Exploring the Ringling Museum of Art | Orange Blossom Tour: Day 2

Photograph by Nicole Suddard

Florida may be best known for sandy beaches, orange groves, a larger-than-life mouse and alligators in virtually every body of water, but that’s not all the Sunshine State has to offer.

Instead, our Classic Motorsports Orange Blossom Tour takes you on an exploration of the Florida you never knew existed, including one-of-a-kind destinations, first-class cuisine and hidden gems known only to longtime residents, all from behind the wheel of your favorite car.

Our 2026 Classic Motorsports Orange Blossom Tour takes place this week, March 8-13, with Tuesday, March 10, the second day of driving.

Here's a look at what you missed out on:

The day began by heading southwest toward Florida’s Gulf Coast for a unique destination located in Sarasota Bay: The John and Mable Ringling Museum of Art, a sprawling complex built by John Ringling–of Ringling Bros. and Barnum & Bailey Circus fame.

Lunch was enjoyed on the property at the Ringling Grillroom before we set the tour group free to tour the museums.

There was one more stop before heading back to the hotel, another private collection. As opposed to the collection visited on Monday, this collection could be best described as “small but mighty.”

After viewing the collection–and learning about its history and how the cars are maintained–it was a short jaunt back to the hotel for the evening.

Our tour participants had the night off to choose their own adventure–whether that meant venturing out or staying close by the hotel.

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

Up close with a dream roster of exotics | Orange Blossom Tour: Day 1

Photograph by Chris Tropea

Florida may be best known for sandy beaches, orange groves, a larger-than-life mouse and alligators in virtually every body of water, but that’s not all the Sunshine State has to offer.

Instead, our Classic Motorsports Orange Blossom Tour takes you on an exploration of the Florida you never knew existed, including one-of-a-kind destinations, first-class cuisine and hidden gems known only to longtime residents, all from behind the wheel of your favorite car.

Our 2026 Classic Motorsports Orange Blossom Tour takes place this week, March 8-13, with Monday, March 9, the first day of driving following everyone’s arrival on Sunday.

Here's a look at what you missed out on:

Central Florida may be best known for Orlando and mega theme parks, but neither was the destination for our first day of driving.

Instead, we first embarked from Lakeland’s Terrace Hotel to the charming city of Mount Dora. Once there, we gathered for lunch at an Orange Blossom Tour favorite: Pisces Rising.

Lunch consumed, it was then time to make the trek to Windermere, home to one of the most impressive private car collections we’ve ever had the privilege of viewing.  While the collection’s owner requested no photography, tour guests were able to get up close and personal with a dream roster of exotic cars.

After leaving the private car collection, we headed back to the Terrace Hotel for a Classic Motorsports Road Tours tradition, the parking lot bar, before enjoying dinner at Nineteen61, an upscale Latin American restaurant just down the street from the hotel.

Day completed, it was then time to head back to the hotel to rest for the next day’s adventures.

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

Classic Motorsports Road Tours: A land-based cruise you get to pilot

Everything that makes a cruise ship vacation so attractive–like all-inclusive lodging, meals and attractions–but on land, and you get to drive the boat? You’ll want to join us on one of our Classic Motorsports Road Tours.

Experience the Old Florida you never knew existed on our Orange Blossom Tour, take in verdant valleys and winding mountain roads on our Shenandoah Valley Tour and explore the majesty of New York’s Finger Lakes on our Empire State Tour.

In addition to some of the country’s finest driving roads, each tour features turn-by-turn navigation through custom-programmed GPS units, professional photography of you and your vehicle, and a hub-style structure that sees each day begin and end at a luxurious host hotel (meaning no packing and unpacking your bags each night).

And, no, you don’t have to buy into a drinks package to make the most of your trip.

2026 Classic Motorsports Road Tours Schedule

March 8-13: Orange Blossom Tour, Lakeland, Florida
June 21-26: Shenandoah Valley Tour, Roanoke, Virginia
September 6-11: Empire State Tour, Watkins Glen, New York

All of the Classic Motorsports Road Tours are made possible thanks to Chubb Insurance.

Classic Motorsports Orange Blossom Tour: Sign up now and save $250

The Classic Motorsports Orange Blossom Tour is all-new for 2026–and now, for a limited time, you can save when you register now.

Use promo code HOLIDEALS25, and you can get $250 off of your registration to the Orange Blossom Tour, as well as all of our Classic Motorsports Road Tours.

Need to stock up on Classic Motorsports gear before you join us for an exploration of the Florida you never knew existed, March 8-13?

Use discount code HOLIDEALS25 to get 25% off your entire order from the Classic Motorsports online store. 

Take advantage of these once-a-year discounts to cover gifts for all the concours-goers, auction-watchers, classic car cruisers and vintage racing thrill-seekers on your holiday gift list. (Or just get a little something for yourself–we won't judge.)

Don’t hesitate: Spots in the Orange Blossom Tour are filling up quickly, and both these offers expire on Thursday, December 4, at 11:59 p.m.

2025 Classic Motorsports Road Tours Empire State Tour | A taste of what you missed

The ultimate car enthusiast vacation? This year’s Classic Motorsports Road Tours Empire State Tour explored the finest back roads and destinations in the Finger Lakes region of New York.

Here’s a look at what you missed–and what you can look forward to on future tours.

Sign up for the 2026 Empire State Tour and learn more about all of our upcoming Classic Motorsports Road Tours.

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

Recap: 2025 Classic Motorsports Empire State Tour

To call our Classic Motorsports Empire State Tour simply a driving tour of New Yorks’ Finger Lakes region would be doing it a disservice, as the participants did much more than drive–they visited historic sites, took in breathtaking scenery, enjoyed hand-selected dining experiences and, overall, enjoyed a once-in-a-lifetime tour through one of the most beautiful parts of the country.

While you can read more about the day-to-day happenings at the links below, here are some highlights of what you missed:

Traveling “The Nation’s First Superhighway,” the Erie Canal, by boat.

Exploring the Finger Lakes' unique history of boating, flying, glassmaking, and, of course, motorsports.

Driving on the legendary Watkins Glen road circuit.

Experiencing the breathtaking scenery of the Ithaca and Taughannock Falls, as well as the flora and fauna lining some of the country’s best driving roads.

And did we mention driving? Nearly 600 miles of it in total–that's a lot of seat time for you and your favorite classic car.

Recap: 2025 Classic Motorsports Smoky Mountain Tour

You, your favorite car and six days of the finest views, experiences, food and–our personal favorite–driving roads the Smoky Mountains have to offer.

No, it’s not a dream, but our annual Classic Motorsports Smoky Mountain Tour, which started on Sunday, June 8, and ran through Friday, June 13.

Here’s a recap of what you missed:

Sunday, June 8

All guests arrived at the host hotel, the Westin Chattanooga, for a chance to settle in before a welcome cocktail reception and dinner at the hotel.

Monday, June 9

It’s not every day you get to slay dragons, but that’s exactly what the participants of our Classic Motorsports Smoky Mountain Tour had the chance to do today.

Of course, we’re talking about the famed Tail of the Dragon, regarded by many as one of the world’s best driving roads.

Also on today’s itinerary? A scenic drive of the Cherohala Skyway, lunch at the Tapoco Tavern in Robbinsville, North Carolina, and dinner at Easy Bistro in Chattanooga.

Tuesday, June 10

Ever go to a new restaurant and leave so impressed that you decide to bring your friends the next time you go? Yeah, that was us after experiencing the newly opened Savoy Automobile Museum.

For the second day of adventures, tour participants taking part in this year’s Classic Motorsports Smoky Mountain Tour were treated to a tour of the Savoy’s extensive collection and a private catered lunch at the museum.

After the trip to the Savoy, we led our guests back to the host hotel, the Westin Chattanooga, along some thrilling southern Appalachian mountain roads.

Wednesday, June 11

Yes, Appalachia is home to some truly great driving roads, but it’s also home to some stunning scenery, too.

For day three of our Classic Motorsports Smoky Mountain Tour, we treated participants to some challenging roads before stopping at Fall Creek Falls State Park to take in the iconic waterfall and enjoy some lunch.

The day’s activities also included dinner at St. John’s Restaurant in Chattanooga.

Thursday, June 12

June 12 might be the last day of adventures for our Classic Motorsports Smoky Mountain Tour participants, but that doesn’t mean we’re dialing back the excitement.

First up was a visit to Chattanooga’s Point Park for the chance to take in the stunning panoramic vistas of the city and surrounding areas.

Our guests then loaded up and headed to The Coker Museum for an exclusive tour of the collection–led by Corky Coker’s daughter, Casey Coker-Jarvis–as well as a private lunch at Corky Coker’s Honest Charley Speed Shop.

Lastly, we took the participants along a lengthy driving loop to give the area a proper farewell.

Friday, June 13

Our guests enjoyed breakfast at the hotel before checking out and parting ways,

Reserve your spot now! Few more spots added for Empire State Tour

Due to overwhelming demand, we have opened up a few more spots for our still-intimate Classic Motorsports Empire State Tour, taking place September 7-12.

That’s right, you now have the opportunity to get in on exclusive experiences around the Finger Lakes. That includes taking in destinations such as the region's famous vineyards, the Corning Museum of Glass and even Watkins Glen International–and yes, you'll get to lap the storied track.

Reserve your spot today. Space sells quickly, especially for our Empire State Tour.

The Classic Motorsports Smoky Mountain Tour is presented by Sunoco in association with Chubb Insurance.

*Itineraries subject to change.

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