Wooden wine barrels stored on metal racks at Port of Leonardtown Winery.

Wine Clubs

Love our wine?  Check out the great benefits of joining our Club!

Become a member and each visit you will receive the option of:

Discounted wine flights, glasses of wine or seasonal beverage (any combination of 2 daily)
15% discount on all bottle purchases

*Please note that Wine Club and other discounts do not apply to already discounted specials*

Navigators Club

Perfect for visitors, travelers and Military

Still navigating the world of wine? Always on the go or just have a few too many bottles waiting on your shelf? Join the Navigators Club — the perfect way to enjoy all the perks of our Captains & Commanders clubs, without the commitment of a 3-bottle pickup. Sip, explore, and enjoy exclusive benefits with a simple monthly $25 membership. Easy, flexible, and made for your lifestyle.

Navigators Club Members Receive:

$25 Monthly Fee, no prorated fee for mid month sign up, gets you the same great benefits as Captains or Commanders

  • 15% discounts on all wine bottle purchases
  • Discounted wine flights, glasses of wine or seasonal beverage (any combination of 2 daily)
  • Convenient 1st of the month charge for a stress free winery experience

Membership Terms:

No bottle purchase required unless you want to!

No Minimum commitment; use seasonally, monthly, quarterly, while you are here on Vacation ect..

Captain’s Club

Dry Wines | February, May, August, & November 

This club is for our dry wine drinkers. On the months listed above you will receive 3 bottles of dry wines selected by us and enjoy discounts on glasses, bottles, flights, and more to make sure your glass is never as dry as the wine in it.

Captains Club Members Receive:

  • 15% off all wine purchases
  • Quarterly wine distributions in February, May, August, and November
  • Discounted wine flights, glasses of wine or seasonal beverage (any combination of 2 daily)
  • Access to limited-production wines
  • The option to pick up club selections at the winery within the first 21 day or have them shipped for $19.99

Membership Terms:

The winery reserves the right to cancel membership at its discretion, including but not limited to declined payments or inability to contact the member using the information provided.

A one year, 4 distributions, minimum with a $50 cancelation fee for early termination. 

Commander’s Club

Sweet Wines | January, April, July, & October 

This club is for our sweet wine lovers, on the months listed above you will receive 3 bottles of sweet wine selected by us and enjoy the same benefits of our Captains club, could this deal get any sweeter?

Commanders Club Members Receive:

  • 15% off all wine purchases
  • Quarterly wine distributions in January, April, July and October
  • Discounted wine flights, glasses of wine or seasonal beverage (any combination of 2 daily)
  • Access to limited-production wines
  • The option to pick up club selections at the winery within the first 21 day or have them shipped for $19.99

Membership Terms:

The winery reserves the right to cancel membership at its discretion, including but not limited to declined payments or inability to contact the member using the information provided.

A one year, 4 distributions, minimum with a $50 cancelation fee for early termination. 

Have questions or interested in joining the fun? Stop by our tasting room today and ask one of our associates!

More fun Club Options!

Admirals Club: Looking for a more exclusive experience with extra perks, special benefits, and VIP treatment? It may be time to upgrade your club membership and enjoy even more of what Port of Leonardtown Winery has to offer. Ask to speak with our Club Manager during your next visit and discover which membership level is the perfect fit for you!

Captains and Commanders Shipping Club: Our Shipping Club puts you in control! From the comfort of your home—or right from your phone—you can fully customize your club shipment and choose the bottles you love most. Enjoy the convenience of a $19.99 flat-rate club shipping fee, plus discounted glasses when ever you are in town and all the perks of being a club member. No guesswork, no hassle—just the wines you want, delivered right to your door!

We ship to the following states: Alaska, Arizona, Colorado, District of Columbia, Florida, Georgia, Hawaii, Iowa, Idaho, Indiana, Kansas, Kentucky, Louisiana, Massachusetts, Missouri, North Carolina, North Dakota, Nebraska, New Hampshire, New Mexico, Nevada, New York, Ohio, Oklahoma, Oregon, Pennsylvania, South Carolina, Tennessee, Texas, Vermont, Washington, Wisconsin, West Virginia, Wyoming