Sailing in Tampa Bay

5 boats available

The best out of 5 deals in Tampa Bay - enter dates to check availability

Top Sailing in Tampa Bay

  • 41 ft
    •
    up to 12
    2 Hour – Private Sailing Charter
    Set sail on a private 2-hour adventure aboard the 41ft yacht Phoenix, perfect for groups of up to 12 guests. Choose your preferred time of day—9:30 AM, 12:00 PM, or 2:30 PM—for a relaxing sail and the chance to spot dolphins. For a magical sunset sail, we typically depart about an hour before sunset. Message us for the exact departure time based on the date of your trip!
    Instant Confirmation
    Price for up to 12 people
    US $908
  • 46 ft
    •
    up to 12
    2 Hour – Fantasea Private Sailing
    Enjoy this beautiful 46' sailing yacht for your private charter for up to 12 guests! Great for any occasion when you want to wow your guests with something different and fun. We take pride in our excellent customer service, and this accommodating yacht brings beverages and finger food, or we can suggest local food and beverage options to top off your outing. Don't forget this vessel is child-friendly!
    Instant Confirmation
    Price for up to 12 people
    US $1,008
  • 51 ft
    •
    up to 14
    2 Hr – Private Sailing Yacht Magic
    Unwind and set sail on this 51ft yacht for 2 hours of pure enjoyment! Perfect for hosting family and friends for any occasion. Our captain and crew are dedicated to providing an exceptional experience!
    Instant Confirmation
    Price for up to 14 people
    US $1,232
  • 55 ft
    •
    up to 25
    2 1/2 Hour – Private Day Sailing
    Set sail and explore all of the natural beauty the area has to offer! With the sails up, we can slip away and get up close and personal with the wild Atlantic bottlenose dolphins in Boca Ciega Bay or the Gulf of Mexico. Complimentary bottled water available. BYOB allowed. Cooler with ice available and a restroom aboard. Most trips venture out into the Gulf of Mexico, weather and conditions permitting. What's Included: Bottled Water Coolers with Ice Available Restroom Aboard What to Bring Sunscreen BYOB
    Price for up to 25 people
    US $1,745
  • 45 ft
    •
    up to 6
    3 Hour – Sunset Sail
    Private captained sail through the protected waters of Boca Ciega Bay, with a beautiful view of the sun on an open Gulf Horizon! You're welcome to bring any of your own food or drinks to accompany you on the evening sail!
    Instant Confirmation
    Price for up to 6 people
    US $900

What boaters said about Sailing

  • 5.0
    /5
    (3 Hour Trip – Sandbar Tour)

    great day on the water with Captain Jon!

    Fantastic boat that was spacious and comfortable. Jon was a great guide and took us to a warm sunny sand bar for floating and swimming. great trip! highly recommend!
    David O.
    David O.
    Reviewed on Oct 4, 2026
  • 5.0
    /5
    (2 Hour – Sunset Cruise)

    Best evening for a sea buria.

    We did not go to fish. We had a sea burial for my mom. Captain Dana was wonderful. She said some really nice and moving words. And even read scripture that my sister provided. We would definitely recommend her. Next time we hope to go fishing!!
    GREGORY H.
    GREGORY H.
    Reviewed on Oct 3, 2026
  • 5.0
    /5
    (3 Hour Trip - Sandbar Tour)

    You won't go wrong with Captain Jon.

    Down here for the weekend visiting my son. Great time. We'll call Cpt Jon every time we visit. Perfect afternoon on the water.
    David V.
    David V.
    Reviewed on Sep 26, 2026
  • 5.0
    /5
    (1.5 Hour Dolphin Eco Tour Afternoon)

    Birthday Gift for the Wifey

    Captain Jon was great! I wanted to take my wife out for a boat ride for her birthday. He took us on a nice cruise, and was very accommodating as it was her first time on a boat. You can talk and laugh with him too which kept the mood light. I would recommend.
    Lance P.
    Lance P.
    Reviewed on Sep 13, 2026
  • 5.0
    /5
    (3 Hour – Sandbar Adventure! - 3:30 PM)

    4 hour trip

    We had a great day out with captain Thomas. Caught some nice fish and also had time for the sand bar. My girl friend and I enjoyed every minute of it. Thank you Thomas.
    Chad W.
    Chad W.
    Reviewed on Sep 11, 2026