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Sailing Anna Maria Island: Your Private Island Escape

Florida Sail in Anna Maria Island, FL offers premium, custom private sails. Now operating from our new home in Bradenton Beach, we specialize in "Old Florida" experiences that get you away from the crowds and into the crystal-clear waters of the Gulf.

Our Signature AMI Charters

Egmont Key Adventure: Sail to this secluded state park to explore the ruins of Fort Dade, walk pristine beaches, and snorkel around the sunken remains.
Sunset Sails: Experience the legendary Anna Maria Sound sunsets while keeping an eye out for bottlenose dolphins and manatees.
Sandbar & Shelling Trips: Drop anchor at local favorites like Jewfish Key or Passage Key for swimming and world-class shelling.

Day Sailing Packages and Recommended Trips

Sunset Sail

Cruise the bay, catch the sunset, and keep an eye out for some wild dolphins. The calm intracoastal waterways and the setting sun create an ideal scene for spotting dolphins.

2 Hour Private Charter

Half-Day Sail

Escape the hustle and bustle with our most popular sailing trip-the half day sail! This charter kicks off with a leisurely sail along the intercoastal waterways to one of the best local shelling islands in Florida. Once at Shell Key, you'll have time to swim, snorkel, and look for shells before we begin our sail back to the marina.

4 Hour Private Charter

Full-Day Sail

Embark on a customized sailing adventure and choose your destination. Egmont Key, Anna Maria, or Shell Key. Opt for Egmont Key to explore a historic island, home to gopher tortoises, remains of Fort Dade, and secluded beaches. Choose Anna Maria for a charming coastal town with picturesque surroundings. While Shell Key is a haven for unspoiled nature with fantastic shelling opportunities. Whichever destination you select, our experienced crew will ensure a fun-filled sailing experience.

8 Hour Private Charter

Overnight Sailing Packages and Recommended Trips

One Night Sail

Embark on an unforgettable overnight sail, including a visit to historic Egmont Key, soaking in the sunset on the water, and anchoring near the charming Anna Maria Island. After a day of adventures, enjoy dinner and activities on the island before returning to Second Wind to rest. In the morning, have the option for an early morning coffee and breakfast on Anna Maria Island before starting our sail back to Treasure Island. Max: 6 Guests.

Two Night Sail

Get ready for a relaxing two-night adventure from Treasure Island making stops at Egmont Key, Shell Key, Anna Maria Island, and Sarasota. This excursion gives you time to soak up the sun, experience the sailor's life, and unwind along the Gulf's picturesque coastline. With ample time for fishing, snorkeling, shell hunting, and exploring charming coastal towns, this trip promises to curate memories that will last a lifetime. Max: 6 Guests

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