Iconic Road Trips

Windows rolled down, breeze blowing in, music turned all the way up—there’s nothing like hitting the open road. This summer and fall, exploring via one’s own four wheels is especially smart. Make a playlist, pack your camera and plot a course along a scenic route within range. These are our picks for the best road trips to take in the U.S., Canada and Europe with, naturally, all the most sumptuous places to stay along the way. Make as many or as few stops as needed—the journey is the destination.

PACIFIC COAST HIGHWAY

Following along much of the California coastline, the full Pacific Coast Highway road trip clocks in at just under 700 miles running between San Francisco and San Diego. Kick off the journey in a room with a view of the Golden Gate Bridge at The Lodge at the Presidio. Hop on Highway 1 and head to Monterey, made more famous by Big Little Lies, and visit Fisherman’s Wharf, then explore Carmel-By-The-Sea. When you’re ready to call it a day, head inland 20 minutes to Carmel Valley Ranch for a good night’s sleep (after a round of golf, if desired). The next day, get back on California 1 and onto to Big Sur, where there are plenty of pretty places to pull over and take in all the jaw-dropping nature and car-commercial-regular Bixby Bridge.

Pull into the Post Ranch Inn when it’s quitting time and watch the sunset from your room. Hit the road again for more scenic coastal stops, such as McWay Falls, before rolling into Santa Barbara and tucking in for the evening at Hotel Californian (hello, rooftop pool). Malibu is only 90-minutes away, so spend the day on one of the beaches, or better yet, in the waves, before retiring at the Malibu Beach Inn. You can end in L.A., or extend the trip with stops and stays at Pasea Hotel & Spa in Huntington Beach, The Ritz-Carlton in Laguna Beach and ending at The Lodge at Torrey Pines in La Jolla, where you’ll want to pull out those golf clubs once again.

ROUTE 66

Although decommissioned and replaced by Interstate 40, Route 66 is so iconic that following in its shadow remains one of the best USA road trips. Also known as the Mother Road, so named by John Steinbeck in The Grapes of Wrath, the Route 66 road trip spans over 2,000 miles through eight states from Chicago to Santa Monica. Start it off in Chicago with city and Lake Michigan views at Park Hyatt Chicago. Head south to Adams Street and look for the “Historic Route 66 Begin” sign before hopping on the I-55 to St. Louis to visit the Gateway Arch and Chain of Rocks Bridge crossing over the Mississippi River. Here, overnight at the Four Seasons Hotel. Next, travel onto Sullivan, Missouri to visit the Meramec Caves, before continuing on to Springfield.

From Springfield, do a little detour to Shell Knob for a night nestled in the Ozarks at Stonewater Cove Resort. In the morning, explore the route until you reach Oklahoma City for an overnight at Colcord Hotel. Then it’s off to Amarillo, Texas, where the accommodation is humbler, to see Cadillac Ranch, before heading into Albuquerque, New Mexico. Take a right onto the 285 to Santa Fe, the oldest continuously inhabited city in the U.S., for a night at The Inn of the Five Graces. It’s a picturesque drive through the Petrified Forest before arriving in Sedona, Arizona for some R ‘n R amongst the red rocks at Enchantment Resort. Next is Needles, California, dipping down through Chambless before staying a night in San Bernadino or pushing through to Santa Monica. Here, overlooking the pier, cheers reaching the end of the road at circa-1920s Hotel Casa del Mar.

NEW ENGLAND

Circling six states, a leisurely New England road trip connects history, mountains, the seaside and utterly charming towns. A good place to begin and end is Boston—here, spend a night at Fairmont Copley Plaza to prepare or unwind. From there, head south to Chatham. Park the car and kayak the Bass River or cycle Main Street, see the Chatham Lighthouse and get fresh fish at the Pier. Come nightfall, enjoy the comforts of Wequassett Resort and Golf Club in Pleasant Bay. Then ride on to Rhode Island where there’s the Flying Horse Carousel, the oldest one operating in the U.S., and miles of beaches. Keep the sea views going with a suite at 122-year-old Ocean House. Leave the oceanside for some time in the Berkshires. Here, in Lenox, Massachusetts, Blantyre was modeled after a Tudor-style Scottish home and so gives its guests the English countryside feeling without the trans-Atlantic flight.

From there, it’s only a 90-minute drive north to Manchester, Vermont where one can canoe on Emerald Lake and hike Mt. Equinox before retiring to The Equinox Golf Resort & Spa—they’ll also broker other kinds of outdoor adventures. Then it’s onto Stowe. Take the scenic Route 100 and stop for ice cream at Ben & Jerry’s factory in Waterbury before continuing on to Topnotch Resort. Loop through the White Mountain National Forest next for all its natural beauty before arriving at the Bedford Village Inn in Bedford, New Hampshire for the night. There’s one last state to grace and that’s Maine. It’s only 90-minutes to Kennebunkport where it’s only apropos to take a lobster boat tour. Staunch landlubbers can stroll in Rachel Carson Wildlife Refuge’s mile-long trail and take pictures. Spend the last night before heading home at the beautiful White Barn Inn.

BANFF TO WHISTLER

Driving any considerable length of the 7,821-kilometer Trans-Canada Highway between the Atlantic and the Pacific is a badge of honor. Arguably the most scenic portion is the roughly 900 kilometers through the Rocky Mountains from Banff to Vancouver, then tacking on a trip up to Whistler through the Coastal Mountains to make it a whole mountainous experience. Starting in Calgary, head to Banff and settle in at the Fairmont Banff Springs—there’s enough splendor right outside its doorstep to fill many days. From there, it’s one incredible backdrop after another as the route passes through Banff National Park, Yoho National Park, Glacier National Park of Canada and Mount Revelstoke National Park.

More than just a reprieve from the nine-hour drive to Vancouver, Sparkling Hill Resort just outside of Vernon is restorative, thanks to lake views and a 40,000-square-foot spa. Head north and get back on the Trans-Canada or go south and dip into some of the Okanagan’s more than 200 wineries, before heading to Vancouver. One of the most stunning places to stay in the City of Glass is the Fairmont Pacific Rim, overlooking the harbor and North Shore Mountains. When you’re ready, hop in your car and trade Highway 1 for the 99 Sea-to-Sky and all its scenic bends leading to Whistler where the journey ends at Nita Lake Lodge with a lakeside champagne toast to completing one of the best Canadian road trips.

WILD ATLANTIC WAY

Stretching from the Northern Headlands down to Haven Coast, the Wild Atlantic Way is a rugged, romantic, weaving coastal route in Ireland covering six distinct regions and 2,500 kilometers. Starting at the top of the isle, Donegal is its most remote parcel, home to both hearty northerners and scores of seabird colonies. There’s no roughing it though at Lough Eske Castle, with a Tesla charging station and all. Next up, Mayo straddles the Surf Coast and Bay Coast, where you can stroll Céide Fields, the largest Stone Age monument in the world, or head out into the waves at Keel Beach. When it’s time to come in, head to Ashford Castle, the oldest and grandest castle hotel in the country.

From there, head back to the coast through County Clare to see the Cliffs of Moher, Burren National Park, and the famous Aillwee and Doolin caves. Tuck in for the night at Dromoland Castle. Then it’s onto Kerry, home to Killarney National Park and its lakes. Nestle in at The Europe Hotel & Resort for the night, which looks onto the largest lake, Lough Leane. The coastal route culminates in County Cork. Drive to the most southwesterly point, Mizen Head before digging into the sands of Inchydoney Beach, and keep an eye out for whales off in the distance there. It’s a very short walk from the waterside to Inchydoney Island Lodge & Spa where the journey ends with a massage and a good night’s sleep.

PORTUGAL COAST

When the wish list of places to go in Portugal is long, the solution is to string them together in a Portugal Coast road trip. The only question is whether or not you want to end with all the wine or all the beaches. If dipping toes in the sand is top priority, start south in the Algarve. Return from a beach day at Falesia to Anantara Vilamoura Algarve Resort, where everything else one could possibly want awaits, including multiple pools and golf courses. From there, head north to Comporta and lap up the Portuguese countryside at the 17-acre Sublime Comporta. Keep venturing north and opt to stay in the capital at The Vintage Lisbon or Sintra at Tivoli Palacio de Seteais, depending on whether you fancy exploring the city more or a fairytale town of villas and palaces.

Either way, stop at the Sado Estuary Nature Reserve on the way—you might see dolphins—and tack on some time in Cascais to watch the waves surge through Boca do Inferno (Hell’s Mouth). It’s three hours to Porto, known as Portugal’s Venice and the place for Port wine. Here, stroll Cais da Ribeira or ride down the river in a traditional Ravelo boat, then check into The Yeatman. Don’t dip too far into the hotel’s 25,000-bottle wine cellar because there’s more where that came from if you plunge deeper—90-minutes inland to be exact—into the Douro Valley. Sample the fruits of local vintners’ labors, along with vineyard views, pool time and spa treatments at Six Senses Douro Valley.

MEDITERRANEAN COAST OF SPAIN

Nothing says summertime like a sun-fueled road trip along the Mediterranean Coast of Spain—you’ll probably want to rent a convertible for this one. Set off from Barcelona, but not before enjoying some of the sights and the big city views coupled with the zen atmosphere of Nobu Hotel Barcelona—it’ll set the chill tone for the rest of the ride. The next stop is Valencia, a wildly underrated city of culture, food and futuristic buildings. Here, soak up the seaside at Hotel Las Arenas before journeying through the Sierra Nevada mountains to Málaga and staying in style, just like Elizabeth Taylor once did, at the seaside Gran Hotel Miramar.

From there, plunge into the heart of Costa del Sol and enjoy a couple nights at Puente Romano Marbella. Continue on to Cadiz, home to over 100 watchtowers and Hotel V…, but not before visiting the Rock of Gibraltar. You can wrap up the road trip there or head inland to explore more of Andalusia. Stop in Seville to catch some flamenco and stay at Mercer Sevilla. Carry on to Córdoba to take in the grand Mezquita and overnight at Hospes Palacio del Bailio. Then complete the circle in Granada, visiting palaces, namely Alhambra, and staying in a converted one, Hospes Palacio de los Patos.

AMALFI COAST

Unfurling along Italy’s Amalfi Coast, Highway 163 or Blue Ribbon Road is 50 kilometers of approximately 1,000 hairpin twists and turns. Every curvy klick is worth it for all the staggering vistas the region serves up. Leaving out of Salerno, the first stop is Ravello where it’s up, up, up 350 meters to Palazzo Avino, a 12th-century pink palace offering those trademark villas-clinging-to-the-cliffside views. From there, wind back down to namesake town, Amalfi, and then up to NH Collection Grand Hotel Convento di Amalfi, a jaw-dropping 13th-century converted monastery. After taking in the cathedral, and dining on a terrace or two, drive onto Praiano, the quieter, quainter of the coastal towns. Post up at Casa Angelina, with all its views, and laze about under the lemon trees.

Showstopper Positano is next, where picturesque pastel buildings are stacked one on top of another. Perched here, Villa Franca provides a panorama of it all, particularly well from the extravagant rooftop pool. Then it’s onto Sorrento, considered the gateway to the Amalfi Coast—whether you start or end here, tuck in a couple of nights at Grand Hotel Excelsior Vittoria looking out onto the Bay of Naples to feel like one of the gods of the coast’s Greek myths. Those who fancy a few more nights of luxury and sea views can hop a boat over to J.K. Place Capri for a little island time.

For more, check out our Destination Guide to the Amalfi Coast.