Things to Do Boating

Annapolis Sailing Cruises: Schooner Woodwind

80 Compromise St., Annapolis, MD 21401
(410) 263-7837
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About Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event cruises, too. The Woodwind and Woodwind II offer a real Chesapeake sailing experience for public sails and private events. Buy a ticket, or privately rent the entire boat. Fun, team match racing, corporate outings, crab feasts and catered sunset sails. Sailing is a great way to celebrate birthdays, reunions, and a wedding weekend. Departs from the downtown, Annapolis Waterfront Hotel.

Attraction

General

- Family Friendly

- Open For Business


Business Continuity

General

- Family Friendly

- Open For Business


Schooner Race Watch Cruise
Annapolis Waterfront Hotel Dock

Schooner Race Watch Cruise

October 15, 2020

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 are at least near 100+ feet. This is going to be incredible. Join the fun! They will be racing to the Norfolk area, we will cheer them on till it’s time to go in. We will be under sail with the schooners (and yes you’ll be sailing on one too). We will not cross the starting line, but we will be sailing around them all as they come down from Baltimore. The sail includes bagged lunch, soft drinks, and bottled water and tax.  Our cash bar includes a selection of Craft Beer, Wine & Bubbly! Gourmet Bagged Lunch includes: Adult Bagged Lunches include dill potato salad, charred corn, and fennel slaw & a Cowboy cookie. Sandwiches (Choose 1 per adult ticket) Cranberry Pecan Chicken Salad Wrap Honey Ham with Boursin cheese, rosemary mustard & arugula on a multigrain baguette Vegetarian Hearts & Greens Wrap with artichoke hearts, power greens, almonds & tarragon mayo Child’s Bagged Lunch includes a cluster of grapes & Cowboy cookie Sandwiches served on thick egg bread (Choose 1 per child ticket) Almond Butter & Homemade Blueberry-Pomegranate Jam Turkey & Cheese Departs Annapolis at 10:30 am & returns at 1:30 pm at the Annapolis Waterfront Hotel,  80 Compromise Street, Annapolis MD 21401 Tickets are $90 per adult/$54 per child under 12 years, with a maximum of 35 guests.

Acoustic Brunch with Tony Luca
Annapolis City Marina

Acoustic Brunch with Tony Luca

October 4, 2020

Join us for an intimate, all-ages acoustic show with Tony Lucca aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will perform for over an hour while at anchor in a secluded cove. After the performance, we will set sail on the 74-foot, classic wooden schooner. Raise the sails, steer the boat, sit back, relax and meet Tony while sailing the Bay. Tony Lucca is a Nashville-based singer/songwriter whose catalog of music runs the gamut from soul-infused pop to tear-jerker folk balladry. His music has been featured in shows like “Parenthood,” “Friday Night Lights,” “Felicity,” and “Brothers and Sisters.” He was a frequent member of the house band on “Last Call with Carson Daly,” where he performed alongside then fellow up-and-comers like Kamasi Washington, Zane Carney, Brian Wright, and stalwarts like Marc Ford and Cordovas frontman, Joe Firstman. In 2012, Lucca took third place on NBC’s “The Voice,” earning himself a record deal with coach Adam Levine’s 222 Records. He has toured alongside such artists as Sara Bareilles, Jonny Lang, Maroon 5, Kelly Clarkson, Rachael Yamagata, Emerson Hart, and Gabe Dixon. Lucca currently resides in Nashville with his wife, Rachel, their kids Liam and Sparrow, along with their dog Apple. Enjoy a light brunch as we cruise to a secluded cove. Mimosas and Bloody Marys will be available from our cash bar filled also with local craft beer and wine. Acoustic Brunch Cruise Menu: Bacon & Swiss Quiche Pinwheel Spinach & Pesto Quiche Pinwheel Seasonal Fruit Salad  Pumpkin Bread Have any old instruments you want to go to a good home? We have partnered with Music 4 More, a 501(c)3 charity organization that launched in Baltimore in 2007 (now based in Annapolis, MD), and we will have a drop off that day for any instruments you would like to donate! Their primary focus is collecting instrument donations, repairing and reintroducing them into struggling schools and music therapy programs for veterans. Since its launch, Music 4 More has donated over 700 instruments to schools and VA hospitals in 13 states.   Music 4 More accepts instruments in any shape (Currently we are not taking donations of pianos/organs or sheet music). Any instruments that are deemed unrepairable will be used for art projects to sell/auction for fundraising activities.  For more information www.music4more.org We do sail rain or shine. If the musicians cannot play due to the weather, but we can still sail- we will refund the performance part of the ticket. There are no assigned seats. There are no refunds or exchanges unless the captain cancels the cruise due to unsafe conditions. Due to the Annapolis Power Boat Show, this sail departs from the Annapolis City Marina Departs Annapolis at 11:30 am & returns at 2:30pm at the Annapolis City Marina, 410 Severn Avenue, Annapolis, 21403 Tickets are $111 per adult, with a maximum of 35 guests

October Lighthouse Cruise
Annapolis City Marina

October Lighthouse Cruise

October 3, 2020

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. Enjoy lunch on board. Adult Bagged Lunch includes: Dill potato salad, charred corn, and fennel slaw & a Cowboy cookie. Sandwiches (Choose 1 per adult ticket) Cranberry Pecan Chicken Salad Wrap Honey Ham with Boursin cheese, rosemary mustard & arugula on a multigrain baguette Vegetarian Hearts & Greens Wrap with artichoke hearts, power greens, almonds & tarragon mayo Child Bagged Lunch Includes A cluster of grapes & Cowboy cookie Sandwiches served on thick egg bread (Choose 1 per child ticket) Almond Butter & Homemade Blueberry-Pomegranate Jam Turkey & Cheese Due to the Annapolis Power Boat Show, this sail departs from the Annapolis City Marina Departs at 11:30 am & returns at 3:30 pm at the Annapolis City Marina,           410 Severn Avenue, Annapolis MD 21403 Tickets are $100 per adult/$62 per child under 12 years, with a maximum of 35 guests.

Classic Wooden Boat Regatta
Annapolis Waterfront Hotel Dock

Classic Wooden Boat Regatta

September 20, 2020

Participate in the Classic Wooden Boat Regatta. The Woodwinds’ have been invited to participate in the race in the “Spirit of Tradition Class”.  The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with a pursuit style race. Each boat has a rating, and by the rating, they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats to win the regatta. This will be an amazing trip for photography (hint B&W or sepia tone) of these old, gorgeous boats.  The participating boats will be on display on Saturday (other than the Woodwinds). This is going to be a fun, challenging race! Join the crew! Ticket Price includes bagged lunch, soft drinks, and bottled water. Our cash bar includes a selection of Craft Beer, Wine & Bubbly! Adult Bagged Lunch includes: Dill potato salad, charred corn, and fennel slaw & a Cowboy cookie. Sandwiches (Choose 1 per adult ticket) Cranberry Pecan Chicken Salad Wrap Honey Ham with Boursin cheese, rosemary mustard & arugula on a multigrain baguette Vegetarian Hearts & Greens Wrap with artichoke hearts, power greens, almonds & tarragon mayo Child Bagged Lunch Includes A cluster of grapes & Cowboy cookie Sandwiches served on thick egg bread (Choose 1 per child ticket) Almond Butter & Homemade Blueberry-Pomegranate Jam Turkey & Cheese Departs at 11:00 am & returns at 2:30 pm at the Annapolis Waterfront Hotel, 80 Compromise Street Tickets are $90 per adult/$54per child under 12 years, with a maximum of 47 guests.

Acoustic Brunch with Michael Tolcher
Annapolis Waterfront Hotel Dock

Acoustic Brunch with Michael Tolcher

August 30, 2020

Join us for an intimate, all ages acoustic show with Michael Tolcher aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Michael Tolcher will perform for over an hour while at anchor in a secluded cove. Michael Tolcher is an American singer/songwriter that blends southern, soul, improv, sincerity and comedy all together to form his art. Best experienced at his live show — he captures his audience and leads them through a vocal adventure of artistic, meaningful, musical expression. He’s a Georgia Boy having grown up just south of Atlanta – and still resides just West of the city. He travels for about 30-40% of his time these days – mostly in the US. He calls it lifestyle touring: “I like to be where I want to be, doing what I want to do” Enjoy a light brunch as we cruise to a secluded cove. Mimosas and Bloody Marys will be available from our cash bar filled also with local craft beer and wine. Acoustic Brunch Cruise Menu: Bacon & Swiss Quiche Pinwheel Spinach & Pesto Quiche Pinwheel Seasonal Fruit Salad  Pumpkin Bread Have any old instruments you want to go to a good home? We have partnered with Music 4 More, a 501(c)3 charity organization that launched in Baltimore in 2007 (now based in Annapolis, MD), and we will have a drop off that day for any instruments you would like to donate! Their primary focus is collecting instrument donations, repairing and reintroducing them into struggling schools and music therapy programs for veterans. Since its launch, Music 4 More has donated over 700 instruments to schools and VA hospitals in 13 states.   Music 4 More accepts instruments in any shape (Currently we are not taking donations of pianos/organs or sheet music). Any instruments that are deemed unrepairable will be used for art projects to sell/auction for fundraising activities.  For more information www.music4more.org We do sail rain or shine. If the musicians cannot play due to the weather, but we can still sail- we will refund the performance part of the ticket. There are no assigned seats. There are no refunds or exchanges unless the captain cancels the cruise due to unsafe conditions. Departs Annapolis at 11:30 am & returns at 2:30 pm at the Annapolis Waterfront Hotel,  80 Compromise Street, Annapolis MD 21401 Tickets are $99 per adult, with a maximum of 35 guests

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

August 26, 2020

The Woodwind will be out on the Bay to watch the Annapolis Yacht Club's Wednesday Night Races.  We will be able to sail as safely as possible to the boats, as they race against each other.  Come join us for a fun sail and a great sunset experience.  (We are limited to 24 passengers per sail in set Zoned Seating Areas.  All sales are by credit card only. Purchase your tickets online starting 6 days prior to the sail date at www.schoonerwoodwind.com )

Wind In The Wind Cruise
Annapolis Waterfront Hotel Dock

Wind In The Wind Cruise

August 9, 2020

Join us for a two-hour sail around the Chesapeake Bay while sampling wonderful wines The representative from a winery will introduce you to four special wines while we are under sail. 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 paired bite (we call them magnificent morsels) Includes a take-home, boat friendly, wine glass by Go Vino with the Woodwind’s logo on it. You will be able to raise the sails, steer the boat or just sit back and relax with your wine and food.  Wines and menu to be determined Departs Annapolis at 4:00 pm & returns at 6:00 pm at the Annapolis Waterfront Hotel,  80 Compromise Street.  Tickets are $83 per adult, with a maximum of 40 guests.

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

August 5, 2020

The Woodwind will be out on the Bay to watch the Annapolis Yacht Club's Wednesday Night Races.  We will be able to sail as safely as possible to the boats, as they race against each other.  Come join us for a fun sail and a great sunset experience.  (We are limited to 24 passengers per sail in set Zoned Seating Areas.  All sales are by credit card only. Purchase your tickets online starting 6 days prior to the sail date at www.schoonerwoodwind.com )