The Villages Wine Walk Logo

Thank you for participating in Wine Walk at Lake Sumter Landing's Market Square® on Friday, December 15, 2023 | 6pm 9pm! The Villages Commercial Property Management team is excited to partner with you, our valued Hometown Business Partners on this upcoming resident favorite event. Direct and engaging activities like this are part of our on-going commitment to offering unique opportunities connecting our community of residents with our Hometown Business Partners.

To support this upcoming event, we are pleased to provide you with the following resources and checklists to better help prepare you and your team for an outstanding evening of interaction, participation, fun, and entertainment.

Supply List

Set Up Necessities
  • Table(s)
  • Table Cloth(s)
  • 10'x10' tent with 25lb weights on each leg (only if you do not have a storefront on the square) *if you do not have a tent or weights, reach out to Bobby Davenport
  • Coolers with ice to chill wines and/or appetizers
Serving Supplies
  • Chafing Dishes with Burner Cans
  • Trays, Dishes and/or Food Display Items
  • Serving Utensils
  • Wine Chillers/Ice Buckets to Display
  • Lighter for Chafing Dishes
  • Ice
  • Garbage Cans
  • Garbage Bags
  • Napkins/Towels
  • Serving Gloves
  • Water
  • Themed Décor & Props
  • Bistro Lighting, Lanterns, Ambiance Lighting
  • Ice Buckets
  • Donation Bucket to Support Buffalo Scholarship Foundation
  • Table Signage (Item Names, Ingredients, Potential Allergens — nuts, soy, etc. — Gluten Free, Vegan, etc.)
  • Promotional Signage or Collateral to Give Walkers (Coupons, Handouts, Brochures, etc.)

*If you intend to use a generator, please be sure it is a “whisper quiet generator” or battery pack generator. If you should need a generator or power from your establishment, please do not run cables or extension cords across sidewalks. For any questions, please reach out to Bobby Davenport.

Event Timeline

Prior Evening


  • Designated square roads and Wine Walk reserved event parking (located behind Coggins Home and West Home Buildings east of the square and south of the Trolley parking lot) are closed off for load-in

Friday - Sunday: Sidewalk Sales!

  • Holiday Sidewalk Sales! All Hometown Business Partners are encouraged to display a merchandise rack and or table on the sidewalk adjacent to your storefront encouraging folks to explore and shop your offerings. Please keep your doorway/entrance clear for ease and accessibility into your store

Event Day

12pm – 2pm

  • Participating businesses load-in and set-up their display area
  • Enter the square at the barricade located at the corner of Old Mill Run and Canal Street catty-corner from Old Mill Playhouse Theater


  • Finish load-in
  • Wine orders will start being delivered to your store or pop-up tent by an Entertainment team member, please have an employee available to receive the delivery
  • For outstanding balances please give the delivery person a check for your order Payable to “The Villages”
  • Keep chilled wines on ice or refrigerated. We recommend having 6-12 bottles of wine uncorked and ready to serve beginning at 5:45pm
  • Questions on the wine delivery please contact: Lisa Gruber, 352-750-5411 ext. 5609


  • Entertainment staff on stand-by for guests parking in reserved parking lots


  • Wine Walker Check-in starts at the designated "Check-In" area north of the square under the covered picnic area
  • Wine Walkers will be given a 2oz wine tasting glass, appetizer snack tray, napkin, bag and lanyard passport with a map showing all of the participating businesses and wine selections. Early arrivals are encouraged to visit the Wine Garden until the Wine Walk commences at 6pm

4pm - 9pm

  • Wine Garden Hours - Opens on the grassy area by lakefront catty-corner from The Grand Hotel Building


  • All participating businesses are set-up and ready to go
  • Please keep chilled wines on ice or refrigerated. We recommend having 6-12 bottles of wine uncorked and ready to serve

6pm – 9pm

  • Wine Walk event commences on the square!
  • Wine Walkers stroll around the square sampling wines and hors d'oeuvres from each participating business
  • Please ensure all Wine Walkers being served are wearing their event wristband and lanyard passport signifying they have purchased a ticket and their ID has been verified

9pm – 11pm

  • Take-down, clean-up, and load out
  • The event runs until 9pm, please ensure your area is set-up until 9pm
  • Double check that your area is clean and restored to the same condition upon arrival
  • Remove and properly dispose of all trash from your area

Employee Preparation

  • Designate a minimum of 4 employees to serve food and wine at your in-store or outdoor pop-up tent event area
  • Wine servers must be at least 18 years of age or older
  • All food safety standards must be adhered to e.g. proper food temperatures, use serving gloves, tongs, spoons, etc.
  • Encourage employees to dress in costume according to your theme and have fun!
  • Review proper technique for opening a bottle of wine
Wine Walk

Participating Vendors - Coming Soon


Wine Walk

Do I need to check IDs Wine Walkers that come to my booth?
No. All IDs will be already be checked when a Walker is given their wristband at the beginning of the event.

What should I do if someone approaches my booth without a wristband?
Please refer the guest to the Wine Garden on the west side of the square where they are able to purchase a flight of two 2oz wine tastings for a $5 or more donation benefitting the Buffalo Scholarship Foundation. Also keep in mind ID's are checked upon receiving their wristband. You don't want to serve someone who is potentially underage.

What should I do if a Wine Walker seems intoxicated?
We encourage all Walkers to drink responsibly and urge you to use your best judgement in serving patrons. If you feel someone has been overserved, you may politely refuse to fill their wine glass and offer them a glass of water.
Please review the DBPR and if you have concerns or need to brush up on identifying if someone is being overserved. While we have not had any issues with over serving in the past, should you need assistance during the event, please contact the CPM on-call line at: 352-750-9455

What should I do if I run out of wine?
Relax and enjoy the event! Limit your pours to the 2oz per guest throughout the event. Focus on selling your goods or services if you run out of food and drink.