Signature Affairs

Indulge an affair in vintage elegance and style. Follow your heart into the rolling country, around the limestone shelves and throughout the vibrant city, exploring all that Kentucky has to offer!

Reserve Your Affair

Make Your Memories Unforgettable

  • A man and woman dining at a candlelit restaurant, smiling at each other while holding glasses of red wine, with elegant table settings and a large chandelier overhead.

    An Evening in Vintage Style

    Some evenings deserve a grand entrance. Whether it’s a proposal, an anniversary, or simply a night meant to be remembered, Charlene adds a touch of vintage glamour to your most intimate moments. Glide up to your reservation in stunning luxury, step out with a smile, and let the night unfold—the story on this special night begins at the curb!

    What’s included:

    - Your own personal chauffeur & host
    - Luxury transportation from Charlene
    - Pickup & drop off at your Louisville location
    - Transportation to chosen pre-dinner cocktail spot
    - Transportation to reserved dining at restaurant
    - Transportation & delivery of personal items

    Sample Itinerary (Cocktail & Dining):

    - Depart your location 6 PM
    - Cocktails 6:30 PM
    - Depart for Restaurant 7:10 PM
    - Arrive for Dinner Reservation 7:30 PM
    - Return home between 9 & 10 PM

    Total time: 3 to 4 hours

    Packages start at $1,050 for the evening.

    Packages are fully customizable & costs vary by specific requests. Please contact us for a quote!

    Reserve Your Evening
  • A narrow wooden walkway in a distillery rickhouse with barrels lining both sides, illuminated by warm lights, leading to a bright doorway at the end.

    Journey Kentucky's Bourbon Trail

    There’s a certain kind of magic in a slow Kentucky drive—limestone fences, rolling hills, and the quiet promise of good bourbon waiting at the end of the road. With Charlene leading the way, your journey becomes more than a distillery tour… it becomes a moving postcard of Kentucky heritage.

    What’s included:

    - Your own personal chauffeur & host
    - Luxury transportation from Charlene
    - Pickup & drop off at your Louisville location
    - 2 or 3 distillery experiences (by region)
    - Optional lunch reservation
    - Transportation & delivery of personal items

    Sample Itinerary (Full Day):

    - Depart your location 8 or 9 AM
    - Distillery visit 10 AM
    - Lunch reservation at Noon (optional)
    - Distillery visit 2 PM
    - Return to home between 4 & 5 PM

    Total time: 8 to 9 hours

    Packages start at $1,050 (Half Day) & $1,450 (Full Day).

    Packages are fully customizable by region & costs vary by specific requests. Please contact us for a quote!

    Reserve Your Journey
  • Two brown horses grazing on green grass in a fenced pasture with a large white house and trees in the background during sunset.

    Experience Majestic Horse Farms

    There’s nothing quite like the hush of rolling bluegrass and the sight of champions grazing beneath the Kentucky sky. With Charlene on the lane, your visit to world-class horse farms becomes a timeless tableau—black fences, country breeze, and the soft rumble of a vintage Cadillac at your side.

    What’s included:

    - Your own personal chauffeur & host
    - Luxury transportation from Charlene
    - Pickup & drop off at your Louisville location
    - 2 horse farm experiences (by region)
    - Optional lunch reservation
    - Transportation & delivery of personal items

    Sample Itinerary (Full Day):

    - Depart your location 8 or 9 AM
    - Farm visit 10 AM
    - Lunch reservation at Noon (optional)
    - Farm visit 2 PM
    - Return to home between 4 & 5 PM

    Total time: 8 to 9 hours

    Packages start at $1,050 (Half Day) & $1,450 (Full Day).

    Packages are fully customizable by region & costs vary by specific requests. Please contact us for a quote!

    Reserve Your Experience