Luxury St. Thomas Trip: Your 4-Day Itinerary
With lavish resorts, breathtaking tropical scenery, and upscale shopping and dining, St. Thomas is an incredible island escape. Our luxury four-day St. Thomas itinerary offers discerning travelers a mix of indulgence, island-hopping adventures and exclusive experiences — all set against a backdrop of the lush Caribbean landscape. From private dinners to world-famous beaches, you’ll delight in every moment.
Friday
Your luxury getaway begins upon landing in St. Thomas at Cyril E. King Airport (STT). A short ride whisks you to your first sanctuary for the weekend: The Ritz-Carlton, St. Thomas. Along the white-sand shores of Great Bay, this impressive resort offers elegance at every turn, with a full-service spa, multiple restaurants and sweeping Caribbean Sea views. Take it all in from your perch on the balcony of a spacious suite or guest room.
After check-in, ease into island time with a cocktail by the infinity-edge pool or take a dip in the crystal-clear waters at the resort’s own beach. Whether you’re lounging in a private cabana or strolling along the shore, the resort’s serene vibe eases you into relaxation mode.
As the sun sets, plan for a four-course, Italian-inspired surf-and-turf dinner on the beach. The gentle lapping of waves and soft twinkling lights dangling from the trees set the intimate mood. Coupled with fine wine and flawless service, your first evening sets a high standard for the days to come.
Saturday
Wake up with a gourmet breakfast at Bleuwater, The Ritz-Carlton’s bayfront restaurant. Sip freshly brewed coffee while perusing a menu of local specialties like the Caribbean lobster omelet, banana bread French toast and the St. Thomas breakfast with salted fish, a boiled egg, spinach, avocado and plantains.
After breakfast, head to nearby Red Hook to catch the ferry to St. John. Soak up the sea breezes during the 20-minute ride to St. John, where two-thirds of the land belongs to Virgin Islands National Park. Once the ferry reaches Cruz Bay, meet a guide for your prearranged island tour with either Explore STJ or Star Fish Tours & Taxi. Both operators customize their tours to your interests, which can include beautiful beaches, sugar estate ruins and stops at scenic overlooks.
One stop is lunch at The Windmill Bar, situated high atop a hill on a former sugar plantation with panoramic views. Order the signature Windmill Breeze mixed with Blue Chair Bay Rum plus orange, cranberry and mango juices. Then, choose a burger, taco or burrito bowl from the casual menu.
The tour continues with a stop at the crescent-shaped Trunk Bay, named the world’s best beach. The powdery sand and clear, reef-filled waters invite you to go for a swim or explore the underwater snorkel trail. Rent umbrellas and chairs, plus pick up refreshments, at The Beach Bar & Snack Shack.
Return to Cruz Bay to take the ferry back to Red Hook. Stop in Moe’s Fresh Market before heading to your next overnight destination, The Hideaway at Hull Bay. Buy fine wine and cocktails to accompany the exquisite five-course dinner that can be cooked by a private chef at your villa. Book this experience in advance with either the Hideaway staff or Island Edge Culinary.
Sunday
Wake up surrounded by nature, ready for an introduction to Hideaway’s beachfront property that features hilly views, a farm-to-table restaurant and a pavilion for gatherings. Take a guided tour of the banana- and palm tree-lined organic gardens at the on-site Hideaway at Hull Bay Farm, which grows herbs, fruits, flowers and vegetables used by the resort’s restaurant.
In the late morning, take a tour of St. Thomas. Whether you choose Godfrey Tours, David’s Fun Tours or the Luxury Sightseeing & Shopping Private Tour, you’ll take in scenic attractions like Drake’s Seat and Mountain Top before heading to Downtown Charlotte Amalie. Wander through the historic district that’s known for its colonial architecture and high-end boutique shopping, especially for jewelry, perfume, designer fashions and local art.
In the afternoon, return to Red Hook to catch a ferry from the D Dock in American Yacht Harbor that takes you to Lovango Resort & Beach Club, an exclusive and stylish oasis on a private cay. Be sure to wear your best beachwear at this see-and-be-seen resort. Relax in a lounge chair and savor the local ingredients infused into a fruity cocktail. Before leaving the island, check out the fashionable finds in five different Lovango shops.
Next, hop the ferry to St. Thomas to return to Hideaway at Hull Bay. Cap off the day with a sophisticated dinner at Blue Eleven, one of St. Thomas’ acclaimed fine dining restaurants. Expect inventive dishes from Chef Benji, along with artful plating and an outstanding wine list. Select from a seven-, nine- or 11-course tasting menu filled with popular local dishes like kallaloo, wahoo, jerk chicken and snapper. Touches like passion fruit butter, pepper jam and plantains bring out the island flavors.
Monday
Take in the breathtaking beauty of Hideaway’s mountain-meets-ocean landscape. Stroll along the Hull Bay shoreline for one last look at this slice of paradise.
Eat your final island meal — a casual one made with locally sourced ingredients — at Hideaway Farm’s eatery, The Shack. Try the conch fritters or mahi bites to start, followed by a Shackburger served on a brioche bun, grilled fish or shrimp tacos.
With bags packed it’s time to return to Cyril E. King Airport (STT) to catch your flight home, with unforgettable memories made in the U.S. Virgin Islands.
