Road trips are a bit more fun when you rent an unusual mode of transportation. Picture this: you’re cruising down California’s famous Highway 1 in a vintage red Mustang, or exploring Michigan’s Kalamazoo Lake in a 1950s retro boat, or maybe even traveling through Kentucky in an old-school motorcycle complete with a sidecar. Whatever you choose, chances are the trip will be that much more memorable. 

Rent a classic car

Choose from a fleet of more than 30 classic and vintage cars at Monterey Touring Vehicles, located in Monterey, a seaside city about an hour south of San Jose. There’s everything from a 1958 Porsche 356 Outlaw to a 1968 Chevy Camaro. Or how about a 1970 Chevy Corvette or a 1965 Ford Shelby Cobra? 

Begin your adventure along super scenic Highway 1 in Monterey, where restored adobe buildings are the norm, redwoods are plentiful and the pristine shoreline is highly Instagrammable. A pit stop here could involve stand-up paddleboarding among the seals and whale-watching.

When you’ve had your fill of marine life, continue south to Big Sur and rest your head at Ventana Big Sur resort. Highway 1 at Big Sur is a National Scenic Byway, recognized for its archaeological, cultural, historic, recreational, natural and visual qualities. In other words, be prepared to be wowed by unspoiled, majestic vistas and villages the whole way. The spellbinding twists and turns are incredibly fun in a flashy ride.

Scenic Big Sur: top sights on your Highway 1 road trip 

Two people ride in a light blue boat in an open body of water
Zoom around Lake Kalamazoo in a vintage boat © Courtesy of Nick Hearn Photography

Rent a vintage boat

Head to Retro Boat Rentals in Saugatuck, Michigan, to get your vintage-boat fix. Choose from a whole fleet of old-school boats that have been retrofitted as electric. 

You’ve got beauties like Jane, a 1958 Geneva, or Ruby, a 1959 Bell Boy Banchee that seats four. Ruby is so photogenic, in fact, its been used for numerous weddings, engagements and senior photos. There’s lot of extra leg room in the back, and it’s a great boat for swimming since it’s easy to get in and out of.

Cruise around Kalamazoo Lake, a picturesque inland body of water, for a while with a giant smile on your face. If you have kiddos, Dottie, a 1960 Dorsett Catalina, is a solid option. It seats four, and the kids love the small cabin area. Note: You’ll only be going about 5mph, so it’s more about the experience and less about speed. 

An orange VW camper cruises down a two-lane highway
VW campers are a popular vehicle for road trippers © Courtesy of Vintage Surfari Wagons

Rent a VW van 

There’s no doubt you will make new friends along the way if you are at the helm of a VW camper. Vintage Surfari Wagons is one of the oldest vintage VW camper rental companies in the USA. It’s located 6 in Costa Mesa, California, about 45 miles south of LAX. Take your pick from 20 highly maintained VW pop-top campers that are between 1973 to 2002 vintage, each brimming with personality. 

Because of the popularity of these quirky vehicles, the company encourages travelers to make reservations several months ahead. And keep in mind, you need to be able to drive standard-shift vehicles. Outdoorsy also rents VWs across the nation. Either way, you have lots to choose from. 

The best destinations for camper van travel 

Rent a motorcycle with sidecar

Known as the Airbnb for motorcycles, Twisted Road offers motorcycle-sharing services for a flat, per day charge. Take your pick from rides like the Ural Retro bikes that come complete with a sidecar or a 1976 Honda Cb550. Tip: wear vintage goggles and a scarf to really get into character.

A yellow bi plane takes off
Take to the skies in a vintage biplane © Courtesy of Gypsy Air Travel

Ride in a biplane

In Brodhead, Wisconsin, you can transport yourself back in time via biplane. Gypsy Air Tours gives you the chance to soar through the sky in a 1930s WACO Taperwing, believed to be one of only seven still flying in the world.  

WACO only produced about 70 Taperwings during the golden age of aviation. The engine on this rare plane is an original Wright Whirlwind that is similar to the engine Lindbergh had on the Spirit of St. Louis when flying over the Atlantic.  

You get to sit in the open cockpit as the engine roars to life with a puff of smoke and a whirling propeller. You will have a bird’s-eye view of the circuitous rivers, the orchards, the round barns and people coming out of their houses to look up and wave.  You are close enough to peek in at what’s going on around the towns that look pretty similar to the way they did 100 years ago. You might see a car show from above or a parade, you never know. It’s exhilarating and fascinating at the same time.

Give the pilot a thumbs-up and they will lightly maneuver the plane so that you can feel the lift of the wings and the agility of the stick and rudder. It’s a gentle, smooth flight, which means you can kick back, relax and pretend you are flying in the 1920s and '30s.  

This area is famous for antique aviation because of the number of vintage planes based there and the knowledge and skill of those caring for and flying the planes. Stick around afterward to watch the sun dropping in the west or pay a visit to Kelch Aviation Museum. Gypsy Air Tours plans to reopen in late July, but is already taking reservations. 

A group of people ride in a body of water in a red amphicar. There is a smaller boat in the the background.
For something truly unique hop in an amphicar © Gustavo Caballero / Getty Images

Hop in an amphicar

Roll into yesteryear by taking an amphicar for a spin. Part-car, part-boat, only about 3200 were made during the 1960s. Today, there are likely about 300 or so of them left. Disney Springs in Orlando is one of the only places in the world where you can take one of these puppies for a swim. Fun fact: Jimmy Carter and Lyndon B Johnson owned amphicars. Afterwards, grab a bite to eat at The Boathouse, where oysters, lobster and the legendary baked Alaska top the menu. End your day at one of the three outdoor bars for a craft cocktail. 

You might also like:

These tiny-home resorts are perfect social distancing getaways 
The USA's top national wild and scenic rivers 
The USA's 11 best road trips and scenic drives 

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