Monterey & Big Sur: Drive a 1961 Cadillac Convertible Rental

If you’re dreaming of hitting the California coast in a style that turns heads, this vintage 1961 Cadillac convertible experience might be just what you’re looking for. While I haven’t personally taken this exact tour, it’s made quite a splash among travelers wanting that classic, open-air feel on iconic routes like Highway 1 and 17 Mile Drive.

What really catches my eye are a couple of standout features: first, the chance to drive a vintage Cadillac with a V8 engine—not something you get every day—and second, the personalized, private group experience that makes it feel like a day spent exploring with friends.

Of course, one thing to keep in mind is that this is a one-day rental and certain costs—like parking fees and tolls—are extra. But if you’re after a memorable, photo-worthy adventure that blends nostalgia with breathtaking scenery, this tour could be just the ticket—especially for those who love a good road trip in style.

Who is this experience best for?

It suits travelers who appreciate classic cars, enjoy scenic drives, and want a flexible yet unique way to explore California’s coast. Whether celebrating a special occasion or just craving a fun day out, this experience offers plenty of charm for solo travelers, couples, or small groups.

You can check availability for your dates here:

Key Points

• Iconic vintage Cadillac: Drive or ride in a pink 1961 Cadillac with a V8 engine.
• Beautiful routes: Experience Monterey, Carmel, 17 Mile Drive, and Big Sur in style.
• Private group: Up to 5 passengers, making it perfect for small groups or couples.
• All-inclusive rental: Fuel, insurance, and a driving map are provided.
• Flexible timing: Usually available in morning or afternoon, with easy cancellation.
• Consider extra costs: Parking and tolls are not included, which can add to the day’s expenses.

A Closer Look at the Experience

The Car — A Head-Turning Classic

Driving a pink 1961 Cadillac convertible is about more than just getting from point A to B. It’s about channeling the glamour of the early ’60s, complete with shiny chrome details and tailfins that still catch the eye. The car’s spacious interior with wide bench seats makes it surprisingly comfortable, whether you’re in the driver’s seat or enjoying the ride as a passenger.

The V8 engine, a 390 cubic inch (ci) powerhouse, promises some fun behind the wheel—though a lot of visitors opt to let someone else do the driving, especially if they’re just here for the sightseeing and photos. Still, for those who want to experience the thrill of steering this classic, the car is maintained professionally, and roadside assistance is included, so you won’t be left stranded.

The Itinerary — Scenic Stops and Iconic Views

The tour starts in Monterey, known for its charming streets and historic sites like Cannery Row. We loved the way the route takes you past Lovers Point and Pacific Grove, with the top down and the engine humming, making every mile feel special.

Next, you’re treated to the famous 17-Mile Drive, which is often called one of the most scenic routes in the world. Picture tall cypress trees, rocky coastlines, and golf courses like Pebble Beach—this stretch alone is worth the price of the tour. As you navigate the winding roads, the views of the Pacific are unforgettable.

From there, the journey continues to Carmel-by-the-Sea, a storybook town packed with boutique shops, art galleries, and seaside charm. It’s a perfect spot for a quick stroll or a coffee break, all while feeling like you’re part of a vintage movie scene.

If you choose to head south toward Big Sur, expect rugged cliffs, crashing waves, and that legendary Bixby Bridge—probably one of the most photographed spots in California. The driver can stop for a picnic lunch (you’ll need to arrange this separately), either nestled among redwoods or perched high above the ocean.

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What the Reviews Say

Many travelers appreciate the flexibility of this experience. One reviewer mentioned, “It’s more than just a drive—it’s a chance to feel like a star.” Others have highlighted how the vehicle is well-maintained and makes for fantastic photo opportunities, especially with the top down.

Some note that parking fees and tolls are extra, which is something to consider for your budget. Also, since the car is a classic, the ride can be a bit bumpy compared to a modern vehicle, but that’s part of the charm—if you’re looking for perfect smoothness, this might not be the best choice.

The Practical Stuff — What You Need to Know

• Duration: A full-day adventure, with options for morning or afternoon departures.
• Price: $599 for the whole group up to five people, which includes the car rental, fuel, insurance, and a driving map of Monterey Peninsula.
• Extras: Parking fees and tolls are not included, so plan for those.
• Group Size: Private, so it’s intimate—ideal for small groups or couples wanting a personalized experience.
• Requirements: A valid driver’s license is needed if you’re behind the wheel.

The Experience Level — Is it for You?

This tour is perfect for those who love a bit of nostalgia, enjoy scenic drives, or want to make memories in a truly unique way. It’s especially popular among couples celebrating something special or groups of friends who want a fun, photo-worthy day.

If you’re someone who prefers a guided tour with a set schedule or dislikes driving, you can also hire a driver, which allows you to sit back and enjoy the views without worries.

The Value of the Experience

When you consider the $599 price point, you’re paying for more than just a car rental—you’re buying a photogenic, memorable experience that’s a real conversation starter. The vintage Cadillac isn’t just a mode of transportation; it’s part of the adventure and adds a layer of fun that modern SUVs or sedans just can’t match.

Travelers have rated the experience as “absolutely worth it,” especially when paired with the stunning scenery. The ability to drive along California’s most beautiful stretches while turning heads in a classic car makes this a premium, yet authentic, way to explore.

Who Should Consider This Tour?

If you’re a lover of vintage cars, classic Americana, or scenic drives, this experience hits all those marks. It’s particularly well-suited for travelers looking to celebrate a special occasion or those who want their trip to include a fun photo op or two.

It’s also a good choice if you want flexibility—you can drive yourself or have a professional driver take the wheel. Just keep in mind that extra costs for parking and tolls can add up, so budget accordingly.

People who prefer a guided tour with a set itinerary or are less comfortable driving a classic car might prefer other options, but for a self-driven, stylish adventure, this one stands out.

FAQs

Can I drive the Cadillac myself?
Yes, a valid driver’s license is required if you want to drive the car. You’ll have the option to drive or ride along in the backseat.

What’s included in the price?
The fee covers a 3-hour rental of the vintage Cadillac, fuel, insurance for one driver, and a driving map of Monterey Peninsula.

Are there any additional costs?
Yes, parking fees and tolls are not included, so you’ll need to plan for those on your day.

How long does the experience last?
Typically, it’s available in either the morning or afternoon and lasts about a full day—so you can pick the time that works best for you.

Is this experience family-friendly?
While the car seats five, the experience is more about the scenic drive and vintage vibe rather than activities for children. If you have young kids, consider if they’re comfortable in the car for the duration.

Can I hire a driver?
Yes, you can hire one of the company’s drivers, allowing you to relax and enjoy the scenery without worrying about driving.

Final Thoughts

For anyone craving a nostalgic, fun-filled day exploring California’s coast in a stylish vintage car, this Cadillac rental experience is tough to beat. It offers a unique blend of scenic beauty, classic Americana, and personalized service—perfect for making your trip truly memorable.

While the costs for parking and tolls are extra, the opportunity to drive or ride in a 1961 Cadillac along iconic routes like Big Sur and Monterey makes this a worthy splurge. It’s especially suited for those who appreciate vintage cars, scenic drives, or simply want a show-stopping story to tell when they get home.

If you’re after a luxurious yet laid-back adventure that blends nostalgia with breathtaking views, this experience could be just the ticket. Just plan ahead for the additional costs, and you’ll be set for a day full of fun, charm, and unforgettable scenery.

You can check availability for your dates here: