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Key West Water Adventures

Let our local experts arrange the perfect tour or rental for you!  Browse through some of our most popular excursions, pick out your dream choices and we'll take it from there.   You can reach the Historic Hideaways Concierge at 305-290-3792 or .

Jet Ski Tours

Blast over the waves and experience the thrill of gliding across the ocean's surface. Speed around the island of Key West on a jet ski with your loved ones or on a solo mission! You can also book a guided tour around the island with knowledgeable guides. You will also learn interesting facts about Key West's history and see historic landmarks. No jet ski experience required and we offer free shuttles. 

All Day Tours
All Day Adventures

This is the package for those who want to experience multiple activities like snorkeling, kayaking, jet skiing, water trampolines, and much more! These adventures last all day and will provide breakfast and lunch for you. Couples looking for some fun or families that are seeking adventure as a group will love this adventure package.

Key West Sailing
Schooner Day Sails

Channel your inner-pirate and storm the seas of Key West Harbor in a conventional wooden schooner. These beautiful vessels allow you to experience how settlers of this great nation made their way across the sea while learning some cool facts about the history of Key West…also the kids love it. You can choose to go during the day (for families and early birds) or sunset sails for couples, historians and sailing enthusiasts.

Sunset Sails
Sunset Sails

There really is nothing more breath-taking and awe-inspiring than the perfect sunsets of Key West. We recommend that you view these perfect sunsets by sea on the deck of one of our glorious sailboats. You can witness sunsets from the deck of a schooner or catamaran. You can even book a chartered tour that is limited to 6 people. Most sunset cruises offer free drinks for all adults of age.

Custom Charters Key West Florida
Custom Charters

Since this is your perfect vacation we offer the option to enjoy a private boat charter. Create your perfect atmosphere while sailing the waters around Key West. We can also coordinate a private charter that offers fishing, lobstering, snorkeling, beach picnics, dolphin watching, and pet-friendly trips!

Dry Tortuga National Forest Trips
Dry Tortuga Trips

Key West is the proud home of Dry Tortugas National Park, which is home to historic Fort Jefferson. You may reach the island by one of 3 ways; ferry, seaplane, or private charter boat. When visiting Key West, this is one of the must-do activities so we encourage you to book in advance…Trust us, it’ll be worth it.

Dolphin Watching Tours Key West Florida
Dolphin Watching

See wild dolphins in their natural habitat! Under the Marine Mammal Protection Act, people are not allowed to swim with the dolphins, but they will entertain you with their antics and enthusiasm! Some trips also include snorkeling the reef or backcountry. Private charters available.

Fishing Trips Key West Florida
Fishing Trips

Key West offers world class fishing in different areas surrounding the islands. Choose from backcountry flat water, coral reef & wreckage areas, and offshore fishing for larger species. Our best in class companies own some of the finest boats available to take you fishing and enjoy what is naturally one of the best vacation fishing spots in the United Sates. We offer trips for experts or novices alike. 

Glass Bottom Boat & Kayaks

View the beautiful wildlife that resides in and around Key West through a glass-bottom boat or kayak. The kayaks that you rent have a completely see-through floor that will allow you to look into the magical world below the ocean's surface. Take this opportunity to peer through the clear blue water to see the wonderful world below. You may also combine snorkeling with the glass bottom viewing boat if you'd like, so there are options for everyone. 

SCUBA Diving

Experience the dark, calm silence of the ocean as you explore all of the wonderful underwater adventures that exist around the Key West area. Key West offers divers a chance to explore the famous USS Vandenberg wreckage, and the planet's third largest living barrier reef, not to mention the colorful marine life. There are various certification courses and resort courses that you can pick up in a day! 


Lucky for you Key West is home to the 3rd largest underwater reef in the world. Only Australia and Belize have larger underwater reefs. We can arrange a snorkeling adventure guide to deliver you to the diving locations by speed boat, catamaran or schooner. We can arrange private charters and combination trips for your party based on your needs. 

Key West Parasailing

Fly like a seagull 300 feet above the electric clear blue waters of Key West Florida. Completely safe and exceptionally exhilarating, this is the only way to see all of the beautiful natural sights in the Key West area. 

Flyboard Adventure

Soar, burst and explode from the ocean's surface like a super-hero after learning from a professional flyboard instructor. This new invention is commanded by the motor of a jet ski that allows you to attach to this powerful board and blast up to ten feet in the air. The sheer rush that comes with this activity is unexplainable, and a must for all thrill-seekers. 

Paddle-board Tours & Rentals

SUP, Stand Up Paddle-boarding is a relatively new sport and it seems to be the perfect sport for the Key West area. There are various operators and rental companies that offer trips for all levels from beginners to experts. Some of the tours around Key West take advantage of exploring the crystal blue waters of the area while gently gliding over the wildlife that resides in the shallow waters. Free shuttle available for most tours, so let us know when you’d like to go and we’ll make the arrangements. 

Kayak Tours
Kayak Tours & Rentals

If you are into self-exploration or even a guided kayak tour, then we can find you the right kayak trip. A professional guided tour will take you about 10 miles from Key West into some less-developed areas. Kayaks come in all shapes and sizes and we can assist you in deciding whether you would need a larger ocean kayak or a smaller single or double kayak. Free shuttle rides for kayak tours and no experience is required.