Private Sailing Charter Experience

A private sailing charter is one of the few gifts that hands someone an entire boat for the afternoon. No strangers on deck, no timetable beyond the tide, just a captain & crew who know the water and the people they chose to bring. To see everything afloat first, browse all of our sailing experiences and narrow down to the private bookings from there.

What a Private Charter Includes

Every sailboat charter here comes with a licensed captain, so nobody needs to know a halyard from a jib sheet. The shortest trips run about two and a half hours, and the longest stretch to full day and overnight sailing on the Chesapeake Bay. Most boats take up to six guests, and plenty of crews are happy for you to bring snacks and a bottle aboard. Your recipient picks the dates that suit them, within the operator's season and availability.

Where These Charters Sail

The private sailing tours here cover both coasts. New York sailing trips leave Manhattan and Brooklyn for skyline and Statue of Liberty views, with matching departures from Jersey City. In Boston, charter a 45 foot classic yacht or a 1967 Chris-Craft out toward the Harbor Islands. San Diego covers morning, sunset, swim and six hour family sails, Maryland opens up the Chesapeake, and there is San Francisco Bay, Newport, Orlando, and an outrigger canoe sail on Maui.

Who It Suits, and How to Send It

Two people and a horizon is a hard combination to beat, which makes a charter a strong engagement plan or anniversary gift, and the longer family sails suit a summer birthday gift or a graduation just as well. Leave it late and the e-voucher reaches your inbox in minutes, ready to forward or print off to add to your card. Plan ahead for Christmas and we will send it in a beautiful Giftory gift box instead. The choice is yours!

Private Sailing Charter FAQs

Does the recipient need sailing experience? No. Every trip here is skippered, and captains are used to first timers. If they want to take the helm or help with the lines, most crews will let them.

What happens if the weather turns? Captains move the booking to another date rather than sail in unsafe conditions. Light rain usually goes ahead, so a jacket is worth packing.

What should they wear? Soft soled shoes or bare feet will be instructed once onboard, layers, sunglasses and sunscreen. It runs cooler on the water than on shore, especially on sunset and evening sails.