Monterey & Big Sur: Drive a 1961 Cadillac Convertible Rental

If you’re dreaming of cruising along the California coast in a vintage Cadillac, this tour promises a glamorous, nostalgic adventure. From the moment you see the shiny pink exterior and chrome tailfins to feeling the V8 engine roar beneath you, every aspect of this experience is designed to make you feel like a star. Whether you’re celebrating an anniversary, going on a unique family outing, or simply want a memorable drive, this is a one-of-a-kind way to explore Monterey and Big Sur.

Some of the highlights that catch our eye include the opportunity to drive a beautifully maintained classic car, the chance to take in iconic coastal views, and the flexibility of a private group experience. Be aware that parking fees and tolls are not included, so plan ahead. This experience suits those who love vintage cars, scenic drives, and a touch of Hollywood glamour in their travels.

Good To Know

• Vintage Charm: Drive a well-maintained 1961 Cadillac convertible with authentic features like a V8 engine and shiny chrome accents.
• Scenic Routes: Cover the stunning Monterey Peninsula, 17-Mile Drive, Carmel-by-the-Sea, and Big Sur’s breathtaking coastline.
• Comfort & Capacity: Seats five comfortably, so it’s great for small groups or families.
• Flexibility & Convenience: Private booking with options for a driver or self-drive, and a flexible refund policy.
• Authentic Experience: A chance to soak in California’s coast roads in a classic car, making it perfect for special occasions or memorable outings.

You can check if your dates are available here:

An In-Depth Look at the Experience

The Car: A Time Machine on Wheels

Driving a pink 1961 Cadillac Series 62 Convertible instantly sets the tone for a fun, stylish day. The car’s broad bench seats and spacious interior mean everyone can comfortably enjoy the ride—whether you’re behind the wheel or relaxing in the back. The V8 engine offers enough power to feel the thrill as you wind through coastal roads, while the automatic transmission keeps the drive smooth and effortless. The shiny chrome and eye-catching tailfins don’t just look good in photos—they add to the sense of stepping back in time.

A common sentiment from previous drivers is how well the car is maintained and reliable, which is vital for a day-long adventure where you want to focus on the scenery rather than mechanical worries. Plus, the convertible top allows you to feel the sun and sea breeze, enhancing the open-road experience.

Starting Point: Monterey’s Historic Streets

The adventure kicks off in Monterey, where you can park and start your day exploring the charming streets. The tour includes cruising through Cannery Row, Lovers Point, and Pacific Grove—all picturesque spots known for their coastal beauty and vibrant history. As you drive, you’ll notice that the car’s nostalgic design turns heads and sparks conversations. We loved how the reliable roadside assistance provided peace of mind, ensuring a smooth ride even if unexpected hiccups occur.

Exploring 17-Mile Drive

One of the tour’s biggest highlights is the world-renowned 17-Mile Drive. This winding route through Pebble Beach and Pacific Grove hugs the rocky coastline, boasting stunning views of the ocean, iconic golf courses, and ancient cypress trees. The open top allows you to fully enjoy the fresh air and panoramic vistas. Past travelers have remarked on how the engine hums happily as you take each turn, and many expressed that the drive felt like a film scene—except it was real.

More Great Thing To Do Nearby

Carmel-by-the-Sea: A Seaside Village

As you arrive in Carmel-by-the-Sea, the town’s quaint, storybook vibe comes alive. Known for its boutique shops, art galleries, and cozy cafes, Carmel is perfect for a leisurely stroll or a quick coffee break. The flexible nature of the tour means you can stop for photos, browse local art, or simply soak in the charming streetscape. Many guests find this part of the trip an ideal balance of scenic driving and downtime.

Heading South to Big Sur

The real showstopper is the drive along Highway 1 to Big Sur. Here, the rugged cliffs meet the crashing Pacific waves, and Bixby Bridge offers one of the most photographed vistas in California. Driving this stretch in a vintage convertible elevates the experience—feeling the wind, hearing the engine, and soaking in the breathtaking scenery. Some reviews mention that stopping for lunch “by a creek surrounded by towering redwoods” adds a peaceful contrast to the exhilarating drive.

The Practical Details

The tour lasts a full day, with most options available in the morning or afternoon. The cost of $599 per group (up to 5 people) provides access to the vintage car, fuel, insurance, and a driving map. This price reflects the exclusivity and novelty of the experience—you’re paying for a memorable day in a classic car, not just transportation.

If you choose to drive yourself, you’ll need a valid driver’s license, but you also have the option to hire a driver and relax in the backseat. This flexibility makes it accessible whether you want to be behind the wheel or just enjoy the ride.

What’s Included and What’s Not

The price covers the 3-hour rental of the Cadillac, fuel, cleaning, insurance for the driver, and the convertible top. You’ll also receive a detailed map of the Monterey Peninsula to help you plan your route and stops. However, additional expenses like parking fees and tolls are on you, so it’s best to budget accordingly.

What to Bring

We recommend bringing sunglasses and a camera to capture the stunning scenery. Dress comfortably, especially since weather along the coast can change quickly—layering is advised. The tour staff emphasizes that smoking, food, and alcohol are not permitted in the vehicle, to maintain its pristine condition.

Who Should Consider This Experience?

This tour is ideal for vintage car enthusiasts who love the idea of driving or riding in a classic vehicle. It’s also perfect for romantic couples celebrating a special moment or families wanting an exclusive, fun adventure. The private group setup ensures a personalized experience without the crowds. Keep in mind that this is a full-day activity, so it’s best suited for those with flexible schedules and a sense of adventure.

Final Thoughts

Driving through California’s coast in a beautifully restored 1961 Cadillac offers more than just sightseeing—it’s about relishing the journey and embracing a sense of adventure and nostalgia. The experience blends spectacular scenery, vintage style, and a touch of Hollywood glamour, making it a memorable way to explore Monterey and Big Sur.

The price provides good value considering the exclusivity, the well-maintained vehicle, and the flexibility to customize your day. Whether you’re a car lover, a scenic explorer, or someone who wants to feel like a star, this tour makes for a memorable chapter in your California trip.

FAQ

Can I drive the Cadillac myself?
Yes, if you have a valid driver’s license, you can choose to drive. There’s also an option for a driver, so you can relax in the back.

How many people can fit in the car?
The Cadillac seats five comfortably, making it suitable for small groups, families, or couples.

Is the tour suitable for children?
While the experience is fun and scenic, the site’s age restrictions aren’t specified. It’s best to consider children’s comfort with long drives and the vintage car environment.

What’s the duration of the rental?
The experience typically lasts a full day, with options available in the morning or afternoon.

Are there any hidden costs?
Parking fees and tolls are not included, so you should budget for those separately.

Can I cancel or reschedule?
Yes, free cancellation is available up to 24 hours before the tour, offering you flexibility if your plans change.

What should I wear?
Comfortable clothes and sunglasses are recommended. Dress for the weather, especially since coastal conditions can vary.

Is insurance included?
Yes, insurance is covered for one driver, giving peace of mind during your drive.

What makes this experience unique?
The combination of a vintage car, scenic coastal routes, and the chance to feel like you’re in a movie scene makes this stand out from typical sightseeing tours.

Is there a specific time of year best for this tour?
Weather can influence your experience, so it’s best to check local conditions beforehand. However, the open-top drive is most enjoyable on clear, mild days.

This vintage Cadillac tour offers a blend of style, scenery, and nostalgia—perfect for those wanting to explore California’s coast in a truly unique way. Whether you drive or sit back and relax, it’s a journey that will leave lasting memories.

You can check if your dates are available here: