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Ft. Myers Sailing Tours

Experience our passion for sailing and being on the water aboard our wonderful 35-foot sailing catamaran, Old Glory. We sail from Salty Sam's Marina, near Ft. Myers Beach — a picturesque place for setting out for a lovely sail in the open waters of the Gulf of Mexico.

Watch One of Our Famous Floridian Sunsets at Sea

Sunset aboard Old Glory Sailing Catamaran One of our most popular sailing charter tours is our sunset cruise. For our sunset sail, typically we'll leave the dock a few hours before sunset and return about an hour afterward; plan for about three hours.

The Old Glory by law is limited to a maximum of six paying passengers only.

We will always attempt to sail with a full vessel, which means you may be sharing your cruise with a few other guests.

Onboard our catamaran there is always plenty of space for everyone, and you shouldn't have to be worried about being crammed or crowded for personal space. That's one of the big advantages of booking your sunset sailing cruise aboard a spacious catamaran like Old Glory. 

Or, if you prefer, charter the entire boat and enjoy a private, romantic cruise for two. A great idea for date-night! 

Allow 3 hrs minimum.

Some of our other popular itineraries include: 

  • Gulf of Mexico/Off-Shore

    Sailing the open Gulf of Mexico Aboard Old Glory CatamaranDepart Salty Sam's and enjoy a leisurely ride through the harbor under power, past the shrimp boat fleet and underneath the Matanzas Pass Bridge before heading into San Carlos Bay.

    Sail out past the 3 Nautical Mile Line and you're officially sailing the wide-open waters of the great Gulf of Mexico. Not a whole lot to see out here except plenty of uninterrupted Western horizon where blue sky meets greenish-blue water.

    A dolphin or two might swim by to investigate the vessel; otherwise, it's just the wind in your hair and the gentle sea breeze on your face — and lots of peace and quiet with the engines off and the sails up. Listen to the relaxing sound of the boat making its way through the water as you lounge suspended above the waves on the trampolines at the bow of the boat.

    Bring snacks or lunch and plenty of cold beverages and just relax.

    For those looking to hoist the sails and really get away from it all. 

    Allow 4 hrs minimum. 

  • Sanibel Island and the Sanibel Island Light

    COLREGS Line of Demarcation

    Leave the marina at Salty Sam's, cruise past the lovely harbor, out Matanzas Pass, where we'll cross the COLREGS Demarcation Line and trade one set of Navigation Rules (the Inland Rules) for another (the International Rules). Don't worry, you'll still be in for a good time, as all of these Rules apply only to the skipper! 

    Steering a Westerly course, we'll cross San Carlos Bay to Point Ybel at the tip of beautiful Sanibel Island where stands the famous 98-foot-tall Sanibel Island Light. Find a nice spot nearby to drop the anchor for a picnic lunch onboard while you watch the fishermen reeling in their catch on the nearby fishing pier.

    You may be lucky enough to see a dolphin or two hunting their own meals.

    Don't forget to bring your camera for pictures of the light tower and your swimming attire if you plan on jumping off the boat for a refreshing swim.

    One of our most popular cruises.

    Allow 4 hrs minimum. 
    Meals not provided.

  • Drawbridge at Big Carlos Pass & Lovers Key

    Head out to San Carlos Bay from the marina and set a East-Southeasterly course toward Big Carlos Pass and Lover's Key. The state park there is home to an abundance of wildlife, and you can often spot dolphins or even manatees in the waters nearby.

    When the weather and water are warm, plan on stopping for a while for a swim. Feel free to go ashore and enjoy the beautiful, pristine beach at Lover's Key State Park — there is no charge for visitors to the park arriving by boat. 
    Allow 3-4 hrs minimum.

  • Scenic Harbor Cruise/Back-bay Waterway Tour

    Shrimping Fleet

    Departing Salty Sam's, take a quick trip around Matanzas Harbor and enjoy the picturesque shrimping fleet, mooring field, and the beautiful private homes lining the shore. Pass by the Matanzas Pass Preserve and enjoy the peace and tranquility of a calm-water cruise.

    Instead of heading for the fixed-span Mantanzas Pass Bridge, we set an Easterly course and motor-sail down the pass in the lee of Estero Island, behind Fort Myers Beach, where the island shelters the shallow waterway from the wind and waves of the Gulf of Mexico.

    Ideal for a quick sightseeing cruise or for days when the weather conditions do not allow for trips into the Gulf. 
    Allow 1-2 hrs minimum.

  • Picnic Island

    Picnic Island is a 7.4-acre salty piece of land owned by the State of Florida and located near the mouth of the Caloosahatchee River, northeast of the Sanibel Causeway, about a mile from St. James City near Pine Island.

    The island is one of the popular stops along the Great Calusa Blueway, a 190-mile canoe and kayak trail that works its way through the area’s coastal waters and inland tributaries.

    There are no docks on the islands, and no facilities nor amenities of any kind. Access to the island is via boat only.

    Bring your kayaks or rent them from us and enjoy a beautiful kayak paddle excursion among some of the most pristine natural-Florida wetlands in the state. 

    We can anchor our catamaran a short distance from shore, where you a free to wade (or row the ship's tender) ashore. Bring beach chairs, beach blankets, fishing poles, a beach umbrella and a cooler to enjoy a nice afternoon beach excursion. The water here mostly offers a sandy bottom, but be careful where you step in case of rocks or sharp shells. A few areas of the island provide some shade from the sun.

    From the north side of the island, take a pleasant stroll beside a shallow wading area along the fine sandy beach or hunt for shells along the shore to the south. 

    During holiday weekends like Memorial Day and the 4th of July, the island gets very crowded with thousands of beach-party goers, many of whom beach their small powerboats ashore or raft them together in groups while at anchor, restricting our vessel's access to the shore. This destination is best enjoyed during the weekdays when the island is likely to be a little quieter. 

    Allow 2 hrs minimum.
    Meals not provided.

  • St James City, Pine Island

    St. James City at the south end of Pine Island is a short sail away from Salty Sam's and makes for a nice morning or afternoon cruise of shorter duration. Depart the marina and cross San Carlos Bay and sail under the fixed-span Sanibel Causeway bridge at Punta Rassa.

    Lots of skinny water here, where you may see a manatee or schools of fish running past the boat. Bring a fishing pole and tackle, along with a valid Florida saltwater fishing license if you want to fish from the boat. 

  • The nearby Pine Island Sound Aquatic Preserve to the north and JN Ding Darling National Wildlife Refuge just to the south on Sanibel Island both make perfect destinations for full day charters as well. 

    Bring a kayak and go explore some of the most pristine coastal wetlands around; abundant wildlife in its natural Florida habitat along the beautiful mangrove-lined shore makes for perfect photo opportunities. 

    Use the Old Glory as your personal water taxi to transport you, your friends and family, along with all of your gear to spots only accessible by shallow-draft boats. 

    Allow 2 hrs minimum.