Heading north from Fort Myers the Intracoastal Waterway winds its way through the barrier islands of Sanibel, Captiva, Cayo Costa, and Gasparilla. These are the islands that make Southwest Florida famous. Our passage takes us first through Pine Island Sound. Fifteen miles long and four miles wide, the Sound is protected by the barrier islands to the West and Pine Island to the East, and affords the cruiser countless islands and keys which offer unlimited anchorages and abundant bird and marine life to observe. If there is a landlubber in your crew, many fine marine facilities and award-winning restaurants dot the islands.

Two resorts, 'Tween Waters and South Seas Plantation offer such things as fine dining, entertainment, specialty shops, canoeing and jet ski rentals. And you will want to be sure to catch the famous Florida west coast sunset from any of the island beaches.

If you prefer anchoring, try the bight on the inland side of the Wildlife Refuge on Sanibel Island. When there's a northerly or northeasterly breeze, you may want to drop the hook in the lee of York or Chino islands on the mainland side of the ICW channel. If you plan to head out into the Gulf from here, Redfish Pass between Captiva and North Captiva is navigable; however, it is best to ask for local knowledge for Mother Nature's latest changes to the cut.

One of the most beautiful of the barrier islands is Cayo Costa. A tropical paradise, the island is now a State Park and offers excellent shelling, beachcombing, swimming and dramatic sunsets. The southern tip of the island offers a lovely day anchorage on your cruising itinerary.

Pine Island Sound - Click Here for enlargement

No cruise through Southwest Florida is complete without a stop at Cabbage Key. This picturesque island has been made famous by such well-known cruisers as Jimmy Buffet. Rumor has is that Cabbage Key was the inspiration for Jimmy's song, "Cheeseburger in Paradise"! And there's nothing quite like a cool libation at the island bar which is decorated in a unique wallpaper - dollar bills! The former home of mystery writer Mary Roberts Rinehart, this island estate has been transformed into a world-famous "watering hole" for cruisers from near and far. A stop at Cabbage Key is a "must" in any skipper's float plan!

The jewel of Southwest Florida’s cruising crown might just be the private tropical paradise of Useppa Island. Useppa is a private island club. As members, Vic and Barb Hansen can offer their charter guests access to Useppa.

Cruisers who visit Useppa may enjoy a drink in the Tarpon Bar, dinner in the historic Collier Inn, or a dip in the pool or hot tub. All of the first-class amenities are set in a beautiful, lush tropical atmosphere.

Collier Inn - Useppa Island

Tarpon Bar - Useppa Island

When the wind picks up, Charlotte Harbor at the northern tip of Pine Island Sound offers beautiful and protected cruising. for this reason, and its close proximity to the enchanting barrier islands, the Harbor is home to our own ASA ( American Sailing Association) Sailing School at Burnt Store Marina, one of the nicest marine resort facilities in the area.

Directly across the Harbor to the west is Boca Grande ( "big mouth" ) Pass, a commercial shipping channel as well as home to the world-famous Tarpon and hundreds of fisherman who pursue them. The Pass is well-marked, providing easy access between the Gulf and Charlotte Harbor in all kinds of weather conditions.

To the north sits the town of Boca Grande on Gasparilla Island. The island was named for one of the most famous early settlers, the Spanish pirate Jose' Gaspar. Gaspar and his roving "banditos" strategically stationed themselves just off the channel where they could easily pillage passing ships of their precious cargoes.