Sunset Sail with Eastport Oyster Boys

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Appointed the Musical Goodwill Ambassadors by the City of Annapolis and the Maritime Republic of Eastport, the Eastport Oyster Boys love to share their musical celebration and stories of life on the Chesapeake Bay. For over two decades they have educated, amused and delighted thousands with their wit, wisdom and special message of stewardship and ... Read more

Sunset Sail with Ship’s Company

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

This jolly band of merrymakers has been seen and heard all up and down the east coast of the United States. Our chanteymen perform at living history events, music festivals, private parties and many other settings. www.shipscompany.org https://www.facebook.com/pages/Ships-Company-Chanteymen/69814067368

Sunset Sail with Ken Wenzel

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Nominated for no less than FOUR Washington Area Music Awards at the 2016 30th Annual WAMMIES – for Best Roots-Rock Vocalist, Best Roots-Rock Instrumentalist, Best Roots-Rock Group (Ken Wenzel & Cross Kentucky) and Best Roots-Rock Record (...Beneath Potomac Skies) – singer/songwriter/saxophonist Ken Francis Wenzel has come into his own as one of the DC/MD/VA region’s ... Read more

Classic Wooden Boat Regatta

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

DISCOUNTED RATE for NO LUNCH OPTION, this rate does not include the bagged lunches. We encourage you to bring a prepackaged lunch to enjoy during the sail (no buffets or displays will be allowed) Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been invited to participate in the race in the "Spirit of ... Read more

Sunset Sail with Chris Diller

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Its all heart playing music from head to toe. ​ The energetic one-man-band has been on the road since 2014 after the release the self titled EP which includes the highly requested "Federal Hill." The music has found new life - the sound of a new wave of beach americana and alt-country music buzzing in ... Read more

October Lighthouse Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Depart Annapolis at 11:30am, return at 3:30pm, includes bagged lunch, soft drinks and snacks, $130 per adult. Maximum of 24 ... Read more

$130.00

Cocktail Cruising

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sail away with great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail.  Depart Annapolis at 4:00pm, return at 6:00pm.  Tickets are $95 per adult with a maximum of 24 guests. Zoned Seating Pricing ~ Limited Capacity (24 person max): ... Read more

$95.00

Annapolis Parade of Schooners & Sail

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Come aboard the Woodwind for a beautiful sail that ends with a Parade of Schooners in Annapolis Harbor. Schooner Lynx, When and If, Adventurer, Sally B, both Woodwinds and the Adventure will hopefully be participating.  Local craft beers, wine & bubbly available for purchase aboard.  Depart Annapolis at 11:00am, return at 1:00pm.  Tickets are $65 ... Read more

Schooner Rally 2020

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Come aboard the Woodwind for a beautiful sail amongst all the schooners that are currently in Annapolis for the Parade of Schooners. We will all be sailing in the company of these other schooners for a fun, 2-hour sail.  Local craft beers, wine & bubbly available for purchase aboard.  Depart Annapolis at 1:30pm, return at ... Read more

Halloween Brunch Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Put on your favorite costume and join the Woodwind crew for a Spook-tacular Brunch Cruise!  Cruise includes brunch (individually bagged for each guest), 2 adult beverages per person and tax. Cruise departs the Annapolis Waterfront Hotel at 11:00 am and returns at 1:00 pm. Zoned Seating Pricing ~ Limited Capacity (24 person max): 2 person ... Read more

$95.00