Planning a trip to St. Thomas soon? You’re in the right place! 

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This beautiful island may be small, but there’s so much to pack into a trip here. You can snorkel in crystal-clear bays, wander the colorful streets of Charlotte Amalie, and finish every day with an incredible meal at sunset overlooking the sea. 

With so much to see and do, a little planning goes a long way. That’s why we’ve mapped out five days’ worth of our favorite things to do in St. Thomas, with plenty of downtime built in so your vacation still feels like, well, a vacation!

Ready to start planning your dream island getaway? Let’s get to it!

Itinerary Overview

Five days gives you plenty of time to experience St. Thomas, as long as you plan your days wisely.

For this itinerary, we recommend visiting Monday through Friday, as this lines up best with the opening days of the restaurants and activities we’ve included. We’d also get a few of the bigger plans locked in before you arrive. Boat trips and popular restaurants are definitely worth booking ahead, but always double-check ferry and tour schedules closer to your trip.

When it comes to getting around, taxis are usually the easiest option. Just keep in mind that fares are charged per person and rides are sometimes shared. We also recommend arranging return pickups in advance when visiting beaches, marinas, and hilltop restaurants, where finding a taxi on the spot can be trickier.

If you decide to rent a car instead, there’s one important quirk to know: you’ll drive on the left, but most cars are left-hand drive, which can be a bit confusing! The roads can also be steep, narrow, and winding, so drive carefully and give yourself plenty of time to get around. 

On day three of this itinerary, you’ll be heading to the neighboring island of St. John. The passenger ferry from Red Hook to Cruz Bay takes around 20 minutes, making this an easy day trip. If you have a rental car, we recommend leaving it on St. Thomas unless you’ve specifically arranged to take the vehicle ferry. 

Now that we’ve got all the logistics out of the way, here’s a quick look at what you’ll be up to:

Day 1: Blackbeard’s Castle, Food & Night Kayaking
Visit Blackbeard’s Castle, eat your way around Charlotte Amalie on this guided food tour, and finish with a nighttime kayak adventure.

Day 2: Ziplining, Magens Bay & Charlotte Amalie
Zipline above Magens Bay, spend the afternoon relaxing on the beach, and return to historic Charlotte Amalie for a cozy Italian dinner.

Day 3: St. John, Trunk Bay & Cruz Bay
Hop over to St. John for a private island tour, snorkel at beautiful Trunk Bay, and stick around for dinner in Cruz Bay before returning on the ferry to St. Thomas. 

Day 4: Cas Cay Adventure & Sunset Sailing
Kayak, hike, and snorkel around Cas Cay, then sail into the sunset on a catamaran before dinner near Sapphire Beach.

Day 5: Beaches, Sea Turtles & Paradise Point
Slow things down at Morningstar Beach, sail to Little Buck Island to snorkel with sea turtles, and celebrate your final night at Paradise Point.

Day 1

Breakfast – Petite Pump Room

Start your first morning in St. Thomas with breakfast at a longtime local favorite, Petite Pump Room. If you can, grab a table by the windows or out on the open-air terrace. The harbor views are fantastic here, especially when there’s a cruise ship pulling into port!

We recommend arriving right when breakfast starts around 8 am. Keep in mind, though, that you’ve got a food tour coming up at 11 am, so you’ll definitely want to keep breakfast on the lighter side. If you’re in the mood for something local, try the fish and fungi, saltfish, or johnnycakes. Or, if you just want something familiar, you’ll also find pancakes, French toast, and classic eggs with toast and breakfast meat.

One thing worth knowing before you visit is that an 18% service charge will automatically be added to the bill, and there’s an additional 3% fee if you pay by credit card. So just bear that in mind when you’re budgeting for breakfast. 

After breakfast at around 9 am, grab a taxi up the hill to Blackbeard’s Castle. It’s only about a six-minute drive to the upper entrance, but trust us, your legs will thank you for skipping the uphill climb before the day has even properly begun!

Morning – Take in the views from Blackbeard’s Castle

After breakfast, head up the hill to Blackbeard’s Castle for opening time at 9 am. This historic property has finally reopened to visitors, so you can once again climb Skytsborg Tower and explore the surrounding grounds.

Despite the name, the tower wasn’t actually built by Blackbeard. It dates back to 1679, when the Danes constructed it as a watchtower overlooking Charlotte Amalie Harbor. The pirate connection came later, but honestly, the views are reason enough to visit!

Climb to the top, and you’ll be rewarded with panoramic views over Charlotte Amalie’s red-roofed buildings, the harbor, Hassel Island, and the cruise ship docks below. General admission currently includes access to the grounds and tower, plus a tasting in the Rum Room and pool access at Jolly Roger’s. You won’t have time for a swim this morning, but definitely squeeze in the rum tasting before you leave.

We love this activity because it’s excellent value for the price! Admission is currently $15 USD for adults and $10 USD for seniors aged 60+ and military members, and best of all, kids under 12 and USVI residents with ID can visit for free. 

At around 10:15 am, it’s time to start making your way back down the hill via the famous 99 Steps. Thankfully, you’re tackling them downhill! Just watch your footing, as the path can be steep and uneven, especially after rain.

Lunch/Early afternoon – Eat your way through Charlotte Amalie

Food, history, and Caribbean flair – this food tour ticked all of our boxes! We actually booked it on a whim, but it ended up being one of our favorite experiences in St. Thomas.

After making your way down the 99 Steps, head to Fort Christian to meet your guide outside the front doors at 10:45 am. It’s about a 13-minute walk from Blackbeard’s Castle, or you can hop in a taxi and be there in roughly three minutes. The tour begins at 11 am and lasts around three hours, finishing nearby at approximately 2 pm.

Over the course of the tour, you’ll follow your guide through the charming streets of Charlotte Amalie, stopping at locally owned restaurants while learning about the city’s history and architecture along the way. We loved how our guide blended interesting historical tidbits with visits to local foodie hotspots, so we got a real sense of the island’s flavor – pun fully intended!

The exact tastings can change, but expect plenty of Caribbean favorites. We tried dishes like curried chicken and Creole fungi, and you may also sample seasoned rice, plantains, island slaw, and other local specialties. The portions are generous and collectively make up a substantial progressive lunch, so there’s no need to plan another midday meal.

And then come the cocktails! You’ll learn how to mix a Painkiller, one of the Virgin Islands’ most famous rum cocktails, and enjoy another rum drink along the way. All of the food and drinks are included, so just arrive hungry!

Afternoon – Explore Charlotte Amalie’s historic center

After the food tour, spend the next couple of hours exploring Charlotte Amalie’s historic center at your own pace. You’ve already done plenty of walking today, so we recommend keeping this afternoon nice and flexible!

Since you met outside Fort Christian earlier but didn’t have time to explore inside, head back after the tour if it finishes on time. This is the oldest standing structure in the U.S. Virgin Islands and now houses exhibits exploring the islands’ history. Admission is currently $10 USD per person, and we’d allow around an hour to look around.

From here, pop next door to Emancipation Garden, which commemorates the abolition of slavery in the Danish West Indies on July 3, 1848. Then, wander along Main Street and the surrounding pedestrian lanes, where old Danish warehouses have been transformed into jewelry stores, boutiques, galleries, and souvenir shops.

Charlotte Amalie is famous for duty-free shopping, but we recommend looking beyond the jewelry stores and designer boutiques. Keep an eye out for locally made hot sauce, spices, artwork, woven goods, and Virgin Islands rum if you’re looking for something to bring home.

Finish the afternoon with a stroll along the waterfront. The center can get very busy when cruise ships are in port, but things usually start to quiet down as passengers make their way back to their ships.

Dinner – Stone House Cafe

After a busy afternoon exploring downtown, head to Stone House Cafe for an early dinner. This cozy spot is tucked away from the busier harborfront, and with its old-school Caribbean tavern feel, it’s a fun place to wrap up your first day of sightseeing. Plus, the air conditioning will feel very nice after a warm afternoon outside!

The menu here is absolutely huge and packed with Caribbean-inspired dishes, fresh seafood, and even a few American favorites. Personally, my ideal meal here would start with the conch fritters, coconut shrimp, or crab cakes, and then I’d go with the crispy bang bang snapper or fish tacos for the main. 

Make sure to check the daily specials too, as there are usually a few extra dishes to choose from. Recent favorites have been Cajun pan-seared salmon, shrimp and spinach pasta, and lobster with their famous bacon-pineapple fried rice (trust me, it’s a 10/10!). 

We recommend booking a table for around 5:30 pm so you have plenty of time to enjoy dinner. Afterward, head back to your hotel for a little downtime before getting ready to kayak under the stars!

Evening – Paddle beneath the stars on a night kayak experience

This night kayak tour is perhaps the most unique thing we did in St. Thomas! It really felt like stepping into another world, and it’s the perfect adventure to finish off your first day on the island.

After dinner, take a prearranged taxi back to your hotel at around 7 pm. Change into some quick-drying clothes, grab anything you need for the water, and then head to The Westin St. Thomas Beach Resort & Spa. Aim to arrive by around 8:45 pm for the 9 pm departure.

The experience starts with glow-in-the-dark face paint to get everyone into the spirit before you climb into a clear kayak fitted with LED lights underneath. Not only do they look super cool, but the lights also illuminate the water below, making it easier to spot marine life as you paddle!

We saw rays, tarpons, turtles, and tropical fish gliding beneath us, which was incredible. It almost felt like snorkeling without having to get wet! Our guide was also fantastic at pointing out marine life and sharing interesting facts along the way.

Another bonus is that kayaking after dark means cooler temperatures and no worrying about the Caribbean sun. The entire experience lasts about an hour, so arrange return transportation for around 10 pm.

We’d recommend this tour for everyone from couples and solo travelers to families and groups of friends. Just be sure to book in advance, as spots can sell out. It’s such a magical and unique way to end your first day in St. Thomas!

Day 2

Breakfast – Gladys’ Café

For breakfast on day two, we’re sending you to the lovely Gladys’ Café (you don’t need a reservation here unless you’ve got a group of six or more). It opens at 8 am, and we recommend arriving right when it opens, so you’ll have plenty of time to enjoy breakfast before heading off to your zipline adventure. 

The menu here is absolutely huge, so good luck on deciding what to order! If you’re open to trying something a little different, go for the lobster, avocado, and cream cheese omelet. It’s a combination we wouldn’t have thought of ourselves, but it works so well. You also can’t go wrong with the grits, home fries, and toast, or keep things simple with a fruit bowl or egg sandwich. 

You’ll probably want a coffee, but make sure to drink plenty of water too, because you’ll be spending most of the morning outside (and it gets hot in St. Thomas). 

Once you’re finished, aim to leave by 9:30 am at the latest and grab a taxi or drive to Tree Limin’ Extreme. It’s only about 10 minutes from downtown, but give yourself some extra time for traffic on those steep hillside roads. And don’t forget to bring your swimsuit with you, because you’ll be heading straight to the beach after ziplining! 

Morning – Fly above the rainforest at Tree Limin’ Extreme

Get ready for an adrenaline-filled morning because after breakfast you’re going ziplining high above Magens Bay! We loved this zipline tour because it delivered plenty of adventure with a side of jaw-dropping views, and it ended up being one of the most exhilarating experiences of our trip.

We recommend choosing the 10:20 am departure and arriving at the Tree Limin’ Extreme office on St. Peter Mountain by 9:50 am. You need to check in 30 minutes beforehand, which gives you time to complete the waiver and get fitted with your helmet and harness. From there, you’ll hop into the operator’s vehicle for a ride up to the top of the course, where you’ll have a safety demonstration before the real fun begins!

The course features six ziplines, two elevated sky bridges, and eight platforms tucked throughout the tropical forest. You’ll fly through the trees at speeds of up to 35 mph (56 kmph), but our favorite part was the Yo-Yo line. It’s the only one of its kind in the Caribbean and sends you whizzing backward and forward!

However, this experience isn’t just about adrenaline. Several platforms offer incredible panoramic views over Magens Bay, St. John, Hans Lollik, and even the British Virgin Islands. Our guides also shared stories about the island’s culture, legends, and wildlife along the way.

The tour wraps up at around 12:50 pm, making it perfectly timed for an afternoon relaxing at Magens Bay. Whether you’re a first-time or experienced zipliner, we think this is a must-do in St. Thomas, and clearly we aren’t the only ones—read over 2,000 five-star reviews here!

Early afternoon – Look across Magens Bay from Mountain Top

After ziplining, hop in a taxi or drive about five minutes along the ridge to Mountain Top. You’re really here for the views, so head straight out to the open-air observation deck, where you’ll get an incredible look over Magens Bay and the surrounding islands. On a clear day, you can even see St. John and several of the British Virgin Islands in the distance!

Once you’ve taken way too many photos, head inside for a quick look around. There’s a huge duty-free store selling everything from clothing and jewelry to rum and souvenirs, but Mountain Top is probably best known for its frozen banana daiquiris. The drink is said to have originated here in the 1950s, so share one or grab a nonalcoholic version if you want to see what all the fuss is about.

In terms of timing, we’d keep this stop to around 30 minutes. There’s no admission fee, and while the views are definitely worth stopping for, you’ve still got Magens Bay itself to explore this afternoon!

If you’re getting around by taxi, ask your driver to wait and take you down to Magens Bay afterward. It’ll save you the hassle (and time!) of trying to find another ride from up on the hillside.

Lunch – Magens Point Bar and Grill

By now, you’ll probably be ready for lunch, so make the short drive down from Mountain Top to Magens Point Bar and Grill. It’s a casual poolside spot overlooking the area around Magens Bay, and it works perfectly for a quick bite before heading to the beach.

The menu has a mix of both American and Caribbean favorites, with plenty of lighter options if you don’t want a huge meal before an afternoon in the sun. We’d go for one of the fish or jerk chicken wraps, or share some conch fritters, coconut shrimp, or blackened tuna bites. Definitely check the daily specials too, as you might also find fresh snapper, curry goat, oxtail, or another local favorite on offer.

Aim to wrap things up by 2:45 pm so you can be down at Magens Bay by around 3 pm. We wouldn’t linger too long over lunch today because you’ll definitely want as much time at the beach as possible!

One more thing we’d recommend is checking the latest details before you visit. The restaurant appears to have recently changed operators, so the name and opening hours may change. One thing to note is that the restaurant appears to have recently changed operators, so double-check the current name and opening hours before you visit.

Afternoon – Swim and relax at Magens Bay

After lunch, head down to Magens Bay for a well-deserved afternoon at one of the most beautiful beaches in St. Thomas. This mile-long stretch of sand curves around a sheltered bay surrounded by lush green hills, and the water is usually nice and calm, making it perfect for swimming and floating! 

We recommend arriving at around 3 pm, when some of the larger cruise ship groups may already be starting to clear out. The area near the main entrance is the most convenient, with restrooms, showers, food, drinks, and rental facilities all close by. However, if it feels a little crowded, just wander farther along the beach until you find a quieter patch of sand.

You’ll be able to rent beach chairs, umbrellas, cabanas, kayaks, and paddleboards here, so there’s really no need to do much besides settle in and enjoy! Magens Bay isn’t known for incredible snorkeling, but keep an eye on the water anyway, as you may still spot fish or even the occasional sea turtle.

Entry currently costs $7 USD per person for nonresidents, while children under 12 get in free. If you’re driving, parking is also an additional $2 USD per vehicle.

The park does close at 5:30 pm, so start packing up shortly after 5 pm. There’s usually a taxi stand here, but we’d arrange a 5:30 pm pickup ahead of time just for peace of mind. Then, head back to your hotel for a shower and a little downtime before dinner.

Dinner – Virgilio’s

After a shower and some downtime at your hotel, head back into historic Charlotte Amalie for dinner at Virgilio’s Italian Cuisine. This intimate restaurant is tucked away upstairs on a quiet side street, with hand-painted murals, soft Italian music, and the warm atmosphere of a traditional trattoria.

We recommend booking a table for around 7 pm. There’s nothing else planned for tonight, so settle in and enjoy a slower meal after such an active day. The tableside Caesar salad is one of the restaurant’s signatures and is prepared for two, making it a fun way to begin dinner!

For your main course, the Lasagna di Maria is made using the owner’s grandmother’s recipe and is one of the dishes Virgilio’s is best known for. Seafood lovers have plenty to choose from too, including linguine with clams, shrimp and scallop fettuccine, and a hearty seafood cioppino filled with clams, mussels, calamari, octopus, scallops, and fish.

Virgilio’s is currently open until 10 pm from Monday through Saturday and closed on Sundays. It is a popular dinner spot, so reservations are strongly recommended, particularly around 7 pm. When day two falls on a Sunday, head to The Greenhouse Restaurant & Bar instead. This casual waterfront restaurant is open until 9 pm and serves a large menu of seafood, steaks, burgers, and Caribbean-inspired dishes.

Evening – Take it easy after dinner

After dinner, there’s really no need to rush off anywhere. Linger over dessert or order one last drink before grabbing a taxi back to your hotel. You’ve spent the day ziplining through the trees, taking in incredible island views, and relaxing at Magens Bay, so we think you’ve earned an easy night!

Plus, tomorrow is a big one because you’re heading over to St. John for the entire day. Before you call it a night, confirm your morning taxi to Red Hook and get your beach bag ready so you’re not scrambling in the morning. We’d also bring a little cash for the ferry and any small purchases along the way.

Then, get some rest because there’s another full day of island adventures ahead!

Day 3

Breakfast – Lattes in Paradise

Today starts bright and early, but trust us, it’ll be worth it because you’re heading to St. John! Start with breakfast at Lattes in Paradise, a locally owned coffee shop inside American Yacht Harbor in Red Hook. It’s just a short walk from the ferry terminal, making it the perfect place to grab something before you set off.

If you’re pretty hungry, the breakfast burrito packed with eggs, sausage, potatoes, onions, black beans, and cheddar cheese will definitely do the trick! There’s also a gluten-free bowl version, or you can go with a simple egg and cheese sandwich or salmon bagel if you want something a little lighter. 

Of course, you’ll want some caffeine for the early start too. Grab a coffee, tea, smoothie, or one of their flavored lattes, but make sure to bring plenty of water with you for today’s island adventure.

Lattes in Paradise opens daily at 6 am, and we recommend getting here by around 7:15 am. If you’re staying in downtown Charlotte Amalie, allow roughly 25 minutes to reach Red Hook by taxi. Then, at around 8:10 am, wrap up breakfast and make the short walk over to the ferry terminal. 

Morning ferry – Cross from St. Thomas to St. John

After breakfast, make the short walk over to the Red Hook ferry terminal and aim to arrive about 20 minutes before the 8:30 am departure. That gives you plenty of time to check in, join the boarding line, and get settled without feeling rushed.

The ferry takes around 20 minutes to reach Cruz Bay, so it’s a nice and easy journey. Adult fares currently cost $8.15 USD each way for nonresidents, while kids aged 2 to 11 pay just $1 USD. One personal item is generally included for free, but you may have to pay extra for additional bags, so we recommend sticking to a small beach bag for the day.

If the weather is nice, grab a seat outside for the ride. You’ll get some beautiful views across Pillsbury Sound and the surrounding islands, so have your camera handy!

Ferry schedules and fares can change, so definitely double-check your ferry times before your trip. Thankfully, ferries run regularly between Red Hook and Cruz Bay throughout the day, so you’ll have plenty of options for getting back to St. Thomas later.

And if you have a rental car, leave it behind on St. Thomas today. You won’t need it for this itinerary, and taking a vehicle across requires a separate car ferry.

Early morning – Take a first look around Cruz Bay

Once you step off the ferry, you’ll have a little time to get acquainted with Cruz Bay before your private tour begins. Take a quick stroll around the waterfront as you slowly make your way toward Franklin A. Powell Sr. Park, which is where you’ll meet your guide.

We’d save any serious exploring and souvenir shopping for later, but this is a nice chance to get your first look at the colorful waterfront. Before joining the tour, do yourself a favor and use the restrooms near the ferry terminal too, as facilities can be limited during parts of the day.

At around 9:20 am, head back to Franklin A. Powell Sr. Park and look for your guide holding a Star Fish Tours & Taxi Services sign. And before you join the tour, do yourself a favor and use the restrooms near the ferry terminal. Facilities can be limited during parts of the day, so it’s a good opportunity to take advantage of them!

Late morning – See St. John on a private island tour

At 9:30 am, it’s time to see a whole lot more of St. John on this private island tour. We love this tour because it offers such an easy way to get an overview of the island without renting a car, and since the tour is completely private, there’s also some flexibility to customize the experience to your group.

The tour starts with a drive along the beautiful North Shore Road, where you’ll pass some of St. John’s most famous beaches, including Caneel Bay, Hawksnest Beach, Trunk Bay, Cinnamon Bay, and Maho Bay. There are several stops at overlooks along the way too, so you’ll get some incredible views over the turquoise bays and surrounding Virgin Islands. 

Most stops on this tour are fairly quick, but that’s exactly what we like about it! You get to see a lot of the island in just two and a half hours, while still leaving plenty of time to enjoy St. John afterward.

One thing to know before you go is that you’ll be riding in an open safari-style vehicle, so bring plenty of sun protection and hold onto your hat (trust us on this one!).

Then, after a whirlwind introduction to the island, you’ll finish back at Franklin A. Powell Sr. Park at around 12 pm. Just in time for lunch! 

Lunch – Cruz Bay Landing

After your tour, head to Cruz Bay Landing for lunch. It’s right across from the ferry dock and close to the taxi stand, so it couldn’t be more convenient for grabbing a bite before heading to Trunk Bay.

Like a lot of places in this itinerary, the menu here is huge, with lots of tasty choices like fish sandwiches, mahi tacos, burgers, wraps, salads, and fresh seafood. Since you’ll be snorkeling this afternoon, we’d keep things relatively light, and definitely ask about the catch of the day and any local specials!

We recommend giving yourself at least an hour for lunch, then at around 1:15 pm, head over to the taxi stand and grab a ride to Trunk Bay. The drive usually takes around 10 to 15 minutes, so you should have your toes in the sand before 2 pm.

If you can, arrange for the same driver to pick you up later too. Cell service can be a little unreliable at Trunk Bay, and having your ride back sorted means you can relax and enjoy the afternoon without worrying about it.

Afternoon – Swim and snorkel at Trunk Bay

Spend the rest of the afternoon at Trunk Bay, which is one of St. John’s most famous beaches with white sand, clear turquoise water, and green hills surrounding the bay. 

Once you’ve soaked up the views and taken some photos, grab your snorkel gear and head out to the marked underwater trail around Trunk Cay. There are signs beneath the water pointing out different coral formations and marine life, and you’re likely to spot plenty of colorful tropical fish. You might even get lucky and see a ray or sea turtle!

Snorkel gear, beach chairs, and flotation equipment are usually available to rent, and there are restrooms, showers, picnic tables, a snack counter, and a bar too. Just make sure to bring reef-safe sunscreen, water, a towel, and some cash, as visitors aged 16 and over currently have to pay a $5 USD Amenity Fee according to the Virgin Islands National Park website.

Of course, snorkeling conditions depend on the weather, so use your judgment if the water looks rough or visibility is poor. And while you’re out there, remember to stand only on the sand and never on the coral.

At around 4:30 pm, return your rental gear and make use of the showers and changing facilities before meeting your prearranged taxi at 4:45 pm. 

Late afternoon – Browse Mongoose Junction

Once you’re back in Cruz Bay, spend a little time wandering around Mongoose Junction, a beautiful open-air shopping complex, before dinner. Here, you’ll find lots of independent shops selling locally designed jewelry, handmade art, clothing, and irresistible spices. Most shops are open until around 6 pm, so you should have enough time for a quick look around. 

We’d keep this stop pretty flexible, though, as your taxi back from Trunk Bay may make a few stops along the way. And there’s no need to worry about getting to dinner afterward, because it’s right next door! 

Dinner – Morgan’s Mango

After you’ve had your fill at Mongoose Junction, head over to Morgan’s Mango. This popular open-air restaurant specializes in Caribbean-inspired dishes and fresh seafood, so it’s an excellent spot to finish your day on St. John.

We recommend booking a table for 6 pm, so you have plenty of time before the 8 pm ferry. Seafood is definitely the main event here, with options like coconut-panko-crusted grouper, grilled mahi-mahi, seafood paella, and the catch of the day. And if you happen to be visiting on a Tuesday or Saturday, you can also try the locally caught Caribbean lobster served with sweet plantains, rice, and black beans!

If seafood isn’t your thing, there are plenty of other choices, including ginger and sugarcane pork tenderloin, rib eye steak, and citrus chicken, plus a vegetarian coconut paella.

Whatever you order, though, try to save room for dessert. The key lime pie, tres leches, and passion fruit semifreddo all look divine! 

Before you book a table, know that reservations require a credit card, and there’s currently a $50 USD per-person fee for no-shows or cancellations within 24 hours (so you’ll want to make sure your plans are firm before booking). 

As tempting as it might be to linger, you do have a ferry to catch! Aim to wrap up dinner by 7:30 pm and make the short walk back to the ferry terminal.

Evening – Return to St. Thomas

You’ll want to arrive at the Cruz Bay ferry terminal no later than 7:45 pm for the 8 pm sailing. Then, the crossing only takes about 20 minutes, so you should be back in Red Hook by around 8:20 pm.

We recommend double-checking the return ferry schedule earlier in the day, just in case anything has changed. It’s also worth arranging a taxi from Red Hook ahead of time, although you can usually join the taxi line outside the terminal if you’d rather keep things flexible.

Once you’re back at your hotel, call it a night! After a full day of island hopping, sightseeing, and snorkeling, you’ll probably be more than ready for some rest.

Day 4

Breakfast – Barefoot Buddha

Day four starts with breakfast at Barefoot Buddha, a laid-back café in Havensight that’s perfect for fueling up before a busy morning. We recommend arriving around 7:30 am so you can really take your time and enjoy breakfast before the day gets going. 

The menu has everything you’d ever want from an island cafe, including breakfast burritos, egg sandwiches, quiches, oatmeal, yogurt, and bakery items, plus plenty of vegetarian, vegan, and gluten-free options too. There’s really no wrong choice here; just make sure it’s something filling because you’ve got a few hours of kayaking, hiking, and snorkeling ahead of you! 

Once you’re fueled up and ready to go, aim to leave around 8:45 am and grab a taxi or drive to the Virgin Islands Ecotours base at Estate Nadir. It takes around 20 to 25 minutes to get there, and you’ll want to arrive by 9:15 am. You’ll be getting straight into the action once you arrive, so come prepared with your swimsuit, sunscreen, and water. 

Morning – Kayak, hike, and snorkel around Cas Cay

After breakfast, it’s time to get out on the water for one of our favorite adventures in St. Thomas! This Mangrove Lagoon eco-tour combines kayaking, hiking, and snorkeling over three action-packed hours, so you’ll get to experience several sides of the island’s natural beauty in one morning.

Head to the Virgin Islands Ecotours base at Estate Nadir and check in by 9:15 am, 15 minutes before the 9:30 am departure. Once you’re geared up, your guides will run through some kayaking instructions and a quick safety briefing before you paddle into the protected Mangrove Lagoon Wildlife Sanctuary and Marine Reserve.

The calm waterways wind between mangrove islands, and paddling through them was incredibly peaceful. Along the way, our guide taught us how this unique ecosystem provides a nursery for juvenile fish and supports birds, turtles, and other wildlife while helping us spot animals around the lagoon.

From there, you’ll paddle toward Cas Cay, an untouched island that really does feel like a private paradise! After pulling your kayak ashore, you’ll take a short hike to discover tidal pools, volcanic cliffs, and the island’s unique blowhole.

Then it’s time to cool off with some snorkeling. We swam in a coral-fringed mangrove nursery where you may spot stingrays, tropical fish, turtles, and other marine life. It was the perfect ending to the adventure!

The tour finishes back at the meeting point at approximately 12:30 pm. There are restrooms, changing rooms, and lockers at the launch site, so you can dry off and change before heading to lunch.

Lunch – The Smoking Rooster

After a morning on the water, we have a feeling you’ll be ready for a big lunch! Once you’ve changed into dry clothes at the tour base, make the 15- to 20-minute drive to The Smoking Rooster in Havensight Mall.

This casual barbecue joint is all about meat smoked low and slow over American oak. The brisket and pulled pork are two of the most popular choices, but you’ll also find smoked chicken, pork ribs, and jerk chicken wings. Add some mac and cheese, seasoned fries, or baked beans on the side, and you’ve got yourself a pretty satisfying post-adventure lunch! 

We love this for a lunch spot because you can either sit inside or outside at one of the picnic tables. And while we usually prefer to sit outside, after several hours in the sun, we wouldn’t blame you for heading straight for the air conditioning inside.

Once you’re finished with lunch, head back to your hotel and give yourself a few hours to recharge before heading back out for tonight’s sunset sail.

Afternoon – Rest and recharge before the evening cruise

Once you’re back at your hotel, take a shower, relax for a bit, and get changed before heading back out for the evening.

For the sunset sail later this evening, you’ll want to wear resort-casual clothes and flat, secure shoes. We’d also bring a light layer, as it can feel a little cooler out on the water once the sun goes down.

Aim to arrive at the tour’s meeting point at Sapphire Beach by 4:30 pm. It’s around a 25- to 30-minute taxi ride from downtown Charlotte Amalie, but give yourself some extra time for traffic. 

If you’re driving, bear in mind that you’ll also need time to get through resort security, park, and walk down to the beach. And if you’re taking a taxi, we recommend arranging your ride home ahead of time. That way, once the cruise and dinner are over, all you need to worry about is enjoying the evening!

Evening – Toast the sunset from a catamaran

After a few hours of downtime, it’s time to head back out for one of our favorite ways to spend an evening in St. Thomas – this sunset catamaran cruise! Sunsets here are absolutely magical, but watching one from the water with a cocktail in hand makes the experience even better.

Make sure you’re at the meeting point by 4:30 pm to check in. This is required 30 minutes before the scheduled 5 pm departure, and late arrivals unfortunately can’t be accommodated. Once everyone is aboard, you’ll set off for a relaxed two-hour sail along the St. Thomas coastline as the sun begins to drop over the Caribbean.

There’s plenty of open deck space, so find a comfortable spot and enjoy the breeze and changing coastal views. We were welcomed with a glass of champagne before the cold beer and cocktails started flowing as we cruised along the coastline toward the outer keys.

The scenery only gets better as the evening goes on. We watched the sky turn incredible shades of pink, purple, and orange while St. Thomas glowed in the fading light. We even spotted Billy goats wandering along the shoreline in the distance!

The crew kept the atmosphere fun with great music and plenty of interesting stories about the island, but the cruise still felt wonderfully laid-back. There’s lots of space to kick back, sip a drink, and enjoy the views.

The catamaran returns at around 7 pm, leaving you perfectly timed to continue the evening with dinner near Sapphire Beach.

Dinner – Pangea Terra & Ocean to Table

Once you’re back on dry land, make your way to Pangea Terra & Ocean to Table for dinner. It’s just a short drive from Sapphire Beach, and we recommend booking a table for around 7:30 pm to give yourself plenty of time to get off the boat and over to the restaurant. You can walk, but we’d definitely grab a taxi or drive after dark, as parts of the route don’t have sidewalks.

We absolutely love Pangea because it has such a beautiful tropical setting, with tables tucked beneath the trees in an open-air courtyard. The menu is fairly small and changes with the seasons, so you can always expect something fresh and seasonal.

To start, we always recommend trying the ceviche or poke with house-made tostones, or share the Mediterranean mezze. For your main, you can’t go wrong with the fish of the day. You can have it grilled or cast-iron fried, and you can also choose your sides and sauce. If you’re not in the mood for seafood, there are plenty of other options too, which often include coconut curry chicken, wild shrimp pasta, flank steak, and eggplant Parmesan, plus several vegan and gluten-free dishes.

Since there’s nothing else on the itinerary tonight, take your time over dinner and grab a taxi back to your hotel whenever you’re ready to call it a night. Pangea currently serves dinner Monday through Saturday from 5 to 9 pm, although it typically closes for hurricane season from early September until late October. If your trip falls during this period, don’t worry – Sudi’s Caribbean Bar & Grille is conveniently located near Sapphire Beach and makes a great alternative for dinner.

Day 5

Breakfast – Bumpa’s Sandwich Shop

After a couple of busy days, there’s no need to rush this morning! Head to Bumpa’s Sandwich Shop when it opens at 8 am and grab a table upstairs overlooking the harbor. It’s a casual little spot and a nice place to ease into your final day in St. Thomas.

Menu-wise, you’ll find lots of classics like breakfast sandwiches, omelets, pancakes, and French toast. Go for something filling enough to keep you going through the morning, but don’t overdo it because you’ve got an afternoon of snorkeling ahead!

One thing to keep in mind is that Bumpa’s is closed on Mondays and Tuesdays. So if your day five falls on either, head back to Gladys’ Café in Royal Dane Mall instead. It’s just a short walk away and has plenty of breakfast favorites plus a few more local options.

Once you’ve finished eating, grab a taxi or drive the 10 to 15 minutes to Morningstar Beach for one last morning by the water.

Morning – Slow down at Morningstar Beach

After breakfast, head to Morningstar Beach for a couple of hours of doing absolutely nothing! This beautiful stretch of sand sits on Frenchman’s Bay and is perfect for swimming, sunbathing, or simply finding a spot to relax and enjoy the views.

We’ve intentionally kept this morning nice and open. After a few busy days of tours and sightseeing, take the chance to slow down and enjoy one last laid-back morning at the beach.

Morningstar is a public beach, but loungers, umbrellas, towels, and other resort amenities may be reserved for hotel guests or those with a day pass. We’d bring your own towel and beach essentials, so you’re not relying on anything being available when you arrive.

Plan on staying on the beach until around 11:15 am before packing up and walking to lunch, which isn’t too far away!

Lunch – Sunset Cove Poolside Bar & Grill

For lunch, head to Sunset Cove Poolside Bar & Grille. It’s right by the departure point for your afternoon catamaran trip, so you won’t have to worry about rushing across the island afterward.

Aim to arrive around 11:30 am and keep lunch fairly light since you’ll be back out on the water soon. Fish tacos, a salad, or a sandwich are all good options, or share a couple of appetizers if you’re not too hungry.

Try to wrap things up by around 12:15 pm, which gives you plenty of time to find the VI Cat dock and check in by 12:30 pm. If you’re not sure where to go, just ask your server to point you in the right direction. The marina can get busy, so we definitely wouldn’t leave it until the last minute!

Afternoon – Sail and snorkel with turtles at Little Buck Island

After lunch, it’s time for our FAVORITE experience in St. Thomas! This snorkeling adventure to Little Buck Island National Wildlife Refuge was hands down the highlight of our trip and is the perfect way to spend your final afternoon on the island.

From Sunset Cove, it’s around a 15-minute walk to The VI Cat dock at Marriott’s Frenchman’s Cove, or you can ask the restaurant to arrange a taxi for the five-minute ride. Make sure you’re checked in by 12:30 pm, 30 minutes before the 1 pm departure. Frenchman’s Cove is separate from The Westin at Frenchman’s Reef, so follow signs for public beach access and continue to the wooden dock.

From there, you’ll board a spacious 54-foot (16-meter) catamaran and sail across the turquoise water toward uninhabited Little Buck Island. There’s plenty of room to relax in the sun or shade, but the real highlight comes when you reach Turtle Cove!

Masks, snorkels, fins, and flotation vests are all included, and the crew can help beginners get comfortable in the water. We couldn’t believe how many sea turtles we saw swimming around the refuge! The visibility was fantastic, and there were plenty of other colorful fish to spot too. If snorkeling isn’t your thing, you can swim or simply relax aboard the catamaran instead.

Afterward, kick back with snacks and unlimited drinks from the open bar as you sail toward St. Thomas. The tour returns to Frenchman’s Cove at around 4 pm, so head back to your hotel afterward to shower, unwind, and relax before dinner.

Dinner – Prime at Paradise Point

For your final dinner in St. Thomas, we’re sending you somewhere special! Prime at Paradise Point sits high above Charlotte Amalie, with incredible views over the city and harbor below. Try to time your reservation around sunset so you can enjoy the views in daylight, watch the sky change, and see the harbor light up after dark.

As the name suggests, steak is the star of the show here. You’ll find filet mignon, rib eye, New York strip, and larger dry-aged cuts made for sharing. If you’re more of a seafood person, go for the whole fried snapper or locally caught Caribbean lobster. 

If it were us, we’d start with something to share, like the octopus tacos or local lobster cake, then add a couple of sides for the table during the mains. And since it’s your last night, you might as well go all out and finish with key lime pie or rum-raisin bread pudding!

Prime is definitely one of the pricier meals on this itinerary, but between the food and those views, we think it’s worth the splurge for your final night. Reservations are a must, and we recommend requesting a table near the windows or terrace when you book.

Evening – Admire the lights over Charlotte Amalie

Before you leave Paradise Point, take a few more minutes to soak up those incredible views. Charlotte Amalie looks completely different after dark, and it’s a pretty incredible way to get one last look at St. Thomas. 

Getting back down does require a little planning, though. The Skyride’s operating hours can vary depending on cruise ship schedules, so we recommend arranging a taxi ahead of time rather than relying on it after dinner.

Once you’ve had your fill of the views, meet your driver and head back to your hotel. We’ve left the rest of the evening completely open, so all that’s left to do is pack, relax, and get some sleep before heading home tomorrow.

Where to stay in St. Thomas

Now that your St. Thomas itinerary is sorted, you need somewhere great to stay! Whether you want a beachfront resort, a hotel with incredible harbor views, or a budget-friendly base in Charlotte Amalie, we’ve picked three great options for every budget. Just be sure to book early, as the best places to stay in St. Thomas can fill up fast, especially during peak season!

Luxury – $$$

If you really want to treat yourself while also staying somewhere super convenient for this itinerary, The Westin St. Thomas Beach Resort & Spa is the perfect place to stay. 

We especially love the location. Your night kayaking tour on day one leaves right from the resort, and you’ll already be at Morningstar Beach for the relaxed beach day on day five. 

The resort itself is pretty incredible, too. You’ll have direct beach access, three pools, a full-service spa, and plenty of places to eat and grab a drink without leaving the property.

Rooms typically range from around $470 to $800 USD per night, so it’s definitely a splurge. But if your budget allows, we think the location and resort amenities make it a fantastic base for this trip. Check availability and book your stay at The Westin St. Thomas Beach Resort & Spa here!

Mid-range –  $$

The Mafolie Hotel is a great mid-range pick if you want incredible views without paying luxury resort prices. Perched high above Charlotte Amalie, this family-owned hotel has been around since 1952 and overlooks the harbor, so the scenery is a huge part of the appeal.

The rooms have a breezy tropical feel and range from a tiny 120-square-foot (11-square-meters) room that’s ideal for solo travelers to spacious suites and villas with harbor views. There’s also an outdoor pool overlooking Charlotte Amalie, complimentary breakfast, and an open-air bar and restaurant, so you can end a busy day with dinner and drinks without going anywhere.

Rooms are about $200 to $300 USD per night and can be reserved on Booking.com.

Budget – $

If you’d rather save your money for tours and beach days, Galleon House Hotel is a charming budget-friendly option right in Charlotte Amalie. This historic B&B dates back to 1852 and puts you within walking distance of downtown shops, restaurants, bars, and historic sights, which is especially convenient for several days in this itinerary.

The rooms are simple and cozy rather than fancy, but you’ll have air conditioning and everything you need for a comfortable stay. There’s also a freshwater pool and terrace where you can relax while taking in views over Charlotte Amalie and the harbor. We think it’s a great choice if location and value matter more to you than having all the bells and whistles of a big resort.

Prices range from $85 to $150 USD per night. Check availability and book this stay on Booking.com.

Looking for more great options? Browse through all the hotels listed for St. Thomas here!

Thanks for Reading!

We had such an incredible five days exploring St. Thomas! Between snorkeling with sea turtles, beach hopping, kayaking through mangroves, and even taking a day trip to St. John, we packed in so many amazing experiences without feeling like we were constantly rushing around. And, of course, there was still plenty of time for good food, sunsets, and relaxing by that gorgeous turquoise water!

Before you go, browse more of our Caribbean travel guides here for helpful tips, travel inspiration, and ideas for your next island getaway. You can also scroll below to discover more of our favorite destinations. Cheers!

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