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Duo The Roadside singing on the schooner

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. Band's website: www.theroadsideband.com Band's Facebook Page: www.facebook.com/theroadsideband

$46.00

Tickets go on sale 6 days in advance
Jason Ager entertainer holding a tuba at a train yard

Sunset Sail with Jason Ager

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

Jason Ager is a dedicated father, a passionate college professor, and a hyper-literate original songwriter. Balancing a PhD in German Literature with a few days a week as a stay-at-home dad, Jason still plays more than 100 shows a year in the Mid-Atlantic region and beyond. On his third album, Porchlight, Ager’s talent as a ... Read more

$46.00

Tickets go on sale 6 days in advance
Fathers Day Sailing Cruises Annapolis MD

Father’s Day Brunch

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

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche lorraine squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and ... Read more

$90.00
Mike and Kelly Lange singing on the Woodwind

Sunset Sail with Mike & Kelly Lange

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

Mike and Kelly Lange are a husband and wife ukulele duo.  Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach. Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has ... Read more

$46.00
Entertainer Dirk Schwenk with guitar

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

$46.00

Tickets go on sale 6 days in advance

Celebrate the 4th of July in Annapolis enjoying a sunset sail complete with fireworks from the water

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 6:30 pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the ... Read more

$89.00
Eastport Oyster Boys jammin' on the Chesapeake Bay

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

$46.00

Tickets go on sale 6 days in advance
Tony Lucca

Brunch Sail with Tony Lucca

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

Back for a 5th performance on the Schooner Woodwind! An Intimate, Acoustic Show with TONY LUCCA aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Tony Lucca captured America’s hearts in 2012 as the Team Adam finalist on NBC’s hit TV show “The ... Read more

$107
Mike and Kelly Lange singing on the Woodwind

Sunset Sail with Mike & Kelly Lange

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

Mike and Kelly Lange are a husband and wife ukulele duo.  Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach. Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has ... Read more

$46.00

Tickets go on sale 6 days in advance
Heavy Seas vs. Flying Dog Breweries both schooners racing

Maryland’s Brewer’s Cup Race

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

Join Heavy Seas and Union Craft Breweries aboard the Seventh Annual “Maryland’s Brewer’s Cup”. Buy a ticket aboard your favorite brewery’s boat!  Union Craft vs. Heavy Seas! Battle of the Baltimore Brews. During the race, passengers (guest crew) will be able to participate in helping to sail the boat, where appropriate, of course. This will be ... Read more

$46.00