(800) 814 COOL Questions? Call Us Now!

Naples Luxury & Special Occasions

105 Results
Sort by:
Traveler Rating
Filter
Languages Clear
Time of Day Clear
88
84
44
Duration Clear
0
99
14
0
1
Price Clear
$0 $500+
Rating Clear
85
104
105
Specials Clear
98
32
0
22
0
Features Clear
2
50
97
24
59
0
Accessibility Clear
11
61
93
Families Clear
62
40
5

Naples Tours

Attractions

Guides

Calendar

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
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
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
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
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
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
Guided Tour Pick your Ride Trikes Mopeds Segways and Bike Tour

Your Ride, Your Adventure - Trikes, Mopeds, Segways & Bike Tour. Choose your ride when you arrive at our store! Guided tour all goes together …More

5.0 (3)

Guided Tour Pick your Ride Trikes Mopeds Segways and Bike Tour

Your Ride, Your Adventure - Trikes, Mopeds, Segways & Bike Tour. Choose your ride when you arrive at our store! Guided tour all goes together...

1 hour 30 minutes • Free Cancellation
5.0 (3)
from
$50
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 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
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
Your Ride Your Adventure Trikes Mopeds Segways and Bike Tour

Experience the charm of Downtown Beautiful Naples like never before! Join us for an unforgettable guided tour where you get to pick your ride - …More

5.0 (2)

Your Ride Your Adventure Trikes Mopeds Segways and Bike Tour

Experience the charm of Downtown Beautiful Naples like never before! Join us for an unforgettable guided tour where you get to pick your ride -...

1 hour 30 minutes • Free Cancellation
5.0 (2)
from
$50
Naples Famous Sunset Tour -Electric Trike Tour at Sunset All Ages

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 (2)

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

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 (2)
from
$50
Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours

Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering …More

5.0 (1)

Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours

Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering...

4 days • Free Cancellation
5.0 (1)
from
$36
Electric Trike & Moped Tour of Downtown Naples - Fun For Everyone

Discover Naples the fun, easy way on a 90-minute guided ride by electric trike or moped. After a quick safety briefing and practice loop, glide …More

5.0 (1)

Electric Trike & Moped Tour of Downtown Naples - Fun For Everyone

Discover Naples the fun, easy way on a 90-minute guided ride by electric trike or moped. After a quick safety briefing and practice loop, glide...

1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$50
Bicycle Tour of Naples Florida Scenic Ride

Embark on an unforgettable adventure through the stunning streets of Downtown Naples, Florida, with our exquisite guided bicycle tour. Led by knowledgeable local guides, glide …More

5.0 (1)

Bicycle Tour of Naples Florida Scenic Ride

Embark on an unforgettable adventure through the stunning streets of Downtown Naples, Florida, with our exquisite guided bicycle tour. Led by knowledgeable local guides, glide...

1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$50
Guided Segway Moped Tour of Downtown 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

5.0 (1)

Guided Segway Moped Tour of Downtown 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
5.0 (1)
from
$50
Guided Trike and Moped Tour in Downtown Naples

Experience the charm of Downtown Beautiful Naples like never before! Join us for an unforgettable guided tour where you get to pick your ride when …More

5.0 (1)

Guided Trike and Moped Tour in Downtown Naples

Experience the charm of Downtown Beautiful Naples like never before! Join us for an unforgettable guided tour where you get to pick your ride when...

1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$50
Segway Tour Of Naples Florida Fun Family Experience

Glide through the vibrant heart of Naples, Florida, on an exhilarating Segway tour! Feel the Gulf breeze as you effortlessly zip past stunning coastal vistas, …More

5.0 (1)

Segway Tour Of Naples Florida Fun Family Experience

Glide through the vibrant heart of Naples, Florida, on an exhilarating Segway tour! Feel the Gulf breeze as you effortlessly zip past stunning coastal vistas,...

1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$50
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
E Bike Tour - Explore Downtown Naples Florida - Fun & Scenic Tour

Discover the charm of Naples, FL, on an engaging eBike tour that combines fun and education. This AAA-approved tour allows you to navigate downtown Naples …More

5.0 (1)

E Bike Tour - Explore Downtown Naples Florida - Fun & Scenic Tour

Discover the charm of Naples, FL, on an engaging eBike tour that combines fun and education. This AAA-approved tour allows you to navigate downtown Naples...

1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$50

Frequently Asked Questions

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

Recent tour reviews
Best time ever
New York City
E Bike Tour – Explore Downtown Naples Florida – Fun & Scenic Tour
Linda_V, Sep 2026
Best time ever
Great guide and very fun. You should try it. You see lots of sites and it is easy to follow along. They make sure you are taken care of. And very accommodating.
Read more
Lots of fun
New York City
Guided Tour Pick your Ride Trikes Mopeds Segways and Bike Tour
Debra_G, Sep 2026
Lots of fun
We loved it. Our guide was fantastic. Energetic, outgoing and very knowledgeable of the area. We would highly recommend this tour and the 3 wheel bike are so much fun.
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
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 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
Great evening
New York City
Private Luxury Sunset Cruise in Naples Bay and Keewaydin
robertgT7711JY, May 2026
Great evening
Amazing sunset and really nice boat. We thoroughly enjoyed our trip!
Read more
Highlight of our trip!
New York City
Private Luxury Sunset Cruise in Naples Bay and Keewaydin
sophiegU9443MH, May 2026
Highlight of our trip!
This private sunset boat tour was hands-down one of the best experiences of our trip to Naples. Our group of six had an amazing evening on the water — the captain was professional, friendly, and made the entire trip feel effortless and fun. Cruising toward Keewaydin Island during golden hour was absolutely stunning, and the sunset itself was unforgettable. The colors over the water were incredible, and the peaceful atmosphere made it such a relaxing experience. The highlight for all of us was seeing dolphins swimming right alongside the boat! It felt surreal and made the night even more special. The boat was clean, comfortable, and perfect for a private group outing. If you’re considering a sunset cruise in Naples, book this tour — you won’t regret it. Truly a five-star experience from start to finish!
Read more
Very fun activity with me...
New York City
Naples Famous Sunset Tour -Electric Trike Tour at Sunset All Ages
Aarushi_P, May 2026
Very fun activity with me...
Very fun activity with me and my parents. The tour guide was a really nice guy and knew a lot about the towns history!
Read more
Naples tricycle tour
New York City
Naples Florida Guided Electric Mix and Match Tour – Family Fun
Shahid_N, Apr 2026
Naples tricycle tour
Very informative and laid back. The guide was very patient and would wait for everyone to catch up. Learned a lot about Naples Florida
Read more
Fun riding motorized trikes
New York City
Naples Florida Guided Electric Mix and Match Tour – Family Fun
JulieS969, Feb 2026
Fun riding motorized trikes
Very fun riding motorized trikes! Great guide showing us some sites around Naples. Just an all around very fun time going along the streets of Naples.
Read more
Excellent way to experience Naples
New York City
Naples Private Boat Charter with Keewaydin Beach Setup
TMcCarthy4, Feb 2026
Excellent way to experience Naples
This was such an awesome experience. Tyler was literally a dolphin whisperer and my daughters got to see so many! He was super knowledgeable about the area and between drinks snacks dolphin sightings and more, we truly had the best afternoon!
Read more
Tour Day!
New York City
Electric Trike & Moped Tour of Downtown Naples – Fun For Everyone
John_C, Feb 2026
Tour Day!
Great time and tour guide! Tour was so much time and our tour guide was a lot of fun too and knowledgeable of Naples!
Read more
Experience of a lifetime!
New York City
4 Hour Keewaydin Island Beach Tour
Audra C, Feb 2026
Experience of a lifetime!
Wonderful experience of a lifetime! It was my husband, me & Captain Stephen on board. Captain Stephen was very knowledgeable and took the time to show us dolphin, osprey, pelicans and more and educate us on the special mangroves and the unique coastline of Florida. On Keewaydin we found amazing shells at every step! There were food trucks available. The boat was very clean and nice and even had a bathroom. From the boat, the captain and Keewaydin, I can’t imagine a better experience! My expectations were exceeded in every way! If I’m ever fortunate enough to visit Naples again, this tour & Captain Stephen will be a must!
Read more
Diego was a great guide....
New York City
Your Ride Your Adventure Trikes Mopeds Segways and Bike Tour
Stephen_B, Jan 2026
Diego was a great guide....
Diego was a great guide. He gave a lot of really interesting information. We got to see a lot of really neat places in Naples. I would recommend the electric trikes tour if you want to see the sites of the city of Naples.
Read more
Naples Tours
Attractions
Guides
Calendar
View more
View more