Discover Pensacola Beach on a private 2-hour sailing adventure. Learn to sail, explore scenic spots, and create lasting memories. Perfect for families and couples.
- 715 Pensacola Beach Blvd - 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 27’ 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 Northwest Florida’s 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.
- Carbonated beverages
- Bottled water
- USCG Licensed Captain
- Alcoholic drinks for travelers 21+; non-alcoholic drinks for travelers under 21
- Gratuities
This 2-hour sailing trip takes place in Pensacola Bay, passing by Sabine Island, Deer Point, Fair Point, and Deadman’s Island. We might also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring Quietwater Beach and the Santa Rosa Sound. The small group setting makes this tour very enjoyable. The Jolly Mon can host up to 6 guests. Sailing is a unique and fun experience for all ages. This tour is perfect for families, couples, adventurers, and those seeking relaxation! Guests can learn from the Captain about local wildlife, history, and the art of sailing. Take the helm and learn to sail or simply sit back and enjoy the scenery. Once we leave the dock and motor through the channel, we set sail for a peaceful excursion. There’s something special about traveling across the water powered only by the wind. Every tour is different but always a fun and relaxing activity, creating many lasting memories!
For a full refund, cancel at least 24 hours before the scheduled departure time.
