Sunset Sail with Don Shappelle

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

Facebook LIVE stream of this Event Singer-songwriter and guitarist Don Shappelle has a positive energy and vibe that gets an audience singing along with their upbeat songs.  From traditional folk to songs about the Chesapeake Bay Don has a repertoire of music that everyone will enjoy while sailing aboard the magnificent Woodwind, and virtually. www.donshappellemusic.com ... Read more

Eastport Oyster Boys

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

Facebook LIVE stream of this Event 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 ... Read more

Sunset Sail with Stefan Heuer Music

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

Facebook LIVE stream of this Event Stefan Heuer is a signature Breedlove artist residing in Annapolis, MD. Heuer blends elements of Motown, Soul, and RnB in his original and cover music. His debut EP entitled "Jungle Dreams" is a sonic portrayal of his journey through losing a loved one. Stefan frequently performs all over the ... Read more

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

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

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

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

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

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    

Sunset Sail with “R’n’R”

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

Capt Ron and Ray have been playing together for over a year in the Annapolis music groups Burlwood and Deep Fried Ribs. Their unique takes on classic blues and country tunes make you want to kick back and enjoy the music. The shared love of artists like the Allman Brothers, Waylon Jennings and Johnny Paycheck ... Read more