Friday Night Sailor’s Delight Cocktail Cruise

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

Sail away on one of our first sunset sails of the season. Enjoy 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 5:30pm, return at 7:30pm.  Tickets are $61 per adult with a maximum of 35 guests. ... Read more

$61.00

Port City Beer Tasting Paired with Oysters

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

Join us for a 2-hour sail tasting four delicious beers from Port City Brewing Company paired with outstanding oysters from the Chesapeake Bay.  A brewery representative will be on hand to teach how to taste beer in addition to what you are tasting with the oysters.  Brad from War Shore Oysters will be on hand to talk about how he farms ... Read more

CANCELLED – 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

Sunset Sail with Victoria Vox

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

Victoria Vox has taken the artful sound of the ukulele into eclectic new directions. Her music ranges from upbeat and clever to honest and moving, while incorporating her signature “mouth trumpet” and occasionally singing in French. Her whimsical songwriting uses a unique palette of sounds and beats that delight audiences of all ages. Her songs ... Read more

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

(Rescheduled to August 6) 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

Wedding Crashers 10th Anniversary Brunch Sail

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

Can you believe its been 10 years?  Enjoy a movie themed brunch and 2 adult beverages.  Join Captain Jen as she tells tales about the filming of the movie and share your favorite memories of this cult classic. Food includes crab cakes (of course), meatloaf & egg sliders, scallops wrapped in bacon and other fun themed items. ... Read more

CANCELLED – 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 Victoria Vox

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

Victoria Vox has taken the artful sound of the ukulele into eclectic new directions. Her music ranges from upbeat and clever to honest and moving, while incorporating her signature “mouth trumpet” and occasionally singing in French. Her whimsical songwriting uses a unique palette of sounds and beats that delight audiences of all ages. Her songs ... Read more

Sunset Sail with Ken Wenzel

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

With the brand -new release of  “…Beneath Potomac Skies”  -  a 12-song, full-band collection of moments and memories culled from time spent in Washington DC, and many other locales – singer/songwriter/saxophonist Ken Francis Wenzel is eager to introduce his own roots-rock, country jazz-tinged take on love, learning, and life in contemporary America. Featuring several guest ... Read more