Virginia Wine & History Group Getaway
In Partnership with Monticello Wine Tour & Coach Co.
An Experience That Blends the Best of Both Worlds
A visit to Monticello is a must when exploring the Charlottesville area. The home of Thomas Jefferson offers more than history. It also tells the story of early American wine. Jefferson planted some of the first grapevines in the United States right here in Charlottesville, Virginia, helping spark what we now know as American viticulture. Today, you can sip wines grown from the very land that started it all.
Our Virginia Wine and History Group Tour Package blends the best of both worlds. Explore iconic landmarks, then unwind with curated tastings at some of the region’s top wineries—all in one seamless weekend, including neighboring Pippin Hill Farm & Vineyards. Whether you are visiting Monticello, James Monroe's Highland, or the University of Virginia, we are partnering with Monticello Wine Tour & Coach Co. to offer transportation and a personalized itinerary for history lovers, including private guided tours to make each stop more meaningful.
Your stay at Crossroads Inn adds to the experience. Our 1820s property surrounds you with history while offering modern comfort. From arrival to departure, our team takes care of every detail so you can simply relax and enjoy.
Seamless Transportation, Thoughtfully Arranged
We are proud to partner with Monticello Wine Tour & Coach Co. to provide seamless transportation. Groups lodging at Crossroads Inn receive a special rate when booking with them, making it easy to explore safely and comfortably. During your stay, in addition to tour transportation, they offer airport transfers and can even arrange transportation for an evening out, so you can relax and enjoy every moment.
Why 2026 is the Perfect Time to Visit
250th Anniversary of America's Independence
The year 2026 marks VA250, the 250th anniversary of the United States. Virginia is at the heart of this milestone, and Charlottesville offers a uniquely immersive way to experience it. With its deep ties to the nation’s founding, preserved landmarks, and thriving wine scene, there is no better place to celebrate America’s story while enjoying its flavors.
Below is a sample 48-hour itinerary designed in partnership with Monticello Wine Tour & Coach Co. to help you experience VA250 in a memorable and relaxing way.
Minimum stay requirements may apply.
Sample Itinerary for Your Group
Friday | Arrival & Historic Exploration
Customized breakfast or brunch at Crossroads Inn
Visit Monticello
Lunch at Michie Tavern
Tour James Monroe's Highland
Private wine pairing dinner {Chef’s Table Experience} at Crossroads Inn
Saturday | Wine Country Experience
Customized breakfast or brunch at Crossroads Inn
Estate Tour and Tasting experience at Pippin Hill
Greenhouse Grazing Experience, featuring seasonal boards and curated wine pairings in a sunlit greenhouse overlooking the Blue Ridge
Evening to explore Charlottesville’s dining scene, with curated restaurant reservations and private dining options arranged for your group
Sunday | Departure
Customized breakfast at Crossroads Inn
Depart Virginia Wine Country, with plans to return again soon!