Florida Sailings: July - September

Week-Long Trips


  • Duration 7 nights.

  • Destinations include a variety of itineraries along Florida's West Coast. Explore cruising grounds around Dunedin and Clearwater, Captiva and Sanibel Islands, or for the sailor and want-to-be cruisers, venture to Key West or Dry Tortugas National Park. (see itineraries here)

  • Depart Dunedin marina on Kuma Too, a 47-foot sailing catamaran and sail past the scenic Clearwater Beach waterfront.

  • Depending on the chosen itinerary, enjoy time on the water cruising while the gulf winds fill the sails and dolphins play in your wake.

  • Explore, relax, and immerse yourself in the local fare of Florida's diverse keys and towns.

  • As Kuma Too visits uninhabited islands, you will be immersed in the raw beauty of the gulf waters and star-filled nights.

  • A customized pre-planned menu is provided prior to sailing. (see sample menu here)

  • The professional crew prepares tasty full breakfast, lunch and dinners to include local cuisine.

  • A delicious spread of snacks and hors d’oeuvres is also included daily.

  • Beer, wine, soda, ice and bottled water are provided for your enjoyment.

  • No need to pay extra for a sunset cruise, snorkeling, booze cruise, or any other water activities from vendors in town. We do them all!

Check out detailed itineraries: Dunedin & Pinellas Beaches, Egmont Key & Sarasota, Captiva & Sanibel Islands, Dry Tortugas & Key West Combined, Dry Tortugas, Key West, 10-Day Dry Tortugas & Key West, Virgin Islands

Come aboard Kuma Too and see what the cruising lifestyle is all about! Take a week-long trip along Florida's West Coast to explore the nation's top-rated beaches, secluded keys, and old Florida towns.

If you're ready to experience a sailor's life, venture to the infamous city of Key West boasting its clear turquoise waters, local fare, and legendary nightlife.  We are sure you’ll be the talk of social media. 

If a more remote destination is something you seek, Dry Tortugas National Park has what you are looking for.  68 miles west of Key West lays the unspoiled islands and clear waters of Dry Tortugas National Park and Fort Jefferson. Kuma Too is 1 of 30 permitted vessels allowed by the state to conduct charters to this amazing area.

Click Here for more itineraries down the west coast of Florida.


Get away from it all! Disconnect for a weekend and let Kuma Too take you to your own piece of paradise.   Island hop, explore the endless coastline or bar hop down the Intracoastal Waterway. Boost your Likes on social media with pictures from your sail on Kuma Too proving to your friends that your weekend was truly memorable.



  • Duration 3 days.

  • Destinations include uninhabited keys and bustling beach towns. (see itineraries here)

  • Depart Dunedin marina on Kuma Too, a 47 foot sailing catamaran and sail past iconic Clearwater Beach

  • Enjoy the weekend lounging on board, swimming, snorkeling, sunning, and/or exploring the islands while listening to your favorite tunes.

  • A customized pre-planned menu will be provided prior to sailing. (see sample menu here)

  • The professional crew will provide delectable full breakfast, lunch and dinners with local cuisine.

  • Fresh snacks and a tasty spread of hors d’oeuvres will be provided throughout your cruise.

  • Beer, wine, soda, ice and bottled water provided for your enjoyment.




  • Duration 8 hours.

  • Destination includes a 3-hour sail up the coast past the iconic Clearwater Beach waterfront with a stop at Three Rooker Island or Anclote Key. (see itinerary here)

  • Spend 2.5 hours swimming, lounging, snorkeling, sunning, and exploring the beautiful waters of the island only accessible by boat.

  • After enjoying the island, Kuma Too makes its way back south along the scenic Intracoastal Waterway where multimillion dollar homes and vibrant towns line the shore.

  • Fresh snacks and a delicious lunch with local ingredients are included.

  • A tasty spread of hors d’oeuvres is  provided for the 2.5 hour sail back to Dunedin.

  • Beer, wine, soda, ice and bottled water are included for your enjoyment.


Aboard Kuma Too you'll enjoy cruising, swimming, lounging, music, and maybe a friendly dolphin visit as you sail along the Gulf Coast or through the Intracoastal Waterway.  Experience the tranquility of the smooth seas and flowing air as you cruise along the shores of the nation's top beaches.



  • Duration 4 hours.

  • Sail by the iconic Clearwater Beach, rated #1 beach in the USA on TripAdvisor and Honeymoon Island while you relax to white sandy coastline, colorful water, and an occasional visit from the curious dolphin. (see itinerary here)

  • Kuma Too’s staff provides fresh snacks and a tasty spread of
    hors d’oeuvres.

  • Beer, wine, soda, ice and bottled water are also included for
    your enjoyment.



Come aboard Kuma Too and experience Florida's picturesque sunsets.  Watch the last glimpses of the day fall into the calming waters of the Gulf of Mexico as the sky turns a myriad of colors before your eyes. Whether you're looking for a romantic evening or pregaming for the night's festivities, let the crew of Kuma Too get your night started off right.  You might even get to see the elusive green flash...



  • Duration 3 hours.

  • Sail either by vibrant Clearwater Beach or down the scenic Intracoastal Waterway where everybody onshore will be wishing they were you! 
    (see itinerary here)

  • Kuma Too’s attentive crew will prepare a fresh spread of tasty snacks and hors d’oeuvres throughout your cruise.

  • Beer, wine, soda, ice and bottled water are also included for your enjoyment.


Make Kuma Too part of your next special occasion.  The possibilities are endless.



-Dinner cruise

-Tortuga Music Fest  

-Fantasy Fest  

-Power boat races

-Boat parades

-New/full moon cruise

-Corporate team building

-Business meetings

-Burial at sea

-Holiday celebrations

Contact us for options and pricing.


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