Then & Now: Our Favorite Convertibles for the End of Summer

The days of shorter days, longer pants, and shirts with sleeves are quickly approaching but before we give in to the cold months ahead, we thought that we'd share our favorite vintage convertibles and their modern contemporaries that are perfect for lazy Sunday drives in the last days of summer.

The vintage and classic covertibles we chose were picked from the eclectic selections on show at the recent 2014 Historic Festival 32 at Lime Rock Park in the verdant (and humid!) hills of rural Connecticut. The contemporary cars chosen are the convertibles that we think best capture the sporty, breezy, summer freedom that only a droptop can deliver.

Triumph TR6

Built between 1969 and 1976, the Triumph TR6 was a best-selling primarily exported model for the British brand. The sweet little 2-seater has a inline 6-cylinder engine and, in its collectible form, has a reputation for overheating. Still, we love the classic British roadster look and would drive this on any warm Sunday.

2015 MINI Roadster

The miniest of the MINIs is the MINI Roadster. Available since 2012, the 2-seat convertible and British-born roadster has a more modern motivator than the Triumph TR6: the MINI-ster boasts a 4-cylinder turbocharged engine that can top 140 mph.

Saab 900 Turbo

The classic Saab 900 was first imported as a convertible in 1986. The Swedish designed and Finnish made cabrio sported a backwards engine, but that was just the start of many quirks that created Saab fans worldwide. The final year of the classic, first generation Saab 900 Convertible was 1994. This convertible is as comfortable touring fjords on sunny Sundays as it is farmfields.

Audi A5 Cabriolet

The contemporary car that brings a European flavor to our modern tastes is the German designed Audi A5. Turbocharged with 4 cylinders but full of a fun 220 horses, the Audi A5 has all of the infotainment and technology that would make a Sunday cruise zippy.

Megan

Porsche 356

The classic Porsche 356 is a head-turner on Sunday drives. The first cabriolets were a huge hit in the Summer state: California. Made rare by the prevelance of rust on the unibody convertibles, buying one can set a collector back many thousands of dollars.

2015 Audi TT

The Audi TT is said to take its name from the Isle of Man Tourist Trophy motorcycle race but this sun-loving convertible also is a a nice blend of technology and tradition (as many have also attributed the TT nomenclature).

Lotus Elan

The Lotus Elan is a Bristish-made roadster. Revolutionary for its steel backbone with lightweight fiberglass body, the Elan is seen as the direct inspiration for the more modern Mazda Miata.

Mazda MX-5 Miata

The counterpart to the early-70s British roadster is a new legend: the Bristish roadster-inspired Mazda MX-5 Miata. Celebrating its 25th anniversary in 2015, the Mazda MX-5 Miata is a nimble, and fun roadster that has become a modern day classic. New or used, we'd love to be carving the California canyons in a Miata on any given Sunday.

Megan

Jeepster Commando

The Jeepster Commando was created to compete with the Toyota Land Cruiser, the Ford Bronco, and the International Scout and later became the Cherokee. Perfect for an off road Sunday scrabble, the rag top Commando is legend amongst fans of dirt and mud.

Jeep Wrangler

The Jeep Wrangler is the only modern off road capable truck that still comes in a rag top but it still carries on the legend of Muddy Sunday everywhere.

1972 Mercedes-Benz 280 SE

An elegant convertible, the Mercedes-Benz 280 SE was not designed to be a sportscar but rather the perfect touring droptop for summer Sunday drives with panache.

Mercedes-Benz E-Class Convertible

Similarly, the more modern E-Class convertible is a touring car, even though it is available in a sportier E550 variation.

280 SE

Fiat500 Topolino

The FIAT 500 Topolino was one of the smallest cars in production from 1936 to 1955, with the convertible variant having a sliding canvas roof. It only did about 50mph but could get almost 40 mpg. Perfect for those who want to take a leisurely drive and not leave all of their money at the gas station.

Fiat 500C

The modern FIAT 500C also has a sliding canvas roof and is still one of the smallest convertible cars in production. Even with heavy modern safety and technology piled into the car, the current 500C can compete with the Topolino's 40 mpg and add style and adds more speed to a Sunday drive.

Cisitalia 202

The stunning Cisitalia was an Italian convertible designed by Pininfarina that is still in the Museum of Modern Art's permanent collection. With race car underpinnings and revolutionary aerodynamic design, the Cisitalia is a luxurius and speedy roadster for an exhilarating summer drive.

Mercedes-Benz SLK Convertible

The SLK roadster embodies everything that the Cisitalia set out to do but in a contemporary package. SLK stands for Sportlich (sport), Leicht (light) und Kurz (short).

Cadillac El Dorado

Innovating the "sharkfin" tailfins, the Cadillac El Dorado was at the top of Cadillac's luxury line up and even today is  a treat to glide one of these classic 50s land yachts around on sunny Sunday drives.

Aston Martin V8 Vantage S

Like the El Dorado, the Aston Martin Vantage S has a hungry shark-inspired design and has a V8 engine that can make any Sunday drive scenery a blur.

1967 Ferrari 330 GTS

Unlike the rest of the Ferrari line up, the 330 GTS was never meant to be a race car but was designed to be an elegant, sporty and lightweight grand touring car.

2014 Mercedes-Benz SL 550

Also, a grand tourer the Mercedes-Benz SL-Class is also sporty and light weight and in its contemporary form, has all of the luxury features that anyone would want on a Sunday drive.

1962 Chevrolet Corvette Convertible

The 1962 Chevrolet Corvette was the fastest of the 1st generation Corvettes and in a convertible, is an eye-catching classic bit of American muscle.

2015 Chevrolet Corvette Z06 Convertible

The modern version of the 1962 Corvette convertible has the curvy design cues of the original and will be the fastest Corvette to leave casual Sunday drivers in its dust, to date.

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1962 Bentley Continental GT Drop Head Coupe

The Bentley Continental was a very exclusive car in 1962 with variations being built by several coachbuilders, one of which produced the GT Drop Head Coupe convertible.

2015 Bentley Continental GTC Speed

Still on the more exclusive side of ownership but less rare due to changes in how the cars are manufactured is the contemporary Bentley Continental GTC Speed, which has modern amenities and performance that points directly back to the racing history of Bentley.

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1956 BMW 507 Roadster

The BMW 507 Roadster was not a successful endeavor for the manufacturer meaning that with well under 300 examples imported into North America in the 1950s, this little droptop is a rare sight on Sunday drives.

2014 BMW Z4

On the much more successful side and following on the heels of the extremely well-received Z3 Roadster, the BMW Z4 captures the iconic design elements seen on the 507 and carries on the sporty fun that BMW's Z nameplate is known for.

1936 Cord Westchester

Known for technical innovations and streamlined designs, the American-made Cord Westchester convertible was beautiful to see both then and now. Unfortunately, Cord was not successful in producing cars for the American market and was shortlived.

2015 Infiniti Q60 IPL Convertible

The Infiniti Q60 IPL convertible shares a technology and streamlined design-oriented philosophy with the ill-fated Cord but has a global footprint. With performance-driven aerodynamics and luxury appointments, the Q60 IPL is a comfortable and fun alternative for a Sunday summer drive when your Cord won't start.

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