2 Hours Private Guided Sailing Adventure in Pensacola Beach
Overview
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!
What's Included
- Alcoholic beverages We only serve alcoholic drinks for travelers 21 years old and above. Minor travelers below 21 years old will be served non-alcoholic drinks.
- Carbonated beverages Soda/Pop
- Bottled water
- USCG Licensed Captain
- Gratuities
Meeting Location
715 Pensacola Beach Boulevard
Gulf Breeze, FL 32561, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Sailing in Pensacola has been a tradition since 1559, when Don Tristan De Luna of Spain
landed on the shores of Pensacola Bay, marking the first European settlement in mainland America.
The tradition continues today, as the area is training headquarters for the New York Yacht
Club America's Cup team sailing vessel, American Magic.
On the Jollymon, our sporty custom American
Mariner sailboat, you can experience a sailing adventure just like the early explorers. Your Captain
will be happy to show you the ropes, and even let you steer the boat,
if you feel adventurous!
Sailing is a wonderful experience that is relaxing and exciting at
the same time.
Sit back, relax and enjoy the scenery, along with a cold beverage or
two! Complimentary beverages, including beer and wine, are offered on this cruise for guests of
legal drinking age.
Sailing with dolphins on the Northwest Florida Gulf Coast is a unique experience.
Wild dolphins seem naturally attracted to sailboats, often swimming alongside us, crossing our wake, playing
and feeding nearby. Though we cannot always guarantee a sighting, we do cross paths with
dolphins and other sealife often on sailing excursions.
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Operated by a business
Frequently Asked Questions
(8)Q: Will I get seasick on 2 Hours Private Guided Sailing Adventure in Pensacola Beach?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-136320P5
Traveler Photos
Reviews
Average 5.00 out of 5 stars based on 6 traveler reviews collected by Cool Destinations and partner sites such as Trustpilot, Viator, and TripAdvisor
Additional Info
Similar Tours & Activities
Pensacola Beach Kayak Tour
Kayaking with a knowledgable, science-educating nature enthusiast is an unparalleled experience. Every tour is unique, we have a set starting point and destination but what...
$94
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...
$535
Enjoy your private boat for up to 6 passengers, with restroom aboard, full shade, and a friendly, informative Captain to show you around the Pensacola...
$535
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...
$910
Travelers Who Bought This Tour Also Bought
Experience good times and Jollification aboard the Jolly Dolphin or the Jolly Explorer! Featuring Jolly Dolphin, Pensacola Beach's NEWEST dolphin boat. Both vessels feature full...
$40
Experience Pensacola Beach's most reviewed dolphin cruise aboard the 52-foot Frisky Mermaid — 3,000+ five-star reviews and a crew called the Disney of the Beach....
$34.99
One kayak accommodates TWO people. This is an experience unlike anything else. Experience crystal clear kayaks and paddleboards with led and solar lights. The kayaks...
$74
Hop-on Hop-off Tour in Pensacola
For the best introduction to Pensacola, try the Hop-on, Hop-off Tour. Fully narrated, this tour includes 13 stops for customers to explore areas of interest....
$44
Frequently Asked Questions (8)
The answers provided below were previously given in response to questions from Cool Destinations customers.
Filter by:
If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.
Feb 2023- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CDT).
- Alcoholic beverages. We only serve alcoholic drinks for travelers 21 years old and above. Minor travelers below 21 years old will be served non-alcoholic drinks.
- Carbonated beverages. Soda/Pop.
- Bottled water.
- USCG Licensed Captain.
- Gratuities.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025There is no minimum age for this tour, so bring your wee one along for an adventure..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the 2 Hours Private Guided Sailing Adventure in Pensacola Beach is as follows:
- Service animals allowed
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for 2 Hours Private Guided Sailing Adventure in Pensacola Beach will be included in your confirmation email from Cool Destinations. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024What's Included
- Alcoholic beveragesWe only serve alcoholic drinks for travelers 21 years old and above. Minor travelers below 21 years old will be served non-alcoholic drinks.
- Carbonated beveragesSoda/Pop
- Bottled water
- USCG Licensed Captain
- Gratuities
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Operated by a business
