Sun, Fun, and Island Adventure in Beautiful Key West, FL.

Located at the end of the 113-mile Overseas Highway of US 1, on the southernmost tip of Florida, the city of Key West is home to soft sand beaches, calm blue water, lively nightlife, and a laid-back island vibe.

Spanning just two miles by four miles, it’s not the largest island in the Florida archipelago, but it is one of the most popular, filled with opportunities for exploration, outdoor fun, and a variety of year-round pursuits on land and in the water. 

For this trip, you’ll have deluxe accommodations at one of Key West’s high-end boutique hotels, set within lush tropical landscaping and conveniently located in the heart of Old Town. Here you’ll enjoy restful nights in a spacious room complete with luxury linens and bath products, classic Key West beach details, and all the comforts of home. You’ll also have access to hotel amenities, sparkling outdoor pools with loungers and bar service, daily continental breakfast, and more—all designed to make your vacation special.

We’ve also arranged for you to have three unforgettable adventures during your stay. 

First, you’ll take a private, guided bike tour through the streets of Old Town Key West, seeing some of the city’s major landmarks, pedaling out to the Southernmost Point Buoy for panoramic ocean views, and learning more about the interesting history and people of the island, as well as its Cuban and Caribbean influences. It’s a sweet, leisurely ride that takes you through town and along quiet neighborhood streets and is a great way to kick off a Key West vacation..

Later in the day, you’ll head out for an unforgettable small group sunset sail and dolphin watch tour, passing Key West landmarks along the coast before reaching open water for an authentic luxury sailing experience. As part of the cruise, you’ll search for dolphins, enjoy a fabulous tapas dinner and drinks, and have picture-perfect views of the breathtaking pink and orange sky overhead and reflected in the water around you.

For the third scheduled adventure, you’ll enjoy an incredible half-day seaplane and snorkel trip to Dry Tortugas National Park—one of North America’s most remote and inaccessible National Parks, renowned for its diverse and colorful marine life, pirate legends, and unspoiled natural beauty. Here, you’ll be able to take a self-guided tour of historic Fort Jefferson, sunbathe on a quiet, white-sand beach, and snorkel the incredible living coral reef (the third largest barrier reef in the world) located just off-shore. Beverages and snorkeling gear are provided, and you can bring a lunch or snacks with you if you want to picnic by the water.

Between excursions, you’ll have time to relax at the hotel or do some exploring of your own. Stroll the palm tree-lined sidewalks of bustling Duval Street in the heart of downtown—stretching 14 blocks from the Gulf of Mexico at one end to the Atlantic Ocean at the other—and take in the unique mix of shops, bars, restaurants, and historic buildings. Tour the Hemingway Home & Museum across from the lighthouse. Grab breakfast at Pepe’s Café or a fresh Caribbean-inspired lunch at Turtle Kraals. Get out on the water for jet skiing, kayaking, fishing, or swimming. Or just spend your afternoons relaxing on one of Key West’s beaches, enjoying ocean breezes, warm water, island cocktails, and fun in the sun..