Your 24-Hour St. Thomas Itinerary
Let this itinerary be your inspiration for turning a quick getaway into island bliss. Book a nonstop Southwest Airlines flight from Orlando, Florida, to St. Thomas and discover just how much paradise you can fit into 24 unforgettable hours. When the airplane lifts off from Orlando and banks toward the Caribbean, you can almost feel the frenetic pace of life shifting gears into vacation mode.
Fly from Orlando to St. Thomas
Arrive at Orlando International Airport (MCO) in plenty of time to board your 11 a.m. Southwest Airlines flight to St. Thomas in the U.S. Virgin Islands. Sit back and relax as the color palette below changes from mainland greens and browns to the topaz blue of the glittering Caribbean Sea. Soon, the aircraft will descend over a collection of cays, rolling hills and impossibly clear waters surrounding St. Thomas.
The plane lands at Cyril E. King Airport (STT) at 2:55 p.m. Atlantic Standard Time. Look out the window and you’ll spy the blue expanse of Lindbergh Bay nearby. The airport’s open-air design immediately signals that you’ve arrived somewhere special. Secure a licensed taxi driver to take you from the airport to your resort.
Check into the Resort
To keep your St. Thomas itinerary on track, check in to The Westin St. Thomas Beach Resort & Spa at Frenchman’s Reef by 3:30 p.m. Sitting high on a peninsula between Pacquereau and Morningstar bays, the resort’s contemporary design complements the surrounding Caribbean hues. Airy spaces, sea-facing terraces and panoramic views stretch out toward Charlotte Amalie Harbor.
From a comfortable seat at the infinity-edge pool deck, pause to watch cruise ships glide in and out of port, see sailboats bobbing in the harbor and take in the late afternoon shimmer across the water.
Kick Back on a Sunset Sail
Experience St. Thomas from the water during the leisurely Days End Sunset Sail offered by Marriott Bonvoy Tours & Activities at The Westin. As the luxury catamaran launches just before 5 p.m., the hills rise dramatically, activity unfolds along the waterfront in historic Charlotte Amalie and the silhouettes of Water Island and Hassel Island are visible.
As the sun begins to dip below the horizon, the sky turns gold, then coral and purple. Trade winds keep the air comfortable, and the gentle motion of the vessel feels like a reset button for your soul. This is USVI at its cinematic best.
Dinner at Isla Blue Restaurant
After the sailing excursion, return for a 7:30 p.m. dinner reservation at The Westin, where the experience is as much about ambiance as it is about flavor.
At Isla Blue Restaurant, the chic mood is sophisticated, but relaxed. The water views with lights twinkling in the distance are hypnotic. The menu highlights fresh seafood and island-inspired cuisine. You might begin with tuna sashimi, fresh-catch ceviche or caviar. Outstanding options for the main course include grilled Caribbean lobster with a banana pepper-beurre blanc, whole fried snapper with passion fruit-pepper ponzu or a grass-fed filet mignon. Tropical cocktails — such as the Killer Bee made with passion fruit rum or a Coco Refresher featuring coconut rum — are fantastic complements to your meal.
Breakfast & Magens Bay Beach
After a good night’s sleep, it’s time to pick up where you left off on your St. Thomas itinerary to make the most of your day on the island. Wake up refreshed at 7 a.m. and visit the resort’s Frenchman’s Roast for a quick barista-made cup of coffee or head to Sugarfin for the daily breakfast buffet. You’ll want to fuel up for the active morning ahead.
At 8:30 a.m., take a 20-minute taxi ride to Magens Bay Beach, which is consistently ranked among the most beautiful beaches in the world. It’s easy to see why. The mile-long crescent of powder-soft sand curves around calm waters in shades of aquamarine and teal. In the morning, the bay feels serene. Palm trees frame the beach, and the water is typically gentle — perfect for swimming. You won’t want to leave this peaceful setting.
Scenic Drive & Photo Ops
On your way back to The Westin, stop for photo ops at some of St. Thomas’ most celebrated overlooks.
Drake’s Seat: Named for Sir Francis Drake, this vantage point offers sweeping views of Magens Bay and neighboring islands. The Caribbean Sea stretches across the horizon at one of the island’s most-photographed spots.
Mountain Top: Situated 1,200 feet above Magens Bay, this is the highest point on St. Thomas, offering the best views. Beyond the amazing vistas, Mountain Top is famous for its banana daiquiris and colorful souvenirs.
Skyline Drive: This winding roadway delivers dramatic harbor views of Charlotte Amalie. From here, you can see cruise ships docked below, historic buildings and the expanse of the Caribbean Sea.
Lunch at Mi Casita
In Charlotte Amalie, stop at 11:30 a.m. for lunch at Mi Casita, offering authentic Caribbean and Dominican cuisine. Expect generous plates and complex flavors. Popular dishes include seafood pasta alfredo, fried snapper in coconut sauce, churrasco steak and mofongo (an island side dish with plantains as the main ingredient).
The restaurant is casual, delicious and a perfect final taste of St. Thomas before you depart. After lunch, return to The Westin to gather your belongings and take one last look at the harbor from your private balcony.
Airport Departure
Your itinerary wraps up with a taxi back to the airport. Make sure to leave no later than 2 p.m. to catch your 3:55 p.m. Southwest Airlines flight. By early evening you’ll be back in Orlando, sun-kissed, refreshed and no doubt already thinking about your next trip to St. Thomas.
Discover More Things to Do on St. Thomas
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