top of page

Take Your Next Adventure With Mainsail Naples!

Home: Welcome

About Mainsail Naples

Come explore Florida's beautiful Paradise Coast aboard a Telstar 28 trimaran sailboat! Take in one of Naples' famous sunsets, watch dolphins put on a show, scour the beach for shells, or simply cruise offshore and experience the freedom of feeling the wind in your sails. As a Florida native with over 30 years boating experience, Captain Art Rodriguez finds his greatest joy in sailing and will happily help you create the adventure you seek. Contact us for more information. Se habla español.

Home: About
Home: Video

Private, Chartered Day Sailing

Sunset Sail

A Naples sunset is unlike any you will ever witness. Residents and tourists alike gather on the beaches and applaud each night at sunset at the awe-inspiring dance of colors. Take in the view while under sail. What a romantic way to enjoy an evening! Duration: Approximately 3 hours.


Sails and Shells Tour

Sail to Keewaydin Island, a seven mile barrier island south of Naples that is only accessible by boat. The island boasts excellent shelling and is a picturesque place for a swim. Duration: Approximately 3 hours.

Create Your Own Day Sail Adventure

Let Captain Art help you plan a custom sailing adventure. Contact us directly for more information.

Home: Travel Services
Home: Current Specials

Frequently Asked Questions

Home: FAQ

What should I bring on my sailing excursion?

Wear a bathing suit, clothes, and shoes that you don't mind getting wet in. Bring a hat, a long sleeve and lightweight coverup, sunscreen, water shoes, a dry change of clothes, a towel, a waterproof camera, and any food and drinks you may want. Bring your own cooler or utilize ours. Feel free to bring your own beer and white wine, keeping in mind we do not allow red wine, liquor, or glass containers aboard. We will provide waters and sodas.  If you are prone to seasickness or are unsure, check with your doctor and consider bringing an over-the-counter seasick medicine.

What can I expect from my day aboard?

Captain Art will pick you up at Bayview Park and motor the boat out through Gordon Pass, cruising past the beautiful mangroves and mansions that characterize Naples Bay. Once out in the Gulf of Mexico, the sails can be raised and your sailing adventure begins! You will likely see dolphins and a variety of fish. If you're really lucky, you might see a sea turtle or manatee. Perhaps you'd like to just relax and sunbathe or maybe you'd like to learn a little about sailing or about Naples. If you want to go to the beach, Captain Art can anchor very near Keewaydin Island and assist you to swim to shore. Keewaydin is a beautiful island south of Naples that is only accessible by boat. It's rife with shells and wildlife: you may see iguanas, turtles, and an array of fish and birds. Partaking in a sailing day is a very physical thing especially when considering the sea conditions and weather factors, so participants should be physically capable and strong swimmers. Swimming is at one's own risk.

What if there's inclement weather?

The Captain will determine if weather conditions will deem the trip unsafe and/or unenjoyable. If such determination is made, the Captain will cancel and make every effort to reschedule with you. Not having enough wind to raise sail will not warrant cancelling a scheduled trip.

Is there a bathroom on board?

Yes! The "head" (that's boat lingo for "bathroom") is located at the forward part of the main cabin and made separate by a thick privacy curtain.

How many people can I bring? Is it kid-friendly?

The boat can comfortably fit four passengers, not including the Captain. We welcome children ages 12 and older, and minors must be accompanied by a parent or guardian.

Can I bring alcohol aboard?

Yes, you may bring beer and white wine. Due to our liability insurance, liquor is not permitted aboard. As beverages often spill while under sail, we do not permit red wine. For everyone's safely, we ask that you do not bring glass containers on the boat. We will provide water and sodas.

Do you take credit cards?

No, we do not accept credit cards at this time. We accept cash and payment through Venmo, Paypal, Cash App, and Zelle.

Talk to me about safety...

Our vessel and business meet all local and federal safety requirements. Each passenger is provided a life jacket and the vessel is equipped with a first-aid kit and all Coast Guard required boating safety equipment. The boat is up-to-date with all regularly scheduled maintenance. Each time the boat is used, all surfaces are fully sanitized in accordance with CDC guidelines in an effort to protect against the spread of Covid-19 and all other communicable germs. The cockpit and inside cabin of the boat have non-slip flooring, though all areas of the boat get wet and can get slippery, especially when under sail. We strongly suggest non-slip, close-toed water shoes or sailing shoes and exercising awareness and caution at all times. Situations and weather can change unexpectedly, so in order to keep you safe, the Captain needs your constant cooperation.

Home: Video

Contact Us

At Mainsail Naples, Captain Art is ready to help you plan your upcoming day sail so all that’s left for you is to enjoy it! Call, text, or send us an email and we’ll get back to you as soon as possible.


  • Facebook
  • Instagram

Thanks for submitting!

Home: Contact
bottom of page