Sample Date Itineraries

Real-life couples preview sample dates from the fun & exciting to the laid back and relaxed.


There are so many great date options in Leonardtown. We have gathered together a wonderful variety of date options to suit everyone's taste. View the fun and interesting Sample Date Itineraries below to get started with your plans for a great date.


Grey Paint

Jess & Andrew

Discovering Leonardtown Host, Andrew Ponti, and his lovely wife, Jess chose Date Option No. 1: A Couple's Sip & Paint Night at Wine & Design followed by  enjoying a Raspberry Truffle Latte by the fire pit at
Social Coffeehouse.

Discovering Leonardtown_VD_Andrew and Je

"We really liked being able to do something different and creative..."


Phillip & Stephanie

Our First Couple, Phillip & Stephanie chose Date Option
No. 2
: Dinner at
Salsa's Mexican Cafe followed by a game of pool at Action Lounge & Billiards

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"We love any opportunity we get to try something new."


Derek & Destiny

Our Third Couple, Derek & Destiny chose Date Option
No. 3: A Wine Tasting and enjoying Live Music at the
ort of Leonardtown Winery

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"The staff was extremely welcoming and knowledgeableThis was a great 
afternoon out.



Emily & Nick

Our Fourth Couple, Emily & Nick chose Date Option No. 4: Dinner at The Front Porch a Challenge at the Escape Rooms Southern Maryland

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"We really enjoyed our date in Leonardtown. - from the fantastic meal to reinforcing our bond by working together as a team. We had a great time!


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Check out our Info Guide for planning an event or a group visit in Leonardtown.



Find out what there is to see and do in this eclectic Southern Maryland Town.


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