The Villages Wine Walk Logo

Thank you for participating in Wine Walk at Lake Sumter Landing's Market Square® on Friday, December 15, 2023 | 6:00pm–9:00pm! Early check-in will begin at 4:00pm. The Wine Garden will be open 4:00pm–9:00pm. 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.

Participating Hometown Business Partners and Vendors

Wells Fargo Advisors Financial Network, Todd Blankenship
Sabal Trust Company
Charter Research
Legacy Clinic Of Chiropractic
Arden's Fine Jewelers
Designer Floors By Nickel Tile
Naples Soap Company
Orangetheory Fitness
Lighthouse Point Bar & Grille
Sun Kool Air Conditioning, Inc.
RJ Gators
Epic Theatres Old Mill Playhouse

Properties Of The Villages
Merrill Lynch
Chop House
Gifts & More at The Paper Store
The Villages Grown
Zenith Advisory Group
Fenney Grill
City Fire
Buffalo Scholarship Foundation
The Waterfront Inn
Craig Curtis
Hawkes Bay Dental Care
Peterbrooke Chocolatier

Employee Preparation

  • Designate a min. of FOUR (4) employees to serve food and wine at your 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 of serving gloves, tongs, spoons, etc.
  • Employees are encouraged to dress in costume according to your theme - have FUN!
  • Review proper technique for opening a bottle of wine
Wine Walk


Wine Walk

Do I need to check the ID's of Wine Walkers that come to my booth?
No. All ID's were already verified at Check-In when the participant was given their wristband at the start of the event.

What should I do if someone approaches my booth without a wristband?
Please refer the guest to the Check-In area for information or directly to the Wine Garden where they are able to purchase a flight of two 2oz wine tastings for $5.00, with the donation benefitting the Buffalo Scholarship Foundation. ID's are checked upon receiving their wristband.

What should I do if a Wine Walker seems intoxicated?

  • Wine Walkers are encouraged to drink responsibly, please 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 website to brush up on identifying if someone is being overserved.
  • While we have not had any issues with overserving, should you need assistance during the event, please contact the CPM representative on-call line at: 352-750-9455

What should I do if I run out of wine?
Keep your pours to the 2oz's per guest throughout the event. Focus on promoting your goods and services should you run out of food and drink.

Supplies List

SET-UP: Pop-Up Tent or In-Store
  • Table(s)
  • Table Cloth(s)
  • 10'x10' pop-up tent (25 lb. weights on each leg)
  • Coolers with ice
Generator (if needed)
  • Whisper Quiet or battery powered only
  • Do not run cables or extension cords across sidewalks
SERVING Supplies and Essentials
  • Chafing Dishes, Burner Cans, and a lighter
  • Trays, Dishes, Serving Utensils and Gloves
  • Individual serving cups for liquids or sauces
  • Wine Chillers/Ice Buckets, and Ice
  • CORKSCREW - at least two
  • Garbage Cans and Can Liners
  • Napkins/Towels for clean-up
  • Hand Sanitizer and or Wet Wipes
  • Bottled Water
  • Themed Décor & Props
  • Bistro Lighting, Lanterns, Ambiance Lighting
  • Table Signage
    • Appetizer Names, Ingredients, Potential Allergens; nuts, soy, Gluten Free, Vegan, etc.
  • Coupons, Handouts, Brochures, In-store specials, etc.
  • Donation Bucket to Support Buffalo Scholarship Foundation - provided by CPM

Please, reach out to | 352-750-9455

Wine Walk

Setup Event Timeline

Prior Evening - Thursday


  • 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

Event Day

Sidewalk Sales! 12:00pm - 6:00pm

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

12:00pm - 2:00pm

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


  • Finish load-in
  • Wine orders will start being delivered to your store or pop-up tent, please have an employee available to receive the delivery from the Entertainment team member
  • For outstanding balances please give the delivery person a check for your order
    • Payable to The Villages Operating Company
  • 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 - Under the covered picnic area, northside of the square
  • Wine Walkers will be given their swag with a map showing all of the participating businesses and wine selections. Early arrivals are encouraged to visit the Wine Garden before the Wine Walk commences at 6:00pm

4:00pm - 9:00pm

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


  • All participating businesses are set-up and ready to go
  • Keep chilled wines on ice or refrigerated. We recommend having 6-12 bottles of wine uncorked and ready to serve beginning at 5:45pm

6:00pm - 9:00pm

  • Wine Walk event commences on the square!
  • Please ensure all Wine Walkers being served are wearing their event wristband indicating they purchased a ticket and their ID has been verified

9:00pm - 11:00pm

  • Take-down, clean-up, and load out
  • The event runs until 9:00pm, please ensure your area is set-up until 9:00pm
  • 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
Wine Walk

Thank you for participating in Wine Walk - Lake Sumter Landing!