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US Virgin Islands Itinerary – How to Spend 9 Days in the Caribbean

Today I want to share my US Virgin Islands itinerary with you. This part of the United States is a great place to escape to if you love Caribbean beaches, warm weather, and stunning scenery. From St Thomas to St John and St Croix, there’s a lot you can do and see here. Read on for my guide to how to spend your time in paradise.

US Virgin Islands Itinerary

US Virgin Islands Itinerary

My US Virgin Islands itinerary covers 9 days in this part of the Caribbean (7 if you don’t include travel days). I’ve been here twice before, and I’m excited to return to see more of this United States territory.

I’m going to visit all three islands, and I can’t wait to experience some of the best things to do on each one.

Cinnamon Bay, USVI

Day 1: St Croix

I’m starting my trip on a Saturday afternoon. My flight arrives on St Croix at 3pm, and I head into Christiansted. It’s the largest town and one of the best areas to stay on the island.

I’m staying with locals just outside the main part of town like I did on my last trip to St Croix. Their house is on a hill overlooking the sea, and it’s a beautiful place to call home-away-from-home.

I spend the first evening getting acclimated to the time difference and enjoying tropical cocktails and dinner on their terrace overlooking the Caribbean. It’s the perfect way to ease into island life.

St Croix, USVI View

Day 2: St Croix

The next morning my US Virgin Islands itinerary officially kicks off with a trip to the beach. We drive over to The Buccaneer, a pink hilltop hotel in Shoys with great beaches and a waterfront restaurant called The Mermaid.

We settle in for the day, soaking up the sun on lounge chairs and taking a walk along both of the hotel’s beaches. We spot all kinds of shells on the sand, and we love the feel of the water on our feet.

We order lunch and cocktails to our lounge chairs, enjoying seafood salads and burgers under our sun umbrellas as the waves lap the shore.

St Croix beach in Shoys

When evening comes, we head out to a restaurant called Salt Great Pond for dinner. We tuck into the delicious daily specials to start, then order everything from jerk mahi to steak and pork chops for our mains.

Sitting outside in the Caribbean breeze, it’s a great way to end our first full day in St Croix.

Day 3: St Thomas and St John

The next morning our US Virgin Islands itinerary continues with a seaplane ride to St Thomas. Our flight takes off from the Christiansted Harbor Seaplane Base, so it’s an easy drive to get to the departure gate.

USVI Seaplane

The 20-minute ride offers spectacular views over the Caribbean Sea and the green hills of St Thomas. It’s a fun and beautiful way to travel.

When we arrive, we ask the pilot for a recommendation for breakfast. He sends us to the Frenchtown Deli and Coffee Shop, which is a short walk from the Charlotte Amalie Harbor Seaplane Base.

We order hot meals at the counter, then settle in at a picnic table outside to eat with a view of the sailboats. It’s sunny and warm, and we can’t help feeling like we’ve landed on the perfect spot to start the next leg of our USVI itinerary.

St Thomas, USVI Deli

From breakfast we walk over to the ferry terminal next to the seaplane base and catch a taxi to Red Hook. We buy tickets for the ferry to St John when we arrive, then board the next boat for the 20-minute crossing.

We arrive on St John around 11:30am and spend a bit of time browsing the shops and open-air market. There are all kinds of things for sale here, from clothing to wine and souvenirs.

Soon we’re picked up by the owner of the apartment we’ve rented in Cruz Bay. He kindly drives us up the hill so we can drop off our bags, then back into town to catch a ride to the beach.

St John, USVI Bar

Once there, we hop in one of the big shared taxis that take people all over the island. We’re heading to Cinnamon Bay, a beach we’ve heard is beautiful but not as crowded as some of the more famous beaches in St John.

The ride offers spectacular views from the hills above the Caribbean Sea, and soon we alight at the beach ready to relax.

Cinnamon Bay is everything we hoped it would be. Pristine white sand, turquoise water, and views of the British Virgin Islands fill our eyes as we lay out our towels.

We sunbathe and swim for a while, then pick up sandwiches for lunch at the kiosk near the waterfront. It’s the perfect way to spend our first afternoon on the island.

Cinnamon Bay Beach, St John, USVI

Back in Cruz Bay, we take a taxi to The Westin St John Resort, where I stayed on my last trip to St John, and head out on a sunset cruise.

A catamaran whisks us out of Great Cruz Bay and along the coast as we sip cocktails, nibble canapes, and watch the sky turn golden.

After the cruise we head back into Cruz Bay for pre-dinner drinks. We walk around trying to find a place, surprised how busy everything is.

We manage to snag the last table on the beachfront deck at High Tide and settle in for cocktails by the big outdoor bar.

St John, USVI Sunset

Afterwards we have dinner one street over at Lime Inn. We’ve heard great things about the food here, and the four-course tasting menu lives up to its reputation.

Everything from the tuna tartare to the Caribbean lobster risotto is delicious, and the whole red snapper might just be the best fish we’ve ever had.

Day 4: St John

The next morning our US Virgin Islands itinerary begins with breakfast at St John Provisions. This local spot in Cruz Bay came highly recommended by the owner of our apartment rental.

The coffee and za’atar bagels are excellent, and the meal sets us up well for the day.

Cruz Bay, St John

Afterwards we hop in a shared taxi by the waterfront and settle in for the 25-minute drive to Coral Bay. We’re here to see something we’ve never seen before: a floating taco bar.

Called Lime Out, it’s the sister restaurant of Lime Inn, where we ate the night before. We’ve pre-arranged a dinghy ride out to the bar thanks to a tip we got from the owner of Lime Inn the previous night.

Our captain ferries us out into the bay, and a couple minutes later we’re sitting on big foam lily pads surrounding a taco shop. It’s everything we hoped it would be.

We order from a menu the server floats out to us on a foam tray, then settle in for cocktails and tacos as boats pull up around us. The catamaran from our sunset cruise the previous night even sails up to join the fun.

Lime Out floating taco bar, St John, USVI

After lunch our dinghy captain takes us back to the shore and we call a private taxi to take us to the next stop on our US Virgin Islands itinerary: Maho Bay.

Maho Bay is another of the most beautiful beaches in St John. As soon as we arrive, we’re impressed by both its colorful beachfront bar and its beautiful sand and water.

We rent beach chairs, then head to the sea to set down our things and start sunbathing. The snorkeling here is great, not least because of the sea turtles.

We spend the afternoon here, then head over to the beach bar to order rum cocktails and play cornhole as we wait for a shared taxi to Cruz Bay.

Maho Bay Beach Bar

Back in town we have a drink at the famous Woody’s Seafood Saloon, then walk back to our apartment to freshen up for dinner. We’re headed to Morgan’s Mango in Mongoose Junction, and we’ve heard their lobster is legendary.

It is. We sit at a table with a view in the multi-level dining room and feast on Caribbean lobster. It’s everything it was promised to be, and we love both the food and the buzzing atmosphere.

Day 5: St John, St Thomas, and St Croix

The next morning our US Virgin Islands itinerary continues with a big breakfast of crab cake Benedict and Huevos Rancheros at Cruz Bay Landing.

Table at a St John, USVI Restaurant

Afterwards we store our luggage at Connections of St John and walk over to Mongoose Junction to go hiking. We’re off on the Caneel Trail, a moderately challenging out-and-back route with beautiful views of the bays and islands.

One of the most popular hikes in Virgin Islands National Park, it features wooded areas, vista points, and a platform with panoramic views at the top of the hill.

It’s well worth the climb, and we’re grateful for the exercise after all the eating and drinking we’ve done.

St John, USVI View

Back down in Cruz Bay, we spend our last hours on the island browsing the boutiques, walking along the beaches in town, and sipping drinks in Adirondack chairs on the sand in front of a waterside bar called the Rum Hut.

At 2pm we board the ferry to Red Hook in St Thomas. When we arrive, we hop in a shared taxi to get back to the Charlotte Amalie Harbor Seaplane Base.

It’s a long ride, not least because there are five huge cruise ships on the island and lots of people around. We get a glimpse of the waterfront as we go, then board our flight back to St Croix and enjoy the views along the way.

St Thomas, USVI Ferry

When we land, our USVI itinerary continues with dinner at AMA at Cane Bay restaurant at The Waves Cane Bay hotel.

We start with excellent cocktails at the seaside bar as the sun goes down. From there we step over to the restaurant and sit outside on a deck over the water.

We dine on everything from steak to mahi as the sound of crashing waves serenades us. It’s one of the most memorable meals of our trip.

St Croix Hotel Restaurant

Day 6: St Croix

The next morning our US Virgin Islands itinerary takes us into Christiansted for a bit of shopping. There are great boutiques here, and they have everything from clothing to jewelry, home goods, bathing suits, and decorative items.

We love the bracelets at ib designs, the dresses at Asha, the gifts and interior decor at Adorn, and the beachwear at Island Saint.

When we’ve finished shopping, we have lunch at Shupe’s, a casual restaurant and bar on the boardwalk. It has views out over the harbor, and we enjoy cocktails, burgers, and grilled cheese sandwiches as we take in the scene.

St Croix Shops

After lunch we walk along the boardwalk and do some more shopping in Christiansted.

As we go, we spot a number of churches and historic government buildings interspersed among the colorful shopfronts around the town. The heritage facades are redolent of St Croix’s Danish colonial past.

In the evening we participate in one of the most unique local traditions on St Croix: Disco Bingo.

Hosted at the Deep End Bar and Grill between the Tamarind Reef Resort and the Green Cay Marina, it’s a lively night of games, dinner, and dancing that draws locals and visitors from across the island.

Disco Bingo on St Croix

We settle in at a table in the packed open-air beach bar and tuck into heaping plates of food as the games begin. There are five bingo sessions, each with a stint of music and dancing in between.

Everyone gets into the spirit, and we have so much fun we stay late to keep the party going. I never thought I’d enjoy it so much, and it ends up being a highlight of the trip.

Day 7: St Croix

The next day our US Virgin Islands itinerary takes us over to Frederiksted on the west end of the island. Established in 1751, it’s the second largest town in St Croix.

Our first stop is The Fred, a hip adults-only hotel on the beach. The colorful pool bar and stylish gift shop lure us in, and we spend a while exploring the grounds and taking in the historic buildings that make up the property.

Frederiksted Hotel

Afterwards we drive over to the main part of town to pop into a few shops, admire the clock tower, and take in the views from the waterfront.

From there we make our way to Rainbow Beach, one of the most famous stretches of sand on St Croix. We settle in for the afternoon, breaking for lobster tacos at Rhythms restaurant when the sun gets hot. It’s a blissful way to spend a few hours.

Sign on Rainbow Beach, St Croix

In the evening we enjoy a special island festival in Christiansted. Jump Up takes place four times a year, and we’ve planned our visit to coincide with it.

The historic streets fill with stalls selling everything from barbecue to sugarcane cocktails, and the shops stay open late for the occasion.

Live bands play music and moko jumbie stilt-walkers dance through the streets in colorful costumes. It’s amazing to be here for the occasion.

Moko Jumbie at Jump Up in St Croix

We walk around for an hour to take in the scene, then head to dinner in the courtyard at Too Chez. With fresh seafood and good wine, it’s an enjoyable way to end the evening.

Day 8: St Croix

The following day our US Virgin Islands itinerary continues with a bit more shopping. We hit up the gift shops at The Buccaneer, then drive into Christiansted to go to Sampson House.

The home goods and clothing here are swoon-worthy, and we could spend all day buying things to decorate our houses and selves with.

Street in Christiansted, St Croix

Tearing ourselves away, we continue our USVI itinerary by driving to lunch at La Reine Chicken Shack.

This casual open-air restaurant in the middle of the island is said to have the best barbecue chicken on St. Croix. Martha Stewart even called it her favorite restaurant here.

We tuck into everything from kingfish to goat stew, savoring every bite. It’s a great experience, and we’re glad to have made the trip.

food at La Reine Chicken Shack

From La Reine, we drive over to St George Village Botanical Garden. Set among historic structures of colonial-era plantations, this place has plant species spanning 16 acres.

It’s a peaceful haven with historical and living collections of over 1,500 native and exotic species and varieties.

St Croix Botanical Garden

After the garden, we drive to a road that runs along the northwest side of the island. From Butler Bay to North Side and Hams Bay, we pass everything from a geological blowhole to rock formations like Monk’s Bath and secluded beaches.

With its rugged scenery, it has a more remote feel than other places we’ve been to in the USVI.

We drive all the way down the dirt Hams Bluff Road to a trail that leads to Hams Bluff Lighthouse. It’s amazing to take in the wild landscapes and seascapes along the way.

St Croix Coast

As the sun sets we head into Christiansted for dinner at a Thai restaurant called Galangal. Everything from the summer rolls to the curries is delicious. And that’s to say nothing of the cocktails.

After dinner we drive over to the Caribbean Community Theater. There’s a show on tonight, and we’re excited to see the production.

It’s a hit, and something I never expected to discover on the island. Enjoying such a local experience is a great way to end our last full day here.

Caribbean Community Theater

Day 9: St Croix

The next day is the last on our US Virgin Islands itinerary. We go into Christiansted for brunch at Caroline’s, a pretty restaurant in the King Christian Hotel.

There’s a long wait for a table, so we busy ourselves walking over to the 18th-century Fort Christiansvaern, a bright yellow building with green trim.

We do a self-guided tour, reading the plaques with the history of St Croix (did you know Alexander Hamilton spent a good part of his youth here?) and taking in the views from the top.

Fort Christiansvaern

When our table is ready, we tuck into unique dishes like Bananas Foster French toast and loaded hash browns. Afterwards we walk through the open wall to Cream & Co for ice cream.

By the time we’re finished, we need to start packing for our flight home. It’s been a memorable trip to the US Virgin Islands, and I’m sad to say good-bye. St Croix, St Thomas, and St John have all impressed me, and I’d love to return and see more of them.

Christiansted Restaurant

US Virgin Islands Itinerary

I hope you’ve found this itinerary for the US Virgin Islands helpful, and that you get a chance to visit this part of the Caribbean someday. It’s a really unique place, and an amazing island escape. Happy travels!

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