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 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

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

Blue Angels Practice Cruise

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

Watch the Blue Angels practice their aero-acrobatics during this special cruise. Depart from Annapolis at 11:00am 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 “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

May Lighthouse Cruise

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

Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Depart Annapolis at 11:30am, return at 3:30pm includes soft drinks and snacks, $77 per person, $50 per child. Maximum of 35 ... Read more

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 10:00am 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

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

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 5:30pm, return at 7:30pm.  Tickets are $61 per adult with a maximum of 35 guests. ... Read more

$61.00