Monticello and Highlands: Touring After Christmas

Beautiful Downtown Charlottesville, VA

Touring Monticello and Highland estates just after Christmas felt like an ideal way to slow down, reflect, and begin the New Year with a deeper appreciation for American history. Winter break brings fewer crowds, which allowed us to explore both estates at a relaxed pace and take in details that we would have missed during the busier seasons.

Monticello

Monticello: Thomas Jefferson’s home

Monticello, Thomas Jefferson’s mountaintop home, is as impressive for its views as it is for its architecture. We booked a “Behind the Scenes” tour, which was worth every penny! Our tour guide held a master’s in history and truly brought the tour to life with stories of Jefferson’s personal and professional achievements and challenges.

It took Jefferson 40 years to complete his beloved home with treasures he collected all his life as a US statesman—it is impressive! Don and I recognized the French influence in the small hidden stairwells, octagonal domes, alcove beds, wine and wheeled dumbwaiters, and much more.

Thomas Jefferson family cemetery

Touring his home, ground exhibits, and family cemetery offered us a personal view of Jefferson’s life, innovations, and contradictions, making the visit both educational and an opportunity to reflect. I highly recommend it!

Highland

James Monroe’s Highland, early historic home

Highland, James Monroe’s estate, is a more understated but equally meaningful experience. The property offers an intimate insight into Monroe’s early years and highlights Thomas Jefferson’s influence as his lifelong mentor.

James Monroe’s Highland living room

This experience complements Monticello but differs in that it is self-paced with aspiring college graduates as interpreters (included in admission price). They explain the history and artifacts of the property, which is more intimate and interpretive—great for travelers who enjoy storytelling.

The Forum Hotel

The Forum, beautiful lobby

We stayed at the Forum Hotel, a Kimpton property, which was delightful and quiet as the UVA students were out for Christmas break. Perfect for our peaceful long weekend, which was just what we were looking for.

The staff was attentive, including the valet for our car—the best! We shared two meals during our stay, both were delicious, especially breakfast, which included healthy options. The icing on the cake for us was seeing all the owners spoil their beloved pets as Kimptons are pet-friendly hotels. Good to know!

Good Sport: Forum Hotel casual eatery

In sum

This was the perfect long weekend that focused on celebrating two past American presidents’ legacy in honor of America’s 250th birthday. We relaxed, ate wonderful local food, learned new pieces of history, and admired breathtaking mountain scenery.

It’s exactly what we hoped for and we would happily return.

Tavola: Authentic Virginia-Italian

• The Forum Hotel is an ideal base. Located near UVA, it offers quick access to both Monticello and Highland, making Charlottesville easy and convenient. Quieter when students are on break and bustling when they are in session, but regardless, it is a great place to stay!

• Plan around winter daylight. Visiting in winter means fewer crowds also shorter daylight hours-plan Monticello early in the day. You could plan Highlands in the afternoon or the next day for a more relaxed pace as we did.

Monticello

• Accessibility at Monticello is limited. Only the first floor is accessible to guests with mobility challenges, and there is no elevator for upper floors.

• Expect steep, narrow stairwells at Monticello. Jefferson’s French-inspired staircases are tight and quite steep. On our tour, one guest hand-carried her oxygen tank up the two flights of stairs with family assistance. Something to keep in mind if stairs are a concern.

• Highland Tour stays on the main level. Upstairs is not part of the tour, and the historic floors on the main level can be uneven, which may be important for guests with mobility concerns.

Restaurant recommendation: Tavola

This rustic, upscale “Virginian Italian” spot was a highlight of our trip. The menu is homemade and seasonally sourced, and the owner makes his own music soundtracks—my husband and I found ourselves singing along all evening.

• Tip: Make reservations—this gem is about quality, not quantity. $50-$100 range pp.

Breakfast must-try: Bodo’s Bagels

Who expects to find an authentic New York deli in Charlottesville, VA? There is always a line, but they are quick, inexpensive, and downright delicious. See for yourself!

For more inspiration and insider recommendations, visit our Virginia page.