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Southwest Florida Sample Itinerary 

Day 1 - Charlotte Harbor Yacht Club to Boca Grande or Cayo Costa State Park

Meet Catatonic at Charlotte Harbor Yacht Club and get started on your SWFL adventure!  Hop aboard and set sail for Boca Grande 

Located on Gasparilla Island off the Gulf Coast northwest of Fort Myers, Boca Grande is an affluent residential community recognized for excellent fishing. 

Among Boca Grande's many charms is the Gasparilla Inn & Club, a hidden gem. Built in 1911 but maintained through renovations and updates, this luxurious resort preserves its old Florida charm.


From Boca Grande, it’s just a short hop to Cayo Costa, a relaxed barrier island destination that moves at its own pace.  With great fishing, oak-palm hammocks, mangrove swamps and miles of beautiful beaches, Cayo Costa retains its natural wilderness and sense of remoteness because you can get there only by boat.

Day 2 - Venice Inlet

Venice Inlet is located to the north of the city of Venice in Sarasota County. The inlet divides northern Venice from the barrier island that is called Casey Key that continues north until meeting Siesta Key, a town and beach popular as a tourist destination. Venice is home to Venice Beach, another popular beach for tourists.

Day 3 - Longboat Key

Gorgeous Longboat Key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. 


Day 4 - Egmont Key

Accessible only by boat, Egmont Key has a unique natural and cultural history, including a lighthouse that has stood since 1858. During the 19th century, the island served as a camp for captured Seminoles at the end of the Third Seminole War and was later occupied by the Union Navy during the Civil War. In 1898, as the Spanish-American War threatened, Fort Dade was built on the island and remained active until 1923.

In addition to touring the historic sites and trails, visitors can enjoy swimming, fishing, wildlife viewing and picnicking. Egmont Key is located at the mouth of Tampa Bay, southwest of Fort DeSoto Beach.


Day 5 - Sarasota Bay

Sarasota Bay, the largest and deepest coastal bay between Tampa Bay and Charlotte Harbor. The bay lies between barrier islands called keys, that separate the body of water from the Gulf of Mexico and the Florida mainland. Longboat KeyLido KeySiesta Key, and Casey Key are the major keys that delineate the main bay and its smaller portions.

Day 6 - South Venice


Play in the surf, hunt for prehistoric shark teeth, shop through downtown, bike around the Venetian Waterway Trail in this adorable area of Southwest Florida.


Day 7 - Captiva Island

Captiva is all about the outdoors – kayaking, paddleboarding, sailing, birding and other water activities abound. Captiva Island has a slightly off-kilter and almost magical feel. You might discover a giant frog in Captiva Island, a restaurant where it’s Christmas all year long, or even a tiny starfish.


Gorgeous South Seas Island Resort on the tip of Captiva Island boasts 2.5 miles of beaches and several options for lounging poolside.  An overnight berth at this resort can be added to your itinerary, but keep in mind that this is in addition to your charter fee.

Day 8 - Charlotte Harbor Yacht Club

 Head back to Charlotte Harbor YC to disembark the yacht and start planning your next adventure aboard!

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