Saturday 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 5:30 pm, return at 7:30 pm.  Tickets are $78 per adult with a maximum of ... Read more

$78.00

April Lighthouse Cruise

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. Sail to as many as three different lighthouses on the Chesapeake ... Read more

Sunset Sail with Stefan Heuer Music

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

Stefan Heuer is a singer songwriter residing in Annapolis, Maryland. His original music as a solo performer has reached ears all over the world. Stefan performs at venues in Annapolis and around the DMV area. Stefan mirrors elements of folk, but his original music holds a strong foundation of blues and soul.   Band's Website ... Read more

Brunch Sail with Tony Lucca

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

Back for a 7th 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 is a Nashville-based singer/songwriter whose catalog of music runs the gamut from soul-infused pop to tear-jerker ... Read more

$111.00

Sunset Sail with Ship’s Company

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

Ship's Company is a living history organization dedicated to the preservation of the American maritime heritage. They interpret many aspects of maritime life between 1775 and 1865. For more than a decade, the Ship’s Company Chanteymen have shared sea salts' songs with tens of thousands, all over the East Coast. Aside from being scurvy-free, they ... Read more

Mother’s Day Brunch

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

Our Mother’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 $94 per person, $54 per child. Maximum 35 guests.             Mother's Day Brunch Menu: Bacon, Ham, Caramelized Onion and ... Read more

$94.00

Sunset Sail with Ken Wenzel

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

With the 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 appearances from ... Read more

Dodon Vineyards Wine Dinner

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

Established in 2007, the vineyards at Dodon are fortuitously situated on rolling hills just south of Davidsonville, Maryland. When they began their first experiments with 150 vines, the goal was clear: to practice sustainable agriculture and produce exceptional wines. As ninth generation custodians of this historic farmland, and as demanding winemakers, they are committed to using ... Read more

$113.00

Blue Angels Performance Cruise

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

Watch the Blue Angels perform their aero-acrobatics during this special cruise. Depart from Annapolis at 11:30 am and return at 3:30 pm. Typically, we sail for a 2 hour cruise and then we anchor up front in the "spectator zone" for the best view of the performance which usually happens around 2:00 pm. Advanced ticket ... Read more

$110.00

Sunset Sail with Don Shappelle and Don Sennett

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

Don Shappelle is a singer/songwriter and guitarist who grew up on the banks of the mighty Susquehanna River and sings about the people,history and boats of the Chesapeake bay and it's many beautiful rivers.  Sailing songs and sing-alongs are part of Don's repertoire and always get an audience involved.  Performing with Don Shappelle is bassist ... Read more