#1: Aston Martin DB5
More than just a “romantic” classic car—arguably the most sophisticated car of all time—the 1963 Aston Martin DB5 is for those who wish to make a grand entrance this Valentine’s Day. Imagine being dressed to the nines and hitting the road in this beauty for an elegant dinner at the finest restaurant in the city.
The Aston Martin DB5 has 282 horsepower and tops out at around 150 mph, making it both fast and gorgeous. It’s also first on our list because James Bond showed the world its beauty and mystique in the movie Goldfinger.
More recently, Aston Martin revived the Vanquish nameplate, marking the third generation of the brand’s flagship grand touring sports car. “A true halo model in every respect, Vanquish makes an emphatic statement,” said Lawrence Stroll, Aston Martin Executive Chairman of the 2025 Vanquish. “One that further delivers on our mission to create the most potent, most beautiful, and most exciting cars in the ultra-luxury sports car market.”
#2: 1957 Chevrolet Bel Air
You may live in Southern California and want a classic car that lets you put the top down and drive the coast before your dinner reservations. Or maybe where you live in the Midwest, it’s going to be an unusually warm Valentine’s Day. If so, one of the most romantic classic cars is from the bowtie brand.
The 1957 Chevy Bel Air will make for a memorable evening, especially if you are lucky enough to have the optional Competition V8 with fuel injection and 283 horsepower. The product brochure in 1957 promoted the convertible’s new vinyl interior and foam rubber seats for a more comfortable drive.
With something like a Bel Air, you can go for an American Graffiti-type nostalgia this Valentine’s Day. The convertible Bel Air also had a power-operated top, always good for admiring the stars with your date.
#3: 1962 Ferrari 250 GTO
While you and your date may already have a need for speed, you can go a step further by adding in an element of rarity. For many, the most famous sports car that fits this definition is the Ferrari 250 GTO. This mighty Prancing Horse has a V12 engine and a top speed of 174 mph, and it’s one of the finest Ferraris ever to see the light of day.
The only problem is locating one. There were only 36 made between 1962 and 1964.
You will turn heads at every stop if you are fortunate enough to get your hands on one for Valentine’s Day. While the Ferrari 250 GTO was built for racing, lucky owners now keep them in pristine condition.
#4: Porsche 550 Spyder
Porsche designed the 550 Spyder primarily as a race car (it won the Nürburgring Eifel Race in 1953, among many other races of the day). First introduced at the 1953 Paris Salon, the word “Spyder” was added to signify it as an open and light two-seater. This beauty rides low and actually drove under closed railroad crossing gates in the 1954 Mille Miglia.
There were only 90 made, although 43 were non-race cars as public demand grew for its sleek design and sophistication. Famous designer Ralph Lauren owns the 61st Porsche 550 Spyder.
Imagine the look on everyone’s face when you and your date arrive in this widely-recognizable sports car. It would be understandable if you took February 15th off from work to continue your road trip, following a late-night Valentine’s dinner and dessert.
#5: 1965 Ford Mustang
Given its near-universal appeal (unless your date is really into the Camaro!), the original pony car is the perfect choice for a night on the town.
By 1966, Ford had sold its one-millionth Mustang, with data showing that the median age of Mustang buyers was 31. More than 28 percent of Mustang buyers were younger than 25, a noticeable contrast from the median age of a regular Ford car purchaser at 42. If there is any car that can make you feel young again, a Mustang is it!
After a night out, if you and your date still want more Mustang feel-good vibes, we suggest watching A Faster Horse or playing a game of Mustang-themed Monopoly.
Most Romantic Classic Cars Conclusion
While these are our top five most romantic classic cars for Valentine’s Day, let’s be honest: any popular classic will make the day memorable. And even if you don’t own one of the classic cars on this list, you can still have a fun and romantic Valentine’s Day this year. Just don’t forget the flowers and chocolates!
Carl Anthony is the Managing Editor of Automoblog and the host of AutoVision News Radio and AutoSens Insights. As a respected automotive industry thought leader, Carl has appeared on numerous podcasts and radio shows, including Wrench Nation, Cars Yeah, The Car Doctor, and Digital PR Explained, in addition to appearing as a regular contributor on MotorMouth Radio on WHPC 90.3 FM. His work can also be seen and heard 24/7 on the Automoblog YouTube channel.
