Custom Itinerary

Sample Luxury Itinerary

While we have put luxury accommodations and the finest of dining experiences as the top priority on this tour, you will find that the accommodations are very unique and you will likely never experience touring quite like this again. 

Group Size:    5, 6 or 7 couples or singles

Trip Highlight:

Presidential Homes, Wineries, First Class Dining, Unique Accommodations.

Length of Visit:

5-7 Nights.  The itinerary below is based on five nights.  To lengthen to six nights we recommend adding a night to either Ragged Mountain Farm or The Inn at 1804.  To lengthen to seven nights, we recommend keeping the itinerary below and adding a wonderful in on Charlottesville’s Downtown Mall.  Both the six and seven night options allow you the opportunity to explore Thomas Jefferson’s Monticello and Charlottesville’s Downtown Mall.

Terrain:

All of our destinations are in the foot hills to the east of the Shenandoah National Park.  We will tailor your rides to meet your desires ranging from gently rolling hills, to roller coast style climbs and descents, or the difficulty of climbing to Skyline Drive and enjoying the gently graded multi-mile hills of the Shenandoah National Park.  This territory is our home base for daily riding, so it is easy for us to adjust riding daily if your riding has been too easy or difficult. All riders are equipped with Garmin GPS to make changes on the fly easy.

Destinations:

Ragged Mountain Farm – West of Charlottesville, VA

The 1804 Inn at Barboursville Vineyard

The Inn at Little Washington – Washington, VA

Ragged Mountain Farm – Luxury Vacation Home

We have chosen Ragged Mountain Farm for multiple reasons.  But as you arrive on your first day, your group will have this wonderful estate to yourself with pool and hot tub on the back patio.  So, relax this first day as you get in from your flights.  Everything is about relaxing tonight; therefore we will have dinner catered in the house. 

Day two, we will again stay at Ragged Mountain Farm, and we will choose between a rolling ride by a couple of the well known wineries in the area, or we will set you on a challenging ride to the top of Wintergreen Mountain and then head back to Ragged Mountain Farm along the Blue Ridge Parkway and Afton Mountain.  Lunch will be a catered outdoor lunch on the grounds of one of the local wineries or on the Blue Ridge Parkway.  If you finish your ride early enough, we will spend the afternoon visiting the well renowned local breweries of Blue Mountain Brewery and Star Hill Brewery within a few minutes from the Farm.  Tonight we will go for a walk and dinner in historic Staunton before catching a show at The American Shakespeare Center which is the only reproduction of the original London Theatre that was home Shakespeare.

Days Three and Four

Barboursville Winery – The 1804 Inn

Day Three - Barboursville Winery is arguably Virginia’s finest winery with a deep Italian heritage.  Today is one of the most challenging days of riding; so you will enjoy the luxury of this English and Italian influenced décor with relaxing balconies and patios.  Enjoy the vineyard grounds after the days ride and we will meander over from the Inn to Paladio’s for a afternoon socializing at the wine tasting, then experience dinner at Paladio’s where Chef Melissa Close Hart has been recognized at one of the Mid-Atlantics top chef’s.

Day Four

 After a wonderful breakfast, provided by Palladio’s staff, you will be happy to realize that we are spending another night at The 1804 Inn.  Today we will be riding in historic Orange and Madison Counties where you will have great mountain views with short rolling hills.  After a morning of riding and refreshing yourself, we will head over to James Madison’s Montpelier where we will cater lunch on the grounds of this recently restored Presidential mansion to the Father of the Constitution.  We have arranged a private tour of the mansion, formal garden and landmark forest.  Time allowing, we will take a short drive to Virginia’s finest French winery, Sweely Estate Winery.  Tonight we have yet another dining experience as we visit The Inn at Meander Plantation for dinner.  Hors d’oeuvres start at six before we sit down for dinner at seven.  Then we return to The 1804 Inn for the night.