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Our Wine Tasting Tours in Charlottesville, Virginia

Whether you want a leisurely afternoon of wine tasting with your special someone, are planning to shop and fill your wine rack, or just want to figure out what kinds of wine you like so you can order in a restaurant with confidence, Monticello Appellation Wine Tours has you covered with more than 13 years of touring experience in the Charlottesville Wine Country!

More than just transportation, the owners/guides of Monticello Appellation Wine Tours are ready to take you tasting at three wineries and escort you through your tastings. Three tour amenities are offered. All tours take you to three popular local wineries for tasting with pickup at 1pm, returning around 5pm.

1. The most popular tour amenity is the local deluxe cheese plate which is served at the second winery. The cheese plate offers a generous serving of local cheeses, local artisan chocolate, and fruit. This tour is available any day of the week at $145 per person.

2. The Food Pairing Tour offers cheeses with the first winery tasting, finger snacks with the second, and at the third winery dessert samples from our most popular bakery in town. This tour is offered Thursdays and Fridays when the wineries are less busy. Fee per guest is $165 per person

3. The picnic lunch is available any day of the week but Saturday. The lunch includes a small cheese plate appetizer, gourmet sandwich and kettle chips, and local bakery pastry dessert. This tour is $165 per person.

We regret we cannot include tasting fees as the wineries do not allow tour companies to pay tasting fees. These fees run $8 – $12 per person and all the wineries take credit cards.

All tours include plenty of chilled bottled water.

Each tour can book from 2 to 6 guests. Taste of Monticello does not book groups of more than 6.

Currently two routes are offered:

The Western Tour Route: Tour guides create an itinerary for every tour depending on wines available and weekend versus weekday tours from the following local wineries: Pollak Vineyards, King Family Vineyards, Grace Estate Winery, Stinson Vineyards, Cardinal Point Winery, Afton Mountain Winery, Knight’s Gambit and Veritas Vineyards.

The Southern Route: For this route, itineraries are selected for every tour depending on wines being poured from the following: Michael Shaps Wineworks, First Colony Winery, Trump Winery, Blenheim Vineyards, Jefferson Vineyards and Gabriele Rausse Winery.

Our daily tours include:

  • Pickup and return to your Charlottesville or Scottsville address, B&B or hotel
  • Driver/guide to assist you through your tastings
  • Personalized Itinerary & Virginia Wineries Guide
  • Chilled bottled water
  • Deluxe plate of local cheeses, crackers, artisan chocolates, and fresh fruit

“The highlight of our trip. A terrific itinerary, comfortable ride, gorgeous scenery, and attentive guide providing local history and education. The wine! We learned a lot from Chris and from the three wine tastings.” ~ Guest Comment

“I contacted Monticello Appellation Wine Tours based on TripAdvisor, to reserve for a party of 10. Spoke with Chris who told me he can only handle up to six. I was instantly referred to others who could accommodate our group. Chris was selfless, still assisting me. This must be why Monticello Appellation has a great rating. We were not even their customers, and they still served our needs. Thanks Chris!” ~ Guest Comment


Lunch Package[Read Details…]

Add our beautiful gourmet picnic served Lunch Package, for $20 per person! The total cost of tour and lunch is $165 per person,

The lunch is available Sunday through Friday, and served at a winery indoors or out, depending on the weather, using upscale linens, silver, and heirloom china. No box lunches on our tours!

Included is chilled bottled water. Wine may be purchased at the winery.

Lunches include a cheese plate appetizer, hearty sandwich on a home-baked
roll, crunchy kettle chips, and a local freshly baked pastry for dessert.

Sandwich menu for the Western Tour:

  • Devon – all-natural Roast Beef with horseradish-chive spread and arugula on focaccia
  • Blue Slate – smoked Turkey Breast with havarti cheese, lettuce, tomato and ancho-lime mayonnaise on country bread
  • Chester – panini- All-Natural Ham with provolone, spicy sweet mustard and roasted
    peppers on focaccia
  • Italian – thinly sliced Sopressata and Genoa Salami with provolone, sliced peppers, lettuce and homemade Italian dressing
  • Orpington – tuscan grilled chicken salad with mixed greens on sliced country bread
  • Landrance – prosciutto and fresh mozzarella on baguette with roasted tomatoes, arugula and garlic vinaigrette(also available as a vegetarian sandwich)
  • Melrose – panini -Grilled Portobello Mushrooms and red onions with roasted peppers,
    homemade pimento Cheese and arugula
  • Riviera – our Italian Tuna salad with capers, roasted tomatoes and olive oil, served with mixed greens on sliced country bread
  • Galloway – panini -Pastrami and Swiss with mustard and vinegar slaw on rye bread

Sandwich menu for the Southern Tour:

  • Jefferson – maple turkey cranberry, relish cheddar, lettuce, herb mayo, French bread
  • Farmington – smoked turkey, bacon, havarti, slaw, lettuce, tomato, herb mayo, French bread
  • Rivanna – cajun roast beef, provolone, bacon, onion, lettuce, tomato, BBQ vinaigrette
  • Ednam – maple turkey, havarti, bacon, avocado, lettuce, tomato, herb mayo, French bread
  • Montpelier – rare roast beef, cheddar, lettuce, tomato, horseradish mayo, French bread
  • Belmont – peppered ham, salami, bologna, provolone, hot pepper relish, lettuce, tomato, onions, oregano, vinaigrette, French bread. **VERY SPICY**
  • Keswick – Country ham, Swiss, honey mustard, lettuce, tomato, herb mayo
  • Earlysville – sweet ham, turkey, smoked Gouda, bacon, lettuce, tomato, herb mayo, sourdough
  • Birdwood – cracked pepper turkey, onion, pepper jack, avocado, banana peppers, lettuce, herb mayo, French bread
  • Afton – corned beef, Swiss, cole slaw, brown mustard, rye bread
  • Crozet – chicken salad, cranberry relish, Dijon mustard, lettuce, sourdough
  • Batesville – Cajun roast beef, smoked gouda, lettuce, tomato, onion, brown mustard, horseradish mayo
  • Walnut Creek – deli chicken, pepper jack, chipotle mayo, lettuce, tomato, whole grain ciabatta
  • Vegetarian:Ivy – carrots, avocado, cucumbers, lettuce, tomato, sprouts, herb mayo, French bread
  • Vegetarian:Yogaville – cheddar, havarti, Swiss, sprouts, cucumber, lettuce, tomato, herb mayo, French bread

Birthday Package[Read Details…]

For those who are doing a birthday tour, here is something you can order to make it extra special!

We offer a selection of elegant 6-inch birthday cakes from our FAVORITE bakery, Albemarle Baking Company. We’ll bring the box as well so you can enjoy the remainder as a midnight snack!

The first is the white cake – layers of vanilla sponge with Bavarian cream Cake, iced with a marzipan frosting.

We also offer a chocolate cake – bottom layer of chocolate cake, then a layer of dark chocolate, white chocolate, and milk chocolate mousse, covered with a milk chocolate glaze. The price of this package is $30.

Monticello Appellation’s B&B Travelin’ Through Wine Country Package[Read Details…]

Driving through Charlottesille? Make your overnight stop a stay to remember! This tour is available any Sunday through Thursday.

For this package contact one of our favorite locally owned Charlottesville B&Bs for your room reservation from our pickup list below.

Then book your tour at our secure site here. Be sure in the notes section to let us know you are staying local in Charlottesville at one of our favorite B&Bs for your discount. The regular tour cost is $145 per person, and our B&B discount is $125 per person.

Our B&B list in alpha order is:

 Arcady Vineyard B&B

Foxfield Inn

Inn at Court Square

Inn at 400 West High

200 South Street Inn

Be sure to let your B&B know that you will be arriving earlier than check in time for us to pick you up for your wine tour so they can be ready for you. Your room will not be ready as we pick up for wine tours at 1pm and rooms are not generally ready until 4pm so you will probably do your check in after the tour returns around 5 – 5:30pm

Arrive at your inn by 12:50 for your 1pm tour departure. 

Available from Sunday through Thursday.

Tour includes: 

  • Driver/guide to assist you during your tastings
  • Deluxe local cheese plate and all expenses except tasting fees
  • Plenty of bottled water
  • Personalized itinerary

The Wine Lovers Package gives guests a discount from our regular $145 per person rate to $125 per person. This is in addition to the B&B which you book through the innkeeper. Your wine tour is booked through us at Monticello Appellation Wine Tours, not the innkeeper.


Arrive in Charlottesville by 12:50 pm, and we’ll whisk you off for an afternoon of wine tasting in our Monticello Appellation- guaranteed to unwind you from your hours of driving!

Don’t have time for lunch before you get to your Bed and Breakfast? No problem! We’ll serve you a deluxe cheese/chocolate/fruit platter at the second winery, or you can pre-order the lunch package, an additional $20 per person served to you.

After touring, we’ll drop you off to enjoy your stay in Charlottesville!

Bed and Breakfast Wine Lovers Package[Read Details…]

Enjoy our Wine Country with everything arranged for your comfort, convenience and pleasure! This tour is in addition to your room rate which you book first directly with the innkeeper at the B&B you choose from our pickup list here in alpha:

 Arcady Vineyard B&B

Foxfield Inn

Inn at Court Square

Inn at 400 West High

200 South Street Inn

After you have your room booked, contact us at Monticello Appellation Wine Tours to book your wine tour portion of the package. Be sure to let the innkeeper know we’ll be picking you up for a wine tour.

On your tour day of your stay at your B&B, we’ll pick you up at 1pm for your wine tasting tour! We’ll visit 3 wineries, and everything is included but your tasting fees (per local law):

  • Driver/Guide to assist you through your tastings
  • Personalized itinerary
  • Virginia Wineries Guide
  • Chilled bottled water
  • Cheese plate of specially selected local cheeses, crackers, local artisan chocolates, and fresh fruit.

NEW!! Food Pairing Wine Tour

Monticello Appellation Wine Tours is excited to offer a unique tour not available anywhere else in the area!

We have been touring guests since 2003 and have found that tour guests have evolved. They no longer wish to taste at as many wineries as possible. This drink and dash experience is getting “old”. Guests have been asking for something more relaxing – an experience where they can take the time to savor the different wines and really find the ones that they want to take home.

Wine is made to enjoy with food. There’s no doubt about that! So we have created a food-pairing wine tour we are offering on Thursdays and Fridays, when the wineries are not so busy and can accommodate this special kind of tour. The tour runs from 1pm to 5 – 5:30 depending on traffic.

At the first stop we have paired wonderful cheeses with every wine that is poured.

At the second stop we have paired different snacks with the wines.

The third stop we have local pastry samples to enjoy with the wine.

Monticello Appellation Wine Tours and Arcady Vineyard Bed and Breakfast, LLC, license # 217, located in Charlottesville, Virginia, provides personalized tours of the area’s best wineries, and accommodations designed for wine lovers. Guests who book accommodations at our favorite B&Bs enjoy a 10% discount on wine tours.

“We looked for a quiet, scenic, fun place to celebrate our 33rd anniversary and Arcady Vineyard Bed and Breakfast was all that! The greeting was warm, nicely entertained, our room was wonderful as was the breakfasts. The winery tour was a lot of fun, and Chris and Erika are extremely knowledgeable without being wine snobs!! The B&B has a terrific feel of casual luxury, and is in a quiet, private setting just a few minutes from downtown Charlottesville. We are looking forward to a return visit to taste at even more wineries!!” ~ Guest Comment



Contact Us:

Monticello Appellation Wine Tours
1493 Milton Road Charlottesville, VA 22902
Phone: 434-960-0820
Toll-Free: 888-824-7273