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Naples Cruises, Sailing & Water Tours

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Naples Tours

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Private Luxury Port Royal Real Estate Cruise
Likely to Sell Out
Likely to Sell Out
5.0 (6)

Private Luxury Port Royal Real Estate Cruise

We aim to set the standard when it comes to experiencing Naples from the water. Enjoy a private and intimate experience on a luxury deck...

2 hours • Free Cancellation
5.0 (6)
from
$550
Private Luxury Keewaydin Island Beach & Dolphin Excursion
Likely to Sell Out
Likely to Sell Out
5.0 (8)

Private Luxury Keewaydin Island Beach & Dolphin Excursion

Discover the serene beauty of Keewaydin Island on a luxury boat tour to this hidden gem of Southwest Florida. Accessible only by boat, the island...

3 hours • Free Cancellation
5.0 (8)
from
$595
Private Guided Kayak Tour on Big Hickory Pass
5.0 (37)

Private Guided Kayak Tour on Big Hickory Pass

Enjoy paddling through the mangrove tunnels on Estero bay. Our kayak tours are available for all ages. If anyone wants to bring their own SUP...

2 hours 30 minutes • Free Cancellation
5.0 (37)
from
$135
Naples Private Dolphin Cruise with Breakfast & Port Royal
Likely to Sell Out
Likely to Sell Out
5.0 (2)

Naples Private Dolphin Cruise with Breakfast & Port Royal

Begin your day with a peaceful private cruise through Naples Bay, where the calm morning waters create one of the most beautiful times to experience...

2 hours • Free Cancellation
5.0 (2)
from
$500
Private Luxury Sunset Cruise in Naples Bay and Keewaydin
Likely to Sell Out
Likely to Sell Out
5.0 (3)

Private Luxury Sunset Cruise in Naples Bay and Keewaydin

A serene escape awaits on a private luxury sunset cruise through the tranquil waters of Naples Bay. As you glide past elegant waterfront homes and...

3 hours • Free Cancellation
5.0 (3)
from
$625
Tiki Boat Bachelorette and Birthday Celebrations Tours in Naples
5.0 (5)

Tiki Boat Bachelorette and Birthday Celebrations Tours in Naples

Discover Naples from the water with our vibrant tiki boat tours, perfect for special celebrations or simply unwinding in the sun. Enjoy custom experiences, from...

2 to 4 hours • Free Cancellation
5.0 (5)
from
$1,095
Private Fishing Boat Charters in Naples Bay and the Gulf
4.9 (51)

Private Fishing Boat Charters in Naples Bay and the Gulf

Price as shown is for the boat trip (it is a group price) and not per adult! The Private Fishing Charters are either 4, 3 or...

3 to 4 hours • Free Cancellation
4.9 (51)
from
$495
Bark on the Ark
5.0 (10)

Bark on the Ark

This cruise is exclusively once a month with your pup. We cruise the beautiful Naples Bay passing by the gorgeous multi-million dollar homes on our...

3 hours 30 minutes
5.0 (10)
from
$89
Private Half-Day Charter Tour in Naples, Florida
5.0 (24)

Private Half-Day Charter Tour in Naples, Florida

Have the chance to choose the itinerary of your day here on the beautiful waters of Naples. We can cruise to Keewaydin Island for the...

4 hours • Free Cancellation
5.0 (24)
from
$700
Marco Island Private Tubing, Dolphin Watching and Shelling Tour
5.0 (13)

Marco Island Private Tubing, Dolphin Watching and Shelling Tour

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...

3 hours • Free Cancellation
5.0 (13)
from
$695
2 Hour Naples Sunset Adventure
4.9 (32)

2 Hour Naples Sunset Adventure

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....

2 hours • Free Cancellation
4.9 (32)
from
$78
Private Holiday Light Cruise Tour and Sunset Port Royal Naples
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Private Holiday Light Cruise Tour and Sunset Port Royal Naples

We start the evening with the glamorous sunsets of SW Florida on the Gulf of Mexico and Naples. We see the city in a way...

2 hours 30 minutes • Free Cancellation
5.0 (1)
from
$750
Marco Island Dolphin Watching & Tubing Adventure
5.0 (8)

Marco Island Dolphin Watching & Tubing Adventure

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....

2 hours 30 minutes • Free Cancellation
5.0 (8)
from
$575
Marco Island and 10,000 Islands Sightseeing with Dolphin Tour
5.0 (9)

Marco Island and 10,000 Islands Sightseeing with Dolphin Tour

With our 2 hour tour, experience a complete boat ride through Marco Island and the surrounding 10,000 Islands Wildlife Refuge with a small group. This...

2 hours • Free Cancellation
5.0 (9)
from
$99
Heart of Rookery Bay Kayak Tour
5.0 (15)

Heart of Rookery Bay Kayak Tour

Join SWFL's only active local biologist guides for an adventure through the Rookery Bay Reserve at the start of the 10,000 islands on the #1...

2 hours 30 minutes • Free Cancellation
5.0 (15)
from
$70
Naples Private Boat Charter with Keewaydin Beach Setup
5.0 (3)

Naples Private Boat Charter with Keewaydin Beach Setup

Begin your private charter with a scenic cruise through Naples Bay and the waterways of Port Royal, home to some of Naples' most impressive waterfront...

4 hours • Free Cancellation
5.0 (3)
from
$850
Private Lake Trafford Fishing Charter Near Naples
4.8 (17)

Private Lake Trafford Fishing Charter Near Naples

Just minutes from Naples, Lake Trafford offers one of Southwest Florida's premier freshwater fishing experiences and a refreshing escape from the busy coastline. This natural...

4 to 8 hours • Free Cancellation
4.8 (17)
from
$163
Naples Inshore Fishing Charters
5.0 (5)

Naples Inshore Fishing Charters

Experience and explore the backwaters of the Ten thousand Islands! A short distant and boat ride to great fishing. Enjoy fishing one of the most...

4 to 8 hours • Free Cancellation
5.0 (5)
from
$700
4 Hour Keewaydin Island Beach Tour
5.0 (3)

4 Hour Keewaydin Island Beach Tour

Ditch the concrete and crowds for an unparalleled escape to Keewaydin Island, a pristine slice of paradise only reachable by boat, making it a truly...

4 hours • Free Cancellation
5.0 (3)
from
$194
Private 4 Hour Shelling Adventure 10,000 Islands and Marco Island
5.0 (2)

Private 4 Hour Shelling Adventure 10,000 Islands and Marco Island

*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*...

4 hours • Free Cancellation
5.0 (2)
from
$540

Frequently Asked Questions

These answers are based on answers previously given to Cool Marco Island customers' questions.

Recent tour reviews
Marco Island Dolphin Tour
New York City
Marco Island and 10,000 Islands Sightseeing with Dolphin Tour
LoveTravel755135, Sep 2026
Marco Island Dolphin Tour
We had a fabulous time on the boat. The captain of the boat was so nice and answered all our questions. He got the dolphins to interact with us which definitely was the highlight of the tour.
Read more
A Guide A Tour A Friend
New York City
Private Guided Kayak Tour on Big Hickory Pass
cassieq860, Aug 2026
A Guide A Tour A Friend
Joey was a fantastic guide, knowledgeable, patient, timely, and fun. Well worth the money and time. We actually left feeling like we made a friend, which is worth more than the great service we received. We will be back & thanks to Joey we are trained on where the good spots are.
Read more
Always a blast!
New York City
Marco Island Private Tubing, Dolphin Watching and Shelling Tour
Trail756927, Aug 2026
Always a blast!
Captain Clay was awesome! Eco-endeavors is the company you want to go with. We have used them for this particular event multiple times, every trip is different but always so much fun. Thank you captain Clay for the alphabet cone, and an amazing time out on the water!
Read more
Pleasant trip for all
New York City
Private Lake Trafford Fishing Charter Near Naples
dominichX6103LA, Aug 2026
Pleasant trip for all
4hour Largemouth bass trip around Lake Trafford, Mark knows his clint and where the fish are. we caught lots of bass, some big bass. Good value for money; highly recommend.
Read more
Perfect kayak experience
New York City
Private Guided Kayak Tour on Big Hickory Pass
kaylakG7709CN, Aug 2026
Perfect kayak experience
Super worth it! Great guides and great service! They helped greatly with the kayak boarding. There were so many manatees! Weather was beautiful and perfect amount of time💛
Read more
My dad's birthday Fishing Trip
New York City
Private Lake Trafford Fishing Charter Near Naples
risksd, Aug 2026
My dad's birthday Fishing Trip
Wanted to get a fishing trip booked for my dad's 70th birthday. I know Lake Trafford pretty well for adventure, but I didn't know the best way to go about finding the best charter. Googled and came upon Bass Online Charters; saw they were also on Cool Marco Island, so came to look here too. So many positive reviews made my mind up, and I booked with captain Mark. Today was the day, and we were not disappointed; in fact, we were hugely impressed with Mark. Cool and professional, plus he managed to catch 20-plus largemouth bass, some 6 lbs. Loved the trip and would highly recommend this as a good way to spend a couple of hours and fantastic value for money, and my dad really enjoyed it. Thanks, Mark.
Read more
Shelling Adventure
New York City
Private Luxury Keewaydin Island Beach & Dolphin Excursion
Matthew_T, Jul 2026
Shelling Adventure
Great tour by Captain Matt. We had a beautiful day shelling. Captain was not only very knowledgeable, he was great with our family. Perfect weather and timing!
Read more
Best Day Ever!!!
New York City
Tiki Boat Bachelorette and Birthday Celebrations Tours in Naples
G5115DXstaceyb, Jul 2026
Best Day Ever!!!
Captain Evan and Varonnica were first rate from the minute we arrived. They made the trip fun, were ready to accommodate anybody our requests. I would highly recommend them!!!
Read more
Great day with Captain Clay!
New York City
Marco Island Private Tubing, Dolphin Watching and Shelling Tour
Z5255DSmelissaw, Jul 2026
Great day with Captain Clay!
We had an incredible trip with Eco Endeavors! Captain Clay was fantastic, taking us out for high-energy wakeboarding and tubing. We also found great shells and spotted both dolphins and manatees. It was the perfect mix of water sports and wildlife. Highly recommend!
Read more
The captain called and...
New York City
Private 4 Hour Shelling Adventure 10,000 Islands and Marco Island
William_M, Jul 2026
The captain called and...
The captain called and suggested we change the time from morning to afternoon so we would have shelling at low tide.
Read more
This rocked!
New York City
Marco Island Dolphin Watching & Tubing Adventure
Fearless566830, Jul 2026
This rocked!
Excellent! The kids loved tubing & we got to see dolphins & a whole family of manatees
Read more
Generous & Flexible
New York City
Tiki Boat Bachelorette and Birthday Celebrations Tours in Naples
avamarieg98, Jun 2026
Generous & Flexible
Captain Paul and Evan were beyond accommodating. They were thoughtful and flexible when the bachelorette group decided to add an extra hour. They were generous enough to bring beverages to the beach for us when we stopped off at the island.
Read more
Book your trip now!
New York City
2 Hour Naples Sunset Adventure
Susan_H, Jun 2026
Book your trip now!
We enjoyed our trip! It was such a relaxing time and Captain Marty was very informative! We even saw some dolphins and got out to the Gulf, just in time for a beautiful sunset. I highly recommend booking this tour.
Read more
Stephen was an amazing...
New York City
2 Hour Naples Sunset Adventure
Adianes_R, Jun 2026
Stephen was an amazing...
Stephen was an amazing guide and very knowledgeable. He made the experience an unforgettable one. Thank you
Read more
Tubing close to the dolphins!
New York City
Marco Island Dolphin Watching & Tubing Adventure
Carla_S, Jun 2026
Tubing close to the dolphins!
We had the best time! The four 18 year olds tubed for a long time and even had dolphins join us in our wake! Captain was fabulous and very knowledgeable! Would highly recommend!!
Read more
10k Islands Private Tour!
New York City
Private 4 Hour Shelling Adventure 10,000 Islands and Marco Island
Laura_D, May 2026
10k Islands Private Tour!
Great private shelling transport! Visited 3 islands and Jason was a great captain! Thank you for the fun excursion!
Read more
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