Bourbon & Bluegrass Soirée 2018

October 24 – October 28, 2018

Join us as we indulge in

Oak barrels filled with 23-year old Pappy Van Winkle
Genuine hillbilly tales and prodigious banjo pickin’
Fall foliage as far as the eye can see
5th generation owners with Civil War tales
Porch swings and a family cookout
Scratch-Made apple butter, aged country ham & maple pecan pie
Ticking 3 off of the National Landmark list
Fields blanketed with bluegrass and embroidered with black fences
Sipping along the Bourbon Trail
Autumn races at Keeneland clad in felt hats and feather ties
Betting with the odds of a handicapper
mingling over mint juleps
Sleeping in a contemporary art museum
The best buttermilk biscuits in the world?

Let us take you home

We will take care of all the details.  
All we need is you.

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A Note From Dana:

Over the years during dinner parties in far flung places, I’ve told colorful –sometimes seemingly unreal – stories about growing up in Kentucky on a tobacco and cattle farm.  Along the way, friends have asked if I would be willing to take them home to meet my characterful family and see the best Kentucky has to offer. This itinerary, the Bourbon & Bluegrass Soirée 2018, is my best attempt at bringing my story to life, blending downhome authenticity with the most intriguing venues central Kentucky has to offer. Bourbon distilleries, Thoroughbred horse farms and heritage architecture are never far apart. Over the course of 5 days, during the peak of fall foliage, we will be attending the elegant races at Keeneland accompanied by a professional handicapper, privately touring legendary horse farms, staying in a museum hotel, attending a private bluegrass concert, sipping our way along the Bourbon Trail and dining at the most acclaimed restaurants in the region.

Thanks to local guides and our faithful historian Professor Adam Tooze, we will piece together how the Revolutionary War, the Whiskey Rebellion and actual buffalo trails led Scotch-Irish settlers to the ideal conditions for brewing up the world’s best Bourbon.  Our experts will touch upon slavery, how the Civil War divided Kentucky families and the changing landscape of local agriculture.  We will have the chance to examine contemporary issues facing Kentucky such as the opioid crisis, education, the coal mining industry and healthcare.  Fierce Secretary of State Alison Grimes (D) has agreed to meet with us to discuss the current political climate in Trump’s Kentucky.  As the youngest Secretary of State in the U.S. and one of only two democrats elected statewide, she will explain how she took on her own party’s establishment and gained the respect of this deeply saturated red state.

We hope you will join us for fun-filled Bourbon & bluegrass days experiencing the best Kentucky has to offer. It’s gonna be a barn burner of a soirée!


Our Soirées

The goal of our small group trips, which we affectionately call our “Soirées,” is to capture the energy of a perfect dinner party—great food, fine spirits, excellent conversation, beautiful company—and extend it for an entire trip.  The group must be curious, intelligent, and fun.  That’s you.  The hosts need to be witty, charming, and full of great stories.  We hope that’s us. The location needs to be saturated with art, culture, history, stunning sights and culinary delights. Where to this time? We’re going to Kentucky y’all!!


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Day 1 – Wednesday, October 24th – Arrive Lexington

Arrive into laidback Bluegrass Airport (LEX) this afternoon where you will be greeted by one of our team members and accompanied to the 21c, our boutique hotel strategically located in the heart of downtown Lexington.  The 21c isn’t your average inn: its forward-thinking concept splendidly combines a modernist hotel with a cutting edge contemporary art museum.  Our new 21c home for the next four nights is one of the trendiest spots in town where you will find an eclectic mix rubbing elbows at the bar—southern bells, hipsters and pop stars alike mingle over mint juleps late into the night.  After settling in, we will gather at said bar to say hello to both old and newly minted friends as we sip carefully crafted bourbon cocktails and local brews effectively putting our day of travel behind us. 

With a glass in hand, a docent will lead us through the current exhibition adorning the walls and halls covering over 7,000 square feet of gallery space within the hotel. Dinner this evening will be in our own privatized gallery, skillfully prepared by Lockbox’s Executive Chef Jonathan Searle, who serves up the best darn biscuits in town. They’re to die for! Known for country cooking with a modern twist, our chef will showcase an array of locally sourced products drawing upon a bounty of fresh ingredients fed by Kentucky’s unique limestone-rich soil. During dinner, we will be joined by renowned handicapper Ellis Starr (aka the “Ubercapper”) who, over the course of our stay, will make us comfortable and familiar with racing and wagering while at the same time helping us cash a few tickets!  We’ll have Ellis by our side at Keeneland on Friday. After a slice of delectable pie, we will roll ourselves back to our rooms just steps away for some shut eye.

21c MUSEUM HOTEL (Reception (R), Dinner (D))


Day 2 – Thursday, October 25th

Put your mud boots on, today we are going to be knee-deep in history and good times. We will start with a brief driving tour of downtown Lexington, getting a look at National Landmark Transylvania University, the first college west of the Allegheny Mountains.   Our drive continues east toward the town of Paris, winding through Bourbon County and finally to historic Runnymede Farm, owned by the Clay family and recognized as the oldest continuously owned Thoroughbred farm in Kentucky.  Brutus Clay, the fifth-generation owner, will greet us and take us on a private tour of their exquisite farm fully dedicated to breeding champion Thoroughbred horses.  Mr. Clay will surely delight us with bewildering tales of Civil War intrigue and show us historic buildings from the 18th and 19th centuries that dot the land where three Kentucky Derby winners were raised.  If the stars are in alignment and we keep our fingers crossed, we will meet some of the current champions before settling down to lunch on the farm, an exclusive event arranged solely for us. 

This afternoon we will head onto Maysville, not far from where Dana grew up, for a rare and exceptional stop at the craft distillery The Old Pogue. En route, our local guide will explain the history buff version of the birth of bourbon going all the way back to the Revolutionary War. Perched above the Ohio River, The Old Pogue dates back to 1876, and is on the site of the first Bourbon distillery in Kentucky.  We will be welcomed by the fifth and sixth generation of Pogues, who are still using the original unaltered and time-honored Pogue recipes, consistently offering superior quality small-batch bourbon and rye spirits.  Try not to fall too deeply in love as there is often nothing left for sale, but they always keep a little on hand for tastings—phew!

Now folks, if this day weren’t special enough, we are actually headed home for supper. Yes, home.  Dana’s mom Marcy and her husband Jim have invited us to come on over for an old-fashioned family cook-out in their backyard. After getting so far out in the sticks, you’ll wonder how my mom even found this place, and you’ll feel the world melt away as you rock on the porch swing or go for a hike through their 26 acres with oak and maple trees in full fall flame.    

And guess who’s coming for dinner? Wait for it…… The Moron Brothers. Headliners at Renfro Valley and major Bluegrass festivals, Burly & Lardo, a brilliant and hilarious duo, have agreed to play a private concert for us comprised of their authentic hillbilly stories backed up by talented banjo picking. Does it get any better than this? 


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Day 3 – Friday, October 26th

Ladies and Gents, gussy up and crack open your piggy banks because today we are headed to Kentucky’s most elegant and exciting racing venue, Keeneland!  Races are held each April and October, and we will be watching from the best seats in the house*. Don’t just happen to have a fancy hat or flamboyant feather bowtie laying around?  No worries, we will hit an outrageously dapper shop on our way and pick up all we need as we enter this National Historic Landmark. To gear up for the day ahead, we will take a private tour of the beautifully landscaped grounds and get a behind-the-scenes look at race day operations, including a walk through the stables and a stop by the Jockeys’ quarters. Before the races start, our good friend and professional handicapper, Ellis Starr, will introduce us to the strategies of betting at the horse track. He will join us throughout the day to give advice on assessing the horses and honing our betting tactics. Between jumping up and down, betting, screaming and shouting, we’ll need a few gather-ourselves breaks in our private area for nibbling and, of course, nursing mint juleps.

This evening is free to explore Lexington on your own.  Let us help you book tickets to a fanatical UK basketball game** at legendary Rupp Arena or dinner at the best steakhouse in town, both are just a short walk from our hotel.  


* We plan to book a private box at Keeneland, however boxes are assigned just a few months in advance of the race, and thus we cannot guarantee that we will have a box at the time of printing, but we will get the best seats and access available. 

** 2018 schedule not available at time of printing.

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Day 4 – Saturday, October 27th

After breakfast, we will take a scenic drive through the heart of bluegrass country passing picturesque horse farms lined with their signature black fences.  Our first stop today will be in Georgetown, just north of Lexington, to visit Old Friends, a heartwarming retirement farm for racehorses. Old Friends, a living-history museum for horse racing, invites racing fans to revisit their turf heroes.  We will have the opportunity to swoon over Breeders’ Cup Champions, Belmont Stakes winners, and Kentucky Derby and Preakness champions Silver Charm and War Emblem. 

At the epicenter of the Thoroughbred industry, we will visit the charming village of Midway, a small railroad town with a rich history.  Stroll the quaint streets chockfull of shops selling local arts & crafts and country antiques.  We will dine together at celebrated Heirloom, a favorite restaurant of Midway’s local celebrity, the late beloved playwright and actor Sam Shepard.

This afternoon we continue west towards Frankfort, the capital of Kentucky, and the site of 200-year old Buffalo Trace Distillery, a National Landmark and winner of over 500 awards. Bourbon aficionados will know that this distillery makes over 20 brands of spirits, including the very rare Pappy Van Winkle Bourbon aged for 23 years.  The tours here are exceptionally educational and fun, and always end in with a ruckus tasting around the bar, the brouhaha likely due to one of the tastings being moonshine/white lightening.   

Back in Lexington we will dine at Coles, a favorite of some of Dana’s local friends and foodies, where Lexington-born Executive Chef Cole Arimes showcases reinvented American classics and eclectic artisan dishes; hand crafted like fine pieces of art.



Day 5 – Sunday, October 28th

Waving farewell to the 21c, we will take one last scenic drive, a pilgrimage really, to nearby Holly Hill Inn for Chef Ouita Michel’s beloved brunch. We might have to drag you out of Kentucky kicking and screaming after you’ve had her silver dollar buttermilk biscuits with aged country ham and scratch-made apple butter.

Before heading to the airport, we will tick one last distillery off of the Bourbon Trail with a stop at Woodford Reserve. Boasting the most beautiful grounds and elegant interiors, this National Landmark is a truly gorgeous place to say our good-byes. With a raise of the tasting glass and a nibble of a chocolate bourbon ball, we will toast to one heck of trip—packed with some of the most traditional, rare and bespoke experiences only a local gal could think up. 

21c MUSEUM HOTEL (Brunch)


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RSVP & Deposit

We would be thrilled if you’d like to join us!  First come, first serve for booking space.  Even if you have already told us that you wish to join, we still need for you to respond now that you are “in” through our online booking using the RSVP button below. If that is confusing, then just send us and email at

Once we have confirmed your reservation, we will send you a copy of our standard Waiver and Release of Liability form for you to return and an invoice with instructions for remitting a deposit of $1,500 per person, due within 15 days of your RSVP.  The final invoice will be billed on May 1st and due by June 1st, 2018.  As all payments are non-refundable, we strongly recommend getting trip insurance.  Once we receive your deposit, we will send you a trip insurance quote from our partners at AIG/Travel Guard so you have a place to start with comparisons.

Can’t wait to take you home!!
Dana Conley

For more information, call Dana Conley at 1 347.951.7948 or email at





21c Museum Hotel

The 21c Museum Hotel in Lexington is a boutique hotel, contemporary art museum and cultural center rolled into one. Woven into the fabric of downtown Lexington, 21c welcomes both visitors and the local community to enjoy curated exhibitions and cultural programming. It was rated as Top 5 Best New Hotels by USA Today in 2016.  Hotel amenities include: 7,000 square feet of museum exhibition space open 24 hours a day for viewing, a spa, the Lockbox restaurant expertly led by chef Jonathan Searle, in-room dining provided by Lockbox, a 24-hour fitness center, Business center, Laundry service, a Museum shop and free Wi-Fi. 

Note:  Breakfast is served à la carte at the Lockbox, so we thought we’d let you choose your own vittles each morning versus binding you to a fixed menu.  For this reason, kindly note that breakfast is not included in the rate. 

Check out the hotel website here.


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Your Hosts

Dana Marseille.jpg

Your Tour Director, Dana Conley, grew up in Hillsboro, Kentucky, on a tobacco and cattle farm.  She majored in International Relations at Stanford and has traveled to over 50 countries in search of authentic adventures, beautiful meals, and life-changing moments to share with her private and organizational clients.  Via Conley & Silvers LLC, her goal is to provide guests with the highest level of customer service while creating unique and magical itineraries and events.  Before co-founding Conley & Silvers with long-time Stanford mate Alison Silvers, Dana’s career spanned from being a researcher at the Pentagon and international security think tanks, to appraising art and directing a gallery.  When Dana is not tour managing or on a reconnaissance mission, she divides her time between Europe and New York City where cheese consumption, museum going and urban biking reign as her favorite pastimes.


During our trip, we will have the privilege of learning from top local guides and experts. We also have the great pleasure of having historian Professor Adam Tooze on board with us. Adam is good fun, a tireless conversationalist, and an experienced travel-study leader.  Adam studied and taught at Cambridge as well as the London School of Economics and Yale University. He is now a professor at Columbia University, where he is Director of the European Institute. Adam will be joining us to help place the sites we are visiting into historical, political, and cultural context. Full disclosure: Adam stole Dana’s heart after giving an eye-opening lecture on Scotch-Irish migrations to the US. 

What to expect

This is an easy trip for getting around.  To experience all of our planned activities, you’ll need to be happy with being on your feet for up to an hour at a time, walking on the farm or in town and shuffling around in distilleries.  The farms of Kentucky can have uneven terrain, but we will find you a place to rest if needed.  While we hope that you love the itinerary outlined above, we, of course, reserve the right to mix things up and swap things in to maximize the good times.


The Nitty Gritty

To enhance personal attention and limit costs, we need a minimum of 12 and a maximum of 20 attendees.  If you can vouch for your friends and think they would enjoy our company and style, we’d love to have them join.  Ages 21 and up only, there’s a lot of Bourbon drinking.

Included in the Trip:

❖  4-night accommodation at the boutique 21c Museum Hotel
❖  1 epic brunch
❖  3 delicious lunches
❖  3 gorgeous dinners
❖  Welcome reception
❖  Local wine, beer, and soft drinks at lunch and dinner
❖  All group entry fees, tasting fees and tickets
❖  Transfers to/from Lexington (LEX) Airport

❖  1 private Bluegrass concert
❖  Group transportation via private coach
❖  Expert & local guide fees
❖  All gratuities
❖  Expert & local guide fees
❖  Movie and book list to get you excited
❖  Concierge services by Conley & Silvers* 
❖  Lots of good stories and great memories

* To help you make the most of time on your own, we will happily help you arrange restaurant reservation and other activities, such as spa sessions, horseback riding and getting tickets to local events.

Not Included in the Trip:

❖  Airfare.
❖  Travel, medical, or evacuation insurance.  We strongly recommend you purchase any insurance policies for your specific needs.
❖  Breakfast and any meals and beverages other than those specified as included.
❖  Personal charges such as telephone calls, laundry, and mini-bar blowouts.

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Notes for Flights

If you are flying into Lexington (LEX), you will want your flight to arrive no later than 4:00 p.m. on Wednesday, October 24th. For those flying into LEX, one of our team will pick you up from the airport and bring you to the 21c Hotel. If you are driving or coming from another airport, such as Cincinnati’s CVG located only 1h15min away, please keep in mind that our first activity will start at 5:30 pm.   Transfers from CVG are an additional $200 each way.

Flights should be scheduled out of Lexington after 6:00 pm on Sunday, Oct 28th.  If you need to fly out earlier, no problem, we’ll make it work.



All prices are for paying via bank transfer or via check.  If you would like to pay via credit card, let us know and we will add a transaction fee of 3% to your invoice. 

Double Occupancy - $3,995.00 per person

Single Occupancy - $4,995.00 per person

RSVP & Deposit

We would be thrilled if you’d like to join us!  First come, first serve for booking space.  Even if you have already told us that you wish to join, we still need for you to respond now that you are “in” through our online booking using the RSVP button below. If that is confusing, then just send us and email at

Once we have confirmed your reservation, we will send you a copy of our standard Waiver and Release of Liability form for you to return and an invoice with instructions for remitting a deposit of $1,500 per person, due within 15 days of your RSVP.  The final invoice will be billed on May 1st and due by June 1st, 2018.  As all payments are non-refundable, we strongly recommend getting trip insurance.  Once we receive your deposit, we will send you a trip insurance quote from our partners at AIG/Travel Guard so you have a place to start with comparisons.

Can’t wait to take you home!!

Dana Conley

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