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Naples Luxury & Special Occasions

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Naples Tours

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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
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 …More

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
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 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
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
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
Electric Trike Tour of Naples

Join one of our local guides for a 90-minute Trike Tour through Naples, Florida. Our tours will take you through one of Southwest Florida's most …More

5.0 (13)

Electric Trike Tour of Naples

Join one of our local guides for a 90-minute Trike Tour through Naples, Florida. Our tours will take you through one of Southwest Florida's most...

1 hour 30 minutes • Free Cancellation
5.0 (13)
from
$50
Naples Florida Guided Electric Mix and Match Tour - Family Fun

Effortlessly explore the city with our brand-new electric Trikes and electric mopeds, perfect for the whole family. Our tours offer a unique perspective of the …More

5.0 (5)

Naples Florida Guided Electric Mix and Match Tour - Family Fun

Effortlessly explore the city with our brand-new electric Trikes and electric mopeds, perfect for the whole family. Our tours offer a unique perspective of the...

1 hour 30 minutes • Free Cancellation
5.0 (5)
from
$50
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
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
Guided Electric Trike Tour - Downtown Naples Florida

Join one of our local guides for a 90-minute Trike Tour through Naples, Florida. Our tours will take you through one of Southwest Florida's most …More

5.0 (7)

Guided Electric Trike Tour - Downtown Naples Florida

Join one of our local guides for a 90-minute Trike Tour through Naples, Florida. Our tours will take you through one of Southwest Florida's most...

1 hour 30 minutes • Free Cancellation
5.0 (7)
from
$50
90 Minute Guided Moped Tour in Naples Florida

Experience a brand-new way to explore Downtown Naples, Florida, with our guided Segway Electric Moped tour—a perfect adventure for all ages! Glide effortlessly through the …More

4.6 (14)

90 Minute Guided Moped Tour in Naples Florida

Experience a brand-new way to explore Downtown Naples, Florida, with our guided Segway Electric Moped tour—a perfect adventure for all ages! Glide effortlessly through the...

1 hour 30 minutes • Free Cancellation
4.6 (14)
from
$50
Naples Famous Sunset Tour -Trike Tour at Sunset All Ages Electric

Embark on our renowned Sunset Tour, a captivating two-hour journey through the heart of downtown Naples. Glide effortlessly on our state-of-the-art electric trikes, capable of …More

5.0 (5)

Naples Famous Sunset Tour -Trike Tour at Sunset All Ages Electric

Embark on our renowned Sunset Tour, a captivating two-hour journey through the heart of downtown Naples. Glide effortlessly on our state-of-the-art electric trikes, capable of...

2 hours • Free Cancellation
5.0 (5)
from
$50
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
Guided Safari-Style Jeep Tour

Experienced Guides: Your tour boasts knowledgeable and passionate guides who bring the wilderness to life. Their expertise in local flora, fauna, and conservation efforts ensures …More

5.0 (2)

Guided Safari-Style Jeep Tour

Experienced Guides: Your tour boasts knowledgeable and passionate guides who bring the wilderness to life. Their expertise in local flora, fauna, and conservation efforts ensures...

2 hours • Free Cancellation
5.0 (2)
from
$100

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
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
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
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
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
Fun and informative
New York City
90 Minute Guided Moped Tour in Naples Florida
dlY9812VC, Jun 2026
Fun and informative
Diego was very knowledgeable about the locals and area. He pointed out some very nice houses and talked a little about who lived there. He recommended that we take the trikes which were very comfortable and very fun. I would highly recommend this tour.
Read more
Great 1/2 day shelling adventure
New York City
Half-Day Super Shelling Tour
jayweso, Jun 2026
Great 1/2 day shelling adventure
Amazing day on the water with captain Nate and his pup. We visited 3 stops and found everything we were looking for and learned about the islands as we cruised around
Read more
Best time !
New York City
Naples Famous Sunset Tour -Trike Tour at Sunset All Ages Electric
teribB7160PF, May 2026
Best time !
Our guide, Diego, was fantastic. So very knowledgeable and fun ! He provided a lot of helpful facts and knew all the best places to show us. I would highly recommend this tour and Diego.
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
Naples luxury boat tour
New York City
Private Luxury Port Royal Real Estate Cruise
chriseP738OW, May 2026
Naples luxury boat tour
I liked that it was exclusive to just our family and not with a bunch of strangers. The boat is brand new and is a super smooth ride which the kids enjoyed. Our captain was dressed well and highly professional. His knowledge of the area and the wildlife was really appreciated. They have shelling tours as well and we booked one those for our next adventure. Highly recommended
Read more
Recommend!
New York City
Private Luxury Port Royal Real Estate Cruise
N2170DNstephanieg, May 2026
Recommend!
If you’re visiting Naples and want a luxurious, relaxing, and truly unique excursion, this cruise is an absolute must. Whether you love real estate, architecture, boating, or simply beautiful scenery, this experience delivers on every level. We would absolutely book again and highly recommend it to anyone looking for a high-end coastal experience!
Read more
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