Is it possible to be a tourist in your own town? I’ve called the Naples/Bonita Springs/Ft. Myers area home now for 12 years now and I still can’t get enough. I still hit the beach every chance I can get, I find myself in the fun touristy beach bars and I still find Gulf sunsets truly magical every time.  It doesn’t matter, I’ve seen hundreds of them, but each one captures my attention like it does for the first time tourist.

Last Friday my buddy L. Bond and I celebrated our birthdays (age is top secret) and decided to take the pirate girls out for a little something different. Sure, watching sunset from the Fort Myers Beach pier is nice but you know what’s better, watching it from the deck of a catamaran under sail.

Touristy? Not if you’re in love with the sea. Not if you’re a Castaway.

I’m a catamaran guy, these vessels are stable, offer a large amount of deck space and are just plain sexy. When I started researching the area for sexy cats to charter their was only one or two options. Their were several monohull sail boat choices, but catamarans were slim-pickins. I originally reached out to Happy Charters but he wasn’t doing Ft. Myers Beach charters at the time and turned me onto Captain Bud and the Old Glory–I’m very glad he did.

Fort Myers Beach Sunset Cruise

The “Old Glory” is a 35 foot sailing catamaran boasting a large air conditioned salon, 2 sleeping cabins and room for 6 sea loving passengers. I called captain Bud and made a date to rendezvous at Salty Sam’s Marina for a sail into the sun.

We boarded Old Glory at 5pm and were joined by Kris and his girlfriend Liz. Kris is a lover of the sea, just like all us Castaways, and is learning how to sail. So whenever Captain Bud has room Kris becomes part of the crew and helps sail Old Glory, collecting valuable sea hours in the process. Sign me up for that gig!

Fort Myers Beach Sunset Cruise

Fort Myers Beach Sunset Cruise

We get underway and round Bowditch Point, the northern tip of Ft. Myers Beach (Estero Island). There was only a light wind when we turned off the engines and raised canvas. It might just be me, but watching sails rise into the sky to collect the wind is a surreal experience. Maybe because that’s what the very first sailors did when humans began exploring the sea. It’s a back to the roots type of thing.

Fort Myers Beach Sunset Cruise

The cruise was filled with friendly conversation, cold beer, and lessons about isobars and how they affect the wind. Dolphins cruised by and a large stingray jumped near the boat, but the star of the evening was the sun falling from the sky and dipping behind Sanibel Island. Like I said, it’s a spectacle I’ve seen a hundred times, but some how each one is just as magical as the first one. Conversations on the boat seemed to pause as all eyes were focused on the glowing horizon.

Fort Myers Beach Sunset Cruise

Fort Myers Beach Sunset Cruise

Fort Myers Beach Sunset Cruise

Fort Myers Beach Sunset Cruise

As the sun disappeared we sailed towards port. Now it was the eastern sky’s turn to put on a show of its own off the starboard of Old Glory. The full moon began to peak in and out of some high level clouds and took over as the star of the show for the remainder of the cruise. Moonlight sparkled off the tops of the waves and illuminated our journey back into port.

Fort Myers Beach Sunset Cruise

Fort Myers Beach Sunset Cruise

Fort Myers Beach Sunset Cruise

As all things that you wish would last forever, the sail aboard Old Glory came to an end. It was a fantastic time and I feel as if new friends were made with Captain Bud and Kris. That’s not surprising though, salty sailing souls seem to flock together. Castaways through and through.

There’s nothing wrong with being a tourist in your own town, especially if that town sits on the coast of somewhere beautiful. Be a tourist in your own town, be a sponge and soak in as much as you can. Then when you don’t think you can soak in any more beauty, take an intimate catamaran cruise on a boat like Old Glory. You’ll find that the sponge is never quite full.

If you would like to have the same experience as we did, contact Captain Bud at or give him a call at 239-200-9899.

You can find more photos from the sunset cruise aboard the Old Glory on the RumShopRyan Facebook page.

Cheers to sailing the sea.

caribbean bloggers

What You Will Learn

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By |2016-12-31T11:57:43-05:00October 23rd, 2013|RSR Stories, Sailing / Boating, Southwest Florida|5 Comments

About the Author:

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty.


  1. fabian christopher November 7, 2013 at 10:10 am

    Awesome photos Ryan, and sounds like a great way to spend a birthday.

  2. mm
    RumShopRyan November 7, 2013 at 8:18 pm

    Thanks Fabian, it was a great day spent on the sand and sea.

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  5. Carrie Thieman August 1, 2014 at 2:11 pm

    Great blog about the boat charter industry! We’d love to take you out with us on a boat charter if you are ever down in St. Thomas or St. John!

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