Glide through Pensacola Bay aboard the 27' Jolly Mon sailboat, spot dolphins, and dive into refreshing Gulf waters. This 3-hour coastal sailing trip blends wildlife, relaxation, and adventure.
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Difficulty
moderate
Duration
3 hours
Fitness Level
Suitable for moderate fitness; ability to move steadily on a sailboat deck is recommended.
Wildlife
History
Pensacola Bay has a rich maritime history dating back to the 16th century as one of the earliest European settlements on the Gulf Coast.
Conservation
Local efforts focus on protecting seagrass beds and water quality to sustain the vibrant marine ecosystem guests experience.
Jolly Sailing
Glide through Pensacola Bay aboard the 27' Jolly Mon sailboat, spot dolphins, and dive into refreshing Gulf waters. This 3-hour coastal sailing trip blends wildlife, relaxation, and 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.
Check Weather Forecast
Pensacola Bay conditions can shift quickly; ensure calm winds for a smooth sailing experience.
Bring Swimwear and Towel
The optional swim stop is a highlight—pack swimwear and a quick-dry towel.
Use Reef-Safe Sunscreen
Protect yourself and local marine life by applying eco-friendly sunscreen before boarding.
Arrive Early for Safety Briefing
Arriving 15 minutes early ensures you won’t miss important safety and sailing instructions.
Light Jacket
Offshore breezes can be cool during spring excursions.
spring
Swim Gear
Essential for the swim stop in warm summer waters.
summer
Sunscreen
Protects skin during long exposure to sun on open water.
summer
Hat and Sunglasses
Helpful for glare reduction and sun protection while onboard.