Sunset Sail with “The Roadside”

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

The Roadside is a blue's influenced, roots-rock acoustic band that features music from the turn of the century to modern day hits. Bringing over 40-years of musical experience together, The Roadside Show is the latest musical venture for Robert Nolan and Randy Lusk. Both are transplants to Maryland, having lived and jammed in Alaska, New ... Read more

Sunset Sail with Don Shappelle

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

Don Shappelle sings and writes many songs about the Chesapeake bay,it's people,it's boats and the many rivers that flow into the bay. Don grew up on the banks of the mighty Susquehanna River so many of his songs are influenced by that great river. Don also performs sailing and water oriented songs by other artists.Don ... Read more

Sunset Sail with Crab Alley Lite

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

Crab Alley founders Jeff Holland and Janie Meneely will join up for a Woodwind cruise and regale the crew with their original songs of the Bay and beyond. Serious or saucy, their songs shed light on recreational boating as well as Chesapeake traditions here on the Bay. www.janiemeneely.com  

Sunset Sail with “The Roadside”

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

The Roadside is a blue's influenced, roots-rock acoustic band that features music from the turn of the century to modern day hits. Bringing over 40-years of musical experience together, The Roadside Show is the latest musical venture for Robert Nolan and Randy Lusk. Both are transplants to Maryland, having lived and jammed in Alaska, New ... Read more

Sunset Sail with Eastport Oyster Boys

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

Recognized as the City of Annapolis and the Chesapeake Bay’s Musical Goodwill Ambassadors The Eastport Oyster Boys love to share their musical celebration of life on the shores of the Chesapeake and its scenic rivers with audiences of all ages. For two decades they have educated, amused and delighted thousands with their wit, wisdom and ... Read more

Sunset Sail with Dirk Schwenk

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

Dirk Schwenk is an award winning singer-songwriter from the great state of Maryland. His formal training includes years of clarinet and symphonic band, but he found rock and roll as a late-addition bass player in the High School talent show, and never went back. He has been singing, playing guitar and songwriting ever since, and ... Read more

Sunset Sail with Calico Jenny

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

From pirates to Point Lookout, the music of Janie Meneely largely celebrates the maritime history, characters and traditions of the Chesapeake Bay. Her songs ramble between the raucous ruminations of ne’er-do-well sea captains to more thoughtful ballads about the people who make a living “working” the water. www.janiemeneely.com

Fireworks Cruise

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

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15pm fireworks display and return to the dock after the show. Tickets ... Read more

$84.00

Sunset Sail with Brandon Hardesty

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

Bumpin Uglies are a polished three piece hailing from Annapolis, MD. Known for their focused approach to not taking life too seriously, Bumpin Uglies have earned a reputation as one of the hardest working bands in the land, constantly touring and perfecting their distinct sound. They also have a knack for poking fun where fun ... Read more

Sunset Sail with “The Roadside”

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

The Roadside is a blue's influenced, roots-rock acoustic band that features music from the turn of the century to modern day hits. Bringing over 40-years of musical experience together, The Roadside Show is the latest musical venture for Robert Nolan and Randy Lusk. Both are transplants to Maryland, having lived and jammed in Alaska, New ... Read more