Saturday Night Sailor’s Delight Cocktail Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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
Blue Angels Performance Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDWatch 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
Fireworks Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin 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
Classic Wooden Boat Regatta
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDReduced 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. Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been ... Read more
Cocktail Cruising
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDSail away with 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 4:30pm, return at 6:30pm. Tickets are $78 per adult with a maximum of 35 guests. Cocktail Cruise Menu: Black Bean Hummus Poblano Pimento Cheese Served with ... Read more
Schooner Race Watch Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDThe Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! ... Read more
Sunrise Schooner Race Watch Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDA rare sunrise sailing opportunity! Departs Annapolis Waterfront Hotel at 6:30am and returns at 9:30am The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them ... Read more
Classic Wooden Boat Regatta
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDISCOUNTED RATE for NO LUNCH OPTION, this rate does not include the bagged lunches. We encourage you to bring a prepackaged lunch to enjoy during the sail (no buffets or displays will be allowed) Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been invited to participate in the race in the "Spirit of ... Read more
Cocktail Cruising
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail away with 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 4:00pm, return at 6:00pm. Tickets are $95 per adult with a maximum of 24 guests. Zoned Seating Pricing ~ Limited Capacity (24 person max): ... Read more
Annapolis Parade of Schooners & Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCome aboard the Woodwind for a beautiful sail that ends with a Parade of Schooners in Annapolis Harbor. Schooner Lynx, When and If, Adventurer, Sally B, both Woodwinds and the Adventure will hopefully be participating. Local craft beers, wine & bubbly available for purchase aboard. Depart Annapolis at 11:00am, return at 1:00pm. Tickets are $65 ... Read more