Orange Blossom Tour: Explore Florida’s best-kept secrets

Photograph by Chris Tropea.

The ultimate Florida vacation? Skip the tourist traps and join our Classic Motorsports Road Tours Orange Blossom Tour for an exploration of the Florida you never knew existed–those hidden gems known only to longtime residents.

Exclusive access to private collections? Visits to breathtaking natural attractions? The chance to drive some of the Sunshine State's finest–and surprisingly twisty–driving roads?

You’ll get all that and more on our Orange Blossom Tour, February 14-19, including hand-selected dining experiences, turn-by-turn navigation through custom-programmed GPS units and a five-night stay at the luxurious, historic Mission Inn Resort & Club in Howey-In-The-Hills.

Spots fill up quickly, so sign up today to reserve your spot.

The Classic Motorsports Orange Blossom Tour is presented by Classic Motorsports Road Tours in association with Chubb Insurance.

Classic Motorsports Road Tours: extraordinary destinations for 2027

Photograph by Chris Tropea.

Too early to start planning next year’s vacations? Consider that 2027 is just four months away. And, for a one-of-a-kind getaway starring you and your favorite car, join us on one (or more) of our three Classic Motorsports Road Tours.

From iconic historic destinations to breathtaking natural sites, hand-selected dining experiences to exclusive automotive collections, you’ll get to experience it all while enjoying the thrill of driving some of the country’s finest–and most twisty–back roads.

Sign up for our Orange Blossom Tour, February 14-19, for a chance to see the Sunshine State’s hidden gems known only to longtime residents.

Join us on our Shenandoah Valley Tour, June 6-11, for an intimate exploration of the area’s verdant valleys, unique history and exceptional winding mountain roads.

Participate in our Bluegrass Tour, October 10-15, for an escape through Kentucky’s rolling hills and horse country–a land made famous for its bourbon, bluegrass and finger-licking-good fried chicken.

As our Classic Motorsports Road Tours fill up quickly, reserve your spot today so you don’t miss out.

All of our Classic Motorsports Road Tours are presented by Classic Motorsports Road Tours in association with Chubb Insurance.

Empire State Tour: Deadline to sign up is tonight

Photograph by Chris Tropea

The deadline to sign up for our exclusive vacation in New York’s Finger Lakes, our Classic Motorsports Road Tours Empire State Tour, is tonight, July 31, 11:59 Eastern.

Join us on our Empire State Tour, and you’ll enjoy unique destinations, including Letchworth State Park, Glenn H. Curtiss Aviation Museum, Watkins Glen International and the International Motor Racing Research Center.

We’ll also treat you to a five-night stay at the Watkins Glen Harbor Hotel, turn-by-turn navigation through custom-programmed GPS units, various hand-selected dining experiences, plus the chance to drive your favorite car on some of the most enjoyable driving roads in the country.

If you can’t make our Empire State Tour, keep an eye out for future Classic Motorsports Road Tours.

The Classic Motorsports Empire State Tour is presented by Classic Motorsports Road Tours in association with Chubb Insurance.

Empire State Tour: Discover the works the Wright brothers’ rival

Photograph by Chris Tropea

Ralph Waldo Emerson may have stressed that the journey is more important than the destination, but, then again, he never joined us on our Classic Motorsports Road Tours Empire State Tour.

While you’ll certainly enjoy the journey of piloting your favorite car along some of the country’s finest driving roads, we’ll also treat you to one-of-a-kind destinations found only in New York’s picturesque Finger Lakes region–like the famed Glenn H. Curtiss Museum.

The 60,000 square foot facility celebrates the life and works of Glenn H. Curtiss, a contemporary (and sometimes-rival) of the Wright Brothers, and houses countless vintage automobiles, aircraft, engines and motorcycles.

Also included in our Empire State Tour? A five-night stay at the Watkins Glen Harbor Hotel, turn-by-turn navigation through custom-programmed GPS units plus various hand-selected dining experiences.

Learn more about our Empire State Tour and keep an eye on the Classic Motorsports Road Tours website for future updates.

The Classic Motorsports Empire State Tour is presented by Classic Motorsports Road Tours in association with Chubb Insurance.

Classic Motorsports Road Tours: Easier than ever to stay up to date

Photograph by Chris Tropea

The easiest way to keep up to date on all of our signature Classic Motorsports Road Tours? By following on Facebook and Instagram, of course.

In addition to the latest news and updates from our upcoming Empire State Tour, Orange Blossom Tour, Shenandoah Valley Tour and Bluegrass Tour, you’ll also find highlights, insights and more from each driving tour.

Why join us on any of our Classic Motorsports Road Tours? Because you’ll enjoy a vacation experience you can’t find elsewhere: We’ll treat you to first-class cuisine, exclusive destinations, luxurious accommodations and some of the country’s finest driving roads–and you’ll experience it all from behind the wheel of your favorite car, just as nature intended.

Our Classic Motorsports Road Tours often sell out quickly, however, so register now to avoid missing out later.

Upcoming Classic Motorsports Road Tours:

All of our driving tours are presented by Classic Motorsports Road Tours in association with Chubb Insurance.

Empire State Tour: Experience the “Grand Canyon of the East”

Photograph by Stephen Crane

Breathtaking scenic views. Join us on our Classic Motorsports Road Tours Empire State Tour, our driving tour of New York’s Finger Lakes, and you’ll experience several–including the stunning, 14,000-plus-acre Letchworth State Park.

Aptly nicknamed the “Grand Canyon of the East,” Letchworth is famous for its strikingly deep gorges and towering waterfalls.

That’s just scratching the surface of our Empire State Tour, as participants will also enjoy a five-night stay at the Watkins Glen Harbor Hotel, turn-by-turn navigation through custom-programmed GPS units, several hand-selected dining experiences and the chance to drive on some of the finest driving roads the country has to offer.

Learn more about our Empire State Tour and keep an eye on the Classic Motorsports Road Tours website for future updates.

The Classic Motorsports Empire State Tour is presented by Classic Motorsports Road Tours in association with Chubb Insurance.

Celebrating decades of racing history | Shenandoah Valley Tour Day 4

We kicked off day four of our Shenandoah Valley Tour by heading to Duncan Imports & Classics, an eclectic collection of Japanese and European imported cars.

After enjoying a tour of the mechanical menagerie, we then made our way to one of Virginia's oldest wineries, Chateau Morrisette, for lunch at the winery's on-site restaurant.

Our final stop of the day–and our tour–took us to the Wood Brothers Racing Museum, a monument to NASCAR's oldest continuously operating racing team, the family that started it and the impact they've had on the sport in their 70-plus years on the track.

Museum visit completed, it was then time to head back to our host hotel one last time.

Before heading our separate ways, however, we hosted a farewell dinner where we also had a few surprises in store for our participants.

Missed out on making our Shenandoah Valley Tour this year? Well, good news: we’re doing it again on June 6-11, 2027. Reserve your spot today. Space is limited and we sell out quickly.

Our Shenandoah Valley Tour takes place this week, June 21-26, and is presented by Classic Motorsports Road Tours, in association with Chubb.

Driving on track at VIR | Shenandoah Valley Tour Day 3

We started day three of our Shenandoah Valley Tour with a long drive towards Alton, Virginia, a perfect chance for everyone to warm up their tires for the day’s destination: Virginia International Raceway.

VIR stands as one of our favorite tracks thanks to its rolling hills and variety of configurations.

Our visit at the track consisted of guided laps of the track, followed by lunch on site at the Oak Tree Tavern.

After lunch, it was then another long, scenic drive back to the Hotel Roanoke for a chance to freshen up before heading to dinner at Downtown Roanoke’s Table 50.

Missed out on making our Shenandoah Valley Tour this year? Well, good news: we’re doing it again on June 6-11, 2027. Reserve your spot today. Space is limited and we sell out quickly.

Our Shenandoah Valley Tour takes place this week, June 21-26, and is presented by Classic Motorsports Road Tours, in association with Chubb.

*Itineraries subject to change.

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