FAQ Questions Are Welcome Here.
You don't need to know exactly what to book before contacting us. In fact, that's part of what we're here for. Tell us when you're coming to Kentucky, who you're traveling with, and what sounds interesting. We'll help you figure out what comes next.
You Don't Have to Have It All Figured Out.
Some guests come to us with every reservation already made. Others simply say, “We're coming to Kentucky. What should we do?”
Both are welcome.
Timeless can provide private transportation around an itinerary you've already created, help refine plans you're working on, or help build a more complete Kentucky experience around Bourbon, Racing & Beyond.
One of the easiest ways to begin is simply to text Joshua directly at 502-262-8216 with your travel dates, number of guests, where you're staying, and a little about what interests you.
Let's Make This Easy.
Click any question below. If your situation is a little different, reach out directly. Custom planning is part of what makes Timeless personal.
Timeless combines private transportation, Kentucky experience planning, local guidance and genuine hospitality.
Some guests only need transportation. Others want help building an entire Bourbon, Horse Racing or Beyond experience.
We can do either—and plenty in between.
Not at all.
You can come to us with a complete itinerary, a few ideas, or nothing more than “We like bourbon,” “We want to go racing,” or “We want a fun night.”
Send your travel dates, group size, lodging location and what interests you. That's enough to begin.
Yes.
Our current Timeless experiences are designed around your private booking party.
You are not being combined with unrelated guests. Your transportation, timing and itinerary are focused on your group.
That's perfectly fine.
Send us what you've already booked. We can review timing, help identify potential travel issues, provide local dining or routing recommendations, and handle the private transportation surrounding your plans.
You do not need a complete Timeless experience package to use our private transportation service.
Absolutely.
Depending on your service level, Timeless can help with destination selection, itinerary development, private transportation, dining recommendations, reservation sequencing, lodging coordination, race-day planning, evening entertainment and more.
Our Crafted, Curated and Legacy experience levels allow you to choose how much help and personalization you want.
Pricing depends on service length, distance, group size, destinations, transportation needs, tickets, dining, lodging and the amount of planning involved.
Current website starting points include Bourbon experiences from $350 and Horse Racing experiences from $450.
More complete Curated and Legacy experiences are priced according to the itinerary.
No.
Most smaller Timeless bookings use a $100 reservation deposit.
Larger premium or multi-day reservations may require a higher deposit, generally around $250 unless otherwise quoted.
Your proposal will clearly explain the payment structure before you commit.
Sometimes—but only when your specific proposal clearly states that they are included.
Transportation-only and many Crafted experiences may leave admissions, dining and third-party costs separate.
Curated and Legacy experiences can involve more complete planning and coordination.
Our goal is to be transparent about what is included and what is not before you book.
Yes.
We can help identify the best region, group distilleries geographically, build realistic travel windows, recommend dining, and help sequence the day around available reservations.
Bardstown, Frankfort and Woodford County, Louisville, and Lexington each offer different kinds of bourbon experiences.
Race-day support can range from simple transportation and orientation to a much more involved Kentucky racing experience.
Depending on your service level, support may include handicapping materials, custom race selections, race-by-race opinions, wagering education, paddock timing, track navigation, seating guidance, dining recommendations and support throughout the race card.
Guests always control their own money and make their own wagering decisions.
Beyond is what happens after the main event—or instead of one.
A Beyond experience can include gaming, dinner, cocktails, live music, nightlife, entertainment or a customized evening built around your group.
Beyond can be booked as a standalone private experience or added to a Bourbon or Horse Racing reservation.
When scheduling allows, absolutely.
Maybe your bourbon day ends and your group wants dinner and live music. Maybe Keeneland finishes and you're ready for gaming at The Red Mile.
Ask Joshua. If the additional time can be accommodated, we'll help keep the experience going.
Timeless places a strong emphasis on guest comfort.
Service may include bottled water, Complimentary Guest Care Packages, a comfortable temperature-controlled vehicle environment, and climate-controlled storage that helps protect bottled purchases, food, beverages and personal items from Kentucky summer heat.
Yes.
Timeless can provide hotel pickup, airport transportation, local transportation, regional transportation, and service surrounding Bourbon, Racing and Beyond experiences.
Send us your arrival details and lodging information and we'll help determine the best arrangement.
Kentucky days don't always unfold exactly as expected.
When timing and existing reservations allow, Timeless tries to remain flexible.
That might mean helping find lunch, making time for bottle shopping, adjusting an unreserved stop, finding cocktails or live music, or recommending somewhere nearby when your group wants to continue the day.
Rideshare is designed primarily to move you from one location to another.
Timeless is designed around the entire Kentucky experience.
You have a private service, a consistent point of contact, planned timing, local recommendations, room for purchases, hospitality throughout the day, and someone who understands where you're going and how the pieces fit together.
You'll often be communicating directly with Joshua, Founder & Curator of Timeless Crafted Experiences.
Timeless is intentionally personal.
You're not simply entering a reservation into a large transportation system. You're connecting with an authentic Kentucky host who wants to understand what brought you here, what interests you, and what would make your Kentucky experience memorable.
For most guests, the easiest first step is to text Joshua directly.
Text 502-262-8216 with your name, dates, number of guests, where you'll be staying, and a little about what you'd like to experience.
Prefer to talk? Call Joshua directly at 502-262-8216 or call the Timeless office at 502-208-6108.
You can also email Joshua at Joshua@timelesstransportnow.com .
That's enough. We can build from there.
Don't Let a Question Stop the Conversation.
You do not have to be ready to book before contacting Timeless.
Maybe you're comparing dates. Maybe you're wondering whether an itinerary is realistic. Maybe you're deciding between Bourbon and Racing. Maybe you're considering adding Beyond. Or maybe you simply want a genuine local opinion.
Reach out anyway.
A short conversation can often save hours of searching and help you avoid building an itinerary that looks good online but doesn't work well once you're actually in Kentucky.
Timeless Crafted Experiences
Authentic. Genuine Kentucky Hospitality.
Timeless was built around a simple idea: visiting Kentucky should feel more personal than following directions between reservations.
Joshua brings local knowledge, deep Kentucky roots, a passion for Bourbon and Thoroughbred racing, and a genuine desire to share the places, stories, traditions and experiences that make Kentucky special.
Whether you're wondering where to eat, how many distilleries realistically fit into one day, how to approach your first race at the track, or where to go after the final race, the goal is the same: help you feel welcomed, comfortable and genuinely taken care of.
You don't have to go through a call center or wait for a generic planning response. You can simply reach out to Joshua directly.
You Bring the Idea. We'll Help Shape the Journey.
Bourbon. Racing. Beyond. Private transportation or a complete Kentucky experience. If you're still figuring out what the trip should look like, that may be exactly the right time to connect with Timeless.