

Sailing
The best out of 416 Sailing deals - enter destination and dates to check availability.
Nearest Sailing tours & charters
Nearest Sailing tours & charters
- Trips fromUS $800
- +2Instant ConfirmationTrips fromUS $500
- Instant ConfirmationTrips fromUS $283
Gone Sailing Adventures
Toronto, OntarioTrips fromUS $1,554Gosailto – 22' Sailing Experience
Toronto, OntarioInstant ConfirmationTrips fromUS $408- Instant ConfirmationTrips fromUS $200
Make a Memory on Optimystic
Baltimore, MarylandTrips fromUS $350- Trips fromUS $500
Annapolis Sailing Adventures, LLC
Annapolis, Maryland+4Trips fromUS $650AM Services
Hampton, VirginiaInstant ConfirmationTrips fromUS $375
Top Sailing tours & charters worldwide
- Afternoon Private Boat Trip+2Instant ConfirmationPrice for up to 9 peopleUS $546
- Romantic sunset dinnerInstant ConfirmationPrice for up to 2 peopleUS $569
- 5 HOURS PRIVATE SAILING TRIPS+3Instant ConfirmationPrice for up to 10 peopleUS $740
- 6 Hour – Lunch & Swimming TourInstant ConfirmationPrice for up to 6 peopleUS $740
- Sailing Experience Half Day at Sea+4Instant ConfirmationPrice for up to 6 peopleUS $911
- 4 Day – Trip in Saronic Gulf+2Price for up to 7 peopleUS $608
- 2 Hour – Sunset Tour (up to 4 Pax)Instant ConfirmationPrice for up to 8 peopleUS $250
- 4 Day – Trip in Saronic Gulf+1Price for up to 6 peopleUS $615
- 3 Hour – Sunset Naunet Experience+1Instant ConfirmationPrice for up to 10 peopleUS $569
- 2 Hour – Daytime Charter - 11:00 AM+4Instant ConfirmationPrice for up to 6 peopleUS $200
What boaters say about Sailing tours & charters
- 5.0/5(Afternoon Sailing Experience)
amazing relaxing trip!
awesome people and experience! the trip couldn’t have been better and the boat was so nice.
- 5.0/5(Special 5 hours trip for Amber Russo)
Wonderful Experience!
I booked a BBQ trip for my husband’s birthday and we had a great time! The crew was very attentive and kept us well fed throughout. They provided a lot of information regarding the island, and were happy to answer any questions we had. Very easy to get along with! Unfortunately there wasn’t enough wind to sail but we were still able to use the motor and go out on our tour. The water was so refreshing and clear! The boat is so charming and well-kept! I would highly recommend!
- 5.0/5(3 Hour Sunset Sail with a meal.)
Awesome experience
Captain Rick and Deb were wonderful hosts aboard the Artemis. It was a lovely day of sailing paired with a delicious lunch. Couldn’t have asked for a better experience!
- 5.0/5(6 Hour – Paklinski Morning Sailing)
Relaxing day with a great lunch stop
The captain and his crew were very helpful and made the day very relaxed. They had snorkeling equipment and a paddle board available for us to use and took us to a great restaurant for lunch.
- 5.0/5(4 Hour – Sail Around The Bay)
Fun time with great people
Captains Lynne and Mason were very engaging and willing to expertly answer all of our questions about sailing. thisnis a great experience!
About Sailing
Sailing is the simple joy of moving by wind. A sailing boat uses its sails to harness breeze and glide across the water. It is calm, quiet, and close to nature. Choose it if you want a relaxed pace, hands-on fun, and a true connection to the sea.
Most sailing boats have a roomy cockpit for relaxing and a protected cabin below. You may find a small kitchen, called a galley, and a toilet, called a head. Monohulls lean under sail, while catamarans have two hulls for a stable ride. Deck space is open, with clear areas to sit, move, and enjoy the view.
Sailing is great for day trips, sunset cruises, and weekend getaways. Crewed trips let you sit back while the skipper handles the helm, which is the steering station. Want to learn? Many crews will show you how to trim the sails and help with lines. You can anchor in a quiet cove, swim, snorkel, or just watch the wake drift by.
This boat type suits beginners, families, and seasoned sailors. First-timers can book with a captain for easy guidance. Bring soft bags, sun protection, a light jacket, and non-marking shoes. Life jackets, also called PFDs, are normally on board. If you get motion sickness, plan ahead with your usual remedy.
Before your trip, check local rules for Sailing. Some places require licenses, permits, or specific captain credentials. Know the capacity rating for your group, follow safety briefings, and avoid BUI, which means boating under the influence. Always follow local navigation marks and no-wake zones. When in doubt, ask your captain or operator about the latest rules.




































