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14 Best Boat Tours In Naples Florida (Sunset, Catamaran, Dolphin, and more!)

March 18, 2021 //  by  Florida Trippers

The best Naples boat tours are waiting for you! If you’re looking for a new way to take to the water, you’ve come to the right place.

Florida’s West Coast beaches are undoubtedly beautiful, but swimming off the shoreline and sunbathing can get boring. If you’ve ever wondered what’s beyond the shoreline, then these Naples boat tours are for you. This is truly one of the best things to do in Naples!

It doesn’t matter your disposition, there’s a boat tour from Naples for everyone! If you want to relax and take in the scenery, no problem. Or if you want a workout and want to kayak through the Ten Thousand Islands or the Everglades, there’s a tour for you!

There are even options for Spring Breakers too! Say goodbye to getting stuck on sandbars or worrying about DUIs. Naples boat tours have an option for you that takes away all the worry and hassle so you can be safe!

So no matter if you’re a tourist, a local, a vacationer, a fisherman, or somebody who just wants more of the great out doors? There’s a boat tour from Naples just for you. We even have a list of the best Everglades tours from Naples if you want an airboat ride. Discover what Southwest Florida has to offer you!

14 Best Boat Tours In Naples Florida (Sunset, Airboat, Dolphin, and more!)

Ten thousand islands boat tour.

For half a day, board a boat and explore one of Florida’s top natural attractions. This tour is one of the most fun Naples boat tours, exploring the Ten Thousand Island!

You’ll depart from Marco Island , about fifteen minutes south of Naples, with 12 other people to ensure an intimate experience. Then you’ll head to a small barrier island only accessible by boat on tour lasting about 3 hours.

The captain will point out sea life, highlight interesting sites, and discuss local history and ecology. While on the island, you’ll be able to swim, go snorkeling , and look for rare seashells!

Book Now : Ten Thousand Islands Boat Tour

Western Everglades Adventure Tour

One of the best Naples boat trips is to explore the ecosystem that is the Everglades . This tour will take you from Naples into the marshes and swamps of this natural wonder.

While you ride, you’ll be looking for native Florida wildlife like birds and turtles. You’ll even see alligators , of which there are more here than anywhere else in the world!

There’s even an interactive reptile show at the end of the day! You’ll spend a half-day on the water with your naturalist guide who will teach you about the ecosystem while you spot herons, egrets, and snakes!

Book Now : Western Everglades Adventure Tour

Cape Romano Boat Tour

For a quaint morning and afternoon on the water, enjoy one of the best Naples boat tours of Cape Romano! With a guide, you’ll explore one of the prettiest areas of the Ten Thousand Islands.

You’ll depart at 9 AM from Caxambas Park Marina at the south end of Marco Island, only 15 minutes away from Naples. The tour only hosts 10 people, so you’re in for an intimate experience.

You’ll learn about the region’s marine life and see the ecosystem of mangroves of the Ten Thousand Islands. Afterward, you’ll stop on one of the islands to go shelling ! Make sure to look out for the Florida Domes !

Book Now : Cape Romano Boat Tour

Ten Thousand Islands Catamaran Tour

On this Naples boat tour hosted by Backwater Adventure , you’ll be in the captain’s seat! As you go through the Ten Thousand Islands, you’ll be operating your own catamaran!

On the morning of your tour, you’ll meet at the Little Bar Restaurant. You’ll be provided with all the required US Coast Guard equipment and bottled water. Complimentary pictures will even be shared with you via Dropbox!

Choose from a 2.5-hour or 5-hour tour, and you will operate your own 2 person catamaran through the waterways of the Ten Thousand Islands. Led by a guide on a separate catamaran, you’ll be able to see the marine life at a closeness not available on other boat tours from Naples!

Book Now : Backwater Adventure

Naples Bay and the Gulf Eco-Boat Tour

Of all the Naples boat tours, this may be the most luxurious. You’ll privately be led on a 3-hour sightseeing/eco-tour to discover Naples’s vibrant ecosystem.

Either departing at 9 PM or 1 PM, you’ll spend 3 hours on a 22-inch motorboat with comfortable seating for all guests! Shade will be provided by a T-Top plus an additional bimini on very hot days.

As you head head north through Naples Bay, you’ll see dolphins, manatees, and a variety of birds including blue herons, roseate spoonbills, ospreys, and egrets!

You’ll be provided with complimentary bottled waters and sodas as well as a cooler with ice for your personal snacks and drinks. You can bring your own alcohol onboard and be provided with cups and a corkscrew! Don’t forget a Bluetooth radio to stream music of your choice!

Book Now : Naples Bay and the Gulf Eco-Boat Tour

Naples Sightseeing Boat Tour

Take a break from the hustle and bustle of life on one of the best Naples boat tours. This cruise will help you discover the top sights that Naples has to offer!

You’ll board a small motorboat where you’ll be able to purchase alcoholic beverages and small snacks. Make sure to bring your camera to take unobstructed pictures of the city.

After stopping at Tin City, a shopping and dining destination, you’ll cruise to the Gordon River Greenway. Along this stretch of water, you’ll see historic buildings and the homes of millionaires in Port Royal, some even owned by celebrity snowbirds!

Book Now : Naples Sightseeing Boat Tour

Dolphin, Birding and Shelling Tour

On one of the best Naples boat tours, you’ll be introduced to birding! You’ll also have the opportunity to see dolphins and then go shelling for rare shells on the Ten Thousand Islands.

These tours are never “canned,” meaning the course changes daily to find the most beautiful Florida wildlife as it migrates. You’ll learn about these species in detail and their ecosystems from an experienced naturalist guide!

You’ll be able to see many different species depending on the season. Expect to encounter manatees, dolphins, sea turtles, bald eagles, ospreys, herons, egrets, pelicans, and roseate spoonbills. You’ll also see many species of fish and shore birds.

Make sure to bring your own water and snacks to last 2 hours. Wear a sunhat, sunglasses, sunscreen, and shoes you don’t mind getting wet. You also won’t regret bringing a camera and a pair of binoculars!

Book Now: Dolphin, Birding, and Shelling Tour

Sunset Catamaran Sailing Excursion

How many Naples boat tours allow you to sail on a catamaran named “Cool Beans?” Cool Beans Cruises will be the perfect way to see Southwest, Florida to make lasting memories.

Choose between a 2.45-hour day-sail or a 2.5-hour champagne sunset cruise! With up to 20 passengers, you’ll depart from Naples and pass by the Rookery Bay National Estuarine Wildlife Reserve.

During the day-sail, you’ll stop by Keywaydin Island for shelling and swimming. Keep your eyes peeled for dolphins, birds, and manatees ! Bring a camera to capture a photo!

On the sunset sail, you’ll have a complimentary champagne toast right as the sun sets on the water. On both cruises, you’ll be able to drink complimentary soda, water, beer, and white wine.

Book Now : Cool Beans Cruises

Mangrove Tunnel Kayak Eco Tour

Kayaking in Florida is always beautiful, but you can experience the best of one of the most fun Naples boat tours! Here , you’ll paddle a kayak through the mangroves of the Everglades.

You’ll discover the exotic beauty of the Everglades’ mangroves forest with the expertise of an experienced guide and naturalist. You’ll spend three hours winding through sleepy creeks and mangrove canopies.

Don’t worry if you’re not an experienced paddler, you’ll learn kayaking techniques from your guide. You’ll also get a larger-than-life view of alligators, herons, ducks, and loads of fish species! Don’t forget the bug spray!

Book Now : Mangrove Tunnel Kayak Eco Tour

Marco Island Dolphin-Watching Tour

Hosted by Florida Adventures and Rentals, this is one of the most relaxing of the Naples boat tours. Traveling through the Ten Thousand Islands, you’ll be looking for dolphins.

With your captain-guide, Captain Steve , you’ll explore the Ten Thousand Islands after departing from Marco Island at 11:30 AM. You’ll only be with 10 other travelers, so it’s an intimate experience.

You’ll be able to see dolphins right up close to the boat! Captain Steve will educate you about the natural environment and the area’s ecosystem. Also be on the lookout for native birds as well as fish in the maze of mangroves.

Book Now : Marco Island Dolphin-Watching Tour

Ten Thousand Island Jet Ski Eco-Tour

When you need to beat the heat, one of the regular Naples boat tours just won’t cut it. To get the best views on the water and from the water, consider the Ten Thousand Island Jet Ski tour !

Take a break from the beach and fly through the waters of the Ten Thousand Islands on a jet ski. From the Naples marina, your guide will point out dolphins and sea creatures often missed by untrained eyes.

Because you’re on a jet ski, you’ll be able to travel to secluded locations on the 30+ mile route that are inaccessible to boats and kayaks. With a small group size, you’ll be able to travel to the Florida Domes as well!

Keep in mind to drive a jet ski, you will have to obtain a Boaters Safety Certificate. You also must be 16 years old to operate the machine. If you were born before January 1, 1988, you do not need any certificate at all!

Book Now : Ten Thousand Island Jet Ski Eco-Tour

Naples Deep Sea Fishing Tour

Anglers, rejoice! Sometimes the pier just doesn’t cut it. Instead of chartering your own boat and going it alone, take one of the best Naples boat tours to go deep-sea fishing !

Departing from the Cocohatchee River Park Marina, you won’t even need your own fishing license on this chartered boat. You’ll drop anchor about 10 miles or 16 kilometers offshore before you cast your lines.

Choose between a 4-, 6-, or 8-hour tour. After you depart at 7 AM, your captain will offer instruction and casting lessons to those who need it. Equipment will be provided. Depending on the season, you might find cobia, mackerel, snapper, and grouper!

Book Now : Naples Deep Sea Fishing Tour

Captain Party Hard Boat Tour

If you’re looking for a fun and different Spring Break destination , consider taking the most fun of the Naples boat tours out there: The Captain Party Hard Boat Tour !

Captain Party Hard will provide you a safe and worry-free boat tour. Departing from Marco Island, you’ll sail around Keywaydin Island and the Ten Thousand Island with multiple opportunities to spy on dolphins.

You’ll be surrounded by great music and a party atmosphere on a 27′ Hurricane Deck Boat. For four hours, you won’t have to worry about DUIs or getting stuck on sandbars.

You’ll be provided with beach chairs, games, beverages, and snacks. Dance with locals on the beaches, too! All you need is a bathing suit and a towel! Captain Brent Wilson provides the rest.

Book Now : Captain Party Hard Boat Tour

Guided Kayak Tour

If sitting on a boat sounds unappealing, then enjoy the water on one of the most adventurous Naples boat tours! With small groups of 6 maximum guests, you’ll be on an intimate kayaking adventure !

Small groups create the best opportunity to quietly kayak so everyone can see as much wildlife as possible. Your naturalist guide will provide information about the incredible flora and fauna of Southwest Florida.

Departing from the Cocohatchee River Park Marina in Naples, your guide will provide you with your equipment: kayak, paddle, life vest, and even a dry bag for your electronics. Bring your own water, sunblock, and bug spray.

After departure, you’ll head to Barefoot Beach Preserve. Through the mangroves, you’ll have the opportunity to see dolphins, manatees, birds, and more! Then you’ll stop by Barefoot Beach to stretch your legs and go shelling and swim!

Book Now : Guided Kayak Tour

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Take a Virtual Journey with Cool Beans

Choose a day-sail, champagne sunset or a private catamaran cruise below to enjoy a sailing adventure aboard our 42 foot sailing catamaran, Cool Beans .

If you’re looking for something different we can explore Keewaydin Island or one of the many other hidden treasures aboard Lil’ Beans , our luxury pontoon.

Day-Sail Cruise

Price includes a delightful escape to the beautiful waters of the Gulf of Mexico. Relax and enjoy your sailing experience on our beautiful catamaran while watching the abundant sea life and native birds of Southwest Florida.

During our day sails, we do stop for approximately 35 minutes at one of the many beautiful beaches of Southwest Florida – Keeywaydin Island, a barrier island in South Naples to swim, explore , and collect shells.

(Please note stopping at the beach is based on weather conditions. If it is too rough/choppy in the Gulf, the Captain may choose not to include a stop at the beach. Also know that to get to shore, you must swim in. We drop anchor in approx. 6 feet of water, approx. 30 yards off shore. Life jackets and floaties provided if needed. You are also welcome to stay on the boat to soak in the sun and scenery during the stop if you do not want to swim.)

• Complementary – soda, water, beer and chardonnay included
• You can also bring aboard additional food/snacks and beverages (no red wine please) on-board. Due to insurance liability, hard liquor is not allowed on our vessels.
• Smoking and Vaping are prohibited.

Gratuity Extra

Please note: 18% Gratuity will be added for parties of 7 or more.

• * Children must be at least two-years old.
• ** 24 hour prior notice cancellation policy for parties of 6 or under
• *** 48 hour prior notice cancellation policy for parties of 7 or more

Champagne Sunset Cruise

See Southwest Florida the way it was meant to be seen . . . by water! Escape from the crowds and set sail to take in our beautiful sunset. Sit back and enjoy a warm breeze in your face, a glass of champagne in your hand and the view of one of the most beautiful sunsets you will ever experience. Sail back to port and marvel at the view of the Gulf of Mexico and Naples/Marco Island beaches with the sunset lighting your way.

• Complementary – soda, water, beer and chardonnay included
• Complementary glass of champagne at sunset

Private Day-Sail or Sunset Cruise

 Would you like to have the boat to yourselves? Booking a “Private Cruise” is the perfect way to celebrate any occasion while enjoying your privacy. Choose from one of our Day Sails or our Champagne Sunset Cruises and leave the rest to us. Price includes items described above for your specific choice of cruise.

• ** 48 hour prior notice cancellation policy

Lil’ Beans Pontoon Island Beach and Sunset Adventures

Enjoy a Private 2 ½ hour Luxury Pontoon Tour for Up to 6 Guests for our Day Excursions or a 2 hour Sunset Excursion. Our Pontoons are perfect for Island hopping, up close Eco/Nature and Shelling on Keeywaydin Island. A “Must Do” while visiting SW Florida! (Sunset Charter arrives back to dock approximately 15 minutes after Sunset)

Keewaydin Island– A Deserted Barrier Island

Keewaydin Island is an 8 mile long unabridged barrier island just to the north of Marco. A fantastic sandy beach stretching the length of the island, with great shelling and opportunities to see plenty of wildlife. It serves as a sanctuary for wildlife and a popular recreational destination, especially at weekends. Keewaydin provides a great opportunity to experience Florida’s natural coast and is a vital nesting ground for Least Terns and Loggerhead Sea Turtles.

Hide-A-Way Beach/Sand Dollar Island – An Unspoiled Gulf Beach

Located just north of Tigertail Beach you’ll find Sand Dollar Island which abounds with wonderful seashells and is absolutely breathtaking and totally natural. Many of Florida’s beach-nesting shorebirds that face conservation challenges can be regularly spotted on Sand Dollar, including the Snowy Plover, Least Tern, Black Skimmer, American Oyster Catcher, and Wilson’s Plover.

• GOOD FOR CHARTERS COMPLETED BY JUNE 20TH, 2024
• * Price includes soda and water
• ** Children must be at least two-years old
• *** 48 hour prior notice cancellation policy

Groups & Special Occasions

Small intimate sunset weddings.

Make memories to cherish for a lifetime when you exchange wedding vows during your Cool Beans private sunset sail. Whether you have something particular in mind or need ideas, we can provide some wonderful options to assure that your wedding is everything you expect and more.

Romantic Sailing Excursions

Create the perfect moment to ask your significant other for their hand in marriage with a private cruise along the beautiful waters of Southwest Florida. Ask us how we can help to make your interlude aboard the Cool Beans a magical event to treasure for a lifetime.

Private Anniversary Cruise Celebrations

Reaffirm your love for one another alone or among special friends and loved ones aboard the Cool Beans. Your private sailing excursion is sure to be fun, romantic and memorable.

The Ultimate Birthday Private Cruise

Making a magical birthday celebration aboard the Cool Beans is one of our specialties. Whether your event is for a family daytime cruise, adventure among friends or a private sunset intimate sail, we are here to make your birthday cruise an event to remember.

Bachelorette Party

What a great way to celebrate the Bride to Be with her “Last Sail Before the Veil!” Specializing in small groups up to 20, booking a Bachelorette Party with Cool Beans Cruises will truly create a lasting memory..

Share the gift of a Cool Beans Cruise!

Miss Naples Online Reservations

Concierge or booking agent, buy gift certificates online.

Reservation / Cancellation Policy

All tickets purchased online are non-refundable. Once purchased, tickets cannot be refunded. All cruises take place rain or shine regardless of weather conditions. In the rare situation where we are forced to cancel, ticket holders will be allowed to reschedule to another time (based on availability) or refunded.

Policy Notices

Your ticket code will be required to attend the activity - this is your proof of purchase. Please arrive early: Cruises depart right on time and you will not be entitled to a refund if you are late or miss the cruise. Your tickets are guaranteed upon purchase. ENJOY! We look forward to welcoming you!

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Naples' Premier Sailing Charter Company

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Island Sailing - Naples, FL​​

​Captained charters

We offer many different captained private sailing adventures, including 2, 3, or 4-hour sunset sails and day sails, overnight/weekend trips, and week-long adventures along Florida's southwest coast, Florida Keys, or to the Bahamas. Enjoy a bay tour, set sail in the gulf, and enjoy what nature has to offer aboard Island Time (47' Beneteau) or Island Dreams (31' Catalina). Be on the lookout for dolphins and various FL birds! We cater to our customers' every need and strive to provide our customers with the very best service possible.  Let your captain be your tour guide on your private charter. 

Experienced sailors can bareboat  Island Dreams , our 31' Catalina, for a half day or full day sail. Enjoy cruising along Naples' sugar white sandy beaches aboard a fun and easy-to-sail yacht. She is well equipped for your sailing needs.  Want to go sailing but don't want to pay the high costs of owning a sailboat? You can! We also offer a boat club (5 and 10-day packages). 

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Island Sailing Naples | 800 12th Avenue South, Naples, FL | [email protected] | 239.398.1483

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Bareboat and Crewed Sailing Charters in Naples, Florida since 1985!

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Choose from a 2 hour “taste of sailing”, a half-day “jaunt along the beach” sailing the wind, a full day “adventure to Marco Island” sightseeing or romantic sunset or moonlight cruise.

Bareboat Charters

Let us help you plan a complete Florida sailing vacation from a simple overnight to a couple of weeks

Types of Charters

Choose your desired charter.

When choosing a sailing charter, you want to choose with confidence. Established in Naples in 1985, providing romantic getaways, sunset/sunrise trips, once in a lifetime sailing experiences for families on vacation, and corporate team building adventures.

About sailboats unlimited, naples most trusted sailboat chartering company since 1985.

The best experience you will have while visiting beautiful Naples, Florida

Located in sunny Naples, Fl, we have specialized in crewed sailing charters, bareboat sailing charters, yacht deliveries, and yacht maintenance since 1985.

When visiting Naples, FL or any of the surrounding areas, you have the opportunity to take our sailboats out onto the beautiful gulf. Let us charter you and your guest, or reserve the entire yacht for your guest. Sunset and moonlight cruises, half day and full day cruises. We have something for every scenario.

Our bareboat yacht charters are on boats ranging from 34′ to 42′. Half day to weekly bareboat charters are available. Preliminary checkout available by phone or fax. Prices vary depending on vessel. 34′ ocean racers and up to 42′ luxury cruising yachts. Large parties can be accommodated, with up to 16 on the Danmark, a 40′ Sloop U.S. Coast Guard inspected vessel.

Enjoy the unique Florida experience sightseeing and watching the dolphins at play. Kick back and be pampered or you take the helm. Free sailing instruction during the charter.

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Rains Continue Battering South Florida, Closing Roads and Grounding Flights

The deluge, which began Tuesday afternoon, dumped more than 10 inches in some areas and was expected to continue through Thursday, forecasters said.

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By Livia Albeck-Ripka ,  Judson Jones and Derrick Bryson Taylor

Judson Jones is a meteorologist and reporter for The Times.

Go here for the latest updates on the forecast in Florida.

Heavy rains battered South Florida on Wednesday, closing major roads, stranding vehicles, forcing delays and cancellations at airports, and causing flash flooding in the Fort Lauderdale and Miami areas.

The severe weather, which began Tuesday, is the result of a cold front parked over parts of the state that has dumped more than 10 inches of rain in some areas, Anthony Reynes, a senior meteorologist with the National Weather Service in Miami, said Wednesday afternoon.

The region was bracing for more heavy rain on Thursday, with forecasters warning that showers and thunderstorms over parts of the region would raise the risk of flash flooding from late morning through the afternoon.

“It will take very little additional rain to aggravate ongoing flooding in rural and urban locations,” the National Weather Service’s Storm Prediction Center said in its excessive rainfall warning, which includes Miami.

Flash flooding was reported on Wednesday from Fort Lauderdale to downtown Miami, Mr. Reynes said, noting that major urban areas, including some homes, had been inundated with water, and that many vehicles had been stranded. By Wednesday evening, more than 10 inches of rain had fallen in Hollywood, Fla.; more than nine inches in Fort Lauderdale; and about eight inches in Miami, he said.

As of Thursday morning, there were no reports of injuries or deaths, but many of the same problems persisted.

Dozens of flights from Miami International Airport and Fort Lauderdale-Hollywood International Airport were either delayed or canceled for the second consecutive day. And plans to begin demolishing Marjory Stoneman Douglas High School in Parkland, where a former student killed 17 people in 2018, were also postponed until Friday, school officials said .

On Wednesday, Gov. Ron DeSantis declared a state of emergency in Broward, Collier, Lee, Miami-Dade and Sarasota Counties. The declaration gives emergency managers the authority to allocate resources, including personnel, to respond to the flooding and other effects of the severe weather.

Mayor Dean J. Trantalis of Fort Lauderdale said on social media that resources were being mobilized across the city. “If possible, please avoid driving,” he said. “It’s crucial to never attempt to drive through high water.”

The City of Fort Lauderdale said in an email Wednesday night that it had responded to “multiple stranded vehicles” and that several city roads were impassable.

On Wednesday afternoon, the Weather Service issued its highest level of warning, a flash flood emergency , for a stretch spanning from North Miami to Dania Beach. “The amount of rain that was falling was quickly overwhelming the drainage systems,” Mr. Reynes, the meteorologist, said. “It was becoming a life-threatening situation.”

Like the cars of a train, storm after storm moved from the west coast to the east coast of the southern Florida Peninsula on Wednesday, soaking an area already saturated from the rain. It appears that little relief is in sight.

The threat of excessive rain over South Florida will decrease only slightly on Friday, meteorologists said. Passing showers will again create localized flash flooding, making urban areas, roads, small streams and low-lying regions vulnerable.

Livia Albeck-Ripka is a Times reporter based in Los Angeles, covering breaking news, California and other subjects. More about Livia Albeck-Ripka

Judson Jones is a meteorologist and reporter for The Times who forecasts and covers extreme weather. More about Judson Jones

Derrick Bryson Taylor covers breaking and trending news and is based in London. More about Derrick Bryson Taylor