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Naples Cruises, Sailing & Water Tours

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Naples Tours

Attractions

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Marco Island Sunset Cruise- Private 2 Hour

Experience the magic of a Marco Island sunset cruise as you sail into the golden horizon over the Gulf of Mexico. This 2 to 2.5-hour …More

Likely to Sell Out
Likely to Sell Out
4.9 (40)

Marco Island Sunset Cruise- Private 2 Hour

Experience the magic of a Marco Island sunset cruise as you sail into the golden horizon over the Gulf of Mexico. This 2 to 2.5-hour...

2 hours • Free Cancellation
4.9 (40)
from
$475
Sunset Eco Tour of Marco Island & 10,000 Islands

Our Sunset Tour is the perfect way to end your day in paradise, offering a front-row seat to one of Marco Island’s most breathtaking sunsets. …More

Likely to Sell Out
Likely to Sell Out
5.0 (38)

Sunset Eco Tour of Marco Island & 10,000 Islands

Our Sunset Tour is the perfect way to end your day in paradise, offering a front-row seat to one of Marco Island’s most breathtaking sunsets....

2 hours 30 minutes • Free Cancellation
5.0 (38)
from
$125
Marco Island Dolphin & Eco Tour – Private 2 Hour Wildlife Cruise

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 …More

5.0 (38)

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

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...

2 hours • Free Cancellation
5.0 (38)
from
$425
PRIVATE Eco Boat Trip out of Naples Bay, FL, island stop incl.

(Price shown is a group price and not per adult - absolutely no extra/hidden fees.) Enjoy a private 2h45min long Sightseeing/ Eco Tour on the …More

4.9 (37)

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

(Price shown is a group price and not per adult - absolutely no extra/hidden fees.) Enjoy a private 2h45min long Sightseeing/ Eco Tour on the...

2 hours 45 minutes • Free Cancellation
4.9 (37)
from
$395
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 …More

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
PRIVATE Sunset & Sightseeing Boat Trip of Naples Bay and the Gulf

Price, as shown, is for the boat trip (group price) and not per adult! Maximum are 5 guests regardless of age. If your group is …More

4.9 (34)

PRIVATE Sunset & Sightseeing Boat Trip of Naples Bay and the Gulf

Price, as shown, is for the boat trip (group price) and not per adult! Maximum are 5 guests regardless of age. If your group is...

2 hours 20 minutes • Free Cancellation
4.9 (34)
from
$385
Afternoon Sightseeing and Sailing Tour

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 …More

4.9 (34)

Afternoon Sightseeing and Sailing Tour

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...

2 hours • Free Cancellation
4.9 (34)
from
$41
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
Private Marco Island / 10,000 Islands Sightseeing & Dolphin Tour

Our private excursion allows you to enjoy the beautiful waters of The 10,000 Islands without the crowds of tourists at a comparable price. Guest enjoy …More

5.0 (24)

Private Marco Island / 10,000 Islands Sightseeing & Dolphin Tour

Our private excursion allows you to enjoy the beautiful waters of The 10,000 Islands without the crowds of tourists at a comparable price. Guest enjoy...

2 hours • Free Cancellation
5.0 (24)
from
$445
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
Private Naples Bay and Port Royal Sunset Cruise

This amazing tour views the Port Royal houses and Mansions with either a guided tour or relax on your own with a captained excursion. The …More

Likely to Sell Out
Likely to Sell Out
5.0 (18)

Private Naples Bay and Port Royal Sunset Cruise

This amazing tour views the Port Royal houses and Mansions with either a guided tour or relax on your own with a captained excursion. The...

2 hours 30 minutes • Free Cancellation
5.0 (18)
from
$750
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
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
Drive Our Exciting 2 man Go Cat Boat in Downtown Naples

The exclusive Go Cat Boat is a luxury catamaran. This is the newest and coolest way to explore the 10,000 islands around beautiful Naples Bay! …More

4.9 (14)

Drive Our Exciting 2 man Go Cat Boat in Downtown Naples

The exclusive Go Cat Boat is a luxury catamaran. This is the newest and coolest way to explore the 10,000 islands around beautiful Naples Bay!...

3 hours • Free Cancellation
4.9 (14)
from
$180
Half-Day Super Shelling Tour

What You’ll Find Expect sand dollars, lightning whelks, alphabet cones, tulip shells, and—on lucky days—the elusive Junonia. Captains share quick tips on reading bars, seams, …More

Likely to Sell Out
Likely to Sell Out
5.0 (13)

Half-Day Super Shelling Tour

What You’ll Find Expect sand dollars, lightning whelks, alphabet cones, tulip shells, and—on lucky days—the elusive Junonia. Captains share quick tips on reading bars, seams,...

4 hours • Free Cancellation
5.0 (13)
from
$199
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
3 Hour Keewaydin Island Shelling Adventure

Embark on an unparalleled 3-hour Keewaydin Island Shelling Adventure that transcends a simple beach trip, transforming into an immersive journey into the heart of Florida's …More

4.8 (10)

3 Hour Keewaydin Island Shelling Adventure

Embark on an unparalleled 3-hour Keewaydin Island Shelling Adventure that transcends a simple beach trip, transforming into an immersive journey into the heart of Florida's...

3 hours • Free Cancellation
4.8 (10)
from
$133
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
Marco Island Mangrove Tunnel and Maze Adventure Small group size

Our industry leading small group tours have only 8 people max verses 15 people for your safety and enjoyment. Our kayaks are very stable, have …More

Likely to Sell Out
Likely to Sell Out
5.0 (9)

Marco Island Mangrove Tunnel and Maze Adventure Small group size

Our industry leading small group tours have only 8 people max verses 15 people for your safety and enjoyment. Our kayaks are very stable, have...

2 hours • Free Cancellation
5.0 (9)
from
$53
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 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

Frequently Asked Questions

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

Recent tour reviews
Amazing!!!!
New York City
Drive Our Exciting 2 man Go Cat Boat in Downtown Naples
91adriennel, Sep 2026
Amazing!!!!
Amazing!!!! Absolutely well worth it! We saw dolphins, the beautiful mangroves, the island we went to was spectacular! Our guide TJ was amazing and we felt very safe as he directed and guided us through the waters. Must do!!!
Read more
Breathtaking experience!...
New York City
Marco Island Sunset Cruise- Private 2 Hour
kalee_l, Sep 2026
Breathtaking experience!...
Breathtaking experience! Excellent communication. We booked this for my birthday and Jason and his crew did not disappoint.
Read more
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 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
Accommodating, flexible and great customer support
New York City
Marco Island Sunset Cruise- Private 2 Hour
Silvia_Z, Jul 2026
Accommodating, flexible and great customer support
Captain Tom was so friendly and nice. I had to make several calls before the trip and the customer service was very good! I would go back and do another tour as they accommodate and go with the flow as to what your family wants to do! My son was even able to do some fishing and the sunset pictures we got were spectacular.
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
Great tour! Highly recommend!
New York City
Drive Our Exciting 2 man Go Cat Boat in Downtown Naples
192pattyl, Jul 2026
Great tour! Highly recommend!
We went to Keewaydin Island, great experience, crystal clear water and they had a food and ice-cream boat! Had a sting ray jump in front of our boat and on the way back, saw several dolphins swimming and playing! Awesome tour!
Read more
Great day out
New York City
Marco Island Dolphin & Eco Tour – Private 2 Hour Wildlife Cruise
josephlD3717RH, Jul 2026
Great day out
it was a beautiful day. boat and driver were awesome!
Read more
Birthday on Boat
New York City
Private Naples Bay and Port Royal Sunset Cruise
kimfH2880FY, Jul 2026
Birthday on Boat
Birthday celebration was perfect! Staff was friendly and professional and everyone had a great time!
Read more
Absolutely the best there is!
New York City
Private Naples Bay and Port Royal Sunset Cruise
OnAir796968, Jul 2026
Absolutely the best there is!
I’ve used Sand Dollar for private sunset tours with visitors and also, a few times, as a floating party venue. They are able to accommodate any occasion and they go far out of their way to make each experience successful. We’ve experienced good and bad weather, large and small groups, elaborate and simple events. The Sand Dollar team is on point in every situation.
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
Excellent day on the water
New York City
Marco Island Dolphin & Eco Tour – Private 2 Hour Wildlife Cruise
robertpH2049QF, Jul 2026
Excellent day on the water
Excellent Adventure, highly recommended
Read more
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