Try Something New for Your Next Gathering
Searching for a different kind of way to bring people together? A new idea for your next family reunion? Something a little more meaningful than another rental house or restaurant dinner? Consider a private windjammer charter. There’s a magic that happens when a group shares a boat for a few days: conversations linger, phones get forgotten, meals stretch long, and everyone settles into the simple rhythm of being together.
We’ve seen families and friends reconnect, school and scouting groups try their first real adventure together, and small wedding parties trade the usual bustle for a celebration that feels intimate and unhurried. It doesn’t have to be fancy to be unforgettable—just time spent sailing, exploring, and laughing with your people.
Private Boat Charter FAQ
How many people can the Windjammers accommodate?
Most windjammers carry between 16 and 29 guests on overnight trips, depending on the vessel. Exact capacities and cabin layouts can be found on each boat’s listing on our Fleet page. For day sails, several boats can accommodate larger groups—some up to 75 guests—since no overnight berths are needed.
Can I book just a one-day trip for a few hours?
Yes—sometimes. While the windjammers run a full schedule of multi-night cruises, they can occasionally fit in a private day sail between trips. Availability depends on each schooner’s calendar, but it’s always worth asking.
When do I need to reserve my charter?
The earlier, the better. A cruise can be privately reserved as long as no one else has booked on that trip yet, so reaching out early gives you the most options. Schedules are usually released in the summer, which is the ideal time to start planning. However, there are often still some timeslots available even into early spring so it’s always worth inquiring
What if I don’t have a large enough group?
No problem. You’re welcome to charter a boat with a smaller group if you’d like the vessel to yourselves, or you can simply join one of the regularly scheduled cruises open to individual travelers.
How much does a private windjammer charter cost?
Pricing varies by vessel, trip length, and group size. Private charter prices are based on the same per-person daily rate as regular cruises, though often groups are offered a discount.
Day sails are also priced differently by each boat. The best way to get an accurate estimate is to reach out directly to the vessels you’re interested in—they’re happy to walk you through options.
Use this link to email all of the vessels at once to inquire about a private charter. The more information you can provide about group size, dates, and any other details, the better each Windjammer can assist you in planning!
