Plan Your Kentucky Trip
Explore your options, get an expert plan, or let us arrange the details.
How Much Help Do You Want?
From simple inspiration to full-service planning, we'll help you create a Kentucky experience that fits your style, schedule and budget.
Louisville · Golf, Restaurants
Discovery experience · Louisville
Refine anything below, or continue and we'll build your day.
Let's build your
adventure, together.
You're never planning alone. Tell us the region and the experiences you love, and our team curates a custom day of recommendations, then we handle every detail from here.
- 1
Choose your region
Louisville, horse country or beyond.
- 2
Pick your experiences
Horses, bourbon, golf or limestone.
- 3
Get your concierge picks
The places we trust and guests love, free.
Pick a Region
Select Experiences
Concierge Services
Get Our LGS Picks
Enter your business email and we'll show the places we'd personally pick for you. Nothing is booked.
Business email required — no Gmail, Yahoo or AOL.
A Custom Plan, Just for You
You know the kind of Kentucky trip you want. We know how to put it together. We create a personalized, day-by-day itinerary built around your interests, travel dates, pace and budget.
$150 per itinerary day
Tell Us About Your Trip
Share your dates, interests, group size and what you already have planned.
We Plan
We research the right experiences, timing, routes and recommendations for your trip.
Your Itinerary
Receive a personalized day-by-day plan with everything organized in one place.
You're Ready to Go
Use your itinerary to make your reservations and enjoy Kentucky with a plan that actually makes sense.
Why professional planning? Google can tell you what's popular. We help you decide what actually belongs in your trip, what works together geographically, how much you can realistically fit into a day, and what is worth your time.
Sample Kentucky Itineraries
Get inspired with a few of our most popular trip styles. Each one can be customized for you.
See what a trip could look like, then let us customize one for you.
We Handle the Details
From hard-to-get reservations to private experiences and transportation, we take care of the logistics so you can relax and enjoy the trip.
Transportation
Private & group options
Accommodations
Hotels, homes & unique stays
Dining & Reservations
Tables and private dining
Private Experiences
Access and special moments
Special Requests
Custom & last-minute needs
Trip Logistics
Every detail, coordinated
Concierge clients receive access to the Madeline & Moe Travel Desk.
Quick Answers
With Expert Itinerary Planning, we create a personalized day-by-day plan and you make your own reservations. With Full-Service Concierge, we create the plan and coordinate the details, reservations, transportation, accommodations and experiences, so you can simply enjoy the trip.
A personalized day-by-day itinerary built around your interests, dates and pace, with experience and dining recommendations, realistic routing and timing, lodging suggestions when needed, booking information and local insight. It includes two rounds of revisions.
With itinerary planning, you make your own reservations using the booking information we provide. With Full-Service Concierge, we handle the reservations and coordination for you.
For ordinary dates, a few weeks is plenty. For the Kentucky Derby and festival weekends, start as early as possible, the best hotels and experiences sell out months ahead.
Yes. We plan for couples, families and large groups, tailoring the pace and inclusions with a single point of contact for the whole party.
All of Kentucky, the Bourbon Trail, Louisville, horse country and Keeneland in Lexington, golf, the Red River Gorge and Mammoth Cave, with scenic drives and transportation handled.
Ready to Plan Your Trip?
Start exploring on your own, or let Madeline & Moe help you put it all together.