Headboat in Key West

2 boats available

The best out of 2 deals in Key West - enter dates to check availability

Top Headboat in Key West

  • 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
    (Half day trip)

    Just what we were looking for!

    Hubby and I were on our honeymoon and this trip was just perfect! We wanted the experience, but not on a boat packed with people. The captain was outstanding, knowledgeable, and took us to the most beautiful spots! Loved it and if we are ever in Key West again we will absolutely be doing this one again!
    Laura D.
    Laura D.
    Reviewed on Aug 26, 2026
  • 5.0
    /5
    (Sandbar Eco Tour - 4 Hour Trip)

    Really good trip

    We went with my whole family including my parents in law who are in there 80’s and our two dogs. We adked for a smooth ride and we got it with the right setup. And when we asked for going snorkeling the Captain found the right plan that fit oir constraints. Great memories !
    Tanguy C.
    Tanguy C.
    Reviewed on Aug 11, 2026
  • 5.0
    /5
    (Dry Tortugas (Fort Jefferson) Park)

    SO MUCH FUN!!!!

    We did the trip to Dry Tortugas with Anthony/Kilo Whiskey. The tour was so informative and interesting. Then Anthony took us to an island for a swim and snorkeling. We headed back for Key West and stopped to fish for a couple hours. Caught enough grouper and yellow tail snapper for a fantastic dinner!! We’ll definitely book again if back in Key West!
    Laura S.
    Laura S.
    Reviewed on Jul 26, 2026
  • 5.0
    /5
    (Half day trip)

    So nice, we did it twice!!!

    Captain Eric is top notch!! We absolutely loved all the great places he shared with us -- so much that we booked again immediately after our first tour! Could not recommend him more highly!!!
    Amanda D.
    Amanda D.
    Reviewed on Jul 23, 2026
  • 5.0
    /5
    (Sandbar Eco Tour - 4 Hour Trip)

    Great trip with Captain Forest.

    Captain Forest is the best! Took our group of six to an island to explore. We got to chill in the shallows and then dip into the deeper water. After we explored for a bit, we moved to a site to snorkel in the grasses for a bit. Water was clear and warm. We took one last stop to a sunken boat and saw lots of fish on the wreck. Great trip. We can’t wait to come back!
    Rob U.
    Rob U.
    Reviewed on Jul 20, 2026