Experience the fun of sailing an authentic historic wooden tall ship  Help raise the sails, take the helm, or just sit back while you head out to sail the waters surrounding Key West. Keep an eye out for the dolphins, Osprey, Sea Turtles, and birds from the island and the sanctuary.Experience Schooner Hindu and discover the beauty and tranquility of tall ship sailing in the clear tropic waters surrounding Key West. Call 305-304-3565 for charter information and details.

Day Sail Join us for a two hour schooner sail around Key West's Historic Harbor. Includes premium beer, wine, Champagne, and soft drinks. Sunset Sail Savor the warm breezes & a spectacular Key West Sunset and FREE Premium beer, wine, Champagne, soft drinks, and cheese platter on the Schooner Appledore, operated by Key West Sebago. GO TO WEBSITE

Key West’s Most Exciting Daily Sails and Private Charters Sail back in time aboard the Schooner Jolly II Rover. Rediscover old world sailing on a classic 80’ Caribbean coastal sailing ship -- the same kind used by infamous pirates, rum runners, and those who first sought the freedom and solitude of the Florida Keys hundreds of years ago. Their spirit of independence and adventure lives on daily as we sail Key West and her crystal clear waters with authenticity; Jolly II Rover is the only square rigged, topsail Schooner sailing out of the Historic Seaport of Key West. Key West Sunset Sails – Romantic Sightseeing Adventures Daily Sunset Sails depart Key West’s Historic Seaport nightly. One of the most sought after things to do in Key West, our regularly scheduled sunset sails are perfect for adventurous families or couples seeking a romantic interlude at sea. Bring your own food and drinks, and let us transport you to a time when sailors were one with the ocean. Join the crew and hoist the sails, or just sit back, relax and take in the experience. Revel in the moment as our magnificent red sails capture the wind and the Rover sails off to a place time ...

When you sail with Danger Charters, you sail to another world and time; to a place where the wildlife is still "wild", and your interaction with nature is intimate and authentic. You  feel as if you’ve stepped back in time, back to the days when the Florida Keys backcountry was home to traditional, shallow-draft sailing craft, captained by local water men that had grown up sailing and navigating the notorious shallows and challenging narrow channels of the Florida Keys. Explore the wondrous and enigmatic mangrove islands with one of our very knowledgeable nature guides. Learn all about the mangrove eco-system, while paddling through a maze of mangrove-canopied canals and streams, that are home to an incredible tropical array of birds, rays, sharks, sport fish, and more. And, no worries if you’ve never kayaked before; our kayaks are very stable sea kayaks that novices from ages 6 to 90 and beyond can easily paddle with a few simple instructions from your guide! Danger’s specialty shallow-draft vessels visit a variety of private and pristine patch reefs in the calm and protected waters of the Florida Keys backcountry to provide you with an exceptional and personal underwater experience. And, due to the topography of islands ...

Classic Harbor Line Key West Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessel in the local schooner fleet: Adirondack II. While visiting Key West, Florida you will find a number of land and water based activities. However, a classic schooner sail – a day sail or sunset sail – is well known to be the quintessential Key West activity that will highlight your stay and be the lasting memory forever. South Florida sightseeing is all about getting on the water, seeing the wildlife, watching the sunset with a loved one, and experiencing the adventure sailing in the great Key West Florida breeze. A 2 hour sailboat ride is a great way to take advantage of your time in Key West to enjoy all of these things. Whether buying tickets for one of our Mimosa Morning Sails, Day Sails, Champagne Sunset Sails, Full Moon, Star-Gazer Sails; or Privately Chartering the schooner for a special family event or corporate event, you will be amazed by Adirondack II’s beauty and comfort. She was built and is maintained by the ...

Boarding at the Historic Seaport at Schooner Wharf, passengers are greeted by our uniformed crew.As the magnificent Schooner Liberty Clipper leaves the dock for a delightful cruise through the Key West harbor and out into the open water, blazing white canvas billows overhead, and passengers enjoy the gentle breeze and the unique sensation of being transported back in time to Key West’s rich maritime past. They are encouraged to take the wheel, or simply kick back and relax for a couple of hours, while the crew hoist the rigging, point the bow to the horizon and cater to their every need. ENCHANTED SUNSET SAIL As Key West slides astern and the bow is pointed ...

Sail into History Towering masts support massive white sails billowing in the wind. Balmy ocean breezes lift the aroma of fresh sea air across the wooden deck as soul-warming sunshine reflects off the crystal aqua water. Captain and crew engage you in tales of the last sailing cable tending schooner on earth. She’s one of the oldest working wooden schooner in the United States, the official flagship of Key West and on the National Register of Historic Places. Aboard the Schooner Western Union Maritime Museum, you’ll be transported to another era as you experience a one-of-a-kind journey through the glory days of this magnificent ship. GO to WEBSITE