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Planning Your St. Thomas Itinerary

Even though it stretches across just 32 square miles, St. Thomas is full of things to see and do. Three days is the minimum you’ll need to get a taste of island life, while a 5-7 day vacation (or more!) will give you time to truly relax and visit some of the less-traveled spots. We’ve created a detailed three-day itinerary to help you pack in all the absolute must-sees, and a more general five-to-seven day extended St. Thomas itinerary for longer trips!


Day 1: Magens Bay and Charlotte Amalie

Magens Bay

Morning: Magens Bay Beach

Start your adventure by basking in the sun at the most famous spot on the island - Magens Bay Beach. This picturesque beach is often ranked among the world's most beautiful and is a great place for swimmers of all ages and abilities. Spend your morning swimming, sunbathing, and enjoying the serenity of this idyllic spot. Grab lunch on the beach, then treat yourself to one of the famous milkshakes at Udder Delite.


Afternoon: A Stroll Through History

Explore the history of St. Thomas by visiting sites like Fort Christian, the oldest standing structure in the U.S. Virgin Islands, and the 99 Steps, a 300-year-old staircase made from the ballast of Danish sailing ships. Once you reach the top, take a look out over the harbor and imagine the pirate days of yore, then head down to the water to explore the high seas for yourself.


Evening: Sunset Sail

End an amazing day with dinner and a sunset sail. Our concierge service can help you book a sailing excursion and meal under the stars. Concierge services are always complimentary for Island Luxury guests!


Day 2: East End Exploring

Coki Beach, St. Thomas

Morning: Coki Beach

Grab your sunscreen and your beach towel and get ready for a day on St. Thomas’s East End. Start at Coki Beach, where you’ll experience some of the best snorkeling on the island. This beach is ideal for swimmers of all comfort levels: experts can snorkel along the rocks on the right side of the beach, while kids and novice swimmers can stand in the shallows and spot fish right below the surface.


Afternoon: Sapphire or Lindquist Beach

Once you’ve gotten your fill of snorkeling, it’s time to head to one of the East End’s other gorgeous beaches. Sapphire Beach is a great place to enjoy a daiquiri or painkiller before taking a dip in aquamarine waves. Lindquist is a less-developed beach with powdery soft sand and picnic tables. Pack a lunch and bring cash for the small admission fee.


Evening: East End Eats

Finish your day in Red Hook, the center of shopping and dining on the East End. You’ll find a variety of great local restaurants to choose from (see our favorites here). If you want to keep the party going, check out Sapphire Beach Bar or Duffy’s Love Shack.


Day 3: Ready to Relax

Limetree Beach

Morning: A Walk to Remember

After two busy days on the island, you’re probably eager for some R&R. Start your morning off right with a peaceful walk along one of the island’s less-traveled beaches. Take a moment to soak in the breeze and the sound of the waves along Limetree Beach or Secret Harbour.


Afternoon: Spa Treatment

Enjoy your last few hours with the ultimate way to relax - a massage or spa treatment right in the comfort of your own condo or villa. Our concierge service is available to help you schedule a special solo, couples or group treatment.


Evening: Sunset Stroll

Find a spot to watch the sunset and start planning your next visit to the Virgin Islands! Hull Bay and Secret Harbour are both great sunset spots, or enjoy the breathtaking view from Mountain Top.


St. Thomas Itinerary: 4 Days or More


Day 4: Visit St. John

St. John, USVI

A slightly longer St. Thomas stay gives you time to check out St. John, another stunning U.S. Virgin Island. Explore the pristine beaches, hike the trails of the Virgin Islands National Park, and discover the charming town of Cruz Bay. Don't forget to stop at Trunk Bay, known for its underwater snorkeling trail. You can access St. John via a ferry that makes the trip from Red Hook to Cruz Bay.


Day 5: Learn Something New

Deep Sea Fishing

Make amazing memories while getting those endorphins flowing! St. Thomas is a great place to learn to scuba dive, explore kiteboarding, try deep-sea fishing or even take surfing lessons if you’re vacationing during the winter surf season. As we’ve mentioned, our concierge is standing by to recommend an excursion and assist you with the booking process.


Day 6: Wander the West End

Mermaids Chair, St. Thomas

A longer trip gives you a chance to explore St. Thomas’s rugged, less-traveled West End. Take the easy hike to Mermaid’s Chair to see the place where the Atlantic Ocean and Caribbean Sea meet, then stop at Brewers Bay Beach to cool off and, if you’re lucky, swim with the sea turtles that frequent this area.


Day 7: Visit a Deserted Island

A stop at Sandy Spit is a critical part of the perfect St. Thomas itinerary

Some of the most stunning places in the Caribbean can only be visited by boat, so charter one of your own and prepare to be amazed! Bring your passport so you can travel to the nearby British Virgin Islands and see places like Sandy Spit, The Baths and White Bay Beach.


What’s Your Perfect St. Thomas Itinerary?

What would you add to our St. Thomas itinerary? Leave a comment below and tell us about your must-see spots when you visit the island. If you have questions or would like help making a reservation at one of our condos and villas, you can reach out to our concierge service. St. Thomas itinerary


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