Private Tour
2 Hours Private Guided Sailing Adventure in Pensacola Beach
Overview
Available languages
2 hours
Mobile ticket
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 may also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring areas of Quietwater Beach and the Santa Rosa Sound. A small group atmosphere makes this tour so enjoyable. The Jolly Mon can accommodate parties of up to 6 guests maximum. Sailing is a unique experience and fun for all ages. This tour is great for families, couples, adventurers and seekers of relaxation alike! Guests can learn from the Captain about the area wildlife, history, and the art of sailing. Take the helm and learn to sail or just sit back and enjoy the sights and sounds. Once we leave the dock and motor through the channel, we set sail for a tranquil excursion. There is something special about traveling across the water with only the power of the wind. Every tour is different, but always such a fun and easygoing activity, so many lasting memories to be made!
Additional Info
Service animals allowed
Not recommended for travelers with spinal injuries
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
Soda/Pop
Bottled water
USCG Licensed Captain
We only serve alcoholic drinks for travelers 21 years old and above. Minor travelers below 21 years old will be served non-alcoholic drinks.
Gratuities
What To Expect
Sailing in Pensacola has been a tradition since 1559, when Don Tristan De Luna of Spain landed on the shores of Pensacola Bay, marking the first European settlement in mainland America. The tradition continues today, as the area is training headquarters for the New York Yacht Club America's Cup team sailing vessel, American Magic. On the Jollymon, our sporty custom American Mariner sailboat, you can experience a sailing adventure just like the early explorers. Your Captain will be happy to show you the ropes, and even let you steer the boat, if you feel adventurous! Sailing is a wonderful experience that is relaxing and exciting at the same time. Sit back, relax and enjoy the scenery, along with a cold beverage or two! Complimentary beverages, including beer and wine, are offered on this cruise for guests of legal drinking age. Sailing with dolphins on the Northwest Florida Gulf Coast is a unique experience. Wild dolphins seem naturally attracted to sailboats, often swimming alongside us, crossing our wake, playing and feeding nearby. Though we cannot always guarantee a sighting, we do cross paths with dolphins and other sealife often on sailing excursions.
Options
2 Hours Private Guided Sailing Adventure in Pensacola Beach
Reviews
4 reviews
Total reviews and rating from Viator & Tripadvisor
Great experience
Resort613096,
Sep 17, 2025
- Review from Tripadvisor
5.00I had never been sailing before. Jolly Sailing gave me a great first experience. It was a relaxing and fabulous way to spend an evening.
Would sail with Jolly and Roger again!
W6696LFkimd,
Jul 13, 2025
- Review from Tripadvisor
5.00Me and my husband thoroughly enjoyed our sunset sail. Roger was the best captain ever!! He was very knowledgeable and explained as we sailed around the bay. Would sail with Jolly and Roger again!!!
Top of your MUST DO list
keetrap2024,
Sep 19, 2024
- Review from Tripadvisor
5.00I did 2 cruises with them 2 days in a row and they did not disappoint! We did the blue angel and dolphin one the 1st day then the next day we did the sunset cruise. My 5 year old enjoyed both. And she got to steer the boat on the private sunset cruise. We had a blast! 10/10 highly recommend. Thank me later. I’ve worked in customer service for many years so I look for a certain level of customer service and everyone was so nice and friendly. Totally worth the money.
Highly recommend
Angie G,
Sep 16, 2024
- Review from Viator
5.00The guide helped us learn how to sail. Such a fun evening. Very relaxing and beautiful views. Highly recommend.
Related Experiences
Operated by Jolly Sailing & Dolphin Cruise