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Naples Cruises, Sailing & Water Tours

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Naples Tours

Attractions

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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 …More

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

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 …More

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
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 …More

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

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 …More

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
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 …More

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

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 …More

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

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 …More

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

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. …More

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
$99
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. …More

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
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 …More

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 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* …More

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
$675
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 …More

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

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 …More

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

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 …More

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
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 …More

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
Private Naples Inshore Fishing Charters

Explore the wild side of Southwest Florida on a private Naples inshore fishing charter through the legendary Ten Thousand Islands. This remarkable coastal ecosystem features …More

5.0 (5)

Private Naples Inshore Fishing Charters

Explore the wild side of Southwest Florida on a private Naples inshore fishing charter through the legendary Ten Thousand Islands. This remarkable coastal ecosystem features...

4 to 6 hours • Free Cancellation
5.0 (5)
from
$238
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 …More

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
$172
Naples Luxury Sightseeing Cruises

Explore Naples Bay and the Gulf of Mexico aboard the Naples Princess, a luxurious yacht offering daily public cruises and private charters. Enjoy breathtaking views …More

Likely to Sell Out
Likely to Sell Out
3.0 (2)

Naples Luxury Sightseeing Cruises

Explore Naples Bay and the Gulf of Mexico aboard the Naples Princess, a luxurious yacht offering daily public cruises and private charters. Enjoy breathtaking views...

1 hour 30 minutes • Free Cancellation
3.0 (2)
from
$71
Naples Deep Sea Fishing Charters

Experience a true Naples Offshore Deep Sea Charter, this charter goes at least 10+ miles offshore into federal waters where the big fish live. We …More

5.0 (3)

Naples Deep Sea Fishing Charters

Experience a true Naples Offshore Deep Sea Charter, this charter goes at least 10+ miles offshore into federal waters where the big fish live. We...

6 to 10 hours • Free Cancellation
5.0 (3)
from
$1,399
Marco Island Inshore Fishing Charters

Explore the wild waters surrounding Marco Island on a private inshore fishing charter through the legendary Ten Thousand Islands. This remarkable Southwest Florida ecosystem is …More

4.7 (6)

Marco Island Inshore Fishing Charters

Explore the wild waters surrounding Marco Island on a private inshore fishing charter through the legendary Ten Thousand Islands. This remarkable Southwest Florida ecosystem is...

4 to 6 hours • Free Cancellation
4.7 (6)
from
$238
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 …More

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

Frequently Asked Questions

These answers are based on answers previously given to Cool SWFL 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
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
Stay cool and enjoy the view!
New York City
Naples Luxury Sightseeing Cruises
VFD56, Aug 2026
Stay cool and enjoy the view!
We purchased tickets for the Sunset Cruise. We chose not to have dinner on board but we able to buy drinks and apps. Both were fairly good. The narration was good and the views were great. Sunset was beautiful. We boarded early and managed to secure an outside table on the back of the second deck which was shaded by the third deck. It was great for viewing however there wasn’t enough of a breeze (in August) to compensate for the heat and direct sunlight streaming in under the ceiling. If you don’t mind the heat, or if you’re sailing in the cooler months, it’s a great spot. Otherwise choose an inside table on the left side of the ship for more shade!
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
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 SWFL, 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
Naples shelling trip.
New York City
Private Luxury Keewaydin Island Beach & Dolphin Excursion
chriseP738OW, May 2026
Naples shelling trip.
This was a great shelling tour. The boat trip was smooth and extremely comfortable. It’s a beautiful boat. The captain was very helpful in pointing out how to shell as this was our first time. He showed us where to look and helped identify what we were finding. I would recommend this trip to anyone.
Read more
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