Share a sunset sail by the seat, or take Windrose or Kestrel for your party alone.
Four charters
Shared, by the seat
5:00 to 8:00 pm · Friday to Sunday · up to 12 guests
Join a skippered sail with other guests: out past Eastport, anchor for the sunset, back by eight. The easiest way to try the Bay.
$65 a seat
Private
11:30 am to 2:30 pm · any day · up to 6 guests
Windrose for your party alone, lunch from the galley served at anchor in Whitehall Bay, a swim if the water is warm.
$890 the boat
Private
10:00 am to 4:00 pm · any day · up to 6 guests
Six hours to go wherever the wind allows: Thomas Point, the Rhode River or St. Michaels for lunch ashore.
$1,650 the boat
Private
Saturday 10:00 am to Sunday 4:00 pm · up to 4 guests
A night at anchor off St. Michaels on Kestrel, supper cooked aboard and breakfast in the cockpit.
$2,400 the boat
Shared or private
A shared sail is the easy way to try the Bay. A private charter is the boat, the crew and the day arranged around you.
Shared sail
Private charter
Who is aboard
Shared sail
You and up to 11 other guests
Private charter
Your party only, up to 6
When
Shared sail
Friday to Sunday, 5:00 pm
Private charter
Any day, the times you choose
Route
Shared sail
Set by the skipper
Private charter
Planned with you
Food and drink
Shared sail
Bring your own
Private charter
From the galley menu, or bring your own
Price
Shared sail
$65 a seat
Private charter
From $890 the boat
“The best four hours of our summer, and the price on the website was the price at the dock.”
Ana P. · Sunset sail for two, August
This weekend
Seats are held for 24 hours when you book; the dock office confirms by phone.
Fri
Oct 16
Sunset sail
5:00 pm
4 of 12 seats left
Sat
Oct 17
Long lunch
11:30 am
Booked
Sat
Oct 17
Sunset sail
5:00 pm
7 of 12 seats left
Sun
Oct 18
Full day
10:00 am
Open to book
Sun
Oct 18
Sunset sail
5:00 pm
2 of 12 seats left
