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Sweet Liberty Catamaran Sailing

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880 12th Ave S
Naples, Florida 34102


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Catamaran Sailing in Naples
Naples Florida’s premier sailing charter company, perfectly suited for any occasion. From the moment you leave the Naples City Dock, you will see magnificent million dollar homes along the Gordon River, passing through mangrove protected areas and out to sail in the beautiful Gulf of Mexico (weather permitting).

Cruising the pristine local waters on one of our daily Naples cruises aboard our 44 passenger 53′ Sailing Catamaran is the perfect way to spend your day. We have a variety of cruises to choose from such as shelling, sunset or sightseeing tours. We are also a unique venue for private occasions such as intimate weddings, large social groups, corporate events and memorial services for burials at sea. Local residents, visitors and our seasonal northern friends have enjoyed the Sweet Liberty trips for over 25 years in Naples.

Naples Florida Sunset Cruises
Join us for the Sunset Celebration nightly! Our sunset cruise has been mentioned as the top thing to do by the NY Times, many SW Florida bloggers and local residents for the last two decades! We pride ourselves on receiving the top award for sunset cruises in Naples, FL. We want you to feel as comfortable as possible and welcome you to bring a small cooler or picnic basket with your food and beverage of choice (beer/wine welcome). Can you imagine anything more relaxing than watching the sails go up while listening to the waves roll and watching the pink and orange hues light up the sky as we say goodbye to another day?

Beach Island Shelling Cruise in Naples
A MUST DO for vacationers and local residents! You will truly enjoy a little slice of paradise on the remote Keewaydin Island on this spectacular 3 Hour Beach Island Shelling Cruise.

Nature Watch & Sightseeing Cruise
On this cruise, you will be entertained by a live narration from the Captain about the area we live in, you will see multimillion dollar homes in the prestigious Naples waterfront community, relax and sail in the Gulf of Mexico, and quite likely see an afternoon Dolphin show!

Private Charter Wedding Cruise in Naples Florida
Looking for a unique and memorable wedding experience? Look no further than the Sweet Liberty. We can customize your intimate wedding for up to 44 guests to make your wedding dreams come true! Imagine getting married in the beautiful Gulf of Mexico during one of Naples, Florida’s glorious sunsets. Sweet Liberty has four tables and the bar area inside the cabin where your food and cake can be arranged. We have performed hundreds of intimate wedding ceremonies over the years for happy brides and grooms!

Burial At Sea Memorial Services in Naples
The loss of a loved one is one of the most difficult situations to face in life. Every family is different, and not everyone wants the same type of funeral. Honoring the life of your loved one means you value the relationship you shared. We look forward to helping you decide how to celebrate that bond, and honor the unique individual you’ve lost.

We offer burials at sea for private bookings. Sweet Liberty can accommodate up to 44 guests for your memorial service and burial at sea. Please contact us for more information and pricing. We typically recommend a two hour cruise for memorials.

Corporate Events
Do your employees deserve the best while they are visiting Naples, FL for a convention or meeting? They will LOVE a private cruise aboard Sweet Liberty! We regularly take private corporate groups out for our cruises. Whether it’s an incentive trip for your sales team, a social gathering for your managers or a cocktail cruise for your executives, they will absolutely love a private cruise on board Sweet Liberty. Over the years our past corporate events have made this a must do for their annual conventions in Naples, FL, and they return back to us year after year. This is the best reward your employees will enjoy!

Sweet Liberty - About Us
Captain Shane Chaplin and Susan Chaplin took over the Sweet Liberty business in December 2015. Captain Shane ran the Sweet Liberty as Captain for 4 years prior to purchasing the business from the original owners, Captain Lenny & Anita Wassmer. The Wassmer’s had the Sweet Liberty custom built by Gold Coast Yachts in St. Croix, USVI. After 24 years of successfully running the Sweet Liberty they retired and “passed the conch shell” on to the Chaplin’s.

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