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Overview

Founding Fathers and Fall Colors in Charlottesville
Charlottesville Virginia
Oct 18 - 20, 2026
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Patty
$875
Deposit: $400

About your trip

Join a  3 day/2 night trip to experience Charlottesville Virginia and the beautiful surrounding countryside.  Located in the eastern foothills of the Blue Ridge Mountains, Charlottesville offers us two days of touring some of the Nation's top historic attractions. October is a beautiful season with breathtaking views of fall foliage from the top of "Little Mountain, the Italian name for Monticello". Trip highlights include a guided tour at Thomas Jefferson's Monticello, a guided tour of James Monroe's Highland with a special appearance by Monroe himself and a guided tour of UVA campus including the famed Rotunda and Academical Village, designed by Thomas Jefferson. Two meals are included, lunch at the historic Michie Tavern, serving guests since 1784 and lunch at Eastwood Farm & Winery.  Charlottesville is in the middle of Virginia Wine Country so our trip would not be compete without a Virginia Wine Collective Experience offered by Eastwood Farm & Winery. This experience includes a personalized behind the scenes look into winemaking, wine tastings and lunch.

 Last year's guests on this trip ranked our accommodations at the Omni on the Downtown Mall very high due to it's beautiful renovation and convenience of being located on the Downtown pedestrian mall with access just outside your door to plenty of dining and cultural offerings.  

A trip extra features another way to experience "colors". We make a stop as we travel north at the Vollis Simpson Whirligig Park in Wison for a little "Art in Motion"'. Simpson has captivated the imagination of the country as he evolved from a farm machinery repairman to a famous folk artist.

**Read all about the trip inclusions and itinerary by scrolling down......



Activity Level

The trip will be best enjoyed if guests are able to stand and manage some moderate walking during tours of the historic homes. 

Deposits and Cancellation policy

A deposit is required to book the trip and the final payment is due on September 5th. Refunds are only possible if the trip can be resold to another guest.

Payment Options

You can register and pay on this website with a credit card with the fees ranging from 2.9% for MC/Visa to 3.9% for Amex OR you can use the ACH bank account option at 1%.

You can also mail a check or use Venmo by contacting Patty at 404-791-3166 or tripsbypatty@gmail.com

What's included

Transportation

On a modern luxury coach

Accommodations

At the Omni Charlottesville

Guided Tour

Historian Rick Britton narrated tour of UVA campus.

Guided Tour

At Monticello with additional time on your own to enjoy the Gardens, Mountain Views and Amazing Gift Shop!

Guided Tour

James Monroe's Highland with a special appearance of Monroe himself!

Guided Tour

Of the Virginia Wine Collective at Eastwood Farms & Winery including tasting Virginia wines!

Lunch

At the Historic Michie Tavern

Lunch

At Eastwood Farms & Winery

Tour Host

Ensures your quality experience!

Extras

Bottled water and snacks on the bus

Wine Tasting

At Eastwood Farms & Winery

What's not included

Breakfast

Enjoy the hotel restaurant or plentiful coffee shops & cafe on the Downtown Mall

Dinner

Plentiful options on the Downtown Mall just outside the hotel door!

Driver Gratuity

Lunch and dinner stop

Lunch and dinner stop to and from Virginia

Charlottesville VA

Charlottesville VA image

Experience Charlottesville

Day One - October 18

8:30am - Departure from the St. James/Southport area with exact location TBA.

9am - Second Departure location from Leland

Approx. 11am - Stop in Wilson for leg stretch and self guided tour of the Vollis Simpson Whirligig Park.

Approx. 1pm - Casual lunch stop in Emporia Virginia

Approx. 4:30pm - Arrive at hotel and enjoy dinner at your leisure that evening on the Downtown Mall.   

Day Two - October 19

8:45am - Depart the hotel and enjoy the day touring UVA campus, Monticello and lunch at Michie Tavern.

Day Three - October 20

9:30am - Morning departure for James Monroe's Highland followed by the Virigina Wine Experience and lunch at Eastwood Farm & Winery.  

8pm - Approximate return time to St. James with dinner stop en route.


About your organizer

P
Patty
I love to travel so in my partially retired life I decided to adapt my passion for travel along with 25 years of experience in Travel & Tourism to create Trips by Patty. I received a BA in American History from UNC-Chapel Hill. Not knowing what I was going to do with that degree, I started working as a desk clerk at a hotel in Raleigh. I enjoyed the hotel business and the career path began. Hotel operations and sales, Convention Center operations and marketing, destination marketing with a Convention Visitors Bureau and even a stint as a tour guide. What happened to the history degree? Well, many times when I am escorting my trips I share the history of the destinations we visit. It's a great feeling to take your career skills and adapt them to your own small business. I love what I do and hope you'll join me on a trip one day!

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