Top Key West Private and Luxury

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.

Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on padded benches and teak decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.

Enjoy a morning in the crystal clear water of The Florida Keys National Marine Sanctuary. This private custom charter will take you on an adventure snorkeling at the reef. See marine life in their natural habitat. Sea Turtles, Tropical Fish, Starfish and a living coral reef abound. Your Captain is knowledgeable and will guide you through the experience. You will stop at a tropical sandbar to splash around and see the home for many bird species while encircling the mangroves on your tour. You will also be welcome to Kayak or use the stand-up paddle board! This will help you navigate the sand-bar and have some fun. If fishing is on your bucket list, we can cast the rod and enjoy some near shore fishing. It's your day and you design the activities that you are interested in. No two trips are alike and we can't wait to help you make wonderful memories!

From local shrimp to the perfect Key lime pie, Key West dining is a food-lover’s dream, but finding authentic flavors can be a challenge in a town packed with touristy restaurants. Discover the very best bites on a gourmet tour that samples a little bit of everything, exploring Key West’s charming neighborhoods, colorful characters, and history along the way.

Join us for a 1.5-hour adventure! Our tour is led by knowledgeable local guides. As we walk through the streets of Key West’s old town, you will discover the history and culture of our island. Shipwrecking, sponging, cigar manufacturing, treasure hunting - it’s all about Key West! What to bring: Hat, sunglasses, and sunblock is a must. Bring at least one bottle of water for yourself. Wear comfortable clothing and shoes. Sneakers are the best option. Camera or your phone to take pictures. Your adventurous spirit :)

Explore the literary highlights of Key West during this walking tour, inspired by David A. Kaufelt’s original literary walking tour. An in-the-know guide whisks you around the Old Town to the former homes and favorite haunts of writers that have called the island home, including Shel Silverstein, Tennessee Williams, and Robert Frost. Since this is a small-group tour, you’ll have plenty of time to ask questions, too.

You will be amazed by how much history and culture our small island has! Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old Town, you will learn how the island was discovered and became one of the richest cities in the USA! Hear the stories of the first industries on the island, such as shipwrecking, sponge harvesting and cigarmaking. Also, learn what key role Key West played in the Cuban fight for its independence and find out why Key West declared the war against the United States. What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.

Private, exclusive tour of the islands near Key West. The only land-based tour in the Florida Keys, operating from Key West. Small groups of up to 12 travel in a comfortable customized air-conditioned vehicle along the Overseas Highway. Drivers are professional tour guides who share fun and interesting information about the Florida Keys and the islands we traverse. Experience the iconic 7-Mile Bridge, relax on the world-famous Bahia Honda Beach, and photograph endangered Key Deer on Big Pine Key. Children are welcome. This tour is customizable. You'll love this tour so much, you'll book it again next year!

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Choose to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. We're licensed like a limousine, so you can enjoy your favorite beverages en route. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.

Enjoy the scenic and breathtaking drive on the Overseas Highway One passing Key Largo and the famous Seven Mile bridge to America’s southernmost city Key West. If you selected the snorkel option in Key West we will board a boat and go out to the reef where we will snorkel and experience Florida's underwater world. After the snorkel tour you will have some time to experience the highlights of Key West on your own. If you selected the transportation only tour option you can enjoy 6 hours of leisure to exploring the islands turquoise waters and white sandy beaches or the small white Victorian conch villas and lush tropical gardens. Stroll along Duval Street with it’s cute shops, galleries and cafes to the famous southernmost point monument only 140 km or 90 miles north of Cuba. Key West’s Caribbean flair and charm will seduce you and is a favorite day tour from Miami. Round trip transportation is included  

Get ready for fun in the sun on this day trip off the coast of Key West. Ride across 42 islands from Miami to Key West, then explore this island city in any number of ways during your free time. See where Ernest Hemingway used to live or visit the Mel Fisher Maritime Heritage Museum. Take a hop-on hop-off trolley tour, see the sites from the famous Conch Tour Train, or take an optional snorkeling tour. Relax, feel the warm sea breeze and enjoy the day. Miami hotel pickup and drop-off included.