Top Pensacola Sailing Tours

Hop aboard the Jolly Dolphin, a 42-foot (12.8-meter) shaded tritoon, and make your way out to sea with a captain and crew to help make your experience enjoyable and educational. As you glide along the waters, you'll learn about the natural environment and the creatures that call it home. You may even spot dolphins frolicking in the surf.

There are dolphin tours and then there’s the Frisky Mermaid: a boat tour that tempts you with a mer-mazing time on the water. Come aboard this boat for a scenic cruise around Pensacola Beach, either in the morning or evening. Depending on which time you choose, you may be able to see a variety of marine life in the waters such as fish, turtles, and dolphins. No matter when you sail, the Gulf breeze and warm sun accompany you.

Discover some of Pensacola’s deepest, darkest secrets on a guided, ghost-themed bus tour. This “frightseeing” tour explores the darker side of this waterfront city, one of the earliest European settlements in the US. Discover the five types of hauntings that are common in Pensacola. Visit the historic downtown district, plus the Seville Quarter, Sanders Beach, North Hill, and a cemetery, of course. This scary, fun and informative adventure is for mature audiences. Parental discretion is advised.

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!