This adventure begins in the bustling metropolis of Chicago, a city renowned for its towering skyscrapers, vibrant arts scene, and delectable deep-dish pizza. From there, we embark on a scenic journey through the heartland of America, traversing miles of rolling hills, picturesque farmland, and charming small towns. As we approach our destination, the landscape transforms into the rolling hills and lush greenery of Kentucky, a state steeped in history and natural beauty.
Our journey culminates in the historic city of Lexington, known as the "Horse Capital of the World." Here, we will delve into the rich equestrian heritage of the region, visit world-class horse farms, and witness the grace and athleticism of these magnificent animals. Beyond the equestrian allure, Lexington offers a vibrant downtown area, charming boutiques, and delectable local cuisine, ensuring a memorable and enriching experience for all who visit.
Throughout this adventure, we will uncover the hidden gems and iconic landmarks that define these two distinct regions of the United States. From the bustling streets of Chicago to the serene landscapes of Kentucky, this journey promises a tapestry of unforgettable experiences, creating lasting memories for travelers of all ages.

Chicago

Chicago to Lexington

Sights & Landmarks

Shopping

Food & Drink

Nature & Parks

Tours

Concerts & Shows

Museums

Other

Lexington

Get ready for an epic road trip from the vibrant streets of San Jose to the charming city of Louisville! This cross-country adventure will span several days, taking you through diverse landscapes and countless unforgettable experiences. Pack your bags and get ready to explore the heartland of America, discovering hidden gems and creating lasting memories along the way.
As you embark on this journey, you'll witness a kaleidoscope of natural wonders. From the towering mountains and shimmering lakes of the West to the rolling hills and verdant plains of the Midwest, every mile will bring a new and breathtaking view. Along the way, you'll encounter friendly locals, each with their own unique stories to share.
Whether you're seeking adventure or relaxation, this road trip has something for everyone. Hike through majestic national parks, marvel at awe-inspiring waterfalls, and visit historic landmarks that shaped the course of American history. Immerse yourself in the lively music scene of Nashville, or stroll through charming small towns that embody the spirit of Americana. The possibilities are endless, so buckle up and get ready for the adventure of a lifetime!

San Jose

San Jose to Louisville

Fun & Games

Outdoor Activities

Classes & Workshops

Water & Amusement Parks

Traveler Resources

Nightlife

Louisville

Get ready for an incredible journey from the bustling city of Dallas to the charming town of Lexington! Along the way, we'll traverse diverse landscapes, witness historical landmarks, and create unforgettable memories.
Our adventure begins in the heart of Dallas, a vibrant metropolis where skyscrapers pierce the sky. As we leave the city behind, we'll embark on a scenic drive through the rolling hills and picturesque countryside of Texas. We'll pass by charming small towns, each with its own unique character and stories to tell.
Continuing our journey, we'll cross into the state of Oklahoma, where vast prairies stretch out before us. We'll marvel at the towering Arbuckle Mountains and visit historic sites that recall the region's rich heritage. As we approach Lexington, the landscape transforms once more, revealing rolling green hills and the promise of new experiences.

Dallas

Dallas to Lexington

Spas & Wellness