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Top Pensacola Cruises, Sailing & Water Tours

Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour
Likely to Sell Out
Likely to Sell Out

Experience good times and Jollification aboard the Jolly Dolphin or the Jolly Explorer! Featuring Jolly Dolphin, Pensacola Beach's NEWEST dolphin boat. Both vessels feature full...

90 to 120 minutesFree Cancellation
90 to 120 minutesFree Cancellation
90 to 120 minutes • Free Cancellation
5.0 (925)
$41
$40

Shared Dolphin Cruise in Pensacola Beach | Frisky Mermaid
Likely to Sell Out
Likely to Sell Out

Experience Pensacola Beach's most reviewed dolphin cruise aboard the 52-foot Frisky Mermaid — 3,000+ five-star reviews and a crew called the Disney of the Beach....

90 to 120 minutesFree Cancellation
90 to 120 minutesFree Cancellation
90 to 120 minutes • Free Cancellation
4.9 (617)
$35.99
$34.99

Pensacola Beach Dolphin and Scenic Tour
Likely to Sell Out
Likely to Sell Out

Ready to meet some dolphins? Hop aboard Chase-N-Fins for a fun, family-friendly dolphin cruise in Pensacola Beach where wild dolphins swim, jump, and surf right...

60 to 90 minutesFree Cancellation
60 to 90 minutesFree Cancellation
60 to 90 minutes • Free Cancellation
4.9 (153)
from
$37

Tiki Boat 3 Hour Fun Cruise

This cruise is all about making incredible memories with your family and friends!! Picture this…you’re cruising through Little Sabine Bay, watching Osprey and Pelicans diving...

3 hours
3 hours
3 hours
4.8 (25)
from
$127.50

2 Hours Private Guided Sailing Adventure in Pensacola Beach
Likely to Sell Out
Likely to Sell Out

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, Deer Point, Fair Point and Deadman's Island. We...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (6)
from
$385

Bay Cruise
5.0 (15)

Bay Cruise

Make some lasting memories with a day cruise on the spectacular waters of Little Sabine Bay and Santa Rosa Sound! You may see Osprey and...

1 hour 30 minutes
1 hour 30 minutes
1 hour 30 minutes
5.0 (15)
from
$75

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
Likely to Sell Out
Likely to Sell Out

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (60)
from
$104

Tiki Boat Sunset Cruise Tour
Likely to Sell Out
Likely to Sell Out

Sunset is the best time of day to be on the water and being on a tiki boat makes it extra fun and special!! Book...

1 hour 30 minutes
1 hour 30 minutes
1 hour 30 minutes
5.0 (22)
from
$95

2 Hour Private Dolphin Cruise & Bay Tour
Likely to Sell Out
Likely to Sell Out

Enjoy your own private adventure on the water for UP TO 6 GUESTS MAX. (Please note, we are limited to 6 people on this boat...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (20)
from
$385

Private 3 Hour Powerboat Dolphin Cruise with Remote Beach Stop up to 6 guests

Enjoy your private boat for up to 6 passengers, with restroom aboard, full shade, and a friendly, informative Captain to show you around the Pensacola...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (32)
from
$535

Frisky Mermaid Dolphin + Sightseeing Cruise in Pensacola Beach
Likely to Sell Out
Likely to Sell Out

Experience Pensacola Beach's most reviewed operator on a private small group dolphin and sightseeing cruise. With a maximum of six guests you get the full...

2 hours
2 hours
2 hours
5.0 (77)
from
$395

Frisky Mermaid Scenic Bay Cruise + Snorkeling Stop + Equipment
Likely to Sell Out
Likely to Sell Out

This tour can accommodate up to a maximum of 6 passengers, including infants. EVERY PERSON COUNTS. Not only will our Mermazing local Captain entertain you...

2 hours
2 hours
2 hours
5.0 (10)
from
$395

Private 3 Hour Sunset Cruise On A 50' Luxury Yacht With Captain
Likely to Sell Out
Likely to Sell Out

- This is a private cruise on a yacht with a USCG licensed Captain. - We have 2 restrooms and an air conditioned cabin with...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (12)
from
$910

Frisky Mermaid Dolphin Cruise with a Secluded Beach Stop
Likely to Sell Out
Likely to Sell Out

Ready for a mermazing adventure? You'll enjoy this open air vessel while cruising the bay searching for dolphins and other marine and wildlife with our...

3 hours
3 hours
3 hours
5.0 (13)
from
$535

Pensacola Beach Kayak Tour
Likely to Sell Out
Likely to Sell Out

Kayaking with a knowledgable, science-educating nature enthusiast is an unparalleled experience. Every tour is unique, we have a set starting point and destination but what...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (9)
from
$94

6 Hour Pensacola Beach Excursion with Snorkeling and Swimming
Likely to Sell Out
Likely to Sell Out

Ready for an amazing adventure? You'll enjoy this open-air vessel while cruising the bay searching for dolphins and other marine wildlife with our USCG Captain....

4 hours
4 hours
4 hours
5.0 (4)
from
$935

Blue Angels Practice on a Private Yacht with Captain

Indulge in a luxurious private yacht charter aboard the Mila Yenin, where elegance meets adventure. Cruise the stunning Pensacola Bay and intracoastal waterway, anchoring at...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (1)
from
$910

Clear Kayak and Glow Kayak Adventures

Explore the beautiful waters on a clear kayak or glow kayak adventure that suits all ages. Experience stunning sunsets, encounter playful dolphins, or paddle under...

1 hour
1 hour
1 hour
5.0 (2)
from
$60

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  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

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  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
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