Wine Weekend: Charlottesville

Let’s Explore the Historic Monticello Wine Trail

February 17th – 19th, 2024

When We're Going

February 17th – 19th, 2024

Presidents’ Day Weekend


Early Bird Price: $745.95 per person single occupancy.

*Price increase to $797.10 after January 15th*

Trip Length

2 Days

Drive Times

Departing: 11:30am
Est. Return: 9pm
2hrs, from Franconia/Springfield Metro.


Did you know that Virginia is the true birthplace of American wine? Join your fellow Wine Lovers on a wine weekend to Charlottesville wine country. 

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 6 of them. Time will surely fly by during this wine adventure.

With spectacular views of the Blue Ridge Mountains to enjoy while we sip our way across the region.


  • Transportation To/From Charlottesville, VA
  • 2 Nights at 4 star hotel
  • Daily Breakfast
  • One 4-Course Dinner with wine pairing
  • Private Driver to Wineries (winery tasting fee not included)


You join a fun group of fellow food and wine lovers who love to travel!  There is never an increase in trip costs once you’ve booked.  As well as no extra fees are charged to those who prefer to use our trip payment options.

Every travel need is handled from the moment you decide to join us. We handle airport transfers, tours, local transportation, and accommodation needs. If you need a roommate, we will connect you with a fellow traveler. Your only responsibility is to enjoy your trip!



Our home for this weekend is the polished Doubletree Hotel Charlottesville. Our Doubletree hotel overlooks the Rivanna River and is within easy access to the University of Virginia, John Paul Jones Arena and the Charlottesville regional airport. After you’ve rested, visit nearby historical attractions such as Monticello, Ash Lawn Highland, Michie Tavern, and the downtown mall.

Enjoy the outdoors as we are minutes from the Appalachian Trail, Shenandoah National Park and world-class snow skiing. The Doubletree Hotel Charlottesville is also conveniently located near local vineyards, championship golf, Virginia antiques and many other area attractions that have made Charlottesville, Virginia a destination for years.

After a full day of activities, relax in one of our 235 spacious guest rooms featuring our Doubletree Sweet Dreams bedding, complimentary WiFi, 24-hour complimentary business center, indoor pool and fitness center featuring Precor fitness equipment.

Also available at the Doubletree Hotel Charlottesville are whirlpool suites, one bedroom suites and an executive level featuring an executive lounge, which is host to continental breakfasts and evening receptions. You can experience a one of a kind dining experience at Root 29 Craft Kitchen & Bar open daily featuring breakfast, lunch and dinner. Dine in your room with room service, offered seven days a week. We are Charlottesville’s largest conference facility with over 16,000 sq. ft. of meeting room space which we can tailor to fit any size function, from a dinner of four to a conference of 600. Our team can customize any meeting, wedding or reunion that you and your guests will never forget.


  • Transportation To/From Charlottesville, VA
  • One 4-course dinner with wine pairing
  • Private Driver To Wineries (winery tasting fee not included)
  • Daily Breakfast
  • Transportation to Meeting Point

  • Meals and beverage not previous indicated

  • Winery tasting fees

  • Optional Tours

  • Travel Insurance (See Our Terms & Conditions)

  • Items of a Personal Nature

  • Lunch 

**You will be responsible for your tasting purchases at the wineries. **

There is nothing worse than missing a vacation…how about also losing the money you paid for your vacation? Because all of Be Relaxed Destinations and Wine Lovers group tours are non-refundable and non-transferable, travel insurance is highly recommended. Your premium is related to your trip cost, so you don’t have to worry about being over-insured. Click here for our preferred travel insurance vendor.

  • Making reservations for this package signifies your acceptance of our Trip Terms and Conditions.

  •  Payments are refundable if canceled before 11:59pm Est on November 3rd. All payments are nonrefundable after 12:00am November 4th.

  • Prices are subject to change without notice. Please make your reservations today at this price to be locked in.

  • Monthly payments are required to keep your reservations current. Your invoice will clearly note your payment plan. We suggest you put this payment plan on your personal calendar.

  • You must ensure your roommate, if applicable, is also making timely monthly payments.

  • Roommate Matching is available. Review our Roommate Matching Program.

  • Declined cards will be tried automatically over three days. If it is declined on the third day your reservation will be cancelled.

  • All late payment requests must be approved by management before the final payment deadline on your account.

  • Note: Your card will not automatically be charged by completing and submitting this form; however, completing and submitting this form does give the agent the right to charge the card for the amount and purpose authorized above.

**The accommodations, activities, and other inclusions and/or their order may change and/or be cancelled due to circumstances beyond our control and/or for any other reason we deem necessary. In the event this occurs, we will try our best to arrange similar accommodations, activities, and other inclusions**

We will host a pre-dinner event one week before our departure to celebrate our upcoming trip and to get to know your fellow wine lovers. This also gives you a chance to ask any additional question you might have.



Early Bird Price: $745.95 per person single occupancy.

*Price increase to $797.10 after January 15th