Loading Events

Upcoming Events

Events List Navigation

July 2016

Everything Local Dinner Cruise

July 31 @ 6:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

Enjoy our “Everything Local” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can purchase locally or grow yourself. Tickets are $109 per adult and include three course dinner, 3 drink vouchers, and unlimited soda & water. Maximum 35 guests. Menu TBD

Find out more »
August 2016

Sunset Sail with Deanna Dove

August 4 @ 6:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

Growing up on Broomes Island, Maryland, Deanna Dove (a.k.a., Island Girl) is best known for her compositional writing style about her lifelong experiences on the Chesapeake Bay. Dove’s songs include elements of rock, pop, alt-country, blues and gospel, melding together with her vocal overtones to form a distinctively engaging roots rock style. Dove is a powerful, multi-talented singer-songwriter, guitar playing, beat making, one woman show. Dove, at age 12, played electric guitar and sang gospel harmonies with the Dove sister’s…

Find out more »

August Lighthouse Cruise

August 14 @ 11:30am
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

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 bagged lunch, soft drinks and snacks, $93 per adult, $56 per child with child’s lunch. Maximum of 35 guests         Gourmet Bagged Lunch includes: Gourmet Sandwich (choose one) Grilled fajita spiced chicken with lettuce,…

Find out more »

Sunset Sail with Don Shappelle

August 18 @ 6:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

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 Shappelle accompanies his songs on 6 & 12 string guitar and harmonica. He has performed up and down the Chesapeake bay in many settings over the…

Find out more »

Brunch Sail with Ernie Halter

August 21 @ 10:00am
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Halter has released 6 albums, toured 50 states, and seen his popularity swell to more than 510,000 Twitter followers, 12,000 YouTube subscribers, and nearly 10,000 Facebook ‘Likes’. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail…

Find out more »

Sunset Sail with Brandon Hardesty

August 25 @ 6:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

Bumpin Uglies are a polished three piece hailing from Annapolis, MD. Known for their focused approach to not taking life too seriously, Bumpin Uglies have earned a reputation as one of the hardest working bands in the land, constantly touring and perfecting their distinct sound. They also have a knack for poking fun where fun should be poked, conjoined with a musical earnestness that is clear all the way through their catalog full of honest songs that cut right to…

Find out more »

August Wine in the Wind

August 28 @ 2:00pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

Join us for a three hour sail around the Bay sampling wonderful wines: The Estate of Louis Latour, Burgundy with Timothe Cousins.  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 paired bite (we call them magnificent morsels) to go with each wine.  After the sampling, there will be a small afternoon appetizer buffet that…

Find out more »
September 2016

Sunset Sail with Eastport Oyster Boys

September 1 @ 5:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

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 special message of stewardship and appreciation for the Bay and its unique maritime culture and history. Anyone who loves being on or near the water…

Find out more »

Sunset Sail with Ship’s Company

September 8 @ 5:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

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 portray the musical part of nautical life in the 1700s and 1800s. Many of their songs originally set a pace to keep ship crews rowing…

Find out more »

Old Westminster Winery Dinner Cruise

September 11 @ 5:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
+ Google Map

Captain Jen fell in love with this winery’s location, wine and people that work at Old Westminster Winery at their grand opening in 2013. The proprietors, the Baker family, are raising a reputation for crafting wines of intrigue. The property is situated on a rocky plot of ground just south of historic Westminster, MD, where patrons enjoy the ambiance of the vineyard and a hands-on winery producing exceptional wines. The Baker family believes this winery represents the American Dream: strong…

Find out more »
+ iCal Import Listed Events

© Copyright 2016. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.