Smooth Sailing Ahead

Book early and enjoy your uncrowded private or shared adventure with us. We offer complimentary refreshments on all trips — including adult beverages!

Owners & Crew Jim & Cindy Bielinski

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Come see dolphins play Pensacola Beach Dolphin Cruise, Dolphin Tour on Pensacola Bay & Santa Rosa Sound. Premium comfort boat tour for the Pensacola area, starting at just $25!

Jolly Sailing is a family owned company established in 2011 in Pensacola Beach, Florida. It all began with the Jolly Mon, our 27′ American Mariner Sailboat, on which we offered sailing, snorkeling and sunset tours.

Over the last few years, we have added JollyDayz, our 34′ Pearson sailing yacht, Jolly’Ventures, a 26′ powerboat tritoon, and our newest vessel, the Jolly Dolphin, a 42′ powerboat tritoon passenger vessel that carries up to 26 passengers. We now offer a wide variety of excursions, both private and shared, for our guests to enjoy.

We have been pleased to welcome several experienced, friendly and informative Captains and crew members to our team. Together we strive to provide a safe, relaxing and entertaining excursion for our guests. It’s not just a job, it’s a lifestyle that we enjoy sharing with visitors to Pensacola Beach and residents of the Pensacola Bay Area.

Jolly Good Times Await!

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Got Questions?

Check Our FAQs or Get In Touch

Should I worry about seasickness?

We sail in the protected waters of Santa Rosa Sound and Pensacola Bay, where conditions are quite favorable for boating. Seasickness is highly unlikely to occur while sailing, as it is generally a much smoother ride than on a powerboat. The sails stabilize the boat and keep it from rolling and pitching. Also there are no noxious engine fumes to contend with, which often contributes to the problem. To date, none of our passengers have experienced seasickness on our vessels.

Is there an age requirement for your trips? Is it safe for young children?

We have had passengers of all ages on board, from 3 months to 85 years of age. Our boats are safe, comfortable and fun for all ages. There are several safety measures in place, including lifelines, a throwable life-sling on deck, and life jackets. Kids are able to move all around deck while we are sailing, can explore the spacious cabin down below deck, and can even steer the boat!  Our young guests especially have a great time, often saying the trip was the highlight of their Pensacola Beach vacation.

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Wear comfortable clothing, and a swimsuit if desired. In cooler months, a jacket is recommended. *Your Captain requests that you wear shoes with non-marking soles, as they will leave stubborn marks on the deck.  We also discourage heels.  Barefoot is the way to go on the boat!  You may want a change of clothes if planning to swim or snorkel.  Other items you might need include sunscreen, sunglasses, hat, towel, and camera. You may also bring your cellphone or mp3 device to plug into our stereo.

On snorkel trips, snorkel gear, including flotation devices are provided.

Are alcoholic beverages allowed on board?

We encourage guests of legal drinking age to bring their favorite libations aboard. We provide complimentary ice, cups, plastic glassware, sodas, and water.  You are welcome to bring any favorite drinks or food you would like, which the crew will be happy to serve up for you. For safety reasons, we request that you bring aluminum cans instead of glass.  Bottled wine or champagne is acceptable, and can be stored below in the fridge.

Do you have a restroom available?

There is an enclosed restroom/changing area (known as a head in nautical terms) located on board, which is clean, private, and ready for guests to use.

What happens in the case of inclement weather?

All trips are subject to the Captain’s approval of weather and water conditions. In the event a trip is cancelled, we will attempt to reschedule the trip on another day. If this is not possible, guests will not be charged.

What is your cancellation policy?

If you need to cancel, we require a 24 hour notice prior to your scheduled trip. If you cancel within 24 hours, you will be charged.

What forms of payment do you accept?

We accept cash and credit/debit cards. If you book directly through the reservation calendar online, you will be charged in full. If you would like to pay in cash you may call us with a credit card number to hold your reservation, and pay in cash or charge to card on the day of the trip. If we need to cancel the trip due to weather or conditions, or if you cancel 24 hours or more in advance of scheduled trip, you will be fully refunded. Please call us with any questions.

Will we see dolphins?

Though we cannot guarantee a dolphin sighting, it is quite likely to see them feeding and frolicking in the bay. It is more likely to spot them on our powerboat tours, as we can go faster and cover more water than we can on the sailboat. We see them on most trips, along with fish and other wildlife. Keep a lookout for pelicans, gulls, herons, ospreys, eagles, cormorants, fish, crabs, sea turtles, rays and other creatures.  You never know what you might see on any given day.

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Gratuity is always appreciated but never expected.

Can I buy a trip for someone else? Do you have Gift Certificates available?

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Pensacola Beach Marina
655 Pensacola Beach Blvd.
Pensacola Beach, FL 32561
(850)723-6142

Shaggy's Marina, Pensacola Beach
701 Pensacola Beach Blvd
Pensacola Beach, FL 32561
(850)723-6142

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