5 Best Yachting Trips from Naples

5 Best Yachting Trips from Naples

  • Armand Alikaj
  • 10/29/22

Naples, Florida, with miles of idyllic beaches that boast calm waters and sugary sands, is a sailor’s paradise. This Southwest Florida city is also the perfect location to travel farther to different islands and far-away seas.

For a serene Naples trip, sail on a private yacht with all-inclusive amenities. If you’re feeling adventurous, cruise your way to a tropical vacation in the sunny Florida Keys!

Regardless of which type of getaway you are looking for, the posh city of Naples has an abundance of luxurious yachts to make your sailing dream come true. Here are the five best yachting trips from Naples, Florida:

LUX Boating Tours

For the most premier yacht trip in Naples, check out LUX Boating Tours. This all-inclusive, luxury boat tour will make you feel like royalty while out on the sea.

LUX’s chartered yacht rentals provide a boat captain for the day so that you don’t have to worry about maneuvering through the waters yourself. Kick back and relax as the captain takes you wherever your heart desires!

Luxurious yacht amenities include a welcome gift, tour guide, professional photographer, and catered lunch. Sunbathe on deck in LUX’s comfortable beach chairs or premium lounge seating. If you get too hot, you can always jump in the gorgeous water, or use one of the yacht’s complimentary chilled face towels.

LUX has a club package that allows sailors the option to buy several yacht rentals for one price. These classy charters are perfect for special occasions like birthday parties, weddings, anniversaries, and bachelor or bachelorette parties.

The upscale charter experience at LUX Boating Tours is the most fashionable way to revel in the waters of Southwest Florida.
Credit: LUX Boating Tours

Island Sailing

Cruise away on a charter adventure with Island Sailing! Island Sailing offers two different types of charters: Captained Charters and Bareboat Sail and Boat Club.

Captained Charters are yacht trips that have a captain on deck and include day or sunset sails, overnight trips, weekend trips, and week-long adventures. Not only do these private charters sail along the waters of Naples, but they will go as far as the Florida Keys and even the Bahamas. Captained Charters take place on either the Island Time yacht, a 47’ Beneteau, or Island Dreams yacht, a 31’ Catalina. Each captained charter can accommodate up to six passengers. Enjoy breathtaking views along the waterways and beaches, and be sure to keep your eye out for dolphins and manatees, too!

Bareboat Sail and the Boat Club are for experienced sailors who wish to rent out the Island Dreams yacht. Rentals are available for either a half-day, full-day, or overnight and can also accommodate up to six passengers. The Boat Club allows sailors to charter a yacht for five to 10 days. Steer to beautiful local areas like Marco, Fort Myers, Sanibel, and the Keys. Sail beside white sandy beaches and sweeping estates. Or, try your hand at birdwatching to see if you can spot pelicans, bald eagles, and herons.

Get in touch with nature as you cruise aboard a fun Island Sailing yacht!
Credit: Island Sailing

Naples Princess

Naples Princess is an elegant yacht that provides public and private charters. Sail through Naples Bay, Port Royal, and the Gulf of Mexico with friends, loved ones, or a small group.

Public cruises include afternoon and sunset tours. Hop aboard the Sea Breeze Lunch Buffet Tour to bask in the midday sun, Naples Sunset Dinner Cruise for a local evening favorite, or Sunset Cruise to admire the glowing twilight. Tours run daily and are a great way to take your sightseeing to a new level.

Private cruises are the ideal choice for important celebrations. These custom charters provide first-class food, drinks, and service with scenic views as the backdrop. Unwind from the bay to the gulf as you party on your personalized yacht charter.

Newly renovated, the Naples Princess Catamaran boasts three exquisite levels. The first and second levels are fully air-conditioned parlors. The third level features a large sundeck with comfortable outdoor seating.

Sail along the extravagant Naples Princess for an unforgettable sea experience.
Credit: Naples Princess

Sweet Liberty

Hop aboard the largest and longest-running sailing Catamaran in Naples! Dating back to 1991, Sweet Liberty is a custom-built yacht that runs 53 feet long. Every year, around 19,000 people set sail on one of Sweet Liberty’s public cruises and private charters.

Sweet Liberty offers three different public cruises that take place daily. Bring your picnic basket and admire the pink and orange hues over the Gulf of Mexico during the Sunset Cruise. This trip is about 35 minutes each way and is serene as it is dazzling. Navigate to Keewaydin Island on the Beach Island Shelling Cruise! This three-hour trip will take you to paradise for some much-needed beach time. Take part in a nature watch with the Afternoon Sightseeing & Sailing tour. This two-hour trip is both relaxing and entertaining, as you are bound to see a dolphin show.

Private charters are also available for special events courtesy of Sweet Liberty. Whether it be a corporate trip, social club, rehearsal dinner, or wedding ceremony, the team at Sweet Liberty knows how to host a party.
Sweet Liberty is so superb that it has received several accolades for its charters. The sailing company was recognized as the Best of the Gulfshore by Gulfshore Life, given the Certificate of Excellence by Tripadvisor, and was rated number one for Top Things to Do While Visiting Naples, Florida, by The New York Times.

For a quintessential sailing adventure, charter with Sweet Liberty!
Credit: Sweet Liberty

Naples Nantucket Yacht Group

For a magical day out on the water, cruise with Naples Nantucket Yacht Group! This fleet of nine luxurious yachts will take passengers throughout lovely Southwest Florida. Are you longing to go a little farther? The Yacht Group even journeys as far as the Mediterranean and The Bahamas!
This boutique yacht charter group offers the most diverse range of trips that sail from Naples. Charters within Naples, as well as to Tampa and Miami, are offered year-round. Specialty voyages to Nantucket and Newport take place from July to October. Vacations to the Mediterranean and The Bahamas are personally arranged, as these are longer customized trips.

The Yacht Group’s attentive crew is all about providing high-quality service, as well. This professional team will cater to the needs of you and your guests so that you have an unforgettable sailing experience. The Naples Nantucket Yacht Group hires award-winning caterers to ensure that the food’s presentation and taste match the elegance of the dreamy yachts themselves. The Yacht Group also works with a professional photographer so that you can capture all of the special moments while aboard.

If you are a sailing aficionado, become a part of the Admirals Club! For a yearly fee, sailors can hop aboard the posh Perseverance — a 75’ Sunseeker yacht — for eight half-day blocks. Blocks are four hours each and can be combined for an entire day trip. Those who wish to stay somewhere overnight can also do so in exchange for one block of time. Admirals Club Members have access to regular special events, too! Take part in onboard wine tastings, the Naples Board Parade, or the annual Christmas Party. The Admirals Club hosts a weekly cocktail hour from November through May as well.

The Naples Nantucket Yacht Group will sail you to some of the most lavish locations throughout Southwest Florida and beyond!

Naples Real Estate

Curious about luxury homes in Naples, Florida? Contact Florida real estate agent Armand Alikaj. As one of the most professional and dedicated real estate agents in the area, Armand provides premier service for those buying or selling homes in Naples.

Work With Armand

As an agent representing one of the most dynamic real estate names in Florida, you can expect the utmost professionalism and dedication to all of your real estate needs.