Florida Sail in St Petersburg, FL offers memorable experiences on the water through custom, private sails. Explore the historical ruins on Egmont Key, snorkel in beautiful water, and relax on pristine beaches- all included in our worry-free packages. 

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

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

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