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Egmont Key Sail boat charter

Full Day or Overnight - Max 6 people

Feel like you are a world away at this Florida National Park.  Enjoy swimming, shelling and exploring the island's fort.  

Egmont Key

Sunset Boca Grande sailing charter

7 Days-Max 4 Adults or 2 Adults and 3 Kids

Explore Florida'a barrier islands and their communities as you travel down the ICW (intra-coastal waterway) or sail on the Gulf

Venice & Captiva

Dry Tortugas sailing charter Fort Jefferson

10 Days-Max 4 Adults or 2 Adults and 2 Kids

A "Try Before You Buy" interactive charter that will give you a taste of the cruising lifestyle.

Dry Tortugas

Anchor 1


All itineraries below are suggestions and are examples of what can be done.  We can tailor-make your charter to suit your interests and time frames.  All charters are captained. 

See our Pricing Tab for costs or call us for customized charters and pricing!


Step aboard Cool Runnings and enjoy a vacation of a lifetime!  The best times for any of these excursions are from November to May, but weather permitting, we operate all year long.  Here are just a few sample itineraries that run out of Madeira Beach, Florida, just a short ride from Tampa International Airport (TPA), or St.Petersburg (PIE):

Egmont 2

Enjoy a fun day or weekend away!

Egmont Key State Park

Enjoy a day or weekend away anchored off Egmont Key, Florida.  Play on the beach or explore the island and the ruins of historic Fort Dade.  A leisurely 2 hour sail will get you from our base in Madeira Beach to Egmont Key (depending on the wind, of course!). 


After anchoring, enjoy a swim off the back of the boat, or we'll take the dinghy to shore.  Look for shells on the water's edge or simply watch the many birds who call Egmont Key their home.

After enjoying lunch on board, you can go back to shore and take a walk around

the island, exploring the ruins of Fort Dade, a Spanish-American war era fort, as well as the historic Egmont Key lighthouse.  If it's a day excursion, we'll up anchor and enjoy watching the sun set over the Gulf.  If you're staying overnight, the beach and exploration activities can be spread out over 2 days. The minimum time required to enjoy this trip is 6 hours, but a full day trip or overnight is a more leisurely pace. 

Venice 2

Also great as a 3 or 4 night Charter!

Venice, Cabbage Key, Boca Grande and Captiva

A day's sail south of Madeira Beach, Florida, will end tied up to the dock at the Crow's Nest Marina at Venice Inlet.  Enjoy a delicious dinner at the Crow's Nest Restaurant, and be ready to head out early the next morning.  Depending on conditions, we can either take the ICW (Intra-coastal waterway), or head out back into the Gulf, but our destination will be Cabbage Key. 

After breakfast at the famous Cabbage Key Inn, explore the island by walking the trails, making sure to say hi to the resident tortoises.  Climb the island's water tower, the oldest wooden structure of its kind still standing.

The next evening will be spent tied up in the South Seas Marina where you can enjoy the amenities of the resort, as well as the island and its unique little town of Captiva. This is a great trip to make with kids, as the South Seas Resort has great pools and water slides and the majority of the sailing can be done on the calm waters of the ICW if needed.  The return trip stops at different destinations depending on weather conditions. The entire trip is 7 days, but can be longer if you'd like to spend more time at each destination. As this is a multi-day trip and weather conditions vary, we may adjust destinations and this itinerary accordingly.

Dry Tortugas 2

A "Try Before  You Buy" Charter

The Dry Tortugas


To really get the most out of this trip, you should allow at least 10 days.  That will give you enough time to get there, enjoy this magnificent place, and get back, all while still allowing for weather windows. 


If you are short on time, and would prefer not to make the longer trip there and back, or do not want to do an overnight sail, we can always pick you up in Key West, FL.  If you have enough time, either one (or both) of the legs can be combined with the itinerary above.  We will customize the trip to suit you!

The Dry Tortugas lie about 70 miles west from Key West, FL., and here you will find the magnificent Fort Jefferson.  There is so much history and beauty here,

you won't want to leave.  There are wrecks to dive or snorkel on, crystal clear water to swim in and white sand beaches to explore.  This is a great trip to make if you are thinking of going cruising, but feel you don't have enough sailing experience, or really want to get a feel for the cruising life before committing to buying a boat.   As this is a multi-day trip and weather conditions vary, we may adjust destinations and this itinerary accordingly. 


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