Best Boating Destinations in Southwest Florida

Captiva Island is home to SYS Yacht Sales annual rendezvous to the South Seas Resort
As a team of seasoned yacht sales experts, the staff at SYS Yacht Sales are also very avid boaters. With our corporate headquarters in Sarasota, Florida, our team members regularly explore the many boating destinations along Florida's West Coast. We've compiled an overview of some of our favorite spots for you, so that you can get out and enjoy new boating locales.

Here are our favorite boating destinations in Southwest Florida...

Cabbage Key, FL

Doug Mashke, Sr. suggests this beautiful Gulf Coast island. "A very small, intimate island with a Jimmy Buffett atmosphere. There is a great little restaurant with perfect fare for boaters. Docks are first come-first serve, but there are also rental cottages and an historic inn to stay for those who wish to sleep on land. Across from Cabbage Key is a nice anchorage that has plenty of swing for large yachts". The island itself is 100 acres of tropical vegetation, where there are no cars or paved roads. Perched atop a 38-foot Indian shell mound, the restaurant is open-air with a front porch that offers sweeping views of Pine Island Sound. Learn more about Cabbage Key.

Boca Grande, FL

Suggested by Rob Welling, and located at the southern end of Gasparilla Island, “Boca Grande has a completely refurbished marina with restaurant and bar. Boca Grande Marina (the old Miller’s Marina) is a very nice facility with excellent staff, good food, and a quaint but lively atmosphere. Inshore charter boats are available at the docks. Downtown is only a short walk or golf cart ride (rentals on site) away, and offers nice shops, ice cream, restaurants, and a couple bars. The area is also world famous for the Tarpon Fishing Season in Boca Grande pass”. Learn more about Boca Grande.

Cayo Costa, FL

Alex Rowe suggests this is a "more intimate experience with a wonderful anchorage in a very well-protected bay near the Cayo Costa State Park. It is perfect for a private single boat experience, or a group can raft up and make their own little party island for the weekend. It is very close to Boca Grande, Cabbage Key, and Pine Island, which offers a ferry service to access Cayo Costa. Learn more about Cayo Costa.

Captiva Island, FL

A favorite of SYS Yacht Sales, we host an annual rendezvous open to all boaters at the South Seas Resort on Captiva. The island features multiple marinas and resorts, as well as private residences and a tropical "downtown" with stores, bars and restaurants. If you are arriving at South Seas, they have a wealth of amenities for boaters, as well as meeting/event spaces, restaurants, beaches, a waterpark and pools with a tiki bar, and a 9-hole golf course along the water. Accessing the rest of the island from South Seas can be done by car or rented golf cart. Highlights for visitors include Doc Ford's pub & grill, The Green Flash restaurant, the Bubble Room, and Tween Waters Marina with a small shopping village and great bar/restaurant for nightlife.

SYS President Gary Smith says "Captiva is an incredibly beautiful and fun destination for families. The island offers so many activities that it is definitely not for those looking to get away from it all". Learn more about Captiva Island.

Sarasota, FL

We may be a bit partial, since our company is based in Sarasota, but there are few destinations that offer such a wealth of sites and activities as this jewel. Just south of Tampa Bay, Sarasota is a boating, dining, shopping, and cultural destination for people from all over the world. Boasting the #1 beach in America (Siesta Key), the area is replete with resorts, marinas, theaters, world-class dining, and fun activities.

Marina Jack is the main marina on Sarasota Bay, offering ample dockage, multiple bars and waterfront restaurants, and direct access to downtown Sarasota's amenities. Lido Beach and St. Armand's Circle are just a quick trip over the John Ringling Causeway, and offer additional tropical venues to explore. Learn more about Sarasota.

Planning a boating getaway in Southwest Florida and need help with your itinerary?

Contact our experienced yachting specialists. We have an abundance of advice for boating in this area and elsewhere in the state and would love to help you plan your next boating adventure!

We can help with choosing:
*Cruising itineraries
*Anchorages
*Marinas
*Restaurants
*Fun activities to do in the area

Contact us today!

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Call 941-365-9095