Schooner Woodwind

2025 Sailing Season Has Ended, we will start sailing again mid-April 2026!

Rates and Schedule

2026 SAILING RATES
FOR 2-HOUR SAILS
Weekday
Daytime
Sunday &
Sunset
Saturday &
Holidays
All Guests  $76.10 per person

$65.77 (Ticket)
+
$3.75 (Booking Fee)
+
$6.58
(A&A Tax)

 $79.55 per person

$68.91 (Ticket)
+
$3.75 (Booking Fee)
+
$6.89
(A&A Tax)

 $84.20 per person

$73.14 (Ticket)
+
$3.75 (Booking Fee)
+
$7.31
(A&A Tax)

Includes a complimentary soda or water.

Everyone has loved having more room, so we are staying at just 30 people per cruise (instead of 48).

Tickets go on sale 6 days prior to the date you want to sail.

2026 Public Sailing Schedule

April 11 – April 21

Seven Days a Week

12:30 pm – 2:30 pm
3:00 pm – 5:00 pm
5:30 pm – 7:30 pm (Sunset Sail) *
* Friday, Saturday & Sunday only

April 22 – May 8

Seven Days a Week

12:30 pm – 2:30 pm
3:00 pm – 5:00 pm
5:30 pm – 7:30 pm (Sunset Sail)

May 9 – August 23

Seven Days a Week

11:00 am – 1:00 pm
1:30 pm – 3:30 pm
4:00 pm – 6:00 pm
6:30 pm – 8:30 pm (Sunset Sail)

August 24 – September 27

Seven Days a Week

10:00 am – 12:00 pm
(Saturday & Sunday Only)
12:30 pm – 2:30 pm
3:00 pm – 5:00 pm
5:30 pm – 7:30 pm (Sunset Sail)

September 28 – October 4

Seven Days a Week

11:00 am – 1:00 pm
1:30 pm – 3:30 pm
4:00 pm – 6:00 pm

October 5 – October 21

Limited sailing cruises during this time. Detailed view of our Sailing Cruises during this time. October Sailing

Private Charters are available

October 15 – October 18 we will be sailing from the US Sailboat Show More Information

October 22 – October 31

Seven Days a Week

11:00 am – 1:00 pm
1:30 pm – 3:30 pm
4:00 pm – 6:00 pm

Schooner Woodwind sails rain or shine

Once tickets are purchased, there are no refunds or exchanges.

We sail rain or shine, unless the captain cancels the cruise due to unsafe conditions. We offer complimentary rain ponchos in case of rain.

Please Remember:

  • Only soft-soled shoes are allowed aboard.
  • All departures are from the docks at the Annapolis Waterfront Hotel across from the City Dock (unless otherwise noted). Rates and schedules are subject to change without notice. Our schedule may vary due to weather, special events, and group charters.
  • Tickets go on sale six days prior to the date you want to sail.   Please call our business office at 410-263-1981.
  • Up-to-date schedule information is available by clicking here or calling (410) 263-7837.
410-263-7837