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Top Florida Sunset Cruises

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Key West Wind & Wine Sunset Sail
Likely to Sell Out
Likely to Sell Out
Key West, USA
5.0 (1,702)

Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Cool Destinations for over a decade. In our opinion, this is the best wine...

2 hours (approx.) • Free Cancellation
5.0 (1,702)
$115
$99
Sunset Celebration Cruise on Tropics Boat Tours
Likely to Sell Out
Likely to Sell Out
Clearwater, USA
4.5 (800)

Sunset Celebration Cruise on Tropics Boat Tours

Our Sunset Celebration Cruise lasts approximately two hours and will take you from Clearwater Bay through Clearwater Pass to the beautiful Gulf of Mexico. Sail...

2 hours • Free Cancellation
4.5 (800)
from
$37
2 Hour Sunset Cruise in Clearwater, Florida
Clearwater, USA
4.8 (711)

2 Hour Sunset Cruise in Clearwater, Florida

Our Evening Sunset Cruise is a 2 hour cruise of the Intracoastal Waterway, Clearwater Pass, and into the Gulf of Mexico (weather permitting). Your crew...

2 hours • Free Cancellation
4.8 (711)
from
$40
Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar
Key West, USA
4.8 (3,789)

Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

2 hours (approx.) • Free Cancellation
4.8 (3,789)
from
$80
Key West Sunset Cruise: Dinner, Live Music & Drinks Included
Key West, USA
4.4 (1,905)

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....

2 hours • Free Cancellation
4.4 (1,905)
from
$93
Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar
Key West, USA
4.9 (1,701)

Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...

2 hours (approx.) • Free Cancellation
4.9 (1,701)
from
$100
Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
Special Offer
Special Offer
Key West, USA
4.9 (128)

Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...

2 hours (approx.) • Hotel pickup offered • Free Cancellation
4.9 (128)
$99
$89
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Likely to Sell Out
Likely to Sell Out
Key West, USA
4.9 (1,701)

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hours • Free Cancellation
4.9 (1,701)
from
$123
Sunset Cruise of St. Augustine
Likely to Sell Out
Likely to Sell Out
St Augustine, USA
4.9 (1,372)

Sunset Cruise of St. Augustine

Get lost with the glorious wonder of St. Augustine's attractions. Our Adults Only 21+ option on vessel GREAT BLUE HERON is specifically made for the...

1 hour 30 minutes • Free Cancellation
4.9 (1,372)
from
$43
Evening Boat Cruise through Downtown Ft. Lauderdale
Fort Lauderdale, USA
4.7 (941)

Evening Boat Cruise through Downtown Ft. Lauderdale

Ready for the best tour in Fort Lauderdale? Come view the yachts and mansions along the beautiful waters of Fort Lauderdale. There are numerous photo...

2 hours • Free Cancellation
4.7 (941)
from
$50
Sunset Dolphin Cruise with Sanibel Lighthouse Views
Likely to Sell Out
Likely to Sell Out
Fort Myers, USA
4.8 (450)

Sunset Dolphin Cruise with Sanibel Lighthouse Views

While enjoying a complimentary alcoholic or nonalcoholic beverage we will cruise the back waters of Fort Myers Beach. During the cruise you may spot various...

1 hour 30 minutes • Free Cancellation
4.8 (450)
from
$62
Sandestin Sunset Eco Dolphin Cruise Aboard Sol y Luna
Likely to Sell Out
Likely to Sell Out
Destin, USA
4.8 (330)

Sandestin Sunset Eco Dolphin Cruise Aboard Sol y Luna

Your Sunset Eco-Dolphin Cruise begins with a leisure cruise into the majestic sunset from the Sandestin Baytowne Marina location. There is simply nothing like watching...

1 hour 30 minutes • Free Cancellation
4.8 (330)
from
$33
Key West "Commotion on the Ocean" Live Music Sunset Sail
Likely to Sell Out
Likely to Sell Out
Key West, USA
4.8 (973)

Key West "Commotion on the Ocean" Live Music Sunset Sail

This is the Key West sunset cruise party everyone talks about — live music, open-bar beer, wine, & margaritas, delicious appetizers, dancing, and a great...

2 Hours (approx.) • Free Cancellation
4.8 (973)
from
$80
Gulf of Mexico Sunset Cruise from Naples
Likely to Sell Out
Likely to Sell Out
Naples, USA
4.8 (506)

Gulf of Mexico Sunset Cruise from Naples

Experience the magical Naples sunset while cruising on the iconic Double Sunshine. This 90-minute sunset cruise takes you from historic Tin City Waterside Shops out to...

1 hour 30 minutes
4.8 (506)
from
$73
Scenic Hakuna Matata Sunset Cruise in West Palm Beach
Likely to Sell Out
Likely to Sell Out
West Palm Beach, USA
4.7 (463)

Scenic Hakuna Matata Sunset Cruise in West Palm Beach

See the Palm Beaches from the only boat in Downtown West Palm Beach! Providing memorable cruises and experiences since 1996! Departing from the Downtown West...

2 hours • Free Cancellation
4.7 (463)
from
$66
Sunset Cruise - #1 Party Boat in St. Augustine, FL
St Augustine, USA
4.9 (250)

Sunset Cruise - #1 Party Boat in St. Augustine, FL

Embark on our breathtaking Sunset Cruise in the heart of historic St. Augustine, Florida! We will be partying, singing & dancing along the scenic Matanzas...

1 hour 30 minutes • Free Cancellation
4.9 (250)
from
$47
Sunset Sail in Key West with Beverages Included
Key West, USA
4.9 (972)

Sunset Sail in Key West with Beverages Included

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...

1 hour 30 minutes • Free Cancellation
4.9 (972)
from
$79
Key Largo Sunset Cruise
Likely to Sell Out
Likely to Sell Out
Key Largo, USA
4.9 (481)

Key Largo Sunset Cruise

Join us on a Pirates Cove Key Largo sunset boat tour to experience a breathtaking, tranquil escape where vibrant skies meet calm waters, painting the...

1 hour 30 minutes • Free Cancellation
4.9 (481)
from
$60
Key Largo Bay Dolphin Sunset Tour
Likely to Sell Out
Likely to Sell Out
Key Largo, USA
5.0 (208)

Key Largo Bay Dolphin Sunset Tour

Great way to see the way locals live and take in the wildlife around. Manatee, dolphins, and birds. Nice quiet cruise around the bay with...

1 hour • Free Cancellation
5.0 (208)
from
$66
Miami Sunset and City Lights Cocktail Cruise with Open Bar
Likely to Sell Out
Likely to Sell Out
Miami, USA
4.7 (1,141)

Miami Sunset and City Lights Cocktail Cruise with Open Bar

Take time out from the daily grind and enjoy wine, beer, prosecco, and frozen cocktails on this two hour cruise along Miami’s coastline. Relax as...

2 hours • Free Cancellation
4.7 (1,141)
from
$69

Frequently Asked Questions

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

Recent tour reviews
If the weather supports...
New York City
Miami Sunset and City Lights Cocktail Cruise with Open Bar
Himanshu_S, Sep 2026
If the weather supports...
If the weather supports it then you won't find a better way to spend your evenings with your better half than in this cruise.Unlimited drinks, relaxed vibes, beautiful sunset views all the while the sweet beach scent hits you. What more could you ask for?One tip though: Get there early so you can get seats on the upper deck where the bar is. I can imagine that if one had to constantly move between upper and lower deck then that would no longer make this a fun or relaxing experience
Read more
DOLPHINS!!!!!
New York City
Sunset Dolphin Cruise with Sanibel Lighthouse Views
358lainiea, Sep 2026
DOLPHINS!!!!!
Captain Carly was awesome. We saw lots of dolphin and the boat was great!!! Worth every penny!
Read more
Beautiful evening cruise
New York City
Miami Sunset and City Lights Cocktail Cruise with Open Bar
Tshu4, Sep 2026
Beautiful evening cruise
Great time! Full two hours, drinks were great. Staff was friendly and the slip was easy to find.
Read more
30th Anniversary Cruise
New York City
Key West Sunset Cruise: Dinner, Live Music & Drinks Included
Kandy_P, Sep 2026
30th Anniversary Cruise
Great love music and good bartender. Was a great night with lots of laughs and plenty of pictures to remember the time.
Read more
10/10
New York City
Key West Sunset Cruise: Dinner, Live Music & Drinks Included
cherykac, Sep 2026
10/10
This was a really nice cruise for couples. The sunset was beautiful and the crew was very friendly and helpful
Read more
Cranky toddler
New York City
Sandestin Sunset Eco Dolphin Cruise Aboard Sol y Luna
B9387BRjessicah, Sep 2026
Cranky toddler
Everyone was incredibly friendly and helpful. We were lucky enough to see manatees as well as dolphins on our tour. Even our 3 year old cranky toddler found something entertaining on the trip (the boat engines, not the dolphins or manatees). Overall, a wonderful ride with a great captain and crew.
Read more
The best cruise of them all!
New York City
Sunset Cruise of St. Augustine
A1315MIelizabethj, Sep 2026
The best cruise of them all!
Sarah and Captain Mike were great and the experience on the water was fantastic! Great music, drinks and good vibes.
Read more
Captain Carly made our tour enjoyable!!!
New York City
Sunset Dolphin Cruise with Sanibel Lighthouse Views
nancykY8295GP, Sep 2026
Captain Carly made our tour enjoyable!!!
I’ve never been on a boat cruise before and I’m so glad my first one was with Captain Carly on the sunset cruise. She was super enjoyable and attentive, and helped us learn about the sea animals and birds. She also took our photos so we can remember this trip. Highly recommend!!!
Read more
Excellent way to spend a evening
New York City
Sunset Cruise of St. Augustine
N4217FFdavidm, Sep 2026
Excellent way to spend a evening
Great crew. The boat was nice nothing over the top but spacious and comfortable. The tour was interesting and the views were awesome. Highly recommend as part of your St Augustine experience.
Read more
Sunset Cruise Worth It!
New York City
Gulf of Mexico Sunset Cruise from Naples
Sara_P, Sep 2026
Sunset Cruise Worth It!
Beautiful sunset and such a fun crew! Absolutely worth going to while in Naples! My friend and I enjoyed every second!
Read more
Simply amazing!
New York City
Gulf of Mexico Sunset Cruise from Naples
gracevW6167CF, Sep 2026
Simply amazing!
Wonderful time. We enjoyed the tour, we saw dolphins and the sunset view was stunning. Very friendly staff. I will definitely go back!
Read more
Great
New York City
Sandestin Sunset Eco Dolphin Cruise Aboard Sol y Luna
129pixels, Sep 2026
Great
We didn’t see any dolphins🥲. But it was relaxing!! I would recommend I got cute pictures!
Read more
Do it!!!
New York City
Sunset Celebration Cruise on Tropics Boat Tours
Heather_S, Sep 2026
Do it!!!
This was the perfect way to close out such a great day. Loved every second of it. And the best part was it was very reasonably priced. I would do it again tonight if we didn’t have other plans.
Read more
Amazing experience!
New York City
Key Largo Bay Dolphin Sunset Tour
Danielle_D, Sep 2026
Amazing experience!
Kevin was an amazing captain, extremely nice and super accommodating! I will definitely be booking again
Read more
Late summer catamaran ride
New York City
Scenic Hakuna Matata Sunset Cruise in West Palm Beach
kennedyprof, Sep 2026
Late summer catamaran ride
Small group on the boat made for excellent viewing and ability to move all around the boat. Dillon did a great job of avoiding some potential rain showers! Full bar available for a charge.
Read more
Awesome Trip
New York City
Key Largo Bay Dolphin Sunset Tour
Jennifer C, Aug 2026
Awesome Trip
Turns out it was only my husband and I who showed up for the cruise, but Kevin, our captain took us out anyway. It was like a private tour without the cost of one. He was very knowledgeable of the area and shared some interesting facts about area we passed. Unable to see any dolphins, but that was ok because the ride itself was enough. I would highly recommend this cruise. The tour only allows 6 people at most so It is an intimate evening and well worth the money. Kevin is awesome!
Read more
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