Naples, Florida isn’t just about beautiful beaches and fantastic seafood; it’s also a prime spot for sailing adventures. With its calm Gulf waters, lush mangroves, and plentiful wildlife, Naples offers a perfect backdrop for both relaxing and wildlife-focused sailing trips. We particularly love the Sightseeing and Sunset Catamaran Sailing Excursion for its relaxed pace, dolphin sightings, and stunning sunset views. But whether you prefer a private charter or a lively day sail, Naples has a sailing experience to match your mood and budget.
If you’re trying to decide among the best options, this guide will help. We’ll walk you through three top experiences, highlighting what makes each unique and who they’re best suited for—so you can pick the perfect ride on the water.
Quick Overview
Naples offers a variety of sailing tours tailored to different interests. For those seeking a quick, scenic cruise with wildlife sightings and sunset views, the Sightseeing and Sunset Catamaran Sailing Excursion is ideal. If a private, personalized adventure sounds better, the Private Sailing Tour through the Ten Thousand Islands provides tranquility and wildlife spotting in a luxurious setting. For a longer, more immersive experience, the Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans combines sightseeing, shelling, and swimming on a beautiful private vessel. Now, let’s explore each in detail.
1. Sightseeing and Sunset Catamaran Sailing Excursion
At number 1 on our list is the Sightseeing and Sunset Catamaran Sailing Excursion, which offers a perfect introduction to Naples’ waters. This 2.5-hour cruise on the vessel “Cool Beans” provides a relaxed, scenic experience with chances to see dolphins, manatees, and a variety of birdlife. The tour’s focus on limited motoring means you’ll experience true sailing, and a stop at a secluded beach for shelling or swimming adds an extra touch of adventure (weather permitting).
The cruise departs from Naples and includes opportunities for wildlife sightings, making it especially appealing to nature lovers. The sunset cruise is particularly popular, with reviews praising the tranquil atmosphere, the chance to see dolphins, and the friendly crew. One reviewer called it the “highlight of our vacation,” highlighting the beautiful sunset and drinks onboard. Its affordability at just $70 per person makes it a great value for a half-day escape.
Bottom line: This tour is ideal for travelers seeking a relaxing, wildlife-rich cruise with stunning sunset views without breaking the bank. It’s perfect for couples, families, or anyone wanting a peaceful sail with memorable photo ops.
2. Private Sailing Tour through the Ten Thousands Islands
For those who prefer a personalized experience, the Private Sailing Tour through the Ten Thousand Islands offers a luxurious, intimate way to explore Florida’s lushest waterways. This 2-hour private charter is perfect for families, small groups, or couples wanting a truly tailored adventure. Departing from Goodland, the guide takes you on a stiletto catamaran through the region famous for its mangrove forests, abundant birdlife, and dolphins.
What makes this tour stand out is its flexibility. You can choose your preferred time, including options for a sunset cruise, and your guide will point out landmarks and wildlife along the way. Reviewers rave about the dolphin sightings and the comfortable boat, with one noting, “Captain Nick was great, and the sunset was spectacular.” The experience offers a perfect blend of relaxation and wildlife observation.
Costing around $440 for up to six people, it’s a higher price point but delivers a private, exclusive trip with personalized attention. It’s best suited for those who want a quieter, more intimate adventure or celebrate a special occasion.
Bottom line: If you’re after privacy, flexibility, and a chance to soak in Florida’s natural beauty without crowds, this private tour is a top choice. It’s a little pricier but delivers a luxurious, unforgettable experience.
3. Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Finally, the Catamaran Day Sail Shelling Excursion combines a luxurious sailing experience with the chance to explore a private island. This 2.5-hour tour takes place aboard the comfortable 42ft MaineCat “Cool Beans,” with a focus on shelling, swimming, and wildlife sightings.
What sets this tour apart is its combination of sightseeing and active shelling on a pristine beach. The crew provides complimentary drinks, and guests can relax indoors or outdoors. The review highlights mention dolphin sightings and the pleasure of gathering shells from a quiet beach, making it a hit with families and couples alike. It’s slightly more upscale, with an emphasis on comfort and immersive nature experiences, for $70 per person.
This tour is ideal for those who want a fuller day on the water, with the chance to swim and explore, all while enjoying music and drinks. The focus on wildlife and shelling makes it suitable for nature lovers and those looking for a leisurely, yet engaging, outing.
Bottom line: If your priority is combining sailing with beachcombing and wildlife, this trip offers a comfortable and memorable day on the Gulf.
How to Choose the Best Sailing Experience in Naples
Choosing among these options depends on your budget, interests, and group size. For a short, scenic sunset cruise with wildlife sightings, the Sightseeing and Sunset Catamaran is perfect. If you want a private and customizable trip, the Private Sailing Tour through the Ten Thousand Islands offers exclusivity and flexibility. For a longer, activity-rich day, the Catamaran Day Sail Shelling Excursion combines relaxation with active shelling and wildlife viewing.
Think about your group size: the private tour is best for small groups seeking privacy, while the other two are perfect for couples, families, or small groups. Also, consider your interest in wildlife, sunset views, or beachcombing—each experience offers something distinct.
Booking early is advisable, especially in high season, as these tours tend to fill quickly. Checking the weather forecast before booking will help ensure your trip is smooth and enjoyable.
Final Thoughts
Naples offers a wonderful range of sailing options, from quick wildlife-rich cruises to private, tailored adventures and full-day excursions. If you’re after a romantic sunset cruise, the Sightseeing and Sunset Catamaran delivers stunning views and wildlife sightings at an affordable price. For a more exclusive, quiet experience, the Private Sailing Tour provides personalized service amid lush scenery. And if you want a mix of active and relaxing time on the water, the Shelling Excursion makes for a memorable day out.
No matter which you choose, these sailing trips in Naples promise a chance to enjoy Florida’s natural beauty from the water—so book early, pack your camera, and prepare for a true sailor’s delight.