Road Rules: The Case for Rallies and Tours

This article comes from our January 2007 issue of Classic Motorsports, so some information or pricing may have changed. What hasn't changed is our unwavering interest in tours. So much so, that almost 10 years ago, we started our own: the Orange Blossom Tour. It proved so popular, that we added the Smoky Mountain Tour. And wouldn't you know it, it too proved popular, so for 2020—our 10th year of doing tours—we're starting the Golden State Tour in 2020. Visit our tour website for more information.

Hobbies are strange things. They consume huge amounts of our time, energy and money, but they are, by definition, largely pointless. While this lack of purpose usually serves in a perverse way to enhance the fun factor of hobbies, it can also help kill their appeal. After all, once you’ve built that ship in a bottle, there’s not a lot you can do with it. Stacks of completed jigsaw and crossword puzzles just make it hard to navigate your own hallways. And the only way off of Everest is to turn around and trudge back down the way you went up. Once the project is completed, all that follows is anticlimactic.

We car enthusiasts have an edge, of course, since the objects of our tinkerings and tradings are useful things born of practical invention. Once we’ve finished that restoration or obtained that long-sought acquisition, we can drive our cars and actively enjoy them.

The rub comes in finding a place to do so. Sure, you can still drive your 1929 Isotta Fraschini on the street, but unless you’re Erich von Stroheim and you’ve got Gloria Swanson in the back seat, you’re probably not going to find it an ideal daily driver. Car shows and concours d’elegance are great, but these static displays pretty much defeat the argument for collector cars as practical things. Vintage racing is anything but static, but not every car—or every car owner—is suited to racing.

Fortunately, there is one venue for classic and collector cars that includes elements of all three of these activities—combined with the added appeal of a first-class vacation. It’s called vintage rallying.

A New Way to Rally

Rally events are nothing new in the sports car hobby, since people have been running TSD (time-speed-distance), map and gimmick rallies, as well as almost endless combinations and permutations of each, almost as long as they’ve had cars to run them in. The TSD rally is what we usually think of when we think of a competition rally event, where teams must travel the route at the correct speed to arrive at each checkpoint at a specific time; scoring is based on how close to the correct time the teams actually arrive. Map and gimmick rallies are pretty much what they sound like; these route-based or playful challenges are usually strictly amateur events run more for fun.

Vintage rallies and tours may follow some or all of these formats; the difference lies in the selection of cars competing, and in the activities and atmosphere surrounding the daily driving activities. Since these events are designed to showcase classic and collectible machinery, entries are often restricted to exotics and cars manufactured before a certain year. That point alone guarantees a more exclusive field, but it’s the resort-level accommodations, elegant catering and first-class sightseeing that elevate most vintage rallies to a whole ’nother level. Think of it as a cruise-ship vacation on dry land with a bunch of like-minded enthusiasts.

“We Could Do a Better Job”

The inspiration for many of these rallies is Italy’s famed Mille Miglia, the prestigious 1000-mile rally from Brescia to Rome and back. Although the original Mille Miglia was discontinued after 1957, the event has been revived in recent decades as an antique- and collector-car rally following the original route.

“We went on the Mille Miglia 15 years ago and never really got to drive the cars,” said Rich Taylor, who runs Vintage Rallies, Inc. with his wife and partner, Jean. “We were in a long line the whole time, the crowds were enormous.

We just thought we could do a better job.” The Taylors returned to their home in Connecticut and got to work organizing their first event, the New England 1000. “We came back and said, ‘New England’s just as pretty, and the roads have no one on them,’” Rich recalls. The couple planned out a five-day, 1000-mile tour that included TSD stages on public roads, like the Mille Miglia, but fleshed it out with catered lunches, gourmet dinners, and top-shelf lodgings to turn it into a pleasurable week’s vacation instead of a grueling speed contest.

“We’re not competing with other rallies,” Rich explains. “We’re competing with fly fishing in Peru, or barge trips in France.” Their dedication to this upscale ideal and their attention to detail extends even to the nightly wine lists, which Jean carefully chooses so that no vintage is repeated during the course of the rally.

That first New England 1000 ran in 1993, about the same time that the Colorado Grand, Copperstate 1000 and California Mille rallies saw their debuts. Although these events all have different organizers, details and locales, the basic concept is the same: Give participants a week-long adventure in their classic cars that’s filled with lots of good food, gorgeous scenery, good-natured competition and elegant accommodations. Shake or rumble slightly, depending on the make of car, and serve.

Everybody’s Doing It

Since those first pioneering events made their debut, they’ve continued to grow and prosper. The Taylors now run two other events in addition to the New England 1000, the Mountain Mille (out of West Virginia) and the Texas 1000; all are run to benefit charity, and all are for sports, racing or GT cars from 1975 or earlier, or exotics of any year. The Copperstate 1000 still puts classics from 1973 and earlier through their paces in Arizona to raise money for the Phoenix Art Museum and other charities. The Colorado Grand, now in its 18th year, just led a group of sports and racing cars built prior to 1961 through a thousand miles of mountain hillsides clad in their autumnal glory—and by doing so provided help to many Colorado charities. The California Mille, which will host select cars of 1957 vintage and older for its 17th running next April and May, has been joined by three other events hosted by its organizer, the Amici Americani della Mille Miglia.

It’s a common feature for these events to be run by nonprofit organizations and/or to benefit charity. Not only is this good for their communities, it no doubt helps them to attract the kind of upscale clientele they’re seeking. And make no mistake, this is a rarified group.

“The people who come with us are a lot of high-powered, type-A personalities,” says Rich Taylor. One regular participant puts it another way: “If you meet a guy named Hilton on one of these, there’s a chance he’s one of THE Hiltons.” Another regular rallyist recalled seeing one entrant, a “tycoon,” show up with a tractor-trailer full of different cars, one for each type of event that was to be held that week.

Nevertheless, snobbery seems to be largely absent from this scene. “It has nothing to do with the money,” Rich says. “It has to do with the interest, and the people who do this are like any other affinity group—you can talk to these people and they know what you’re talking about.” An even more succinct comparison was offered by Sherman Wolf, whom we met driving a pristine 1967 Ferrari 275 GTS on the Barnstorming Maine tour: “These people don’t need flashy diamonds; the cars are the jewels.” (As the owner of Phil Hill’s first Ferrari, he should know.)

Is It for You?

You don’t have to be dripping with jewels—or Ferraris—to get involved in vintage rallies. All you need is a classic car in good working order, a partner with a willing spirit, and the ability to pay $10000 to $15000 per couple, or not much more than you’d spend for the same amount of vacation time on one of those cookie-cutter, huddled-masses cruise ships. What you’ll get in return is a lot of time working one-on-one together and problem-solving in a fun atmosphere, some great meals and terrific sightseeing, as well as the opportunity to meet terrific people in a small, intimate setting, since most of these affairs cap entries at around 75.

“People get involved with this because of the cars, but it’s really about the people,” Rich says. “We try very hard not to be cliquey.” According to John Payson, a regular who’s done rallies in everything from his ’57 Bentley to his ’62 AC Greyhound (one of only 85 or so made), participants’ backgrounds vary, from a platinum country singer to a concert pianist, and from a neohippy with a microbrewery to a retired chair of the M.I.T. physics department. “If I’d met in all those rallies a dozen people I would not invite home,” he adds, “I would be very surprised.”

The cars you’ll encounter come from a wide range as well, from more mundane MGs and Mustangs to the exotic Ferraris and Bugattis. Although the price variable between some of these can range in the millions, the participants treat each other as fellow enthusiasts regardless of what they drive. “Like yachting, no one cares how long your boat is,” Rich says. “If you have one, you’re in.”

These events offer a nice mix of the public and the private, since you’ll spend hours each day driving along with your partner, while evenings are spent in social gatherings around good food and drink. There is a competitive element to almost all of the daytime activities, with TSD rallying, gymkhanas and other non-wheel-to-wheel events spicing up the driving, but entrants approach them with varying levels of sincerity. “We try to make it fun,” Rich says. “The timing and scoring is there; some take it more seriously, but it’s all good.” Some rallies do offer expensive trinkets as prizes, and there are people who approach them in all seriousness. Rich recalled one vintage racer from Canada who actually went so far as to hire John Buffum’s navigator for the week: “They got beat by a guy using his wife’s wristwatch with no numbers on it.”

Most of all, vintage rallies and tours provide a way for couples to enjoy their cars and the hobby together, at speed. This is immensely good for the people as well as the cars, since we all need a little airing out now and then. What better way to do it than on beautiful roads, in the company of friends?

Selecting a Rally or Tour Event

What’s the difference between a road rally, a performance rally and a vintage rally, or a vintage rally and a vintage tour? Don’t be confused by the nomenclature here; although the differences between these various terms are subtle, they can represent wide variations in event type, price and the demands it will place on you and your car.

A road rally is the course-following competition that inspired the world of vintage rallies and tours. It can take many forms, including TSD, map, tulip and gimmick. Road rallies are one of the first types of motorsport competition, and still attract a lot of enthusiasts, from beginners to serious competitors with intricate timing and odometer equipment. In this country, a majority of these events run under the auspices of the Sports Car Club of America, whose regions sponsor mostly weekend rallies that travel public roads at legal speeds. Since these types of rally events are usually club- and volunteer-run, no-frills experiences, they also tend to carry a much lower price tag—in most cases topping out in the hundreds rather than the thousands of dollars. 

Performance rallies are the pinnacle of rally competition, involving Warp Factor 9 runs through closed-to-the-public twisty forest roads. If you’ve got the urge to follow in the footsteps of Paddy Hopkirk or Stig Blomqvist and compete in real stage rally, there are opportunities for vintage car enthusiasts to indulge their fantasies. National Auto Sport Association and Rally America are two sanctioning bodies in the United States that organize performance rally events. Both groups recognize a historic class, which covers just about any older car prepared to compete in a stage rally.

Like the more familiar vintage road racing, the historic performance rally categories tend to emphasize period-correct modifications and improvements, albeit with necessarily modern safety specifications. Popular cars for this class range from MGB GTs, Minis, and Porsche 911s to even the odd Swedish Saab 99 or Volvo 142 or two thrown in the mix. More information on stage rally and historic classing can be found here.  

The format followed by the most of the events we’ve discussed is called a vintage rally. Although participants on these events can expect some competitive activities in the form of TSD stages, gymkhanas and the like, these will be designed to test your mental agility and precision driving abilities rather than the limits of your car’s acceleration or adhesion, and are intended to be fun. Even so, their sporting nature means you’ll probably be better off with something like a classic Corvette or Porsche 356, rather than the Isotta Fraschini (sorry, Erich). Entry fees vary depending on the length of the rally and the level of accommodations, but most run five or six days and cost $3000-$5000 per couple. Entries are usually restricted to around 75.

That price tag may seem steep compared to the local club events, but for your money you’ll be getting a very complete package that in most cases also includes loaner cars in case yours breaks, plus chase vehicles and topflight mechanics to keep everyone in the game. (Some organizers have even told us of people who enter their rallies on a regular basis just to enjoy the mechanics’ talents. Considering a Ferrari tune-up can cost as much as entering one of these events, it’s easy to justify when you look at it that way.)

A vintage tour is very similar in terms of length and upscale offerings, as well as what you’ll pay, but is designed to be a more gentle experience without the timed competitions. These are good choices if your primary goal is sightseeing and touring. Brian Redman’s Barnstorming Maine tour is a good example of one of these outings; organized with the help of the Maine Tourism Association, it offers a wonderful taste of the state through four days of “Down East” scenery and food. This type of event would be a good choice for more antique, or more fragile, classics.

These are just general guidelines as to what you’re likely to encounter; exceptions abound. For instance, Martin Swig’s Amici Americani della Mille Miglia has an event with a $4800 price tag (the first-class California Mille, which restricts entries to approved cars “in the spirit of the Mille Miglia” from 1957 and earlier), as well as one with a $50 entry fee (the decidedly fun and wacky Double 500, which caravans a motley group of $500 cars over its 500 miles and puts up overnight at a Super 8 motel). On the other end of the spectrum is the Great Race, which leads pre-1970 vehicles across the entire continent in pursuit of a $350,000 purse.

And if your driving ambitions extend beyond our borders, there are several companies offering arrive-and-drive vacations in Europe in rented classic cars. Classic Motorsports will be partnering with England Specials again this summer for two weeks of touring Germany and England.

No matter what your speed—literally—there’s an event for you. So find one and get moving. You owe it to your classic, and to yourself.

Rally and Tour Insurance

Once you’ve checked out your car, sent in your entry and made your travel arrangements, you may think you’re ready to pack up for that week-long rally event. But one other item should be on every participant’s pre-event checklist: the insurance review. 

Since these outings are designed to put rare and exotic machinery on the streets, there can be a lot at stake. So we asked the people at Hagerty Insurance Agency, Inc. to provide a few pointers. The agency, which specializes in policies for antique and vintage autos, has extensive experience with varied rallies and tours, including the Colorado Grand, Copperstate 1000, Gauthier Classic, Sugar Valley Rally, Great Race sanctioned events, and many poker runs and mystery tours. 

According to the folks at Hagerty, they recognize and support classic vehicles used in this manner, as these events are designed to enhance the experience of driving a classic vehicle. As long as the event doesn’t require operation of vehicles at above-legal speed limits or usage in an unsafe manner, collector vehicle road rallies are generally acceptable. Coverage exclusions may exist for activities held in conjunction with generally acceptable events that require the use of vehicles in competition held on closed roads, or on-track situations.

“One of the best things about the collector car hobby is the thrilling event of driving your treasured vehicle with friends and family through some of the coolest towns in the country,” said CEO McKeel Hagerty. “We understand that this is a fun time for our customers, so we try to provide the best coverage that will ease their minds with their only worry being what exciting event comes next.”

While Hagerty has continued to make efforts toward offering expansive coverage options for the collector, many standard programs may have moved toward more restrictive coverage. Due to recent increased concerns within the insurance industry regarding performance driving usage, it is important for any collector vehicle owner to review their policy to see what type of language is used to address rallies and tours. Changes in policy language may have occurred since an individual had originally obtained coverage. Some policies may address these events in the same context as competitive racing or high-performance driving events.

We Had So Much Fun, We Started Classic Motorsports Road Tours

Why tour with us? Because we know what you like. Before writing this article, we had done enough tours to see what worked and what could work better. Marry that with a determination to show others that our home state of Florida has some amazing roads, and thus the first Orange Blossom Tour—which turns ten in 2020—was established. 

Each of our road tours is limited to just 25 cars, lending an intimate, luxurious experience that bigger groups just can’t get. Hub-based routes featuring curvy roads mean you won’t have to move hotels each night, but you will enjoy a new experience and breathtaking views each day. Every one of our tours is all-inclusive, with memorable meals, choice lodging, free luggage porting and free traveling mechanics in case something unexpected occurs.

Though we use our access to bring you some truly once-in-a-lifetime experiences like private collections, track driving experiences and more, we don’t use it to exclude anybody: All sports cars are welcome, and you’ll find everything from multi-million dollar Ferraris to nicely-kept Miatas touring together.

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Jordan Rimpela
Jordan Rimpela Digital Editor
8/5/19 3:38 p.m.

Updated with information on our own tours

Gary SuperDork
8/5/19 9:34 p.m.

Good article. It's been my personal objective for the past 10-15 years to do the New England 1000 with Rich Taylor and crew. I just needed the appropriate vehicle to do it. Still selecting. I have the means and the knowledge. What I lack is the resolve and gumption to "pull the trigger and buy the damn car." I'm working on that with the help of wife Annie and a close enthusiast friend. In fact, they had an ad hoc intervention for me last week at a restaurant. BUY SOMETHING they said!!! Annie is an enabler, and that friend just bought a beautiful 2001 NSX out of AZ. So this article is more incentive for me to move my butt. Hell, I'm seventy. I'd better do it soon.

Jordan Rimpela
Jordan Rimpela Digital Editor
8/6/19 10:32 a.m.
Gary said:

What I lack is the resolve and gumption to "pull the trigger and buy the damn car." I'm working on that with the help of wife Annie and a close enthusiast friend. In fact, they had an ad hoc intervention for me last week at a restaurant. BUY SOMETHING they said!!! Annie is an enabler, and that friend just bought a beautiful 2001 NSX out of AZ. So this article is more incentive for me to move my butt. Hell, I'm seventy. I'd better do it soon.

Seems as though you're surrounded by good people. And yes, buy something! You won't regret it. 


Marjorie Suddard
Marjorie Suddard General Manager
8/6/19 2:00 p.m.

Thanks for the comments on the article, Gary--it was fun to write.

Rich and Jean do a great job; we've done several of their tours and greatly enjoyed them all. And if you don’t want to step into something that meets their more restrictive guidelines (1990 or earlier), you’d be welcome on a Classic Motorsports tour with us in a more modern sports car. (Well, you'd be welcome with us either way because you're family. Appreciate your regular comments here.) 

Whatever you choose, yes, listen to your kind enablers and do it sooner rather than later.


stu67tiger Reader
8/6/19 7:07 p.m.

Hey Gary:

Wasn't there a thread on here a while back, along the lines of "fun cars for touring"?  So what sort of car are you thinking of?  Many would suggest an older Miata, but you already have one.  Trade up to a Spit that's done, or at least driveable? Some older Mercedes SLK's can be had for 4 digits.  They would certainly be comfortable and safe for long distances, but are they too new for your plans? 

Tell us what you are thinking, so we can make more suggestions and totally confuse your selection process ;-))


Gary SuperDork
8/7/19 7:08 p.m.

In reply to Margie and Jordan:

Thank you for the words of encouragement. Indeed, I have some supportive people around me (including Stu from Massachusetts). I mentioned the NE 1000, but either The Orange Blossom or Smokey Mountain would be superb as well. They just present a slightly more complex logistical issue from RI. But not insurmountable. Getting the appropriate car is first order of business! 

Gary SuperDork
8/7/19 7:19 p.m.

In reply to stu67tiger :

Hey Stu,

I'm looking at everything from a Bugeye from "The Guy" in CT, to a "reasonably priced" 356 coupe or 230/250/280 SL Pagoda with manny tranny (they're out there). I'll be going to Palm Springs in November and again in February to the Keith McCormick auctions (been to about ten now). There are always some of these crossing the block in SoCal. And also a ton of 560 SL's in superb dry-climate condition and reasonable prices. Great cars. Usually estate sales because the original buyers/owners are ... well no longer with us. So a lot of these sales are estate sales. Best ones have been well-kept and are in the middle of my price spectrum and present a great  value alternative to the 280 SL Pagoda, although in automatic tranny only.

I'll either keep this thread going or start a new one concerning my progress. (So now there's added pressure on me to perform. I thought that all went away when I retired five years ago. I was trying to avoid that with this classic car E36 M3 frown).

(Then again, maybe I should just enjoy my beautiful, unmolested, low milage '96 NA Miata, which I really love, on the back roads of northern RI and Eastern CT. Then have somebody finish the Spit Mk3 for me ... because I'm done with working on it. I lost my gumption. Damn, now you see my dilemma?)

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