Monterey & Big Sur: Drive a 1961 Cadillac Convertible Rental

Imagine cruising the California coast in a pink 1961 Cadillac Convertible, the wind in your hair, and the engine humming beneath you. That’s exactly what this experience offers—a chance to channel Old Hollywood glamour while exploring some of the most stunning scenery along the Pacific. We haven’t personally taken this trip, but from what we gather, it’s an adventure that combines classic style, scenic beauty, and a touch of nostalgia.

Two things we really love about this experience: first, the vintage Cadillac itself. It’s a real head-turner, with its shiny chrome, swooping tailfins, and bold color. Second, the opportunity to cruise along legendary routes like 17-Mile Drive and Highway 1 in style—it’s a very different way to see the coast than a typical guided tour or rental car.

A potential consideration? The experience is limited to just one day, so it’s more about the fun of the drive than in-depth exploration of every stop. Also, it’s best suited for those who want a memorable photo opportunity or a special occasion rather than a comprehensive sightseeing tour.

This tour is perfect for families, couples celebrating a milestone, or anyone craving a unique way to see Monterey and Big Sur. If you love vintage cars, scenic drives, or just want to feel like a star for a day, it’s a fantastic pick.

Key Points

• Iconic Vintage Car: Drive a beautifully maintained 1961 Cadillac Convertible with an automatic V8 engine.
• Scenic Routes: Experience Monterey, Carmel, 17-Mile Drive, and Big Sur in style.
• Comfortable for Groups: Seats 5, making it ideal for families or small groups.
• Flexible Experience: You can choose to be the driver or enjoy the ride with a professional driver.
• All-Inclusive Pricing: Price includes fuel, insurance, and a driving map—no hidden costs.
• Memorable Photo Opportunities: The classic car and stunning coastlines make for great snapshots.

You can check availability for your dates here:

A Classic California Coastal Drive in a Beautiful Vintage Car

This experience instantly appeals to those with a love for vintage cars or a desire to add a touch of glamour to their trip. The 1961 Cadillac Series 62 Convertible is a genuine icon—its pale pink exterior and chrome accents are as much a statement piece as the scenery you’ll be enjoying. We love the fact that this car is reliable and professionally maintained, with roadside assistance included, which keeps the focus on fun rather than worries.

The car’s spacious interior means you won’t feel cramped, even with five passengers. The wide bench seats evoke the classic era of cruising in style, giving everyone a chance to soak in the sights comfortably. Whether you’re driving yourself or sitting back and relaxing, the experience offers a rare blend of nostalgia and adventure.

Detailed Itinerary and Experience

Starting in Monterey

Your day begins in Monterey, a charming harbor town known for its fishing history and art scene. As you set off along the coast, you’ll pass through Cannery Row, once the heart of the sardine-packing industry, now lined with shops, restaurants, and galleries. We love how this area combines history with modern charm.

Driving in a vintage Cadillac makes the experience more immersive—every turn, every curve of the road feels like stepping back in time. The top-down aspect means you’ll get the full sensory experience—the scent of salt air, the warmth of the sun, and the feeling of freedom that only a convertible can provide.

Scenic Highlights: 17-Mile Drive and Carmel-by-the-Sea

The 17-Mile Drive is a highlight, winding through lush cypress groves, rocky coastlines, and past world-famous golf courses like Pebble Beach. It’s a route that’s as celebrated for its beauty as for its exclusivity. Many reviews mention how special it feels to drive this legendary stretch in such a stylish vehicle, with one reviewer noting they felt like they were “living the dream.”

Next, you’ll arrive in Carmel-by-the-Sea, a storybook village packed with boutique shops, art galleries, and cozy cafés. The relaxed, artistic vibe makes it a perfect spot for a quick stroll or a coffee break. The small-town charm combined with coastal scenery makes for a memorable stop.

More Great Tours Nearby

Heading toward Big Sur

The drive south along Highway 1 to Big Sur is often described as one of the most breathtaking routes in the world. With the top down, you’ll enjoy unobstructed views of towering cliffs, crashing waves, and redwood forests. The Bixby Creek Bridge is a popular photo stop, and for good reason—its sweeping arch is one of the most photographed spots in California.

Depending on your schedule, you could stop for lunch in Big Sur—many options offer dining with a view, whether high above the cliffs or surrounded by towering redwoods. Some reviews mention the pleasure of eating in places with a sense of connection to the landscape, often near creeks or on coastal bluffs.

The Experience of Driving

While some might prefer to hire a driver, the option to take the wheel in this classic car adds a layer of fun and authenticity. Imagine feeling the power of the 390ci V8 engine as you navigate curves and enjoy the sensation of being behind the wheel of a true American icon. If you choose to be a passenger, you’ll still enjoy the sights and sounds with the comfort of a professional at the wheel.

Practical Details and Functionality

The price of $599 covers the entire group, up to five people, which makes it quite reasonable when you consider the exclusivity and uniqueness of the experience. Fuel, insurance, and a driving map are included, so there are no surprises. However, you’ll need to handle parking fees and tolls separately.

The tour lasts about one full day, with options for morning or afternoon sessions. It’s a private group, giving you privacy and flexibility. You’ll want to bring sunglasses, a camera, and comfortable clothes—things that will help you relax and enjoy the ride.

Authenticity and Customer Feedback

Many reviewers mention how the vehicle is well-maintained and reliable, which is crucial for peace of mind. One noted, “It’s not just a photo prop—it’s a working car that’s fun to drive.” Others appreciated the personalized service and the flexibility to customize stops or routes.

Some feedback touched on the value of the experience—while it’s a bit of an investment, many feel it’s worth it for the memories created and the chance to drive such an iconic car in such a stunning setting.

Who Should Consider This Experience?

This tour is ideal for vintage car enthusiasts, romantic couples, families celebrating special occasions, or friends eager for a memorable adventure. It’s especially suited for those who want to combine scenic sightseeing with the thrill of driving a classic. If you love the idea of standing out and making a statement on the California coast, this is it.

However, if your priority is a full-day, in-depth tour of every site, you might find this experience a bit limited in scope—it’s more about the journey and photo opportunities. Also, those prone to motion sickness or uncomfortable with open-air drives should dress accordingly.

The Sum Up

This Monterey & Big Sur drive in a vintage 1961 Cadillac offers a truly unique way to experience California’s coast. It’s more than just a scenic drive—it’s a chance to step into a different era, feel the thrill of a powerful classic car, and enjoy some of the most stunning coastal views in the world.

We think it’s perfect for those seeking a fun, stylish, and memorable experience that leans into nostalgia and adventure. The private group setting and inclusive pricing make it a straightforward choice for a special day out. Plus, it’s a fantastic story to tell back home—“Yes, I drove a pink Cadillac along Big Sur.”

While it may not replace a comprehensive sightseeing tour, it’s a delightful addition for anyone wanting a bit of Hollywood glamour and unforgettable scenery in one package.

FAQ

Can I drive the Cadillac myself?
Yes, the experience includes the option for you to be the driver, provided you have a valid driver’s license.

What’s included in the price?
The $599 fee covers a 3-hour rental of the vintage Cadillac, fuel, insurance for one driver, roadside assistance, and a driving map. It seats up to five people.

Are there options for a professional driver?
Yes, you can hire a driver if you prefer not to drive, allowing you to relax and take in the scenery.

What should I bring with me?
Bring sunglasses, a camera, and comfortable clothes suitable for outdoor and possibly variable weather.

Is this experience suitable for children?
Yes, the car seats five, making it feasible for families. Just keep in mind that the experience is primarily about the drive and scenery.

Are there any additional costs?
Parking fees and tolls are not included, so be prepared for those expenses separately.

What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund, offering some flexibility for changing plans.

This experience provides a fun, stylish, and scenic slice of California coast life—perfect for making lasting memories in a truly classic way.

You can check availability for your dates here: More Great Tours Nearby