Louisville

Join us in Louisville for a fun-filled long weekend of bourbon, museums, hat-making and horse racing!

This exclusive Damesly girls’ trip brings together the best of Kentucky charm while supporting some amazing local women making big waves. Sip small-batch bourbon at women-led distilleries, craft your own Derby-worthy hat, and explore the iconic Churchill Downs and Kentucky Derby Museum!

We’ll stay in a beautiful boutique hotel that includes breakfast each morning, dine at top-rated restaurants, and dive deep into the heart of Bourbon Country with a private, female-owned tour company. Whether you're a bourbon lover, history buff, or just in it for the hats, this itinerary blends culture, creativity, and cocktails for a weekend you won’t forget.

Price from

$1,899.00

March 26-29, 2026

Per person based on double occupancy. Solo Rooms available.

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Questions?
Call Us 888-505-DAME

Picture Yourself

  • Sipping delicious bourbon at female-led distilleries
  • Rocking your own hand-made Kentucky derby hat
  • Taking in the magic of majestic Churchill Downs
  • Giggling with new travel friends as you sip bourbon through the town
  • Hanging with some badass ladies who make Louisville such an exciting destination

Day by Day

Day 1 Day 2 Day 3 Day 4

Day 1: Welcome to Louisville!

After arriving to Louisville Muhammad Ali Int’l (SDF), make your way to our gorgeous downtown hotel, The Grady, where the fun will officially begin!

This cute boutique luxury hotel has an on‑site bourbon‑inspired restaurant Wild Swann set in a restored hat factory! It's the perfect location to kick off what will be a fun long weekend together - with bourbon!

Meals: D
Hotel: The Grady




Day 2: Day on the Bourbon Trail

This morning after breakfast at the hotel, we're hitting the Bourbon Trail! We'll set off with the only woman-owned veteran tour company in Kentucky to visit three of Louisville's top distilleries for a fun-filled day! Our stop will take us to the factory of Jim Beam, the luscious grounds at Maker's Mark, and Evan Williams' Heaven's Hill. Lunch will be provided, as well as snacks and beverages throughout the day!

Meals: B, L
Hotel: The Grady

Day 3: Hat Making + Horse Racing

Today we'll learn more about the rich heritage of what Louisville is known for: horse racing! See for yourself world-famous Churchill Downs Racetrack!

Walk through the Grandstands where thousands of people roar with excitement on Derby day. Your Tour Guide will lead you to the rail of the legendary dirt track where every Derby winner has raced, from Aristides, to Secretariat, and many more. Your Guide will share stories of the early days of the Kentucky Derby through its transformation into the iconic event it is today. Have your camera ready!

Then, we'll make our very own Derby hats! The Derby experts from the Kentucky Derby Museum help us to create our very own personally designed Kentucky Derby hat. Big brimmed hats, small brimmed hats, fedoras, cowboys hats, fascinators, the choice is yours! Ribbons, bows, flowers, feathers, staff assistance and all the fanfare are provided - you provide the style!

After a fun morning, we'll return to the hotel for downtime. Later, we'll check out a women‑led cocktail lounge, Trouble Bar, which is famous for its female‑distiller selections. Evening at your leisure.

Meals: B, L
Hotel: The Grady

Day 4: Departures

It's been such a fun long weekend! Today you'll make your way to the airport to align with your flight. We sad to see you go, but we know you're leaving with memories to last a lifetime!

Meals: B

  • Trip Length

    3 nights/ 4 days

  • Activity Level

    Low

  • Perfect For

    A fun weekend away

1 3
1 1

Louisville

Louisville

$1,899.00 USD
$1,899.00 USD
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Low stock: 4 left

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Spaces on tours are sold per person. Deposits are non-refundable. Ensure your payment option is as desired before checkout. If paying deposit only, remaining payments can be made via client portal until 60 days before departure. See our cancellation policy for details.

Love this tour but can’t make the dates? Click here to make this tour private.

Includes

  • Hotel (shared or solo)
  • Bourbon tasting tickets + private transport
  • Hat-making and Churchill Downs tour
  • All entrances
  • All meals listed

Excludes

  • Airport transfer
  • Meals not listed

Meet Your Trip Leader

Kelly Lewis

Kelly Lewis is a women's travel industry maven, author, speaker, business coach and the founder and CEO of Damesly. Raised in Hawaii, she's been to all 7 continents and over 85 countries. She is also the author of the best-selling title "Tell Her She Can't."

Read More

Additional Information

Flights: Fly in/out of Louisville. Check in to the hotel after 2 pm on the first day, depart at anytime on the last day.

Want us to advise on flights? Email us at info@damesly.com

Need to arrive a day early or depart a day late to accommodate your flight(s)? No problem! Let us know if you’d like us to arrange an additional hotel stay for you.

Weather: March is one of the best months to visit Louisville as the weather is cool but sunny (high 70s/lows 50s), and the city is not yet super packed for the Derby.

Packing: Sun protection (hat/sunscreen/sunglasses), comfortable walking shoes, and comfy clothes!

One of the days of this tour is bourbon tasting, but you are of course always welcome to pass on the bourbon, or to have a soda or water instead!

Small group trips require at least 4 people to run. We will confirm as soon as possible when the trip has met its minimum; up to 60 days before departure. For this reason, we recommend waiting until after a trip has been confirmed to purchase airfare. Any tour can be converted to a private departure when a trip does not meet its minimum. Additional costs may incur. Alternatively, apply your credit to any small-group tour departing within 12 months. 

Will you match me?
Of course! If you choose a space in a shared room but you're traveling solo, we will do our best to pair you with a roommate. Roommates are matched based on arrival time and perceived compatibility. Sharing a room is a great way to save costs, and make a new friend! However, we ask you to approach the situation with an open mind, some grace, and maybe a little humor.

While 99% our travelers are amazing, we can't guarantee that you'll hit it off with your roommate, or that your sleeping styles will be compatible.

Is sharing right for you?
If you are a light sleeper, get easily irritated or just know that you need your own space, sharing a room might not be for you. Likewise, if you know that you snore, sleep with a CPAP machine or have other health conditions, sharing a room might not be the best fit.

What if I don't get along with my roommate?
If you've tried but you absolutely can't get along with your roommate and need to separate, your trip leader will either swap things around, or, attempt to get you your own room. If the latter, additional charges will incur.

What if I book a double room, and you can't match me?
We book a certain amount of hotel rooms before any tour, and are bound by their rules. In the event that we cannot find a roommate for you before the tour, and your room converts to a single room, there may be additional charges.

Still have questions? See our FAQ or Contact Us.

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