Experience a private 4-hour sailing tour on the Jolly Mon in Gulf Breeze, Florida. Enjoy scenic bay views, wildlife spotting, and optional swimming stops on this relaxing open-water adventure.
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Difficulty
easy
Duration
4 hours
Fitness Level
Suitable for all fitness levels; requires the ability to move safely around a boat and swim if choosing to snorkel.
Wildlife
History
Pensacola Bay has a rich maritime history dating back to Spanish explorers in the 16th century, with significant naval importance through the centuries.
Conservation
Efforts are ongoing to protect Pensacola Bay’s delicate marine ecosystems, including regulated fishing and responsible boating practices.
Jolly Sailing
Experience a private 4-hour sailing tour on the Jolly Mon in Gulf Breeze, Florida. Enjoy scenic bay views, wildlife spotting, and optional swimming stops on this relaxing open-water adventure.
Jolly Sailing is a small-boat charter operator based in Long Beach, California, that offers a curated range of private and semi-private maritime experiences concentrated in the Pensacola area. The company operates two main vessels: the Jolly Dolphin, a 42' powerboat tritoon used for dolphin cruises, scenic bay tours, and Blue Angels viewing; and the Jolly Mon, a custom 27' sailboat used for snorkeling, sunset sails, and full-day island excursions.
Trips are designed for intimate groups with a maximum of six guests, emphasizing close wildlife encounters, hands-on sailing options, and flexible itineraries. Offerings include short two-hour dolphin and scenic bay tours, multi-hour snorkeling and beach days, Blue Angels practice and show cruises that pause at Sand Island, and extended seven-hour island sails with snorkeling and paddleboarding opportunities.
Jolly Sailing highlights transparency and safety by specifying boat types, passenger limits, and clear trip formats. The focus on small groups supports personalized attention, easy access to secluded islands and snorkeling sites, and enhanced opportunities to spot Bottlenose dolphins and other marine life. Routes often include Pensacola Bay landmarks such as Fort Pickens, Pensacola Lighthouse, Sand Island, and Santa Rosa Sound.
All descriptions reference the operator’s published trip summaries and vessel details. Jolly Sailing positions itself as a specialist in intimate, wildlife-focused maritime tours that combine sightseeing, snorkeling, and specialty Blue Angels viewing from the water.
Location
Long Beach, California
Business headquarters
Group Size
Up to 6 guests
Intimate private and semi-private tours
Trip Lengths
2–7 hours
Options from two-hour tours to full day
Boat Types
Powerboat & Sailboat
Jolly Dolphin 42' and Jolly Mon 27'
Reserve a small-group trip aboard the Jolly Dolphin or Jolly Mon for dolphin sightings, snorkeling, or Blue Angels viewing — limited to six guests per tour.
Bring Sunscreen and Hats
Protect your skin from Florida’s strong sun during the open-water portions of the trip.
Wear Non-Slip Shoes
Opt for shoes with good traction to stay safe while moving around the boat.
Stay Hydrated
Drink plenty of water especially on warm days to avoid dehydration.
Be Ready for Weather Changes
Florida weather can shift quickly; bring a light waterproof jacket just in case.
Sunscreen
Protects your skin from strong UV rays during extended sun exposure.
summer
Swimsuit
Ideal for enjoying optional swimming and snorkeling stops.
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Light Waterproof Jacket
Keeps you dry and warm in case of sudden rain or cool breezes.
spring|fall|winter
Non-Slip Deck Shoes
Ensures safe footing on the boat deck during sailing.