Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature ... More

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More

With your friendly and knowledgeable tour guide, this 4 Hour VIP Tour of the South Keys promises to amaze you. En route, you’ll learn the history, culture, and ecology of the Keys, listen to island music, and enjoy the breathtak... More

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury boat, ensuring a swift and comfortable journey through the stunning turquois... More

Explore the vibrant sights of Key West with the Old Town Trolley, Aquarium, and Shipwreck Museum package. This tour offers unlimited hop-on, hop-off access to 13 convenient trolley stops, allowing you to explore highlights like th... More

A Sunset Cruise with a Twist aboard the Island Pearl Wrap up your perfect day in the Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat for the USS Roosevelt. Set o... More

Experience a relaxing start to your day on a spacious 53’ luxury catamaran as you cruise through the clear waters surrounding Marathon. Enjoy a complimentary morning mimosa as the crew guides you along scenic coastlines with vie... More

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and bein... More

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most legendary paranormal figures. Your experience begins with a 30-minute guided ghost tour ... More

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks such as Boot Key Harbor, the Atlantic Ocean, and the histor... More

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your guide will be talking you through many points of interest ar... More

Key West Water Fun with Snorkeling, Sunset Cruise, Dinner, Live Music and open Bar. Enjoy a bright and early morning snorkel Catamaran cruise departing 9 am for a full morning of Snorkeling fun. Return at 12:00pm and have 4 hours... More

Witness the vibrant hues of a Florida Keys sunset on a 90-minute cruise along the stunning Seven Mile Bridge. This intimate experience aboard a 31’ motorized catamaran offers 360-degree views and a shaded seating area, perfect f... More

Enjoy a Spectacular Key West Sunset Cruise Looking for the perfect way to end your day? Join us on the Seabreeze, your 42-foot Corinthian powercat, and ride in comfort with this relaxing, catered cruise into the horizon on Key We... More

You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District. Experience its amazing architecture and hi... More

Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Tours depart an ho... More

Featured in National Geographic Travel - Over 2000 five-star reviews and ranked #1 on Google Maps for Key West dolphin tours. Small Groups, Big Experience - Maximum 6 guests on comfortable Four Winns (25ft) or Robalo (25ft) boats.... More

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

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 �... More