Beginning from our port at Fort Myers Beach, Southwest Florida offers some of the best cruising grounds in the world, from Tampa in the north to the Florida Keys in the south. Regardless if your interests are to watch the sun slip into the Gulf at a secluded anchorage or a fine dinner ashore at one of the many top notch marinas, south Florida can accommodate your sailing plans. This area makes for very casual coastal cruising at your desired pace.

Heading north from Fort Myers Beach, you can pick up the calm, controlled waters of the Intracoastal Waterway. Click here for chart. This scenic waterway begins at Sanibel Island with Pine Island Sound and winds its way between Pine Island to the east and the Barrier Islands of Sanibel, Captiva, North Captiva, Cayo Costa, and Gasparilla to the west. The anchoring possibilities are endless in this stretch and many of the islands are only accessible by boat. If anchoring out is not for you, there is an abundance of fine marinas and resorts as well. As you pass Captiva and North Captiva Islands, you will approach the pristine barrier island of Cayo Costa. This tropical paradise offers excellent shelling, swimming, or simple sunset watching. Pine Island Sound is also a Mecca for bird-watchers.

At the north tip of Pine Island Sound you approach Charlotte Harbor. This area offers a beautiful and well-protected cruising ground and a perfect alternative to the brisker waters of the Gulf. The marina facilities at Punta Gorda are among the best in Florida.

Heading north past Siesta Key and Longboat Key, you reach the northern tip of our cruising grounds, the Cosmopolitan Seaports of St. Petersburg and Tampa Bay.

Sanibel Island - One of the best shelling, bicycling and relaxing destinations in south Florida. The most developed part of Pine Island Sound.

South Seas Plantation - Located near the northern tip of Captiva Island, South Seas Plantation is one of the finest marinas in western Florida. Great restaurant too.

Cabbage Key - At the northern tip of Pine Island Sound. This "Old Florida" island hideaway features a marina/restaurant (left) that is fabled to have provided the inspiration for the Jimmy Buffet song, "Cheeseburger in Paradise". Check out the wallpaper.

Cayo Costa - This secluded island has nine miles of pristine undeveloped beach, perfect for nature walks and shelling. You may wish to catch an open air tram through the Cayo Costa State Park.

Gasparilla Island - Home to one of the most beautiful Victorian inns in all of America, the Gasparilla Inn at Boca Grande Village.

Sailing south from Fort Myers Beach it is a comfortable 4-5 hour sail via the Gulf of Mexico to Naples. Enter Gordon Pass and anchor out at the very protected anchorage just inside the pass, or put in at the Naples City Dock and take in dinner at one of the excellent local dockside eateries.