

Sailing
The best out of 427 Sailing deals - enter destination and dates to check availability.
Nearest Sailing tours & charters
Nearest Sailing tours & charters
- Trips fromUS $800
3rd Coast Cruising – Legend 31
Chicago, Illinois+2Instant ConfirmationTrips fromUS $500- Instant ConfirmationTrips fromUS $284
Gone Sailing Adventures
Toronto, OntarioTrips fromUS $1,564Gosailto – 22' Sailing Experience
Toronto, OntarioInstant ConfirmationTrips fromUS $411- 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
- 4 Hour – Morning – Private Trip - 9:00 AM+4Instant ConfirmationPrice for up to 8 peopleUS $539
- Afternoon Private Boat Trip+2Instant ConfirmationPrice for up to 9 peopleUS $539
- Romantic Sunset DinnerPrice for up to 2 peopleUS $561
- 5 HOURS PRIVATE SAILING TRIPS+3Instant ConfirmationPrice for up to 10 peopleUS $730
- 6 Hour – Lunch & Swimming TourPrice for up to 6 peopleUS $730
- Sailing Experience Half Day at Sea+4Instant ConfirmationPrice for up to 6 peopleUS $898
- 4 Day – Trip in Saronic Gulf+2Price for up to 7 peopleUS $599
- 2 Hour – Sunset Tour (up to 4 Pax)Price for up to 8 peopleUS $247
- 4 Day – Trip in Saronic Gulf+1Price for up to 6 peopleUS $606
- 6 Hour – Ocean Experience (copy) - 12:00 AM+1Price for up to 10 peopleUS $673
What boaters say about Sailing tours & charters
- 5.0/5(Afternoon Private Boat Trip)
Janko is the skipper to ask for!
Captained by the brilliant Janko this was a fantastic afternoon on the water. You could not ask for a better skipper for a trip like this. Our only regret was that we forgot to draw out some cash to provide a tip. Sorry Janko! Hope the muffins were a small consolation.
- 5.0/5(2 Hour – Sunset Wedding proposal)
Wonderful Trip
Miguel and crew were wonderful, and the boat was beautiful. They were extremely prepared, Miguel was a made great conversation, and the wine, charcuterie, and champagne were great. The moment for our proposal was fanstic, and would not change anything. The photographer wasexcellent, she had a professional camera to capture the moment, us, and the scenery.
- 5.0/5(2 Hour – Burial at Sea)
Wonderful experience despite the task at hand
Andrea and Kurt were great and helped my family as we spread my wifes ashes. Tastefully respectful for our grief. Very helpful as the documented it for us. I couldn't ask for more.
- 5.0/5(3 Hour – Sunset Cruise)
Beautiful Sunset Sail!
We had a beautiful sunset with Capt Michael out of Lavagna. Capt Michael provided plenty of snacks and drinks. The boat had plenty of space to relax and enjoy the sail. Capt Michael shared his boating experiences with us as we snacked and listened to relaxing music. We drove and parked minutes from the boat. We would definitely recommend Set Sail Tours.
- 5.0/5(2 Hour – Sunset Tour)
Lisbon sunser cruise delight
We had a wonderful sunset cruise on the Tagus. Captain Miguel and his mate, also Miguel, were knowledgeable, gracious, and highly skilled. The views of Lisbon at sunset were breathtaking, and the wine and snacks were a lovely touch. An outstanding experience we highly recommend!
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.





































