Book Your Experience

Sunset with a Sommelier

Wine. Water. A historic Eastern Shore winery. What more do you need?
The Windmill Creek Wine Sailing Experience brings the tasting room to the Alyosha — and honestly, we think it's an upgrade. We've partnered with Windmill Creek Winery out of Berlin, Maryland, to pour their handcrafted wines right here on the Alyosha, captained by Steve Butz, while you sail the Assawoman Bay with unparalleled views of the OC skyline and Assateague Island. And here's what makes this more than just wine on a boat —Pam Hall, the Wine Director and Sommelier III, from Windmill Creek will be onboard to walk you through the wines, share the story behind each pour, and answer any questions about their winemaking process.
 
Windmill Creek isn't your average winery — their tasting room is set inside a historic 1858 farmhouse built by Lemuel Showell II, now listed on the National Registry of Historic Places. The wine tasting will include 5 wines poured by Pam who has been working in the wine business for more than 10 years. She is also a Wine Educator and Winemaker who received her certifications from the Wine School of Philadelphia, which is part of the National Wine School based in Los Angeles, CA. Lite fare of cheese and charcutier will be provided during the tasting experience.
 
Sit back, sip something special, and let the salty breeze and golden light do the rest. This is a 21+ cruise — you MUST BE 21 OR OLDER. Two hours, great wine, and the most beautiful backdrop on the Eastern Shore. Book it.
 
Duration: approximately 2 hours.
 
Your Captain, Steve Butz likes wine, mainly reds. But he won't be participating in the tasting… 

This trip will depart promptly at the stated departure time from the pier alongside of PIER 23 in West Ocean City Harbor. (Actual address: 12817 Harbor Road, Ocean City, 21842)

If the boat is not there, don't despair! We are likely running another trip and will be back in time for yours!

This is a two hour event and sometimes it can get a touch chilly on the fall evenings... so bring some layers just in case.

There are restrooms ("heads") aboard Alyosha for use by customers. Keep in mind that the toilets on a sailboat are a little bit more sensitive than land based toilets… so plan accordingly.

Alyosha has plenty of water bottles for guests. There is plenty of room onboard to store coolers, food and drink.

Aligned with the goal of ensuring all Sail Alyosha customers have a great experience, we will only run trips that are deemed safe by our Captains. Generally, the weather on the coast of the Ocean City area is very pleasant but sometimes storms and thunderstorms do occur.

In the event that your trip is cancelled, you will receive a full refund. Sometimes, the weather conditions, particularly high winds causing choppy seas, will allow us to run a safe trip that is a bit unpleasant.

Our captains will always strive to let people know when conditions will be less than ideal and if conditions warrant a possible refund you may choose to not take the trip. (But sometimes those rough passages make for the best experiences!)

$149

How Many Seats?

You can make this trip a Private Charter -- a trip that is exclusvely for you and your group.

By booking all 12 seats on this trip, you'll get a discount and be able to set the itinerary: whether we go sailing, cruising along Assateague, or anchor for a bit and go swimming!

$149

Any Children? (under 12 years old)