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Key West Boat Cruises and Tours

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

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!