48 Hours in the U.S. Virgin Islands: The Ultimate Itinerary

Day 1: Morning

8:30 a.m.: Check-in at the Ritz-Carlton St. Thomas and enjoy a poolside seafood breakfast at Bleuwater to fuel up for your day ahead. The most populated island, St. Thomas is the major tourism hub in the U.S.V.I. making it the ideal base for a trip. It's home to the Cyril E. King International Airport (Charlotte Amalie) and frequently-operating ferry services to St. John and St. Croix (Red Hook).

10 a.m.: After breakfast, hail a cab to Red Hook to catch the 10-minute ferry to Water Island, where you can explore the beautiful Honeymoon Beach and go paddle-boarding in the crystal-clear waters. Check out the vibe at Dinghy's Beach Bar & Grill and maybe order a rum cocktail or two—when in the Virgin Islands, after all. (We suggest the Cream Dinghy, a local frozen favorite that uses Cruzan Rum). Just make sure you don't lose track of time, as you must catch the 12:15 p.m. ferry back to St. Thomas.

Day 1: Afternoon

1 p.m.: To visit all three of the major islands in the U.S. Virgin Islands during your trip, it's important to make a day trip to St. Croix in the afternoon of your first day. We suggest making an afternoon visit to Buck Island National Monument, an uninhabited 176-acre island located just north off the coast of St. Croix. Head to Marriott Frenchman's Cove Dock at 1 p.m. to embark on a three-hour sailing tour of Buck Island aboard a 54-foot Catamaran. During your adventure, you will snorkel at Frenchman's Reef and explore the Buck Island National Wildlife Refuge.

4:30 p.m.: Head to the capital of St. Thomas, Charlotte Amalie, to explore the local landmarks and taste the local flavors of the island. The city was established in 1681 by Danish settlers and travelers can still explore the 17th-century architecture and ruins of this historic city. We suggest climbing the 99 steps (there are actually 103) to Blackbeard's Castle and enjoying the city's picturesque views. Additionally, if you have a bit of an appetite, stop by Gladys’ Cafe, in the Royal Dane Mall, for some Caribbean cuisine and to buy a bottle of the local hot sauce.

6 p.m.: It's officially happy hour, and we recommend celebrating with a craft beer tasting in Historic Frenchtown. The Caribbean may be famous for its rum, but one visit to Frenchtown Brewing will have you interested in the local hops, as well.

Day 1: Evening

6:30 p.m.: Hop in a cab from downtown Frenchtown and head inland towards Crown Mountain Road for the next stop on your journey. Continue the happy hour revelry with a visit up to the historic Mountaintop bar, home to the world's first banana daiquiri. Enjoy your drink while catching an aerial view of St. Thomas at sunset. If you're lucky, visitors can see straight across to Tortola and Virgin Gorda (among other islands in the British Virgin Islands), as well as Puerto Rico.

8 p.m.: Next, head over towards the Mahogany Run Golf Course to enjoy a divinely delectable feast at Old Stone Farmhouse, located in the hills overlooking Charlotte Amalie. Afterward, enjoy more cocktails in the rum courtyard, and enjoy the outdoor ambiance of after-dinner drinks beneath the stars.

Day 2: Morning

10 a.m.: For our second day of adventuring, we're headed to St. John, an island renowned for its natural beauty and gorgeous white-sand beaches. Catch the 10 a.m. ferry for a 20-minute ride from the Red Hook Ferry Terminal in St. Thomas to the Cruz Bay Ferry Dock in St. John.

11 a.m.: While taxis work well for navigating St. Thomas, we suggest renting a car when you arrive on the island of St. John, as the Virgin Islands National Park is best explored on wheels. Head to the Visitor's Center in Cruz Bay to get an overview of hikes and activities, and prepare to be overwhelmed by the gorgeous mountaintop vistas you'll find while exploring the winding roads of the island's National Park. The Virgin Islands National Park accounts for 60 percent of the total land-mass of St. John and is simply a must-visit for travelers.

Day 2: Afternoon

12 p.m.: After visiting the park's visitor's center, enjoy lunch at Woody’s Seafood Saloon, a popular seaside shack located along Cruz Bay in St. John. We suggest Caribbean classics such as the conch fritters and the rum punch. Also recommended on the menu is a B.B.C.—a Banana and Baileys concoction invented in the nearby British Virgin Islands.

1 p.m.: While the environment at Cruz Bay is simply breathtaking, the most scenic shoreline on the island of St. John is found 10 minutes further down the coast, in Trunk Bay.  Trunk Bay is one of the most photographed beaches on the planet, and travelers should set aside an hour or more to enjoy sunbathing in this picture-perfect slice of paradise. Travelers can either pay to snorkel at Trunk Bay or head up to Waterlemon Cay, home to some of the best snorkeling in the U.S. Virgin Islands. Waterlemon Cay is also located within Virgin Islands National Park and is a 12-minute drive from Trunk Bay.

3:30 p.m.: Finally, travelers should return to Cruz Bay to enjoy happy hour on the salt-stained wooden terrace at The Longboard in St. John. Happy hour runs from 3 to 6 p.m. and features The Longboard's world-famous frozen painkillers (a signature drink and a necessary indulgence when visiting the U.S. Virgin Islands).

Day 2: Evening

4:45 p.m.: The U.S. Virgin Islands are famous for their sailing and conditions are always optimal due to reliable trade-winds and the archipelago's geographical composition. Plus, the views can't be topped—you'll find the true meaning for the islands' nickname of "America's Paradise." Though there's no shortage of possibilities for sunset sailing (and daytime sailing, for that matter, as well), we suggest signing up for the hour-and-a-half Champagne sunset sail that departs from the Westin St. John at 4:45 p.m.

6:30 p.m: After you've returned to dry land, we suggest checking out the sophisticated rum bar at 1864, located in Mongoose Junction (a seven-minute cab from the Westin dock). Continue your rum-tasting journey of the U.S. Virgin Islands by ordering the Bird of Paradise, a cocktail mixed with house-infused grilled pineapple rum. 

7 p.m.: After your pre-dinner rum cocktail, get ready to sample the inventive wine menu over at The Terrace, a French-inspired restaurant located in Cruz Bay, St. John. (The wine list has been the recipient of multiple Wine Spectator Awards). The outdoor terrace overlooks the gorgeous Cruz Bay and is the perfect destination to toast the end of your trip. Plus, it's conveniently located right beside the ferry terminal for your return trip home to St. Thomas.

9 p.m.: After your meal, catch the 9 p.m. ferry from Cruz Bay (a short walk from The Terrace) to your final destination in Red Hook, St. Thomas. But be sure not to miss it: This is the last ferry of the evening. (Ferries operate until 10 p.m. on Fridays). If you're up for it, head over to Secret Harbour Beach Resort for one final round of cocktails at the Cruzan Beach Club, a tiki bar that boasts bottle service and outdoor cabanas overlooking the Caribbean Sea.