Captained Charter Sailing Cruises

Private Sailing Cruises

Reserve our catamaran for a private sailing cruise and enjoy any of these splendid destinations! 

Your party of up to six (6) will be able to decide on every detail of your voyage; stop for a swim, take in the sights and soak up the sun...whatever!

We depart daily from Salty Sam's Marina in Fort Myers Beach at scheduled times. 

Check our calendar for availability and departure times here. 

COST: $120/hr 
Duration: 3-8 Hours

Bring up to six (6) total passengers. 3-hour minimum booking required. 


Some of Our Most Popular Private Cruises 


Sunset Sailing Cruise

 Sunset_cruise_Fort_Myers_Beach_SAIL_SWFLOur most popular sailing cruise.

We can't promise a picture-perfect sunset every day, but when the weather does cooperate, the sunsets here make for a spectacular light show.

Depart Salty Sam's and steam into San Carlos Bay for a picturesque cruise past Fort Myers Beach or over to Sanibel Island. Enjoy the beauty of the sea and keep a look out for dolphins.

We'll hoist the sails and time permitting, sail farther out into the Gulf of Mexico where we'll clear the lee of Sanibel Island, allowing you to watch the sun sink beneath the waves on the unbroken horizon. 

The sunsets upon the ocean are truly a sight to behold! ...Don't forget your camera.


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Sanibel Island Cruise

Sanibel_Island_Sailing_Cruise_SAIL_SWFL_CruisesBook the Old Glory for a cruise to Sanibel Island and enjoy a beautiful afternoon, or the whole day, sailing, sun-tanning and spotting for dolphins! 

Departing from Salty Sam's Marina, we'll head up Matanzas Pass under power, and then enter San Carlos Bay through the channel. Then we'll head out into the Gulf of Mexico where we'll hoist the sails and cut the engines. 

A wonderful sail takes us across the bay to picturesque Sanibel Island where you'll see the Sanibel Island Light and the nearby fishing pier. Drop the anchor and have a picnic lunch just off the beach near the lighthouse. Or, just relax and take some great pictures as we cruise past. 

Depending on the weather and water temp., we can drop the hook so that you can go for a swim near the beach or wade ashore to relax on the sand for a while. Makes for a lovely afternoon!

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Lunch or Dinner Ashore Cruise

Lunch_Cruises_Dinner_Cruises_Fort_Myers_Beach_SAIL_SWFL_Cruises For a special private sailing cruise, visit one of the fine local waterfront dining establishments in Matanzas Pass.

For a half-day charter cruise, arrange to have lunch upon returning from a coastal tour of Fort Myers Beach. Or, have a nice lunch first and arrange for a pick-up at the restaurant's dock when you're ready and we'll take you out sailing for the rest of the day. 

For a full-day charter, arrange to have dinner after watching the sunset on the ocean aboard the boat. 

We can also pull up to Fort Myers Beach and drop our anchor near the shore, where you're free to wade/swim ashore to grab lunch from a couple of different establishments located right on the beach. 

Lunch or dinner stops (or pickups/drop-offs) are available as an add-on to any cruise or tour.

A few places we recommend (including a few located at Salty Sam's Marina where Old Glory is berthed): 

Nervous Nellies of Fort Myers Beach

Bonita Bill's Waterfront Cafe

Doc Ford's Rum Bar & Grille

Trico Seafood Market (best fresh seafood in town)

Original Shrimp Dock Bar & Grill

Parrot Key Caribbean Grill

Bongo’s Beach Bar and Grill at The Pink Shell Resort

Pinchers Crab Shack on Fort Myers Beach 

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Lover's Key Cruise

Lovers_Key_Catamaran_Sailing_Tour_SAIL_SWFL_CruisesLovers Key is one of four barrier islands that make up the Lover's Key State Park.

It's a haven for wildlife and home to manatees, dolphins, spoonbills and bald eagles. 

Depart Salty Sam's Marina and motor into San Carlos Bay from Matanzas Pass where we'll turn to port, heading southeast along the shore of Estero Island and Fort Myers Beach.

Then we'll hoist the sails and cut the engines for a wonderful catamaran cruise to Big Carlos Pass.

Weather permitting, we can lower the sails and motor in close to the two-mile-long beach where we can drop our hook just offshore. You're free to wade/swim ashore.

The beach here is popular for shelling, swimming, picnicking and sunbathing. 

Black Island has more than five miles of multi-use trails for hiking and bicycling. The park's concession offers kayak tours, as well as bicycle, canoe, kayak, paddleboard, beach chair and umbrella rentals.

Book the Old Glory for the entire day for your private party of up to six and spend a lovely day exploring the park before heading back to the boat for a sunset sail back to Salty Sam's. 

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Fort Myers Beach & Pier Cruise

Fort_Myers_Beach_Catamaran_Sailing_Cruise_SAIL_SWFL_CruisesReserve the Old Glory catamaran for a leisurely sail along the shore of Estero Island.

Depart Salty Sam's and sail past Bowditch Point Park, entering San Carlos Bay via Mantanzas Pass, turning east-southeast and down Fort Myers Beach where you'll see the fishing pier extending into the bay.

A lovely, leisurely sail along the shore here makes for some great photos, and there's a good chance we may see a dolphin or two along the way.

This cruise is nice for those who don't care much for going offshore and prefer to have the view of the beach homes, condo towers and tourists walking the beach for something to look at.   


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Gulf of Mexico Sailing Cruise

Gulf_Of_Mexico_Catamaran_Sailing_Cruise_SAIL_SWFL_Cruises Our personal favorite. 

Depart Salty Sam's and steam into San Carlos Bay for a nice cruise past Fort Myers Beach or over to Sanibel Island. Spend the day, or at least four hours, enjoying the sea and looking for dolphins.

We'll head out to sea, past the Three Nautical Mile line, where we'll officially be out in the Gulf of Mexico. Head her into the wind, hoist the main, then the jib...and cut the engines. 

Enjoy nothing but the sound of the boat making her way through the water. Not much to see out here...just beautiful Gulf green water in every direction. And no land in sight...but that's part of the appeal. 

For those looking to really get away from it all! 

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Dolphin Watching Cruise

Dolphin Watching Cruises Sanibel Island Fort Myers Beach Join us for an exciting, family-friendly dolphin watching cruise aboard the Old Glory catamaran! 

Depart Salty Sam's Marina and steam under power into San Carlos Bay where we can raise the sails for a relaxing cruise over to Sanibel Island where our dolphin friends often like to congregate.

We'll shut down the engines and keep a watch on all points for the distinctive dorsal fin breaching the water's surface as they take a quick gulp of fresh air.

Spend the afternoon, or the whole day, enjoying the sensation of sailing on the sea and watching for dolphins. Of course, we can't guarantee we'll see them, but if we do, be sure to have your camera ready!

...and bring the kids!

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Learn to Sail A Catamaran Cruise

Learn to sail catamaran SAIL SWFL CruisesHave you ever wanted to learn how to sail?

Maybe you already own a powerboat or a traditional monohull sailboat and you're wondering what it would be like sailing a cat?

Charter the Old Glory for a private learn-to-sail-a-cat cruise! Join Skipper Bud for a half-day or full-day of sailing on San Carlos Bay and the Gulf of Mexico and he'll literally "show you the ropes..." of course, on a sailboat, rope is always referred to as lines, halyards, or sheets depending on its intended use.

You'll learn this and more!

This cruise makes for a great date with that special someone...or a great birthday present for someone who's always wanted to learn how to sail.

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