Top Naples Cruises &amp; Sailing

Sightseeing and Sunset Catamaran Sailing Excursion

Discover the sights and marine life of Naples on a sightseeing cruise. You have the opportunity to see birds, dolphins, and, season permitting, manatees. The cruise also takes you past the area’s top mansions, Keewaydin Island, and more. Relax and learn about local history, wildlife, and celebrity real estate during on board commentary. It’s the perfect time to take unobstructed photographs of the city and its natural surroundings.

4.8

(662)

from $70

Special Offer

Naples Sightseeing Boat Tour

Our 2-hour cruise is designed for relaxation and deeper discovery. While shorter tours offer a quick look, this experience allows your licensed captain to guide you through the winding canals of Aqualane Shores and Port Royal. Enjoy a front-row view of prestigious waterfront estates—architectural masterpieces hidden from the main bay. With extra time on the water, relax, socialize, and take photos as you cruise calm canals and scenic waterways. Watch for dolphins and native birds along palm-lined shores—without the rough Gulf waters. Step aboard our tropical, hexagon-shaped tiki boat for a fun, personal experience with your captain. Book by the seat (up to 6 passengers) or reserve a private charter. This is a BYOB cruise—bring your favorite drinks and snacks. We provide a cooler with ice, cups, leis, photo props, Bluetooth music, and all required safety equipment. Also consider our Bonita Springs tour launching from The Fish House and our pontoon cruises.

2 Hour Naples Tiki Boat Cruise, Port Royal and Luxury Canal Tour

2 Hour Naples Tiki Boat Cruise, Port Royal and Luxury Canal Tour

Don't just witness a sunset, experience a transformation. Our Naples Sunset Adventure is your ticket to the "golden hour" magic that defines Florida's Gulf Coast. Each evening is a unique, ephemeral performance as the sun kisses the horizon, exploding into a symphony of color that paints both the sky and the shimmering water. This is where cherished memories are forged, where the kids gasp in wonder, and where couples find a moment of perfect romance. Let us guide you to the heart of this nightly wonder, creating an unforgettable highlight of your Naples vacation.

(3)

from $75

2 Hour Naples Sunset Adventure

(32)

from $75

Dolphin and Shelling Cruise for up to 12 people

Set sail into the glorious Gulf of Mexico for a luxurious 2.5-hour Catamaran day sail, aboard the beautiful 42ft. MaineCat Cool Beans. Journey to an exclusive island paradise where you can bask in the sun and take part in some exciting shelling (weather permitting). Relax with pristine views as calming island tunes fill your ears, while sipping on complimentary drinks from comfortable seating—with the choice of basking indoors or outdoors. Create memories with your loved ones on the high seas.

(1,019)

from $109

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

Set sail from Naples aboard a spacious catamaran that cruises along the Gordon River, Naples Bay, and drops anchor at Keewaydin Island. This half-day cruise takes you to pristine white-sand beaches where you can go swimming and shelling. Hear live commentary about the sights along the way and keep an eye out for dolphins. The catamaran accommodates up to 44 passengers and is suitable for all ages.

(185)

from $70

Beach Island Shelling Cruise to Keewaydin Island Tour

Beach Island Shelling Cruise to Keewaydin Island Tour

Exploring the Ten Thousand Islands National Wildlife Refuge on your own can be intimidating if you don’t know your way around on the water. Book this Thousand Islands 2-person Catamaran Tour to follow a knowledgeable guide who will keep you from getting lost and ensure you enjoy this pristine preserve to the fullest, with great opportunity to view the wildlife and sea life that inhabit the refuge.

(59)

from $56

Backwater Adventure's CraigCat Tours of the 10,000 Islands

Backwater Adventure's CraigCat Tours of the 10,000 Islands

1 hour 30 minutes to 2 hours 30 minutesFree Cancellation

(952)

from $170

Cruise the beautiful waters of Marco Island while taking in the wildlife and making a stop at a remote island for some shelling and beach time. After the beach we check out some of the local hot spots for some catch and release fishing. This trips is a crowd favorite. We customize each trip to the guests to make a unforgettable experience! This excursion lasts for 4 hours. Pricing is for 6 people max. *** Have a Group Larger than 6? We have 2 boats and can take groups up to 12 people. Please reach out to customer service and they will assist you in booking***

Private 4 Hour Shelling , Fishing and Eco Tour Marco Island FL

Private 4 Hour Shelling , Fishing and Eco Tour Marco Island FL

4 hoursFree Cancellation

(41)

from $725

Experience the natural wonders of Southwest Florida on a private 2-hour dolphin and eco tour through the Ten Thousand Islands. Cruise aboard a comfortable boat with a USCG-certified local captain, spotting dolphins, manatees, sea turtles, sharks, and a variety of coastal birds in their natural habitat. Enjoy a stop at a secluded barrier island for shelling and beach time, where you can explore pristine sands and collect unique shells. This small-group tour (up to 6 guests) offers a personalized adventure ideal for families, couples, and nature enthusiasts. Whether you're a nature lover, photographer, or family looking for a memorable adventure, this tour delivers unforgettable moments in one of Florida’s most scenic coastal regions. Frequent sightings of dolphins, manatees, and native wildlife Visit a remote island for shelling and beachcombing ***Have a Group Larger than 6? We can take groups up to 12. Reach out to customer service and they will assist you in booking***

Marco Island Dolphin & Eco Tour – Private 2 Hour Wildlife Cruise

Marco Island Dolphin & Eco Tour – Private 2 Hour Wildlife Cruise

(36)

from $425

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in Naples Bay and then set sail into the Gulf of Mexico to watch a breathtaking sunset while sipping your favorite cocktail. Cruises are narrated to point out interesting sights along the way. Dolphin sightings are plentiful and fun for all ages. Pack your favorite drinks and snacks in a cooler, and don't forget to take some pictures! We've been cruising the Naples Waterways since 1991 and are family-owned and operated. Guests are welcome to bring small coolers with their favorite beverages and snacks. Alcohol is permitted. Please note this is not a private boat tour, this is a group tour with others onboard Boarding time is 15 minutes prior to scheduled departure time. Please allow enough time to park and walk down the dock. We leave promptly on time.

Sunset Cruise Tour

(53)

from $49

Kick back, relax, and let your captain set sail for the sunset with you and your party on this private cruise from Marco Island, Florida. Feel free to bring a cooler packed with your favorite food and refreshments, alcoholic and otherwise. Stop off at a secluded beach for some shelling, and keep your eyes peeled for local wildlife such as dolphins, alligators, manatees, and coastal birds.

Marco Island Sunset Cruise- Private 2 Hour

Marco Island Sunset Cruise- Private 2 Hour

(38)

from $450

Southwest Florida is home to a diverse ecosystem and marine life. See where the Gulf of Mexico and the waters of the Everglades converge during this sunset cruise. You’ll begin your sail in Naples then head out into the Everglades in search of alligators, sharks, and manatees. Then, you’ll ride through the Everglades National Park to the 10,000 Islands where more wildlife awaits. Finally, you’ll gaze at the sunset before heading back to Naples.

Manatee, Dolphin and 10,000 Islands Sunset Cruise!

Manatee, Dolphin and 10,000 Islands Sunset Cruise!

Pontoon Sightseeing and Shelling Excursion to Keeywaydin Island

4.7

(69)

from $130

(133)

from $325

Naples Florida Sunset Cruise-Complimentary Charcuterie and wine

Nature lovers can spend a day immersed in pristine landscapes on this shelling cruise from Naples, Florida to Keewaydin Island. Join a small group and board your vessel for the journey to the remote island. Cruise past mangrove forests and see wildlife such as alligators, dolphins, and even manatees along the way. Once you reach Keewaydin, take a nature walk and fill your big with beach treasures before heading back.

(81)

from $110

Special Offer

Dolphin Watch Eco Shelling Cruise to Keewaydin Island

Dolphin Watch Eco Shelling Cruise to Keewaydin Island

Explore Marco Island’s best-kept secrets on this exclusive three-hour adventure, combining wildlife encounters, island exploration, and tubing fun. Unlike larger tours, this small-group experience offers a personalized journey through the 10,000 Islands, where you’ll have close-up encounters with wild dolphins in their natural habitat. Step onto a secluded barrier island—only accessible by boat—and search for rare shells along the untouched shoreline. Then, cool off with a tubing ride in the crystal-clear waters, with your captain adjusting the speed to match your comfort level. Whether you’re looking for relaxation, adventure, or family-friendly fun, this tour delivers it all in one unforgettable trip. Book now and experience the perfect blend of nature, excitement, and discovery on the water!

Marco Island Private Tubing, Dolphin Watching and Shelling Tour

(10)

from $695

4 Hour Ten Thousand Islands Shelling Trip

3 hours 15 minutesFree Cancellation

Drive your Own 2 Seat Fun Go Cat Boat on Marco Island

(100)

from $155

4.8

(292)

from $180

Hop aboard the best water experience in Naples, where the shimmering Gulf waters become your highway to paradise. We'll whisk you away to the secluded, white-sand shores of Keewaydin Island. Spend your day basking in the sun, shelling along the beach, or exploring the island's lush flora and fauna. We offer two choices on where to be dropped off. The first option, we call it the secret beach, is a much quieter option. It is way less crowded than the main beach on Keewaydin Island, so if you want a more chilled out, quiet, and relaxing experience this one may be for you. The second option is to be dropped off in the heart of the action at the main beach. This is a favorite hangout for locals, buzzing with activity, and there are usually lots of boats (particularly on the weekends). We also provide each passenger a BEACH CHAIR WITH CANOPY, BEACH TOWEL, BEACH UMBRELLA, SOUVENIR SHELL BAG, BUCKET & SHOVEL FOR KIDS, BEACH GAMES, COMPLIMENTARY WATER, SODA AND SNACK.

NAPLES TO KEEWAYDIN: your luxury water shuttle with all amenities

NAPLES TO KEEWAYDIN: your luxury water shuttle with all amenities

4 hours 30 minutesFree Cancellation

Price varies by group size

(52)

from $175

PRIVATE Eco Boat Trip out of Naples Bay, FL , island stop incl.

2 hours 45 minutesFree Cancellation

(38)

from $395

This is the only tour of its kind around Marco Island! Experience the best of the 10,000 Islands on this exciting dolphin-watching and tubing adventure. Cruise through mangrove-lined waterways, spotting wild dolphins playing in their natural habitat. Then, switch gears for some fun as you float and glide across the water on a tubing ride, perfect for all ages. This private, small-group tour offers a unique mix of wildlife viewing and thrilling water activities, making it an unforgettable way to explore Southwest Florida’s scenic coast. Book now to combine adventure and relaxation on the water!

Marco Island Dolphin Watching & Tubing Adventure

Marco Island Dolphin Watching & Tubing Adventure

(7)

from $575

Immerse yourself in some of Florida’s loveliest scenery—and enjoy a relaxing excursion out on the water—with this private sailing tour. Meet your guide in the afternoon in Goodland, hop aboard your stiletto catamaran, and set sail. You’ll tour the Ten Thousand Islands region, known for its lush seascapes, mangrove forests, and wealth of wildlife. Your guide will point out landmarks and highlights as you go.

Private Sailing Tour through the Ten Thousands Islands

Private Sailing Tour through the Ten Thousands Islands

from $450

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What are people saying about Naples

Private 4 Hour Shelling , Fishing and Eco Tour Marco Island FL

Courtney_B, Jun 2026

Fantastic!

We saw dolphins multiple times, found great shells, caught 5 different types of fish, and a shark!! I think Cole was our guide (I'm horrible with remembering names). He was amazing with our kids and very patient. Our group was Grammy, myself and husband, and our 3 kids (7, 10 and 10 years old).

Marco Island 2 hour Dolphin, Birding and Shelling tour

Kristianne_S, May 2026

5/5 Stars – An Unforgettable Morning on the Water!

We couldn’t have asked for a better experience on our dolphin, shelling, and birding tour. We took the 8:00 AM trip, and it turned out to be the perfect time for shelling—the beach on the tour was loaded with shells due to a SW wind.The highlight of the day was definitely the wildlife. We were lucky enough to spot a mother and baby dolphin right near the boat; seeing the little one nursing was a once-in-a-lifetime moment. To top it all off, we actually saw a manta ray leap completely out of the water! It was truly a breathtaking, once-in-a-lifetime sight.The crew was top-notch. Our Captain and the guides were incredibly knowledgeable, patiently answering every single question we had about the local ecosystem and the birds we spotted.The shelling lived up to the hype, too! We found some great treasures, and it was a nice touch that we were able to keep our shelling bags as a souvenir. With perfect weather and expert guides, this was a fantastic trip from start to finish. Highly recommended!

Manatee, Dolphin and 10,000 Islands Sunset Cruise!

Sarah_C, Apr 2026

The best time on our babymoon!

We had the best time with Capitan Wes! We saw three different manatees and so many birds, including ospreys and their nests! We also had a magical experience with dolphins riding in our wake and jumping around! Capt Wes was so knowledgeable and really made the trip great! Definitely recommend this tour!

Naples Florida Sunset Cruise-Complimentary Charcuterie and wine

Douglas_C, Apr 2026

Great personalized sunset cruise

Captain Ty made the cruise extremely enjoyable. We saw homes of the rich and famous, crazy hugh yachts, jumping dolphins and a beautiful sunset while sampling charcuterie and sipping wine. And captain Ty’s stories really kept us entertained! We look forward to taking this cruise again in the future.

Backwater Adventure's CraigCat Tours of the 10,000 Islands

Edward_B, Mar 2026

Absolute adventure

This was an absolute blast! Didn’t originally feel like 2.5 hrs was going to be enough time. It was. We saw dolphins in a couple area and our guide was great at stopping and pointing them out. They don’t surface much and move pretty fast. The guide helping figure out the direction they moving helped seeing them more. By far the best is just out cruising the catarmaran’s. They are a blast to drive. Very comfortable seats. Not a lot of storage so pack accordingly. They provide a cooler with ice and water you can throw a couple bottle of pop in. Overall great experience and will definitely tour again with them!

4 Hour Ten Thousand Islands Shelling Trip

Todd_W, Feb 2026

Awesome Birthday

Made a very memorable moment for my wife on her birthday. Captain Marco was knowledgeable and made the trip awesome. It’s amazing how there’s so many beautiful shells that you have to be picky and not like being on a public beach where you’re picking up every nice shell. We also found some rare shells. Highly recommend!

Dolphin Watch Eco Shelling Cruise to Keewaydin Island

John_M, Feb 2026

Just do it!

Wonderful excursion! Captain and first mate were extremely knowledgeable about the Eco system and Naples area in general. The island provided the most beautiful and plentiful seashells! Having iguanas great us with a photo opportunity was extra fun! We also had the opportunity to see a pair of dolphins swim alongside the boat!

Dolphin and Shelling Cruise for up to 12 people

Ellen_S, Dec 2025

Amazing trip

Our family loved this trip! Captain Glenn was charming and knowledgeable, and Michelle was lovely and helpful. We saw tons of birds and he knew exactly how to make sure we saw dolphins, too: We went to one shell beach and while there were other tourists there, we were there early (we booked the 830 am tour) and we were all so excited to find a lot of sand dollars. The scenery is gorgeous and the ride, relaxing. Highly recommend!

Drive your Own 2 Seat Fun Go Cat Boat on Marco Island

Kathy_K, Dec 2025

Great day on the water!

This 2 seat Cat Boat water tour was so much fun! Driving your own boat while seeing all of the beautiful mangroves, dolphins and unchartered areas of the 10000 Islands was fantastic! Our tour guide Austin was very personable, and did a great job of explaining how to drive the boats as well as some about the area. It was well worth it.

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

Tiffany_S, Nov 2025

Perfect Day out on the Water!!

These guys are awesome!! We loved Dan & Kyle…who took us out, and Linda and Dave were great too!! From start to finish..everything was organized, and everyone was super knowledgeable and friendly. By the end, we all felt like friends!! We will definitely be back..it was a perfect day on the water!! Highly recommend.