Gal’s Getaways

Take a two-day trip with your friends to Charlottesville, VA, to visit wineries, the downtown area, have a guided painting lesson in the mountains, hike beautiful trails, and much more! This trip is completely tailored to your requests! Overnight options include camping or hotel reservations. Speak with us to work out the details of your adventurous weekend!

Price: $2,240 Private group tour (Based on $140/person for private group-tour (min. 10 / max. 16))

Duration: 2 days


What’s included
  • Expert pre-planning services
  • On-board tour guide
  • Air-conditioned vehicle
  • Transportation
Optional Add-ons
  • All inclusive package: an additional $220 per person
    • Lunch x2
    • Dinner x2
    • Breakfast x1
    • Drink voucher at winery x1
    • Choose one: Hotel room or campsite booking




DEPART – 8:00 am on Saturday, January 18th from REI 350 Independence Blvd, Virginia Beach > Charlottesville, VA!

RETURN TO REI – 6:00 – 8:00 pm (traffic dependent).

7:45 Arrive/board the bus

8:00 – (departure)  174 miles  2 hours, 50 min We will stop mid-way for 1-hour BRUNCH/mimosas along the route (not included in price, bring $; restaurant TBD by group majority)

Directions – We can stay on I-64 W for the shortest route, or we can take a more scenic route (TBD by group majority)


Between noon and 1:00 – Arrive at Boar’s Head Resort. (Check-in time TBD)

1:30 – 2:00 Drive to the Glasshouse vineyard for guided painting with an artist (bring $ for wine tasting)

2:00 – 5:00 Possibly visit a 2nd vineyard if time allows. The vineyards close at 5:00.

5:30 – Drive to “the downtown pedestrian mall” for dinner. List of “cheap eats,” “midrange,” or “high end” dining options will be provided. Individuals can take 2 hours free choice time for dinner.

7:30 – whenever GAME NIGHT! Gift exchange, Bonko, prizes!



Breakfast (9 am place or a later brunch, TBD by majority)

Optional Activities 1. Sleep in until check out ? 2. Monticello $26 basic tour or $49 behind-the-scenes tour (advance tickets online); min 3-hours advised. 3. Pre-book yourself a service at the Boar’s Head Resort Spa 4. Take in other area tourist activities

DEPART – 2:00 pm > 5:30 pm (one ½ hr stop to stretch legs and restroom break)

Optional stop in at Pippin Winery on our way home (add 2 hours to return time) (TBD by majority)

RETURN to REI before 6:00 – 8:00 pm (traffic dependent).

For our pick-up locations please visit our FAQs page

We go rain or shine, see our weather policy FAQson the  page


*All our tours involve walking; guests should expect varying degrees of physical activity.

Plan your group trip now!

We are flexible and can accommodate your groups particular interests.

Please fill out the short questionnaire provided below, and we will contact you soon to choose a date and finalize details.

We know your group will have a great time. This an opportunity to bond with one another. You will leave inspired and feel a deeper connection with the environment. Every moment of your adventure is thoughtfully planned out, from the moment you step on, until you disembark.