Headboat in Florida Keys

2 boats available

The best out of 2 deals in Florida Keys - enter dates to check availability

Top Headboat in Florida Keys

  • 55 ft
    •
    up to 40
    2 Hour Trip –Sunset Cocktail Cruise
    Set sail from Historic Key West Bight Marina and head out onto the pristine and protected waters around Key West. Enjoy music of your choice aound the boat and relax with your friends while taking in a world famous Key West sunset. You are welcome to bring any food and drink that you would like aboard with you. **We can accommodate supplying drinks and snacks for an additional cost and advanced notice**
    Price for up to 40 people
    US $750
  • 58 ft
    •
    up to 12
    Say I Do with a View Sunset Wedding
    Celebrate Your Love on the Waters of Key West: A Simple and Memorable Wedding For couples who want something truly unique, exchange your vows in the beautiful tropical waters of Key West. This no-frills wedding combines the raw beauty of the ocean with an intimate and adventurous ceremony, creating memories you'll treasure forever—without the fuss or high price tag.
    Price for up to 12 people
    US $700

What boaters said about Headboat

  • 5.0
    /5
    (4 Hour – Islamorada Adventure)

    Roman is awesome !

    Roman is awesome ! the local stories mixed in wuth the sceney was awesome - had a great time !! Thanks
    Paul M.
    Paul M.
    Reviewed on Oct 13, 2026
  • 5.0
    /5
    (3 Hr – Afternoon Sandbar & Snorkel)

    Great boat day!

    We had such a wonderful family outing with Captain Dawid! He was professional, courteous, and made sure we all had a fantastic time. He came prepared with plenty of fun floating toys for us to enjoy at the sandbar, which was a huge hit with the kids! A perfect day out on the water in the Keys. Highly recommend Captain Dawid!
    Adriana F.
    Adriana F.
    Reviewed on Oct 12, 2026
  • 5.0
    /5
    (Special 2 hour trip for Jim Dowling)

    great trip

    Matt is a captain with a ton of experience and knowledge of the waters around upper matecombe key/islamorada. i look forward to a great fishing trip out in the near future! Jim D
    Jim D.
    Jim D.
    Reviewed on Oct 12, 2026
  • 5.0
    /5
    (4 Hour – Sandbar Trip (AM))

    amazing day!

    we got to see the most beautiful water and sandbars. the boat is meticulous and so comfortable. it was so amazing to don this with our friends!
    Gina R.
    Gina R.
    Reviewed on Oct 4, 2026
  • 5.0
    /5
    (3 Hr – Morning Sandbar & Snorkel)

    Great group excursion

    We had such a great time with Captain Dave! He was prepared with sunchill chairs, an icechest cooler, a floating lily pad, and trash can to make our sandbar trip perfect! The boat was very spacious with extremely comfortable seating for our group of 4. The company was amazing at communication with the variable keys weather. DEFINITELY BOOK THIS CHARTER!!
    Lauren S.
    Lauren S.
    Reviewed on Oct 4, 2026

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