2024 Sailing Season is coming! See you April 13, 2024!

June Wine in the Wind – Tommasi Family Estates

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Italy.  The representative from the winery will introduce you to four special wines while we are under sail as we explore Italy through the Tommasi Family Estates. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along ... Read more

$81.00

July Wine in the Wind – Masciarelli Family Estate

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from the Masciarelli Family Estate of Abruzzo Italy.  The representative from the 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 ... Read more

$81.00

August Wine in the Wind – Along the Douro

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Portugal.  The representative from the 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 ... Read more

$81.00

September Wine in the Wind – Around the World, New Zealand to California

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from the Goldschmidt Winery, Alexander Valley & Beyond.  The representative from the 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 ... Read more

$81.00

June Wine in the Wind

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Spain.  The representative from the 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 ... Read more

$83.00

July Wine in the Wind

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from France.  Celebrate Bastille Day as the representative from the winery introduces 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, ... Read more

$83.00

August Wine in the Wind

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from South America.  The representative from the 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, ... Read more

$83.00

Wine in the Wind: Women in Wine

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

Join us and sip on women-led wineries who have all broken ground in different ways and challenged the old guard of wine making. We invite you to raise the sails, steer the boat or sit back and relax. Wine Samples paired with "Magnificent Morsels" There will be representatives aboard to talk about the food and ... Read more

$101.20

Wine in the Wind: Coastal/Island Varietals

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

Join us and discover new lesser known grape varietals from the coast and islands in the Mediterranean We invite you to raise the sails, steer the boat or sit back and relax. Wine Samples paired with "Magnificent Morsels" There will be representatives aboard to talk about the food and the wines. 3oz samples of each ... Read more

$101.20

Black Ankle Vineyards Dinner Cruise

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

Captain Jen fell in love with this winery's location, wine and people that work at Black Ankle Winery. Black Ankle Vineyards is the culmination of a long-time dream of founders Ed Boyce and Sarah O'Herron. They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of rolling ... Read more

$148.35
Schooner Woodwind
410-263-7837