Questions

Before you come aboard.

The things people ask most, answered plainly. Anything else, call or email the crew.

Where and when do you sail?

Boca Raton, Florida, from November 1 through May 31, and Annapolis on the Chesapeake Bay from June 1 through October 31. FareHarbor shows the dates that are open.

How do I book?

Use any “Check dates” button. It opens Windsong’s FareHarbor booking page, which has the current charter options, times, prices and checkout. The crew follows up with boarding details.

How many people can come?

Up to 12 guests. It’s a private charter, so everyone aboard is someone you invited.

What’s included?

The captain, two crew and fuel. Paddleboards, a floating dock, floats, a hammock, inflatable bow chairs, a gas grill, hot freshwater showers, a drink fridge, a blender, ice, water, a cooler and Bluetooth sound are all aboard. Gratuity is not included.

Can we bring food and drinks?

Yes. Bring whatever you like to eat and drink; we supply ice, water and a large cooler. If you would rather have the boat stocked before you arrive, ask the crew about concierge provisioning.

Can we celebrate something?

Please do: birthdays, bachelorette parties, family outings, even weddings. Tell the crew what you are planning and they will help with the details before you book.

Will we actually sail?

Yes, when the wind cooperates. Catamarans sail flat and steady, and if you ask, the captain will happily hand you the helm for a lesson or two.

What if the weather turns?

Weather and water conditions affect every charter, and the captain makes the call on safety. Read the weather and cancellation terms shown with your FareHarbor booking before you pay.

Are the dogs aboard?

Frankie and Sammie, our French bulldogs, are part of the crew. If anyone in your group has allergies or concerns, tell us when you book.

Do you teach sailing?

Yes: a standard sailing lesson, a four-day liveaboard course and a three-day sailing vacation. These are booked directly with the crew, who confirm dates, inclusions and the final price.