145th Kentucky Derby Spectacular!

May 2, 2019 thru May 5, 2019

Join us for one of the most iconic worldwide events – the 145th Kentucky Derby! So much more than just a horse race, the Kentucky Derby is the original springtime sports party of extravagance, tradition, and celebrity! Every year, Churchill Downs draws an impressive crowd that includes some of the biggest names in entertainment and sport, as everyone who’s anyone descends upon the Twin Spires for the famed Run for the Roses. Our tour departs from Tucson and has limited space. Make your reservations early!





4 days, 3 nights

Activity Level



6 meals (3 breakfasts, 1 lunch, 2 dinners) included




Livery from / to your home included

Tour Highlights

  • Bourbon, Barbecue and Country Music
  • Louisville Slugger Museum
  • The Hermitage Thoroughbred Nursery
  • Lunch at Claudia Sanders Dinner House
  • Undulata Horse Farm
  • Derby Hat Boutique
  • Bourbon & Chocolate Hotel Reception
  • “Off to the Races” Dinner Party with Kentucky Derby Museum
  • The Kentucky Derby – Reserved Seats
  • Derby Day Riverboat Race
  • Belle of Louisville vs. The Mary M. Miller
  • Churchill Downs VIP Fast Access Pass


  • Roundtrip air transportation
  • Pick-up/drop-off livery service
  • 3 nights lodging
  • 6 meals (3 breakfasts, 1 lunch, 2 dinners)
  • Admissions as described within
  • Services of a tour director
  • Baggage handling
  • Bus refreshments
  • Driver tips

Day 1

We arrive into Louisville this afternoon and settle in for a fun filled three-night stay! Afterwards, we enjoy a Bourbon, Barbecue and Country Music Dinner at the Jeptha Creed Distillery in Shelbyville, a new farm to bottle Distillery. You will enjoy an evening on the patio with a Barbecue dinner and live Country Music. There will be dancing and distillery tours – plus a bourbon tasting opportunity. This is one of the most modern bourbon distilleries in Kentucky and we have a festive evening planned here as our kick-off event to the Derby.

Day 2

Today we visit The Louisville Slugger Museum – You don’t have to be a baseball fan to love Louisville Slugger Museum & Factory. It’s iconic, it’s linked to legends and it is one of Louisville’s best known tourist attractions. This tour is fascinating with interactive exhibits that are fun.

The Hermitage Thoroughbred Nursery – Hermitage Farm is a world-class equine operation where champion thoroughbreds are born and nursed. Last January the broodmares here gave birth to 40 foals. You will see next year’s babies at the age of 4 or 5 months. These soon to be racehorses will just be learning to run. Your guides will talk about them and about the Farm’s past babies that grew into champions including winners of the Kentucky Derby, Kentucky Oaks, Breeders’ Cup and more than 200 other stakes races.

Lunch at Claudia Sanders Dinner House – This restaurant is a replica of the elegant, old home opened by Colonel Sanders of KFC fame, in 1959. It was from this very building that Kentucky Fried Chicken grew into a world-wide organization.

Undulata Farm – Listed on the National Register of Historic Places, this is where Civil War veteran Harry Weissinger and his sons once bred the great stallion, American Born. We will tour the first two floors of the family home, the horse training facility and actually see training in progress.

Day 3

Today’s first event is the Derby Day Riverboat Race. We have chartered space on one of the famous riverboats. It doesn’t get any better than this. Once onboard there is complimentary coffee and tea or start the festivities with a Bloody Mary or Champagne Mimosa from the cash bar.

Once underway we have experts providing a few insider tips on the Derby Race. They will talk about the Horses, how they run in different conditions, who has the post and what does that mean, plus information on the trainers, their Derby History and more. You also enjoy a seminar on how to place a real bet at Churchill Downs.

At the end of the “How to Bet” lesson, our Sternwheeler will turn downstream and with those big red paddlewheels kicking up a feather trail of whitewater they race each other back to Louisville. We encourage you to place a creative bet or two with your travel partners.

The 145th Kentucky Derby – Second Level SeatsNext is the highlight of your trip. You have a VIP Fast Access Pass to Churchill Downs and 2nd Level Grandstand Seating, under cover.  You will be at The Derby all day, enjoy crowd watching, sample a mint julep and place a few bets. This is one of the world’s greatest and most celebrated sporting events, “The Fastest Two Minutes in Sports” and you are on hand to experience it all. The Kentucky Derby is America’s most extravagant springtime sports party, and one of our most celebrated events. While there is a horse race at the heart of this spectacle, there are many other intriguing aspects within this Louisville tradition. It is a festival and fashion show, it’s a Parade and a Race, it’s Mint Juleps and Riverboats; it’s about Horses and it’s about time you see it.

Day 4

This morning, with hat boxes and suitcases loaded, we return to the Airport and depart for home with another terrific event checked off your Bucket List.

***Please contact us for special pricing if you are not departing from Tucson.

Package Pricing

$4,777 per person

Double occupancy

Deposit: $400

$5,597 per person

Single occupany

Deposit: $400

Price Includes

Roundtrip air transportation
Motorcoach transportation in Louisville
Pick-up/drop-off livery service
3-nights lodging
6 meals (3 breakfasts, 1 lunch, 2 dinners)
Admissions as described within
Services of a tour director
Baggage handling
Bus refreshments
Driver tips

Booking Policy

For this tour, we require a $400 deposit, of which $200 is refundable for cancellations prior to 1/1/19. We pride ourselves on great service and an enjoyable experience for all and will go over our booking policies after you make your request for booking. If you’d like to learn more about our booking policies before your trip, give us a call at 520.325.8839, or visit our Booking Policies page. Click here for more information on our booking policies.


For your reference, we send to you a detailed itinerary approximately 3-4 weeks prior to the scheduled tour departure. This has day-by-day times and events, hotel information where you can be reached in case of an emergency, and airline information.

The times listed on the itinerary are all approximate. We cannot be held responsible for schedule changes due to unforeseen circumstances with weather, transportation agents, highway conditions, hotels or contracting agents.


You will be issued your boarding pass the morning of our departure, after your arrival at the Tucson International Airport. If you have an Airlines frequent flyer number, or a TSA number, please call our office at least 3 days prior to the tour to ensure we can note these in your reservation.

If you are joining the tour from locations other than Tucson, we make other arrangements for you to join the tour. Please call our office for more details.


Do not forget to bring your government issued picture ID to show at the airport. A Driver’s License or Passport is preferred. If you do not have proper ID, the airline will turn you away.


We have arranged for handling for one piece of luggage per person regarding the skycaps (where available) and hotels. If you check through luggage note that the maximum weight for the checked piece of luggage is 50 pounds and maximum size is 62 inches (length + width + height). If your bag weighs over 50 pounds the airlines will levy an extra fee that you will be responsible to pay. If you feel the need to lock your checked through luggage and your bag is searched, your lock could be damaged in the process. You can purchase a TSA (Transportation Security Administration) accepted and recognized lock at any luggage store. Make sure you ask for a TSA approved lock. These locks are the kind that TSA screeners can open by using a special tool without breaking. Passengers can carry-on 1 bag (dimensions are limited to 10x16x24 inches), plus a personal type bag, like a purse. We advise that you pack your carry-on lightly. There are restrictions regarding your carryon baggage and contents due to enhanced
security measures. Attached find a list regarding commonly asked about items as well as an update. If you have further concerns, please visit the TSA's Web-site at www.tsa.gov. There is room inside the motorcoach for your hand carried bag.


Unless we travel with Southwest Airlines passengers are assessed a $25 fee per checked in bag, by the Airlines, upon checking in for the flight.


It is always a good idea to carry on your person a list of medications that you are taking and an emergency contact phone number while you are traveling. And we suggest making a copy of the itinerary and provide it to a friend or family member.


The traditional end-of-tour gratuity to your tour director is not included. If you feel your Tour Director helped you enjoy your tour, we suggest you enclose a gratuity in an envelope and present it individually at the end of the tour. Simply as a guideline, one may consider a per person, per day gratuity of $8.00 per tour guide as an average to be modified by one’s own personal experience. All hotel porterage and airport sky cap (when available) fees are included. We also include the gratuities for the coach/livery drivers. Maid tips are not included.


For your convenience we have a (round-tour) door-to-door pickup service with each multi-day tour. (This service is not available to all clients depending on your location.) Approximately 2 to 3 days prior to the departure date you will receive a call from our office and we will tell you your assigned pickup time. (These times can vary up to 15 minutes depending on traffic.)


If you would like to request special accommodations at the hotel(s) where we are lodging, please call us as soon as possible and we will forward these requests for you. The phone numbers of the hotel(s) where we are staying are listed on the itinerary.

Many hotels around the country have instituted a "reconditioning fee" of $300 or more that is levied upon a guest that smokes in a non-smoking room. If this occurs during our tour you will be responsible for paying this fee to the hotel prior to check-out.


We pay close attention to your requests but please realize that these are merely requests and cannot be guaranteed.


Pleasurebent Tours acts solely as agent in arranging hotels, transportation, sightseeing, baggage-handling and other services and does not assume any liability for injury, damage, loss or delay due to any act or default of any company or person. We, along with our subcontractors, reserve the right to make changes to an itinerary if it is necessary for the proper handling of a tour.


Please be sure to bring a sweater and / or rain jacket, along with good walking shoes and a hat.

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