Wineries of Charlottesville

Our Adventure

For three days we'll explore the historic Monticello Wine Trail. With over 33 wineries on the Monticello Wine Trail, we’ll only have time to explore 5 of them. Time will surely fly by during this wine weekend, with spectacular views of the Blue Ridge Mountains to enjoy while we sip our way across the region.

What's Included

• 2-night stay at the English Inn of Charlottesville
• Breakfast every morning
• Transportation to and from Charlottesville
• Transportation to Wineries
• 1 four-course dinner with wine pairing at The Farmhouse at Veritas

Departure & Return:

Departure Time: Saturday 11:30 AM

Return Time: Monday Approximately 7:00pm

Departure & Return Point: Franconia-Springfield Metro

ITINERARY:

Day 1: Saturday

We will meet Saturday morning at Franconia-Springfield Metro at 11:00am, we will depart promptly at 11:30am. Please Park in the multi-day parking area and meet the group down by the bench on the ground floor. Look for our Meetup sign.

Multi-day parking: Between 15 and 17 spaces are allocated for multi-day use of up to 10 days. Availability is on a first-come, first-served basis. There is no charge for multi-day parking beyond the regular fee. Access multi-day parking by entering the garage through the lower-level entrance #1 and proceeding to row J of the facility. Park in spaces signed "Multi-day Parking."

Our first stop of the day will be at Barboursville Vineyards, an magnificent and historic Virginia estate outside of Charlottesville between Monticello and Montpelier, home to Virginia's most honored winery, founded in 1976 by a family prominent in Italian viticulture since 1821. Producer of Octagon, the most renowned red wine of Virginia. where we will enjoy their award-winning wines and beautiful views. They also offer a few food options you can purchase. They have multiple tasting options to choose from.

Next, we will check-in at the hotel and get settled into our rooms. We can meet at the hotel bar for a drink before we head to Veritas Winery for a four-course, wine paired dinner at they're The Farmhouse at Veritas restaurant. Their menu will feature homegrown and house-made Farm-to-Fork ingredients. This dinner is included in the price of the trip.

Day 2: Sunday

Wake up and enjoy breakfast before we head out to Horton Vineyards. Horton Vineyard is one of the most innovative wineries in the country. Utilizing the latest viticultural techniques, Horton is charting a new generation of wines made from Viognier, the premier grape of France's Rhone Valley, and other premium varieties from southern France, Portugal, Spain, Russia/Georgia, and Italy. Horton Vineyards has over forty wines to taste. Their knowledgeable staff will guide us through each of them to help us fully explore our palate to find our new favorite.

Next, we will head to Early Mountain Vineyards. Set against the stunning backdrop of the Blue Ridge Mountains, Early Mountain Vineyards in Madison, VA is one of the true gems of Virginia wine country. With 300+ acres of rolling hills and award-winning wines, this spot knows how to impress.

We’ll relax in their beautiful tasting room—or if the weather’s right, sip and soak up the views outdoors. Each pour is thoughtfully crafted with care and connection to the land, and their food? Next level. The on-site culinary team serves up seasonal dishes made with ingredients from local farms—each bite perfectly matched to the wines. This stop is all about slowing down, sipping well, and tasting the best of what Virginia has to offer. You are responsible for your own lunch.

Finally, we will head to the hotel so that we can freshen up and relax.

Day 2: Monday - Check-out 11am

Sleep in a bit after our previous day of indulgence. Before we head home, we will stop at Pippin Hill Farm & Vineyards. Pippin Hill Farm & Vineyards is unique among the growing number of fine wineries along Virginia’s Monticello Wine Trail. They are known for creating distinguished boutique wines. Here you can also enjoy their amazing Farm-Table lunch. You are responsible for your own lunch.

After having our fill of this weekend tasting and touring, we will make the journey back home

PACKAGE PRICE:

$938.00 per person based on single occupancy only

Deposit: A refundable deposit of $200 is due at the time of reservation. If requested by 11:59 pm on August 15rd.

Monthly Payments: After your initial deposit we will set up a Monthly Payment plan of equal amounts due on the 1st of each month through the full pay date. You may pay in full at any time.

Final Payment: is due August 1, 2026

CANCELLATION POLICY: Payments are refundable if canceled before 11:59 pm Est on August 15th. All payments are nonrefundable after 12:00 am August 16th.

If you're seeking a relaxed wine weekend filled with delightful company, exquisite wines, and breathtaking mountain views—this is the perfect getaway.