OUT ON THE TOWN
DATING IN LEONARDTOWN
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.
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
"We really liked being able to do something different and creative..."
-ANDREW & JESS
Derek & Destiny
Our Third Couple, Derek & Destiny chose Date Option
No. 3: A Wine Tasting and enjoying Live Music at the
Port of Leonardtown Winery
"The staff was extremely welcoming and knowledgeable. This was a great
-DESTINY & DEREK
Emily & Nick
"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!
-EMILY & NICK