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Fort Myers Cruises, Sailing & Water Tours

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Fort Myers Tours

Attractions

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Kayak Eco Tour in Don Pedro Island

Discover the wonders of Don Pedro Island! Dive into adventure on a kayaking eco tour with the areas most experienced tour guides. Your tour guide …More

5.0 (160)

Kayak Eco Tour in Don Pedro Island

Discover the wonders of Don Pedro Island! Dive into adventure on a kayaking eco tour with the areas most experienced tour guides. Your tour guide...

120 to 150 minutes • Free Cancellation
5.0 (160)
from
$85
Naples Guided Sunset Kayak Tour Activity

We are the only Kayak Tour Agency offering Sunset Tours at this location with the Hobie Pedal Mirage Drives. Whether you choose to paddle or …More

Likely to Sell Out
Likely to Sell Out
4.9 (17)

Naples Guided Sunset Kayak Tour Activity

We are the only Kayak Tour Agency offering Sunset Tours at this location with the Hobie Pedal Mirage Drives. Whether you choose to paddle or...

3 hours • Free Cancellation
4.9 (17)
from
$85
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party …More

Likely to Sell Out
Likely to Sell Out
4.9 (55)

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party...

3 hours • Free Cancellation
4.9 (55)
from
$89
Fort Myers Beach #1 Parasailing Experience

Take off and enjoy the highest Fort Myers Beach parasailing flights that Wind and Water Sports has to offer! All while being captivated by amazing …More

5.0 (15)

Fort Myers Beach #1 Parasailing Experience

Take off and enjoy the highest Fort Myers Beach parasailing flights that Wind and Water Sports has to offer! All while being captivated by amazing...

1 hour • Free Cancellation
5.0 (15)
from
$110
2.5 hr Sailboat Tour aboard Orion's Child

Cool SWFL Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple …More

Likely to Sell Out
Likely to Sell Out
5.0 (92)

2.5 hr Sailboat Tour aboard Orion's Child

Cool SWFL Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple...

2 hours 30 minutes • Free Cancellation
5.0 (92)
from
$130
Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the …More

5.0 (11)

Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the...

2 hours 30 minutes • Free Cancellation
5.0 (11)
from
$149
Private ONLY Dolphin Boat Tours

For the price of a boat rental plus fuel, you will get a guided boat tour by our Master Captain with deep insight knowledge of …More

5.0 (34)

Private ONLY Dolphin Boat Tours

For the price of a boat rental plus fuel, you will get a guided boat tour by our Master Captain with deep insight knowledge of...

3 to 4 hours • Free Cancellation
5.0 (34)
from
$160
Private Dolphin & Sightseeing Boat Day Tour

This is the Day-Tour to our widely popular Sunset & Dolphin Boat Tour. You will get very close to wildlife and our first mate will …More

5.0 (14)

Private Dolphin & Sightseeing Boat Day Tour

This is the Day-Tour to our widely popular Sunset & Dolphin Boat Tour. You will get very close to wildlife and our first mate will...

4 hours • Free Cancellation
5.0 (14)
from
$161
Private Lake Okeechobee Bass Charter Near Fort Myers

Leave the Gulf Coast behind and discover one of the world's greatest bass fishing destinations on a private Lake Okeechobee fishing charter near Fort Myers. …More

5.0 (11)

Private Lake Okeechobee Bass Charter Near Fort Myers

Leave the Gulf Coast behind and discover one of the world's greatest bass fishing destinations on a private Lake Okeechobee fishing charter near Fort Myers....

4 to 6 hours • Free Cancellation
5.0 (11)
from
$161
Private Lake Okeechobee Bass Charter Near Naples

Escape the beaches and discover one of the world's most legendary bass fisheries on a private Lake Okeechobee fishing charter, conveniently accessible from Naples. Known …More

Likely to Sell Out
Likely to Sell Out
5.0 (26)

Private Lake Okeechobee Bass Charter Near Naples

Escape the beaches and discover one of the world's most legendary bass fisheries on a private Lake Okeechobee fishing charter, conveniently accessible from Naples. Known...

4 hours • Free Cancellation
5.0 (26)
from
$169
Fort Myers Beach 1.5hr Jet Ski Dolphin Tour

Discover the natural beauty of Southwest Florida from the seat of your own Sea-Doo on an exciting 1.5-hour guided dolphin eco-tour. Follow your experienced guide …More

5.0 (2)

Fort Myers Beach 1.5hr Jet Ski Dolphin Tour

Discover the natural beauty of Southwest Florida from the seat of your own Sea-Doo on an exciting 1.5-hour guided dolphin eco-tour. Follow your experienced guide...

2 hours • Free Cancellation
5.0 (2)
from
$225
Everglades Day Safari from Fort Myers/Naples Area

Spend a full day exploring the wilderness of the Everglades on this adventure from the Greater Fort Myers/Naples area. With your naturalist guide, take an …More

4.8 (336)

Everglades Day Safari from Fort Myers/Naples Area

Spend a full day exploring the wilderness of the Everglades on this adventure from the Greater Fort Myers/Naples area. With your naturalist guide, take an...

9 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.8 (336)
from
$250
90 Minute Private Tiki Cruise

The mission statement is “We build boats that put smiles on people’s faces, one cruise at a time!” Our franchise opportunities extend our mission statement …More

5.0 (16)

90 Minute Private Tiki Cruise

The mission statement is “We build boats that put smiles on people’s faces, one cruise at a time!” Our franchise opportunities extend our mission statement...

2 hours • Free Cancellation
5.0 (16)
from
$270
Private Day Cruise: Explore Cape Coral, Sanibel and Fort Myers

Embark on a guided day cruise with our licensed captain and enjoy a beautiful day on the water with your family and friends. We'll tour …More

5.0 (19)

Private Day Cruise: Explore Cape Coral, Sanibel and Fort Myers

Embark on a guided day cruise with our licensed captain and enjoy a beautiful day on the water with your family and friends. We'll tour...

2 to 6 hours • Free Cancellation
5.0 (19)
from
$280
Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on …More

Likely to Sell Out
Likely to Sell Out
5.0 (2)

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on...

2 hours • Free Cancellation
5.0 (2)
from
$349
Dolphin Tiki Cruise around Fort Myers Beach

Enjoy a private cruise with your friends and family on the Tiny Tiki. The price is a flat rate for a maximum of 6 people. …More

5.0 (75)

Dolphin Tiki Cruise around Fort Myers Beach

Enjoy a private cruise with your friends and family on the Tiny Tiki. The price is a flat rate for a maximum of 6 people....

1 hour 30 minutes • Free Cancellation
5.0 (75)
from
$350
Shelling Tours - Fort Myers Beach / Naples

On this trip, Guests will be exploring the local Islands around Fort Myers and Naples area. The Islands are well known for their excellent shells. …More

5.0 (79)

Shelling Tours - Fort Myers Beach / Naples

On this trip, Guests will be exploring the local Islands around Fort Myers and Naples area. The Islands are well known for their excellent shells....

2 hours • Free Cancellation
5.0 (79)
from
$350
Dolphin Tours - Fort Myers Beach / Naples

On this trip, guests will explore the Bay waters and the Gulf of Mexico in search of Dolphin, Manatee and Turtles. These encounters happen on …More

5.0 (77)

Dolphin Tours - Fort Myers Beach / Naples

On this trip, guests will explore the Bay waters and the Gulf of Mexico in search of Dolphin, Manatee and Turtles. These encounters happen on...

2 hours • Free Cancellation
5.0 (77)
from
$350
2 Hour Private Tiki Cruise

Our mission statement is “We build boats that put smiles on people’s faces… one cruise at a time!” Our franchise opportunities extend our mission statement …More

5.0 (8)

2 Hour Private Tiki Cruise

Our mission statement is “We build boats that put smiles on people’s faces… one cruise at a time!” Our franchise opportunities extend our mission statement...

2 hours • Free Cancellation
5.0 (8)
from
$360
Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to …More

Likely to Sell Out
Likely to Sell Out
5.0 (4)

Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to...

2 hours • Free Cancellation
5.0 (4)
from
$449
4 Hour Dolphin and Sandbar Cruise

 …More

5.0 (29)

4 Hour Dolphin and Sandbar Cruise

...

4 hours • Free Cancellation
5.0 (29)
from
$550

Frequently Asked Questions

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

Recent tour reviews
A Most Enjoyable Trip
New York City
Kayak Eco Tour in Don Pedro Island
Lamboid2, Sep 2026
A Most Enjoyable Trip
Jeff, our guide for the morning made the whole trip for us. He was engaging, knowledgeable, funny but above friendly who gladly gave his time to talk about the wildlife we encountered. The area is beautiful, the paddling not too hard and the wildlife varied. The trip rounded off with Jeff finding us a mother dolphin with her two very young babies teaching them how to catch fish. Mesmerising! Would definitely recommend as we found the whole outfitters to be friendly and efficient
Read more
Excellent highly recommend
New York City
Fort Myers Beach 1.5hr Jet Ski Dolphin Tour
cticich14, Sep 2026
Excellent highly recommend
Tyson was excellent highly recommend this guy when you go on a dolphin tour very knowledgeable on how to get the dolphins once they are spotted very knowledgeable on the waterways also
Read more
So fun!!
New York City
Kayak Eco Tour in Don Pedro Island
irishpostal, Sep 2026
So fun!!
We had a wonderful experience. The young man there was super helpful and knowledgeable. We were challenged at the mangrove and worked hard there. We didn’t see much that day but all in all a great time!
Read more
Fun.
New York City
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
Dennis_T, Sep 2026
Fun.
Kayla was an amazing captain. Sea Turtles, manatees dolphins. Partied in the sand bar. Saw some star fish. So fun.
Read more
great fishing- plenty of Largemouth bass caught
New York City
Private Lake Okeechobee Bass Charter Near Naples
fedrika2026, Sep 2026
great fishing- plenty of Largemouth bass caught
Been on a few fishing trips out of Lake Okeechobee but can highly recommend Bass Online. This is the second time we have been out with Capt. Mark. We took 12- and 15-year-olds with us and caught a lot of big bass. It is still early season, but with approximately 30 plus caught in the 4 hours, there were happy customers all round. I've had experience with some fishing charter companies that only seem to care about the money and have some questionable practices, but I'm pleased to say that Bass Online charters do not fall into this category. I would, and have, recommended Bass Online to others.
Read more
Fantastic experience
New York City
2.5 hr Sailboat Tour aboard Orion’s Child
A8076HVjeffreym, Sep 2026
Fantastic experience
Always a great sail with Orions Child. Captain Dan and Diane are the best. We have been several times and will be back.
Read more
Excellent Trip
New York City
Private Lake Okeechobee Bass Charter Near Naples
nicholaslQ5003GV, Sep 2026
Excellent Trip
An excellent 6 hr and well worth every penny, Paul the Captain was very patient with both us and our 12-year-old; if you've never fished before, they will show you how, and we caught a lot of Largemouth bass...great fun for everyone, if you want to go fishing, go with Paul on the Bass Online.
Read more
Great Dolphin Watching Ride
New York City
Fort Myers Beach 1.5hr Jet Ski Dolphin Tour
198jamessf, Sep 2026
Great Dolphin Watching Ride
Great trip. the staff at the booth was very friendly and accommodating to us. We had to reschedule due to inclement weather in the Gulf but came back the next day for our dolphin tour. It was great, saw several dolphins and got to see a lot of the bay side of FMB. Wed definitely do it again. highly recommend.
Read more
Fun time for all
New York City
Shelling Tours – Fort Myers Beach / Naples
Tammy_H, Sep 2026
Fun time for all
Very fun experience! There were four adults and two children in our party. We all enjoyed! Would recommend!
Read more
Amazing Sunset Tour on our Wedding-Day
New York City
Private ONLY Dolphin Boat Tours
142lennartm, Aug 2026
Amazing Sunset Tour on our Wedding-Day
We absolutely loved our Sunset Dolphin Watching Tour and couldn’t have asked for a better experience!We took the tour on the day of our wedding with our parents, which made the experience even more special. Our captain Martin and his wife René were absolutely incredible – so warm, friendly, and genuinely passionate about making the trip memorable.We saw so many dolphins, enjoyed a beautiful sunset, and created countless amazing memories that we will cherish forever. It was truly the perfect way to celebrate such a special day.A huge thank you to Martin and René for making our wedding day even more unforgettable! ❤️🐬🌅We would absolutely recommend this tour and would book it again in a heartbeat!
Read more
Beautiful sunset tiki cruise
New York City
2 Hour Private Tiki Cruise
972cherib, Aug 2026
Beautiful sunset tiki cruise
We loved our tiki boat tour. It was so beautiful and we had a great sunset and even saw several dolphins right by our boat. Captain Caleb showed us the site's and made our cruise so much fun! I definitely recommend the sunset tiki cruise. Shout out again to Captain Caleb!
Read more
Best most respectful
New York City
Private Day Cruise: Explore Cape Coral, Sanibel and Fort Myers
126steffanieb, Aug 2026
Best most respectful
Carsten was absolutely incredible to our family. He was polite friendly and very courteous. He knew a lot about the area and was able to answer our questions when we had any. The view was amazing the boat ride was fantastic. Swimming at sanibel island was like living a dream! We found sand dollars, seen dolphins, collected shells. I would definitely recommend this trip! Thank you again Carsten for treating our family with the utmost respect.
Read more
Exceptional, amazing
New York City
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
alyssap760, Aug 2026
Exceptional, amazing
Amazing captain. Above and beyond. Our experience was exceptional to say the least. Great conversation. Wonderful! Highly recommend
Read more
Amazing shelling tour!
New York City
Shelling Tours – Fort Myers Beach / Naples
courtneygA1743HJ, Aug 2026
Amazing shelling tour!
We had a truly special time on our shelling tour! Mike took us to some great spots, and we were able to see TONS of dolphins playing! I would recommend this to anyone.
Read more
Dolphin cruise captain was excellent!!
New York City
Dolphin Tiki Cruise around Fort Myers Beach
Bradley_M, Aug 2026
Dolphin cruise captain was excellent!!
The captain is very friendly, knowledgeable and safe. She allowed us to reschedule after our tour started due to bad weather. She was more concerned with our experience then making a profit. Very genuine person, will definitely recommend to friends and family
Read more
Don't hesitate, book this experience!!
New York City
4 Hour Dolphin and Sandbar Cruise
Daniela_V, Aug 2026
Don't hesitate, book this experience!!
It unfortunately rained heavily so we had to turn back, but Lauren did try her best to make the best out of the experience. We appreciate her effort and also fun personality.We will book again and hope for better weather.1000% recommend
Read more
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