Pensacola Bay Sailing Adventure Experience

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!

Meeting Point

715 Pensacola Beach Blvd

715 Pensacola Beach Blvd, Gulf Breeze, FL 32561, USA

The Jolly Mon sailboat is located at Sabine Marina, 715 Pensacola Beach Blvd., Pensacola Beach, FL 32561, behind the Sandbar Sunset Bar & Grill. Park in the lot by the Sandbar, then meet the Captain at the gate behind the restaurant leading into the marina.

What's included:

• USCG Licensed Captain

What to expect:

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.