Inspired Itineraries: Alex Schroeder (@DevourDC)

10AM - Amtrak Arrival (DC -> Charlottesville)

Did you know that Amtrak runs multiple times a day from DC to Charlottesville and the ride is just under 3 hours long? Check the schedule & ticket prices on Amtrak’s website.

Early Check-In at The Draftsman Hotel (1106 W Main St)

Alex stayed at The Draftsman Hotel, a 7-minute walk from the station. We recommend stopping by to see if your room is available early or dropping your bags off at the front desk so that you can explore the area.

11AM Guajiros Miami Eatery (114 10th St NW)

For brunch, Alex headed to Guajiros Miami Eatery, a family-owned, local favorite. Their menu is inspired by flavors of South Florida, Central America, and the foods their family grew up eating. Don’t forget to get some of their Cuban-style coffee too!

12:30PM Downtown Charlottesville

A visit to Charlottesville isn't complete without a stop at the Downtown Mall. It’s a wonderful mix of restored and renovated buildings where visitors can enjoy shopping, dining, and entertainment. Of the roughly 200 pedestrian malls built in the United States during the 20th century, only about 30 remain today, and Charlottesville is one of them!

Recommended stops:

• The Beautiful Idea (shopping)
• Oyster House Antiques (shopping)
• Hedge Fine Blooms (shopping/flowers)
• Darling and Dashing (clothing shopping)
• Old Flame Vintage (clothing shopping)
• Second Street Gallery

4PM Ethos Wine & Tea (817 W Main St)

After exploring the area, Alex took some downtime at The Draftsman Hotel and got settled in. Afterwards, he headed to Ethos Wine & Tea, a 7-minute walk from the hotel. Women-owned Ethos is an inviting spot for wine, tea, small plates, and community gathering.

6:30PM Maggie’s Midtown (606 W Main St)

A newer addition to Charlottesville’s West Main St, Maggie’s Midtown serves elevated pub classics in a polished yet welcoming setting. Check out their menu 👉https://www.maggiesmidtown.com

8PM Up on the Roof (499 W Main St)

After dinner, Alex headed to the rooftop of the nearby Doyle Hotel for post-dinner cocktails. Up on the Roof has an excellent selection of menu items made with locally sourced ingredients that pair perfectly with their creative, hand-crafted cocktails. The sun setting over the Blue Ridge Mountains was a gorgeous bonus and the perfect way to end the day.

9AM The Ridley

Located right inside the Draftsman Hotel, the Ridley was a perfect place for Alex to grab a hearty breakfast in preparation for the day’s activities.

10:30AM Winery Tour with Monticello Wine Tour

Today was all about wine country and Alex decided to explore the area with Monticello Wine Tour, a local transportation company that provides curated wine and craft beer tours! His driver, Ben, picked him up right from the hotel in a cozy Mercedes Sprinter and they headed out for their day exploring the Monticello Wine Trail!

First Stop: King Family Vineyards
Co-owner James King was kind enough to take Alex on a personal behind-the-scenes tour of the winery where they explored the polo barn, vineyards, barrel room, and ended with a tasting of select wines. King Family Vineyards offers an excellent assortment of tasting and experiences – all bookable from their website.

Second Stop: Pippin Hill Farm and Vineyards
Next, Alex headed to Pippin Hill Farm and Vineyards for a self-guided tasting and lunch on their gorgeous veranda. Their tapas-style menu features fresh ingredients from local farms (including their own) and elevated bites meant to pair with their current wine offerings.

Third Stop: Eastwood Farm & Winery
Last but not least, Alex rounded out the day with a stop at women-owned and operated Eastwood Farm & Winery. Known for their award-winning wines, Alex enjoyed a curated tasting and the opportunity to chat with owner Athena Eastwood before heading back to his hotel.

7PM Oakhart Social (511 W Main St)

For dinner, Alex went to Oakhart Social, just a 10-minute walk from the hotel. Their seasonal dinner menu consists of delicious, wood-fired modern American food that’s meant for sharing and made using the best local ingredients! Take a look at the menu 👉https://www.oakhartsocial.com/...

9AM - Cou Cou Rachou (917 Preston Ave Ste B)

Alex started his final morning off right with a stop at Cou Cou Rachou. This beloved French bakery is the perfect stop for savory and sweet pastries that are as gorgeous as they are delicious!

10AM Monticello (1050 Monticello Loop)

Next, Alex headed to the mountaintop for a tour at Thomas Jefferson’s 1769 home, Monticello. With guided tours and 250th events galore, there’s plenty to do at Monticello year-round, especially in 2026. If the weather is right, you can even hike up via the Saunders-Monticello trail, a very manageable four-mile trail with a maximum grade of 5%.

1PM Bodo's Bagels (1609 University Ave)

Before heading home, Alex of course had to stop at Bodo's Bagels! The beloved bagel shop was just a 10-minute walk from the hotel and although the line looked long, service was fast!

2PM - Explore UVA Grounds

Just a few minutes farther down West Main St are UVA Grounds, one of Charlottesville’s most iconic destinations and well worth exploring during any visit.

Recommended stops:

• The Rotunda
• The Memorial to Enslaved Laborers
• Mincers (UVA Gear)
• Moge Mochi Donuts & Boba
• Shannon Library
• Contemplative Commons

5PM Departure Back to D.C.

Alex returned to The Draftsman Hotel to collect his bags before making the short walk back to the Amtrak station for his trip home to Washington D.C.

Now that you know what you'll do while you're here in Charlottesville & Albemarle County, start planning your trip by browsing lodging at the link above. We hope you'll have as much fun as Alex did!