Our Favorite Road Trip Destinations to Escape to this Summer

Every year, as Memorial Day rolls around, we become more and more in need of a vacation.

But not just any trip–the end of May means it's time to plan a summer vacation. And while we love city life, there’s nothing quite like trading skyscrapers and concrete for sand and sea.

As we pull together our summer itineraries, we're sharing a few of our must-visit getaway destinations from around the country. The best part? They’re within driving distance of some of our favorite cities!

From New York: Head to the Hamptons

Courtesy Sant Ambroeus


  • Duryea’s Lobster Deck: You’ve probably seen this spot pop up on your Insta feed nonstop. Whether you’re staying out in Montauk or want to venture out of East Hampton for the day, the seaside restaurant is not to be missed. WE LOVE: The Lobster Cobb salad paired with a sunset view.

  • Sant Ambroeus: With delicious options for lunch and dinner, you'll never regret stopping by Sant Ambroeus. The beloved Italian restaurant is a staple due to its mouth-watering dishes and al fresco dining. WE LOVE: People watching with a crisp glass of wine in hand–you'll have a front-row seat to Southampton’s Main Street.

  • The Golden Pear Cafe: It doesn't matter if you’re off to play tennis or have an afternoon of rosé ahead of you–all summer days should start at the Golden Pear. WE LOVE: The low-key cafe can be your first stop in the morning to pick up an iced coffee and a bagel.


  • Gurney’s Montauk Resort: The rustic seaside resort delivers luxury accommodations with easy beach access. WE LOVE: The resort has private bungalows by the sea that can be reserved in advance.

  • The Maidstone: The charming boutique hotel is set on a picturesque property. WE LOVE: The landscaping is unbelievable–all of your hydrangea dreams will come true.

  • Ruschmeyer’s: The cabin-style hotel offers complete privacy while serving up one of the best restaurants in Montauk. WE LOVE: They have a chic outdoor fire pit for late-night hangs.


  • Sweat it out with SoulCycle Outside: The infamous exercise class will continue outdoor classes in Summer 2021. WE LOVE: The convenience–there are 4 SoulCycle locations between Water Mill and Montauk.

  • Hit the beach: Head to one of the many world-renowned beaches on the Long Island coast. WE LOVE: Don’t miss Ditch Plains in Montauk, one of the most beautiful beaches to visit and a renowned surf spot.

  • Take in the sunset with drinks at Surf Lodge: There are plenty of places in the Hamptons to score a bottle of rosé with your friends, but none are quite in the lexicon like this beachside hot spot in Montauk. WE LOVE: Come for the Insta-worthy vibes, stay for the trendy crowd.

  • Find your zen with a yoga session: Yoga instructor and Hamptons native Hedges Rauscher offers private sessions at your home. Or, stop in for a yoga class at the acclaimed Topping Rose House. WE LOVE: A 60-minute vinyasa class at Topping Rose House’s new pool-side facility.

From Los Angeles: Head to Monterey, California

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  • Café Kevah: Trust us, you’ll go for the view but stay for the food. The casual eatery is located right along the Pacific Coast Highway and serves up California cuisine atop a sky-high terrace. WE LOVE: The sunsets here are next level, so plan your visit accordingly.

  • The Glass House: If you’re looking to commemorate your trip with a truly unique experience, look no further than The Glass House at the Ventana Resort in Big Sur. WE LOVE: The impeccable ocean-front vantage point paired with the restaurant’s famous prix-fixe menu will surely deliver.

  • Seventh & Dolores Steakhouse: This steakhouse in Carmel will tick all of your culinary boxes. The restaurant combines the best of fresh California ingredients with traditional steakhouse menu items for a meal the whole group will remember. WE LOVE: Carmel is in a super charming town, so make time to explore before your meal.


  • Ventana Big Sur: Situated at the top of the mountains in Big Sur, this luxury hotel is adults-only. You'll instantly feel miles away from the city, kids, work–all of the above. WE LOVE: Their luxurious “glamping” accommodations are a once-in-a-lifetime experience.

  • Post Ranch Inn: From ocean-view hot tubs to woodland tree houses (!), there’s no better place to snap that vacation photo than at this luxury hotel. WE LOVE: Between the Yoga Yurt and the Meditation Pool, this is where you’ll find your zen.

  • L’Auberge Carmel: This grand hotel is set in the heart of the quaint seaside town, Carmel-by-the-Sea. WE LOVE: They have a Michelin-starred restaurant and an impressive wine cellar with over 2,500 bottles.


  • Take in the beauty of the Pacific Coast Highway: From Bixby bridge to the Lone Cypress lookout point, the best part of venturing to Monterey County is the drive itself. WE LOVE: Roll the windows down and prepare to pull over often for some incredible vistas.

  • Visit Pfeiffer beach: You’ll find dramatic coves and stunning beaches throughout Monterey, but no spot is quite like Pfeiffer beach. WE LOVE: Be sure to visit the famous Keyhole Arch at sunset.

  • Play a round at the Pebble Beach Golf Club: If you’re traveling with a golf enthusiast, they’ve probably already visualized their drive from the back nine. WE LOVE: The golf course at Pebble Beach is one of the best in the world, but also completely worth the hype–even if you’re just along for the golf cart ride.

From Chicago: Head to Harbor Country, Michigan

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  • Stray Dog Bar and Grill: This waterfront restaurant is known for its sun-soaked terrace and signature cocktails. WE LOVE: Stop by for a sunset drink under the stars and take in the incredible view.

  • Viola Cafe: Whether you're in the mood for a muffin or want to try their signature Afternoon Tea, this local bakery is too sweet to miss. WE LOVE: Their wide-ranging menu has everything from biscuits & gravy to Swedish pancakes–AKA something for everyone.

  • Terrace Room: The upscale bistro is dedicated to local food sourcing and sustainable farming practices. WE LOVE: This is a must-visit for farm-to-table dining obsessives.


  • Rent a house: From lakeside beach houses to charming cottages and sprawling estates, make the most of your shore vacation by renting an entire house for your group. WE LOVE: There’s a rental for every preference available–but lake houses are in high demand during the summer, so make sure you plan in advance.

  • The Brewery Lodge & Supper Club: Nestled onto a woodland estate and only a 15-minute drive from the shore, this rustic boutique hotel is cozy and romantic. WE LOVE: This spot has it all: a craft beer and wine bar, plus 40 acres of wooded land that guests can explore.

  • The Journeyman: These luxe accommodation options include a 7,000 square foot flat, a farmhouse, and a smaller bunkhouse. WE LOVE: They’re affiliated with the well-known Journeyman Whiskey Distillery, so make sure you schedule a distillery tour and tasting during your stay.


  • Enjoy a glass of wine at Round Barn Estate: Spend a day taking in one of the area’s most popular vineyards. WE LOVE: The family-owned business features wine and craft beer tastings as well as live music.

  • Get on the water with Oselka Marina: After all, the best part of being at the lake is being on the lake, and this marina is the perfect place to make it happen. WE LOVE: Sail off on a sunset cruise or rent a pair of jet skis for a few hours.

  • Take a stroll at the Warren Dunes State Park: The white sand dunes and ocean views make this one of the most popular parks in Michigan. WE LOVE: It has nearly six miles of scenic hiking trails–you’ll want to explore every route.

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