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Road Trip Retreats Across America: Places To See & Stay

CALPAK Stevyn Duffel Bag in Pink Sand.

Ready for a real road trip? From classic cross-country odysseys to easy intrastate escapes, we’ve got your trip’s pit stops covered. Check out some of the country’s top road trip adventures – long hauls all the way to quick cruises – with suggested stays along the way, and what you should take with you before you hit the open road.


The Classic Cross-Country Road Trip

Long haul with side trips: Craving a slice of classic Americana for your next road trip? Cruise from the Windy City through the desert to the City of Angels, seeing everything from the world’s largest rocking chair to one of its greatest natural wonders. Start at the very beginning, or pick it up anywhere along the way and disappear into the desert – it's all about feeling present along this historic highway.

Search for places to stay in Chicago on Vrbo.

        • START or stop in CHICAGO

        • The old Route 66 begins at the intersection of Jackson Boulevard and Michigan Avenue.

Search for places to stay in Flagstaff on Vrbo.

        • DETOUR: THE GRAND CANYON

        • Iconic natural wonder alert! Be sure to make a break north for Flagstaff. It’s an awesome escape any time of year, and a perfect place to stop so you can see the Grand Canyon in all its glory.

Search for places to stay in Joshua Tree on Vrbo.

    • DETOUR: JOSHUA TREE NATIONAL PARK

    • If you're coming from Los Angeles or Las Vegas, a stay in or around Joshua Tree is the perfect way to soak up this storied desert’s powerful vibes.

Search for places to stay in Santa Monica on Vrbo.

    • STOP OR START IN SANTA MONICA

    • Classic Americana to the max. Your epic road trip adventure could begin or end with a cool breeze and sand between your toes. Route 66 stops at Santa Monica Pier, so why not celebrate by booking a stay with beach views so you can let the California sunshine in?

        • DIFFERENT CLIMATES CALL FOR VERSATILE BAGGAGE:

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The magical PNW: NorCal/Oregon Coast to Seattle

Medium Haul: The windy parts of Pacific Coast Highway stretching from Northern California to the northern tip of Washington State are nothing short of stunning. Take this manageable drive for the kind of cliffside vistas and sparkling scenery Instagram dreams are made of. This is one of those scenic routes you'll definitely never forget.

Search for places to stay in Big Sur on Vrbo.

        • START OR STOP IN BIG SUR

        • Big Sur is big-time chill. Whether you choose to ease into your drive with this peaceful perch on the Pacific as your starting line or decide wind down here for your big finish, you have to see these ‘grammable shoreline vistas for yourself.

Search for places to stay in Monterey County on Vrbo.

          • DETOUR: Monterey County

        • Monterey County is another scenic stunner and an iconic destination for anyone exploring this part of the country. Pacific Ocean views like these are a must-see, so be sure to make a pit stop here as you crawl up or down California’s magnificent coast.

Search for places to stay in Cannon Beach on Vrbo.

      • DETOUR: Cannon Beach, OR

    • Get your “Goonies” shot! Don't miss the chance to take photos of this crazy-cinematic beach setting with the same stunning arched rock formations, like Haystack Rock, you’ve seen in movies your whole life. Oregon’s epic coast also offers other amazing views – from wildlife to lighthouses, and more.

Search for places to stay in Seattle on Vrbo.

stop or start in SEATTLE

Emerald City, here you come! (Or go!) The food, fun, sights, and sounds of Washington State’s leafy urban wonder are enough on their own to make any stay here a dream. But you can also cruise onto one of many ferries bound for other gorgeous spots, like Bainbridge Island, or stay in your car to cross Deception Pass into Whidbey Island, or even hop a seaplane to Orcas Island for a more remote retreat to top off your adventure.

        • accessories for adventures and luggage to safely pack your camera gear:

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CALPAK PACKING CUBES IN HAZEL
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THE SUPER-SCENIC SOUTHERN MOUNTAIN RANGE

Short Haul: How about a quick getaway from the ATL for a little fresh mountain air and some insanely beautiful scenery? Just jump in the car and head for North Carolina’s coolest city. Asheville has everything...even pleasant temps throughout the summer months. And the kicker is that you’re literally at the gateway to the epic Blue Ridge Parkway if you want to extend your road trip through some one of the country’s most gorgeous mountain ranges.

Search for places to stay in Atlanta on Vrbo.

          • START OR STOP IN ATLANTA, GA

        • Kick off this easy escape (or wind it down) in Georgia’s peachy capital city. This is your chance to experience some of the South’s best art, music, cocktails, food, and history before or after you hit the road.

Search for places to stay in Asheville on Vrbo.

            • START OR STOP IN ASHEVILLE

        • Think booming art scene, food scene, craft beer scene, live music scene, and, of course, mountain landscape scenes ... there’s so much to love about super-chill Asheville. It’s your go-to spot for laidback fun either leg of your trip. It’s also a great gateway to the Blue Ridge Mountains if you want to explore that epic range even more.

        • PACK FOR COZY SWEATER WEATHER:

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CALPAK MEN'S RELAXED FRENCH TERRY SWEATSHIRT IN ONYX
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THE Atlantic seaboard

Long Haul: Whether you’re bound for the bustling isle of Manhattan or the sandy shores of South Beach, this Atlantic Coast adventure is best approached one way: a scenic crawl up or down its historic shoreline between Miami and New York City.

Search for places to stay in Miami on Vrbo.

          • Start or STOP IN MIAMI, FL

        • What a way to begin or end your road trip! South Florida’s wildly vibrant cultural hub is a thrilling place to commence any celebration of any kind. Period. It’s also the perfect place to revel in your adventure after you’ve crossed the finish line.

Search for places to stay in Charleston on Vrbo.

            • DETOUR: Charleston, SC

        • Hard exit ahead! See for yourself why everyone’s crazy for this Southern charmer. South Carolina’s picturesque coastal city has been rated one of the U.S.’s top travel spots for several years running for good reason. There’s amazing food, art, music, history, and even perfect beaches for lounging when you need to recover from it all.

Search for places to stay in Outer Banks on Vrbo.

                • DETOUR: Outer Banks, NC

        • Making time to explore North Carolina’s rugged seashores is a major must. These banks are packed with fun activities – from hang gliding to simply beaching it – and are part of the state’s fragile outer coastline barrier most impacted by erosion and the elements. Be sure to see them while you can.

Search for places to stay in New York on Vrbo.

            • START OR STOP IN New York City, NY

        • What’s better than hitting the streets of NYC to rev up for, or cool down from, your East Coast auto adventure? Now’s the time to cover all the boroughs from top to bottom – by car or by bike. And there’s always the joy of ambling through its eclectic neighborhoods or sauntering over to Central Park for a picnic on a gorgeous day.

        • PROTECT YOUR BELONGINGS AND STAY ORGANIZED:

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CALPAK CLEAR LUGGAGE COVER
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Explore your own backyard

Short Haul: Your next vacay could be an easy drive away! After all, getting away from it all doesn’t necessarily require going far. Just pack up your car (travel light!), and hit the road to explore your own neck of the woods more. Visit Vrbo HERE for suggested stays in awesome destinations within driving distance.

        • BRING YOUR FAVORITE ROAD TRIP ESSENTIALS WITH YOU:

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