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Sunset Sail with Entertainer Deanna Dove playing guitar

Sunset Sail with Deanna Dove

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

Deanna Dove, Island Girl, Americana Roots Rock artist singing the stories of her life and times on the Chesapeake Bay and Patuxent River. If you like the "salt life" then these songs will speak to you. Deanna's deep and powerful voice takes control of these upbeat, lively, tongue-in-cheek songs. www.deannadove.com facebook/deannadove1    

$48.00

Tickets go on sale 6 days in advance
The Wooden Boat Regatta in Annapolis photo by Kate Gahs

Classic Wooden Boat Regatta

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

Reduced Ticket Price - not including Bagged Lunch (the order has already been placed with our caterer).  Be sure to bring your own lunch to enjoy aboard.  Lunch must be self contained (boxed or bagged) - no buffets or displays will be allowed aboard. Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been ... Read more

$71.00

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Duo The Roadside singing on the schooner

CANCELLED – Sunset Sail with “The Roadside”

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

CANCELLED - BOTH BOATS PRIVATELY CHARTERED The Roadside is a blue's influenced, roots-rock acoustic band that features music from the turn of the century to modern day hits. Band's website: www.theroadsideband.com Band's Facebook Page: www.facebook.com/theroadsideband

$48.00

Tickets go on sale 6 days in advance
Entertainer Ernie Halter

Brunch Sail with Ernie Halter

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

An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, ... Read more

$93.00

Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

Cocktail Cruising

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, 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 4:30pm, return at 6:30pm.  Tickets are $78 per adult with a maximum of 35 guests. Cocktail Cruise Menu: Black Bean Hummus Poblano Pimento Cheese Served with ... Read more

$78.00
Schooner Woodwind Chesapeake Bay Lighthouse Sailing Tours in Annapolis, Maryland

October Lighthouse Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Reduced Ticket Price - not including Bagged Lunch (the order has already been placed with our caterer).  Be sure to bring your own lunch to enjoy aboard.  Lunch must be self contained (boxed or bagged) - no buffets or displays will be allowed aboard. Sail to as many as three different lighthouses on the Chesapeake ... Read more

$86.00

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Entertainer Tyrone Wells sitting on steps

Acoustic Evening Sail with Tyrone Wells

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Schooner Woodwind is pleased to announce the return of TYRONE WELLS to perform aboard the boat for an Intimate, Acoustic Show.  We will cruise to a secluded cove for the performance and then enjoy a sunset sail back to the dock.   This will be Tyrone's fourth time singing and sailing on the Woodwind. It all ... Read more

$120.00
Two gentlemen enjoying beverages and a sunny sail

Brews in the Breeze Lunch Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Reduced Ticket Price - not including Lunch (the order has already been placed with our caterer).  Be sure to bring your own lunch to enjoy aboard.  Lunch must be self contained (boxed or bagged) - no buffets or displays will be allowed aboard. Sail on a lunchtime cruise on the Chesapeake Bay.  Tickets are $69 ... Read more

$69.00

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Great Chesapeake Bay Schooner Race Start

Schooner Race Watch Cruise

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

The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! ... Read more

$91.00
Great Chesapeake Bay Schooner Race Start

Sunrise Schooner Race Watch Cruise

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

A rare sunrise sailing opportunity! Departs Annapolis Waterfront Hotel at 6:30am and returns at 9:30am The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them ... Read more

$74.00

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