Top Pensacola Cruises & Sailing

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.

There’s nothing quite like watching the sunset from the Florida Panhandle, especially when you’re out on the emerald waters fed from the Gulf of Mexico. Take advantage of the wide open water and enjoy a relaxing sunset cruise leaving Pensacola Beach. A licensed USCG Captain will take you through Little Sabine Lake and the Santa Rosa Sound where you’ll watch the sun fade into the horizon.

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 for fish, maybe even seeing a few Stingrays in the shallows, as you listen to music and enjoy your beverages. Then you head out into Santa Rosa Sound where you keep your eyes open for Dolphins – they’re thick out here! – and enjoy the scenery. You have a private licensed captain driving the tiki so you only have to worry and relaxing and enjoying your day. This cruise has options! You can stop at one of several sandbars and shallow areas to swim, float, or snorkel or you can check out one or more of our awesome beach bar/restaurants – Sneaky Tiki, Paradise Grill, Flounders, and more. You can hang out on water or land and listen to live music. You'll return back to dock salty and happy! Bring your own beverages & snacks or get refreshments at one of the great establishments along the route.

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 and National Seashore. Or explore the Condor: walk around, do the Titanic pose, sit on the sides and dangle your feet in the water; feel like you're surfing or flying up on the bows; or drive a world-class Condor!

- This is a private cruise on a yacht with a USCG licensed Captain. - We have 2 restrooms and an air conditioned cabin with a flat screen TV. Avoid overcrowded excursions with this private, small-group (up to 6 passengers), sunset cruise on Pensacola Bay and the intracoastal waterway to include: viewing the Pensacola Pass, the Pensacola Lighthouse on NAS, Home of the Blue Angels, Sand Island and the Big Lagoon. As we head out from Bayou Grande in the late afternoon aboard our 50' yacht, your Captain shares details about the area's waterways. As we sail away from the shore and enjoy our local waters, you will take in all that our coastline has to offer. While sipping on a cold drink, we will chase the sunset and look out for dolphins playing in the wake before heading back in— it’s the perfect way to end your day and to make memories that will last a lifetime.

You will have a mer-mazing time on this 4 hour dolphin tour. Cruise through the waters around Pensacola Beach searching for dolphins and other marine and wildlife. MAKE SURE TO VIEW DETAILS ON YOUR TICKET - every passenger 1 day - 100 years old require a ticket. Your local Captain will entertain you on your excursion offering interesting facts, historical sites and information.

Spend your day relaxing in Pensacola Beach with this small-group bay cruise complete with your own dedicated captain. You’ll need very little to enjoy yourself on this sailing trip as your captain makes every effort to keep you happy. The full-range stereo, large ice chest, and bottled water keep the vibes cool while the electric pump can keep your floaties plump. Enjoy cruising on the Little Sabine Lake and Santa Rosa Sound.

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 a scenic spot while enjoying the thrill of the Blue Angels flying overhead. Perfect for relaxation, sunbathe on the bow or lounge with Captain Dan. Refreshments like water, sodas, ice and light snacks are included, ensuring a comfortable experience. - Embark at 9:00 AM for a one hour cruise to Sand Island - Experience breathtaking views and marine life on a 50’ yacht - Relax on board with complimentary refreshments - Watch a breathtaking display of speed, power and patriotism against the Gulf Coast sky as the Blues roar overhead in flawless formation and heart pounding precision - Depart Sand Island for a one hour return cruise to dock at 12:00 PLEASE NOTE: BLUE ANGEL PRACTICES ARE ONLY HELD TUESDAYS & WEDNESDAYS DURING CERTAIN MONTHS. PLS SEE PICTURE OF SCHEDULE FOR DATES PRIOR TO BOOKING.

Ring in the New Year on this Zero-Proof, Sober Fireworks Cruise. Non-alcohlic beverages & snacks for sale on the boat.

This is not just a lesson — it’s a carefully guided introduction to a completely new sensation: flying above the water.

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!

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. This incredible tour includes beaching at a secluded beach for swimming, shelling, and fun. See local historical sites while learning about our beautiful area and amazing sea life. EVERY PERSON counts, including INFANTS. Maximum 6 passengers, no exceptions.

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 on your excursion offering interesting facts about historical sites and information while you cruise the bay, they will also provide information on all of our local marine & wildlife. Keep your eyes peeled for our favorite local dolphins and other marine and wildlife above and below the water at your 30 -45 minute snorkel stop. Fun music, good times and tan lines. You'll dolphinately have a FINtastic time. We provide adult size snorkel sets. You may also bring your own.

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 USCG Captain. This Frisky Stop includes beaching at a secluded beach for swimming, shelling and fun. See local historical sites while learning about our beautiful area and our amazing sea life. EVERY PERSON counts, including INFANTS.

Dive into a unique adventure with our Inflatable Sandbar Excursion featuring cool motorized floats that do all the work for you while you sit back and relax. Explore a beautiful sandbar, a hidden gem known mostly to locals in Pensacola Beach. Our floats excursions offer more than comfort—they provide an extraordinary way to relax and create lasting memories. Join us for an exceptional beach experience that stands out from the rest! Choose the Cooler option and we will provide a cooler, ice, and drinks for you as well!

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.