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 11:30am and return at 3:30pm. Advanced ticket purchase required, includes box lunch, soda, and snacks; $93 per person, $56 per child w/child's lunch. Maximum 40 guests.       Gourmet Bagged Lunch includes: Gourmet Sandwich (choose one) Grilled fajita spiced ... Read more

$93.00

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

Acoustic Brunch Sail with Gareth Asher

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

An Intimate, Acoustic Show with GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. As a touring artist, Asher has shared the stage with Shawn Mullins, Glen Phillips(o/ Toad the Wet Sprocket), Emerson Hart, Angie Aparo, Corey Smith, Sister Hazel, Collective Soul, 3 Doors Down, Steve ... 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  

June Wine in the Wind: A Tour of Bordeaux

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

Join us for a three hour sail around the Bay sampling wonderful wines: A tour of Bordeaux with Patrick De Abreu.  This representative from the winery will introduce you to these special wines. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly ... Read more

$109.00

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

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 10:00am and returns at 1:00pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche lorraine squares, baked citrus salmon with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $88 per person, ... Read more

$88.00

Acoustic Sunset Sail with Paul Pfau

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

An Intimate, All Ages Acoustic Show with PAUL PFAU aboard the Schooner Woodwind for a concert on a beautiful sailing boat. Paul Pfau (rhymes with "wow") is an award-winning singer-songwriter living in Nashville, TN. After graduating from college with an economics degree in 2010 he decided to forgo the 9 to 5 for a career as ... Read more

$63.00

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