Valentines Day Couple

The Five Most Romantic Classic Cars For Valentine’s Day

  • Matt Robertson of Leland-West Classic Car Insurance examines the top five classics for Valentine’s Day.
  • With one of these classic machines, you will make a memorable first impression as you arrive for dinner.

Valentine’s Day is approaching, and it is time to decide where to make the dinner reservations. The cards, chocolates, and flowers are purchased and ready for the perfect delivery. Then comes the planning of the actual date. What will you wear? Did you get your haircut? How will you get to your destination?

Will you take a limo to impress your date or is your current automobile good enough for this special night? How about stepping up your game and making sure this date is memorable?

Pick up that special someone in a romantic classic car. The question then is what are the top classic cars that are also romantic enough for Valentine’s Day? Let’s explore five of the most romantic classic cars ever produced.

#1: Aston Martin DB5

Someone who wants to make an amazing entrance this Valentine’s Day in a classic car would have to begin with the most sophisticated (and sexiest) one ever made: the 1963 Aston Martin DB5. The classic Aston Martin DB5 is one of the most recognizable vehicles of all time. Imagine being dressed in the finest attire possible and hitting the road in this beauty for an elegant dinner at the nicest restaurant in town.

Your date will be amazed when you pull up in this much-sought-after classic. The Aston Martin DB5 has 286 horsepower and tops out at 142 mph, making it powerful and fast in addition to sexy. This car is first on the list because James Bond showed the world its beauty in the movie Goldfinger.

And many women will agree James Bond is forever a symbol of sophistication and class.


#2: 1957 Chevrolet Bel Air

Maybe you are living in Southern California and are wanting a classic car that allows you to put the top down and drive the coast before your dinner reservations. The 1957 Chevrolet Bel Air is the obvious choice.

This beautiful specimen has a 4.6L V8 engine which should impress even the most skeptical of dates. And the classic elegance of the car will bring out the romantic in anyone. states that the Chevrolet Bel Air is “arguably the world’s most popular classic car.”

That being said, your date will be delighted when you pull up in this for the evening.

2011 GM Event Dream Cr36 1
A 1957 Chevrolet Bel Air on display at the GM Renaissance Center during a press conference. Photo: General Motors.

#3: Ferrari 250 GTO

Let’s turn our attention to those who might be looking for a sporty classic car to make the list. Maybe you and your date for the evening envision a need for speed and excitement. Arguably the most famous sports car of the time was the 1962-1964 Ferrari 250 GTO. This powerful car comes with a V12 engine and a top speed of 174 mph, and is one of the finest Ferraris ever to hit the road.

The only problem you will face is locating one. There were only 36 made between 1962 and 1964.

If you are fortunate enough to get your hands on one for Valentine’s Day, you will definitely turn heads at every stop. Some have described this classic sports car as the most desirable and legendary motorcar ever created. While the Ferrari 250 GTO was built for racing, as time has gone by, the lucky owners now keep them in pristine condition. And those that catch a glimpse will certinately stay awestruck.

Ferrari 250 GTO
In August of 2018, a 1962 Ferrari 250 GTO was bid to $48,405,000 at the RM Sotheby’s sale in Monterey, California. The bid makes this 250 GTO the most valuable car ever sold at public auction, beating the previous record for a 250 GTO – $38,115,000 – in 2014.

#4: Porsche 550 Spyder

If mixing that convertible top with sports car speed is something that interests you for Valentine’s Day, then to many the choice is clear. The classic 1953-1956 Porsche 550 Spyder was 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.

Porsche designed the 550 Spyder primarily as a race car. It won the Nürburgring Eifel Race in 1953 among many other races in the day. There were only 90 made, although 43 of them were non-race cars as public demand grew for its sleek design and sophistication. Famous designer Ralph Lauren owns the 61st Porsche 550 Spyder by the way.

Imagine the look on your date’s face if you were able to pull up in this rare, yet widely-recognizable classic sports car. You would be forgiven if you skipped dinner and just continued to enjoy the ride together.

Porsche 550 Spyder
Actor James Dean poses with a Porsche 550 Spyder. Photo: Porsche AG.

#5: 1965 Ford Mustang

The Mustang is for those that still want to impress, but also want to afford their entire Valentine’s Day date. Almost everyone loves the Ford Mustang and there are few better than the 1965 model year. Although this classic car is not as rare as some of the others discussed, it does have a powerful V8 engine, and comes in a coupé or convertible.

Your date will take notice of the time and effort you put into the evening when you pull up in this classic automobile.

1964 Worlds Fair Ford Exhibit 1965 Mustang neg CN3430 805
1965 Ford Mustang fastback in front the Ford Pavilion at the 1964 World’s Fair in New York. Photo: Ford Motor Company.

Picking The Right One

Classic cars are extremely popular as manufacturers cannot afford to make cars like those today. As enthusiasts know, the options are endless when trying to impress someone you cherish with a vehicle. And the opinions are different depending on the driver. Some prefer a head-turning vehicle with plenty of power; some want that elegant and noticeable convertible; others desire race car levels of speed and performance.

But most just want a classic that’s loved and adored by the masses.

While these are our top five romantic classic cars for Valentine’s Day, let’s be honest: any popular classic automobile will make the day memorable and romantic. Just don’t forget the flowers and chocolates!

Matt Robertson is Managing Partner at Leland-West Classic Car Insurance. Matt is a classic car nut and when he’s not wrenching in his garage, you can find him at any number of antique car events.