Monterey & Big Sur: Drive a 1961 Cadillac Convertible Rental

Imagine cruising along California’s legendary coastline in a pink, chrome-laden vintage Cadillac, feeling like a starlet or a Hollywood legend. That’s exactly what this experience offers — a chance to take the wheel of a classic 1961 Cadillac Convertible, explore iconic spots like Monterey, Carmel, and Big Sur, all while enjoying the open air and stunning scenery. Whether you’re celebrating a special occasion or simply want a memorable way to see the coast, this tour promises a ride filled with charm, nostalgia, and breathtaking views.

Two things we love about this experience are the opportunity to drive a genuine vintage American icon and the flexibility of a private group setting, which makes it tailored and intimate. Plus, the inclusion of a detailed driving map ensures you won’t lose your way along those scenic routes. One thing to keep in mind is that parking fees and tolls are not included, so budget accordingly if you plan to stop frequently or visit popular spots. This tour suits those who enjoy a mix of sightseeing with a splash of vintage glamour, particularly couples, families, or groups celebrating something special.

Key Points

• Authentic Vintage Car – Drive or ride in a beautifully maintained 1961 Cadillac convertible, complete with V8 power and classic styling.
• Stunning Scenic Routes – Experience the famed 17-Mile Drive and Highway 1 Big Sur, with views of rugged cliffs, redwoods, and the Pacific Ocean.
• Flexible Itinerary – Full-day private experience with options to start in the morning or afternoon.
• All About Value – For $599, up to five travelers can enjoy a memorable adventure in style, with fuel, insurance, and a detailed map included.
• Authentic & Fun – Feel the wind in your hair, hear the engine roar, and soak in the California coastal atmosphere.
• Ideal for Special Occasions – Perfect for celebrating, making memories, or simply indulging in a unique driving experience.

You can check availability for your dates here:

A Classic California Coastal Drive Like No Other

Driving along California’s coastline in a vintage 1961 Cadillac Convertible is a bit like stepping into a Hollywood film, but with a very real, personal twist. We loved the way this experience combines the nostalgic appeal of a classic American car with the natural beauty of the Monterey Peninsula and Big Sur. This isn’t just transportation — it’s a full-on style statement, an opportunity to feel like a movie star or a vintage car enthusiast for a day.

The Cadillac itself is a showstopper. Its pale pink exterior with chrome accents and tailfins immediately catches the eye and makes a statement without trying too hard. Inside, the wide bench seats and spacious interior give a comfortable ride for up to five people, whether you’re behind the wheel or riding shotgun. The automatic 390 V8 engine provides enough power to make the drive fun without feeling overwhelming, and the convertible top allows you to soak up the sun or enjoy the sea breeze.

The Itinerary: What to Expect

The tour begins in the charming town of Monterey, where you’ll start your adventure on historic streets, passing Cannery Row, Lovers Point, and Pacific Grove. These spots are perfect for a quick photo or a stroll. Monterey’s waterfront is lively, with plenty of spots to grab a coffee or simply admire the view before hitting the road.

Next is the renowned 17-Mile Drive, a route celebrated worldwide for its scenery. As you wind along the coast, you’ll see towering cypress trees, rocky outcroppings, and world-famous golf courses like Pebble Beach. With the top down, you’ll feel every gust of ocean breeze and hear the crunch of gravel under the tires. Travelers have mentioned that “the views of the coast and the golf courses are spectacular,” making this a highlight of the day.

From there, the tour continues to Carmel-by-the-Sea, a storybook village packed with boutique shops, art galleries, and inviting cafés. The town’s fairy-tale vibe makes it an ideal stop for a quick browse or a sit-down drink. For those who prefer the wild side, heading south to Big Sur along Highway 1 is a must. You’ll pass Bixby Bridge, which is one of California’s most photographed spots, and enjoy the drama of cliffs plunging into the Pacific Ocean.

In Big Sur, you might stop for lunch in a scenic spot, nestled among towering redwoods or perched high on the cliffs. The tour’s flexibility means you can choose to linger or keep moving, making it adaptable to your pace.

The Experience of Driving or Riding

Whether you opt to drive yourself or have a professional guide do the honors, the experience is immersive. We loved that the vehicle is maintained professionally and that roadside assistance is available if needed. Reviews indicate that drivers appreciate the smooth automatic transmission and the classic feel of the car, which makes sightseeing feel like a step back in time.

For those who prefer not to drive, some packages include a driver, so you can relax in the backseat and enjoy the scenery while someone else handles the road. Either way, you’ll enjoy the sense of freedom and fun that comes with cruising along one of the most beautiful coastlines in the world in such an iconic car.

The Practical Side: Pricing, Duration, and What’s Included

At $599 per group, the cost covers up to five people, making it a surprisingly good value for such a unique experience. This includes the car rental for three hours, fuel, insurance, roadside assistance, and a detailed driving map. The full-day experience allows for flexibility, with options to start in the morning or afternoon.

It’s important to note that parking fees and tolls are not included, so plan for those additional expenses. The tour is designed for private groups — perfect for families, friends, or couples wanting a more intimate experience.

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What to Bring and What Not To

To make the most of your day, bring sunglasses, a camera, and comfortable clothes suitable for the weather. Since the top is convertible, you’ll want sun protection, and a camera is essential for capturing those unforgettable vistas. Keep in mind that smoking, food, and alcoholic drinks are not permitted in the vehicle, maintaining a clean and respectful environment.

Who Would Love This Experience?

This tour is ideal for travelers who are car enthusiasts, vintage lovers, or those celebrating something special. If you want to combine sightseeing with a touch of Hollywood glamour, this option is perfect. It also suits families or groups who enjoy a relaxed, private experience with a knowledgeable guide or driver.

While the experience isn’t aimed at hardcore adventurers or hikers, it’s perfect for those who want a comfortable, stylish way to see the coast. If you’re looking for a memorable day that blends scenic beauty with the nostalgia of a classic American car, this tour will give you memories to cherish.

Final Thoughts

Driving or riding in a vintage Cadillac along California’s coast is more than just a way to get from A to B — it’s a chance to feel like part of the story. The combination of a classic car, spectacular scenery, and flexible planning makes this experience stand out among coastal tours. It’s a celebration of style, history, and natural beauty in one package.

This tour offers great value for the price, especially considering how unique and Instagram-worthy the experience is. Whether you’re celebrating a special occasion or simply want to add a dash of glamour to your trip, it’s a memorable way to explore California’s most scenic spots in comfort and style.

Who Should Book?

If you love vintage cars, scenic drives, or iconic landscapes, this experience will hit the mark. It’s especially well suited for those who appreciate the finer details, like a well-maintained vehicle and personalized service. It’s also a great choice if you want to avoid the hassle of driving yourself on busy coastal roads.

FAQs

Can I drive the Cadillac myself?
Yes, the rental includes the option for you to drive if you hold a valid driver’s license, or you can select a package with a professional driver.

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

Are there any additional costs?
Yes, you’ll need to budget for parking fees and tolls, as these are not included.

How flexible is the schedule?
You can choose to start either in the morning or the afternoon, and the experience is designed as a full day — giving you the flexibility to linger or move at a faster pace.

What should I bring?
Bring sunglasses, a camera, and comfortable clothing suitable for outdoor sightseeing and weather conditions.

Is the car suitable for families?
Yes, the spacious interior seats five comfortably, making it a fun, family-friendly activity, especially if everyone enjoys vintage cars and scenic drives.

This vintage Cadillac coastal drive is more than just transportation — it’s a chance to step into a storybook California adventure. Whether you’re a classic car enthusiast or simply someone wanting a different way to see the coast, it offers a blend of nostalgia, comfort, and stunning scenery that’s hard to beat.

You can check availability for your dates here: