Kentucky Derby 2027
First Turn Tickets, Premium Hospitality, Event Transfers & 3‐Night Stay for 2
Please note that this package has limited inventory and can only be used in fundraising events prior to February 26, 2027.
This Experience for 2 Includes:
- Two (2) First Turn tickets to the Kentucky Oaks — Friday, April 30, 2027
- Two (2) First Turn tickets to the Kentucky Derby — Saturday, May 1, 2027
- VIP Fast Access Pass — expedited entry into Churchill Downs
- Premium all-inclusive concessions including unlimited gourmet food offerings, specialty vendors, and premium alcoholic & non-alcoholic beverages
- 3-night stay in select Louisville hotel accommodations
- Daily breakfast for two
- Round-trip ground transportation between your hotel and Churchill Downs
- Winspire booking & concierge service — seamless support from start to finish
Few experiences in the world awaken the senses quite like the Kentucky Derby. For more than 150 years, this legendary celebration has woven together pageantry, fashion, sport, and Southern grace into a spectacle unlike any other. Silk dresses ripple beneath towering hats. Mint juleps catch the golden glow of spring sunshine. The air hums with anticipation — until the thunder of hooves sends a shiver through the crowd and history charges down the stretch.
This is where tradition lives and legends are born. Where strangers become friends over shared toasts. Where elegance meets exhilaration in a swirl of color, sound, and emotion.
This is not merely a race weekend — it is a front-row invitation into one of America’s most cherished and iconic traditions.
Kentucky Oaks — Friday: Grace, Glamour & Anticipation
Your unforgettable Derby weekend begins in one of the most coveted locations at Churchill Downs — First Turn seating, where the energy, beauty, and pageantry of the Kentucky Oaks unfold just feet away.
Churchill Downs is washed in blush-pink silks and spring blossoms, transforming the historic track into a living tableau of glamour, tradition, and excitement. The air sparkles with champagne, laughter drifts across the grandstand, and anticipation builds with every race. From your exceptional vantage point, you’ll sip premium cocktails, savor elevated culinary creations, and watch elite fillies thunder past in a blur of grace and power — so close you can feel the rhythm of every stride.
Here, fashion becomes art, celebration becomes tradition, and every moment feels infused with promise. This is more than race day — it’s the breathtaking overture to the most iconic weekend in sport.
Kentucky Derby — Saturday: The Most Exciting Two Minutes in Sports
Saturday dawns with a reverence and electricity unlike anything else. From the moment you arrive, the air hums with history — today, legends will be made.
Your First Turn seating places you at the heart of the action, where the thunder of hooves surges past in a breathtaking crescendo of speed, strategy, and spectacle. Indulge in premium all-inclusive cuisine and handcrafted cocktails as you mingle among racing aficionados, insiders, and fellow enthusiasts — all drawn here by the irresistible pull of the Run for the Roses.
Then, the moment arrives. The bell rings. The gates burst open. Twenty magnificent thoroughbreds explode onto the track, sweeping into the first turn directly before you — a surge of motion, muscle, and momentum so powerful it steals your breath.
For two unforgettable minutes, the world fades away — leaving only the roar of the crowd, the pounding of hooves, and the intoxicating thrill of witnessing history unfold mere feet from your seat.
VIP Fast Access — Effortless Arrival
From the moment you step onto the grounds of Churchill Downs, your VIP Fast Access Pass transforms arrival into a seamless, elegant experience. Skip the crowds, bypass the lines, and glide directly into the heart of Derby weekend — where excitement hums in the air, champagne sparkles in hand, and anticipation builds with every step. This is entrance without effort, style without stress, and the unmistakable feeling of being exactly where you belong.
Your Louisville Retreat
After exhilarating days at the track, retreat to the quiet comfort of your Louisville hotel, a serene haven designed for rest and reflection. Sink into plush bedding, unwind with a nightcap, and relive the day’s most thrilling moments. Each morning begins with a relaxed breakfast, fueling you for another day of pageantry, prestige, and pulse-pounding excitement. It’s the perfect balance — refined calm after unforgettable spectacle.
Seamless Transfers — Every Detail Handled
From hotel to track and back again, round-trip ground transportation ensures your weekend flows effortlessly. No planning. No logistics. No waiting. Just smooth, comfortable transfers that let you stay immersed in the magic of Derby weekend — free to savor every second, every cheer, and every unforgettable moment.
Why This Experience Captivates Donors & Closes Bids
- One of the world’s most iconic sporting events: The Kentucky Derby is instantly recognizable and universally aspirational — a global symbol of tradition, prestige, and celebration
- Coveted First Turn vantage point: Witness the most dramatic moment of the race as the field charges into the turn directly in front of you — an electrifying perspective few ever experience
- Two legendary race days included: Kentucky Oaks and Derby Day deliver a perfect blend of elegance, anticipation, and pulse-pounding excitement
- All-inclusive premium hospitality: Gourmet food, specialty vendors, and premium beverages elevate comfort while keeping guests fully immersed in the moment
- Emotion-driven storytelling: The thunder of hooves, fashion, pageantry, and history unfolding in real time create memories that last a lifetime
- Effortless luxury: VIP Fast Access, round-trip event transportation, and curated hotel accommodations remove every logistical concern
- Broad donor appeal: Ideal for couples, milestone celebrations, corporate gifts, and bucket-list seekers alike
- Auction-proven standout: Highly recognizable, limited-inventory, and excitement-driven — a package that sparks competitive bidding
- Winspire confidence factor: End-to-end concierge support ensures a seamless experience from the winning bid to the final toast
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
VIP Starting Gate Courtyard Access, Premium Hospitality, Event Transfers & 3‐Night Stay for 2
Please note that this package has limited inventory and can only be used in fundraising events prior to February 26, 2027.
This Experience for 2 Includes:
- Two (2) Starting Gate Courtyard tickets to the Kentucky Oaks — Friday, April 30, 2027
- Two (2) Starting Gate Courtyard tickets to the Kentucky Derby — Saturday, May 1, 2027
- VIP Fast Access Pass — expedited entry into Churchill Downs
- Premium all-inclusive concessions including unlimited gourmet food offerings, specialty vendors, and premium alcoholic & non-alcoholic beverages
- 3-night stay in select Louisville hotel accommodations
- Daily breakfast for two
- Round-trip ground transportation between your hotel and Churchill Downs
- Winspire booking & concierge service — seamless support from start to finish
Few experiences in the world awaken the senses quite like the Kentucky Derby. For more than 150 years, this legendary celebration has woven together pageantry, fashion, sport, and Southern grace into a spectacle unlike any other. Silk dresses ripple beneath towering hats. Mint juleps catch the golden glow of spring sunshine. The air hums with anticipation — until the thunder of hooves sends a shiver through the crowd and history charges down the stretch.
This is where tradition lives and legends are born. Where strangers become friends over shared toasts. Where elegance meets exhilaration in a swirl of color, sound, and emotion.
This is not merely a race weekend — it is a front-row invitation into one of America’s most cherished and iconic traditions.
Kentucky Oaks — Friday: Grace, Glamour & Anticipation
Your unforgettable Derby weekend begins beneath a wash of blush-pink silks and spring blossoms, as Churchill Downs transforms into a living tableau of beauty, elegance, and excitement. The Kentucky Oaks is where glamour meets tradition — a dazzling celebration of world-class racing, iconic fashion, and Southern hospitality at its finest.
From your Starting Gate Courtyard seats, you’ll sip premium cocktails, savor elevated culinary creations, and soak in the electric atmosphere as anticipation builds with every passing race. Champagne sparkles. Hats turn heads. Laughter drifts through the air. The crowd hums with possibility as elite fillies thunder down the track, each stride carrying the promise of history in the making.
This is more than a race day — it’s a celebration of grace, style, and the thrilling prelude to the greatest spectacle in sport.
Kentucky Derby — Saturday: The Most Exciting Two Minutes in Sports
Saturday arrives wrapped in reverence, excitement, and pulse-quickening anticipation. From the moment you step through the gates, you feel it — this is hallowed ground, and today, history will be written.
Your Starting Gate Courtyard access places you just steps from the track, immersing you in the raw drama of the sport. Indulge in premium all-inclusive cuisine and beverages, mingle among racing insiders, and feel the thunder beneath your feet as the finest thoroughbreds on Earth prepare to break from the gate.
Then — the moment. The bell rings. The gates explode open. Twenty magnificent horses surge forward in a breathtaking blur of power and grace.
The roar of the crowd swells. Hearts pound. Time stands still. And in the most electrifying two minutes in sports, a champion is crowned — wrapped in roses, forever etched into history.
This isn’t just an event. It’s a once-in-a-lifetime moment, lived from the very heart of the action.
VIP Fast Access — Effortless Arrival
From the moment you step onto the grounds of Churchill Downs, your VIP Fast Access Pass transforms arrival into a seamless, elegant experience. Skip the crowds, bypass the lines, and glide directly into the heart of Derby weekend — where excitement hums in the air, champagne sparkles in hand, and anticipation builds with every step. This is entrance without effort, style without stress, and the unmistakable feeling of being exactly where you belong.
Your Louisville Retreat
After exhilarating days at the track, retreat to the quiet comfort of your Louisville hotel, a serene haven designed for rest and reflection. Sink into plush bedding, unwind with a nightcap, and relive the day’s most thrilling moments. Each morning begins with a relaxed breakfast, fueling you for another day of pageantry, prestige, and pulse-pounding excitement. It’s the perfect balance — refined calm after unforgettable spectacle.
Seamless Transfers — Every Detail Handled
From hotel to track and back again, round-trip ground transportation ensures your weekend flows effortlessly. No planning. No logistics. No waiting. Just smooth, comfortable transfers that let you stay immersed in the magic of Derby weekend — free to savor every second, every cheer, and every unforgettable moment.
Why This Experience Captivates Donors & Closes Bids
- One of the world’s most iconic events: The Kentucky Derby is instantly recognizable — a global symbol of tradition, glamour, and sporting history
- Front-row prestige: Starting Gate Courtyard access places guests at the very heart of the action — a level of proximity few ever experience
- All-inclusive luxury: Premium food, specialty vendors, and top-shelf beverages remove every friction point, letting donors fully indulge
- Two legendary race days: Kentucky Oaks and Derby Day combine elegance, anticipation, and peak exhilaration into one unforgettable weekend
- Emotional storytelling built in: The pageantry, fashion, thunder of hooves, and crowning of a champion create moments that stay with guests forever
- Effortless execution: VIP Fast Access, private transfers, and curated accommodations ensure a seamless, stress-free experience
- Broad donor appeal: Ideal for couples, milestone celebrations, corporate gifts, and once-in-a-lifetime bucket-list seekers
- Auction-proven magnet: Aspirational, limited, and excitement-driven — a package that commands attention and competitive bidding
- Winspire confidence factor: End-to-end concierge support builds trust, eliminates uncertainty, and makes bidding feel easy and secure
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
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