Sail in Florida and the Virgin Islands!
Thank you for another fantastic season! We’re already counting down the days until we can set sail with you again aboard Tall Ship Windy in 2024.
If you’re looking for other ways to sail, we invite you to explore our other exciting locations! Tall Ship Windy is proud to be a part of the Amphitrite Digital family of companies.
Join us at Paradise Adventures in Panama City Beach, Florida, where sun-kissed shores await. If you’re dreaming of a week-long yacht vacation, Charter Smarter in the Virgin Islands promises an unforgettable experience. For a full or half day on the water from St. Thomas and St. John in the US Virgin Islands, our team at Seas the Day Charters USVI is ready to make your dreams a reality.
No matter where your compass points, we’re here to create more unforgettable memories with you. Until then, fair winds and following seas.
Paradise Adventures Catamarans and Watersports
Panama City Beach, FloridaEnjoy top-rated boating adventures on the Florida Gulf Coast at Paradise Adventures Catamarans and Watersports!
- Experience inflatable fun on a Privateer Adventure Tour
- Snorkel and explore Shell Island
- Look for dolphins on a Sightseeing Tour or enjoy a Breathtaking Sunset Sail
- Book a private charter on a catamaran, sailboat, powerboat or pontoon boat
Charter Smarter
Virgin IslandsExplore the wonders of the Virgin Islands with an all-inclusive Charter Smarter yacht charter!
- Each week-long adventure includes a professional captain, a skilled chef and all meals and drinks
- Take advantage of all your catamaran’s amenities, water toys and land-based activities in paradise
- Bring your family or friends and create memories that will last a lifetime
Seas the Day Charters USVI
US and British Virgin IslandsEnjoy a full or a half-day adventure with Seas the Day Charters USVI!
- Luxury sailing excursions & fast powerboat adventures
- Private & semi-private charters available
- Snorkel with beautiful fish, coral and sea turtles and explore white sandy beaches
- Explore the US Virgin Islands or the British Virgin Islands
Explore Chicago’s scenic shores and enjoy this Windy City boat tour with a relaxing sail around Lake Michigan. Take in the world-famous Chicago skyline, enjoy spectacular city views and discover the Windy City from the water. Select from Pirates and Maritime stories at 1pm, Architectural Tour and Skyline at 3pm and 5pm or a Chicago Sunset Cruise at 7pm.
75 Minutes | Starting at $39
Explore Chicago Sailing Special Events
Welcome Aboard Tall Ship Windy
Tall Ship Windy, sailing from Chicago’s Navy Pier, brings you exciting boat tours that are educational, creative and inspiring. From our daily storytelling adventures and field trips for students to our concert sails to lively Chicago Architectural Tours, there is something for everyone. Enjoy the Chicago skyline as you sail on our tall ship!
For group boat excursions and private sailing charters, email us at tickets@tallshipwindy.com or call us at (312) 451-2700.
Tall Ship Windy offers the most spectacular Chicago fireworks cruises during the summer.
Our boat tours are both fun and educational, which makes them the perfect way to see Lake Michigan.
Feel the spirit of centuries past and hoist the sails as part of your Chicago boat excursion on Tall Ship Windy.
There is simply no better way to experience Chicago’s world-famous skyline than on a Windy City Boat Tour with Tall Ship Windy.