Roadside Attractions: Before your departure, head to the Hollywood area for Route 66 landmarks, such as the Griffith Observatory, the giant Chicken Boy statue, the TCL Chinese Theatre and, of course, the Hollywood sign.

Town: Consider a stop in Barstow, California, home of the former Harvey House Railroad Depot, originally built in 1885. Today, it’s the Route 66 Mother Road Museum, featuring a spread of old photos and artifacts. It’s the perfect way to kick off your adventure and learn more about the history you’re going to experience firsthand on this trip.

Eat & Drink: While in Barstow, you can snag some great Mexican food. Lola’s Kitchen, a hidden gem in a strip mall, has tasty green chili worth stopping for.  

Do: In Lake Havasu, visit the world-famous London Bridge. Yes, the London Bridge from the nursery rhyme resides today in Arizona. It was built in the 1830s in London and moved to Arizona in the ’60s. In addition to a wealth of Route 66 attractions, this surprising beachfront resort in the middle of this desert state boasts ample hiking, boating, biking, fishing, golfing, and special events in Lake Havasu — so much, in fact, that you may want to extend your trip and stay here for a few days.

Eat & Drink: Lake Havasu has a good selection of food, mostly casual. A brewery can provide a great glimpse into a community, so refuel at award-winning Barley Brothers Restaurant and Brewery. Wood-fired pizza and local brew with a view of London Bridge. You can’t go wrong.

Stay: It’s an Arizona rite of passage to go camping on the lake, although there are other lodging options, as well.

Breakfast: Fill up on a classic American-style breakfast at Peggy’s Sunrise Cafe before hitting the road.

Town: The small town of Seligman, Arizona calls itself a “birthplace” of Route 66. It feels like you’ve stepped back in time with the retro signs and classic cars.

Eat & Drink: When in Seligman, you must dine at Delgadillo’s Snow Cap (founded in the ’50s), with quirky menu items like Oink Burgers, “male” or “female” sundaes, and a “cheeseburger with cheese.”

Detour: For a slower but more historic drive, you can swap out I-40 for a diversion on Route 66 up to Valentine, Arizona, and see the historic Schoolhouse at Truxton Canyon Training School. Keep on Route 66 and it will dump you back on I-40 around Seligman. Although this historic detour only adds 17 miles, it will tack on an additional half-hour, without stops, and Route 66 has tolls.

Do: Witnessing the 10-mile-wide Grand Canyon is awe-inspiring, even life-changing. Explore it via hike, a mule ride, bike, or even raft down the Colorado River.

Eat & Drink: The best restaurant is hands down El Tovar, which is both exotic and Southwestern–it’s also a bit expensive. For another solid option that’s less pricey, check out the Grand Canyon Lodge Dining Room on the North Rim.

Stay: Stay at the beautiful El Tovar Hotel on the South Rim. Let’s be honest: You’re going to want to stay here for a few days. Not only for the Euro-style hunting lodge feel with canyon-view rooms, but also to fully experience this “grand” wonder.

Breakfast: Hit up Bright Angel Restaurant on the South Rim for an affordable breakfast before you head out for the day.

Town: Although this stretch of the drive is short and straightforward, a bonus site along the way is the 11-acre architectural treasure, the La Posada Historic District in Winslow, Arizona. Stroll through the grounds and pick up a souvenir.

Shops: La Posada’s Trading Post and Book Store is a great place to find Mimbres design replica pottery, Southwestern jewelry, and Native American crafts.

Eat & Drink: The La Posada Hotel houses a restaurant called the Turquoise Room, considered the finest restaurant in the region. It specializes in Southwestern cuisine.

Do: In the Holbrook area, take time to enjoy the fairy tale-esque Petrified Forest National Park and glimpse some fossils.

Eat & Drink: Locals love Sombreritos Mexican Food for unpretentious, authentic Mexican food.

Stay: Stop in the Wigwam Motel on the National Register of Historic Places. Instead of a typical room, guests stay in a concrete teepee.

Breakfast: Joe and Aggie’s Cafe is a local gem when in Holbrook. This family-style restaurant even has a mini-museum inside with old photos, news clippings, and other Route 66 mementos.

Town: If you want to immerse yourself in Native American culture and the Pueblo of Acoma, take a small detour (about 20 minutes) to Sky City, New Mexico. Start at the Sky City Cultural Center and Haak’u Museum and learn about the oldest continuously inhabited settlement in North America.

Eat & Drink: Taste authentic Acoma food at the Y’aak’a Cafe’ inside the cultural center. In addition to traditional fare, you can also find modern American food, all made by a member of the tribe.

Photo Opp: The Rio Puerco Bridge in Rio Puerco, New Mexico is west of Albuquerque on Route 66, after a scenic drive into the valley. You can walk across the bridge, which is on the National Register of Historic Places, and take photos of the old Highway 66 fading into the desert beyond.

Do: There’s so much to do in Albuquerque, but the ABQ Biopark is a true wonderland for animal lovers. Round out the day with a sunset ride on the Sandia Peak Aerial Tramway.

Eat & Drink: Campo at Los Poblanos is the definition of farm-to-table; it’s located on an organic farm in the Rio Grande River Valley.

Stay: Stay in the Hyatt Regency Tamaya Resort and Spa, if you want a luxurious break with Native American culture (it’s actually built on the Santa Ana Pueblo), or at the Hotel Parq Central for a unique and historical experience; the latter is a former infirmary transformed into an elegant hotel with a sultry rooftop bar.

Breakfast: Swing by the healthy and hip Grove Cafe and Market in Albuquerque for a fresh breakfast in a bright, enclosed patio.

Town: Glenrio is unincorporated and considered to be both in Texas and New Mexico at the same time. Here, you can see the Historic Route 66 roadbed in a well-preserved, mid-century ghost town of the American West.

Eat & Drink: Russell’s Truck and Travel Center is a convenience store, as well as an authentic Route 66 diner. It’s not fancy, but it’s the real deal.

Do: When in Amarillo, you have to take photos at the famous roadside attraction The Cadillac Ranch, where a row of Caddys curiously balance, noses down in the ground and tail fins up in the air.

Eat & Drink: Everything is bigger in Texas, right? Then order a 72-ounce steak at the Big Texan Steak Ranch.

Stay: If you attempt the 72-ounce steak challenge, you will be waddling back to your bed. Luckily, there’s a motel and “horse motel” (yes, for your horses) on site. The Big Texan Motel was built to look like an old Wild West town, complete with a Texas-shaped swimming pool.

Breakfast: Ye Olde Pancake Station is where the locals start their day. There’s more than pancakes; you can actually order green eggs and ham (the green here is green chili).

Town: Clinton, Oklahoma is located on Route 66. Stop here to tour (and take some great selfies at) the Oklahoma Route 66 Museum, and learn more about Oklahoma’s part in the historic road.

Eat & Drink: The Route66 Cafe at the Market not only pays homage to the Mother Road, but it also has drool-worthy, old-fashioned comfort food. Meatloaf. Catfish fry. Chicken fried steak. Homemade Frito pie. Just like Grandma used to make it.

Do: Feel like a cowboy at the National Cowboy and Western Heritage Museum, which boasts more than 28,000 Western and Native American art and artifacts.

Eat & Drink: Pops Soda Ranch is exactly the kind of mom-and-pop stop you want to eat at on a road trip like this. Just look for the massive, neon, glowing soda bottle as you cruise down 66.

Stay: The Route 66 road trip is all about time travel, and you can continue that at the Colcord Hotel, built in 1909 originally as a skyscraper office tower. Today, it’s a swanky luxury hotel.

Breakfast: The Colcord has five different restaurants on site. Aravalli is a European-style coffee shop with grab-and-go meals if you want to pack your lunch for the next leg of the trip.

Town: Tulsa, the second-largest city in Oklahoma, may be known for its art-deco architecture, but it’s also home to several Route 66 markers, such as the 11th Street Arkansas River Bridge and the charming, cottage-style Vickery Phillips 66 Station.

Eat & Drink: Get a fresh seafood lunch at Tulsa’s White River Fish Market and Restaurant. Yes, the best restaurant in this land-locked state is surprisingly from the sea.

Do: While it might be easy to drive right past this tiny town in Oklahoma, it really is a Route 66 mecca, with a ton of different related museums, classic Route 66 architecture, and nostalgic attractions. Visit multiple stretches of the original Route 66 that are only nine feet wide.

Eat & Drink: Waterway Cafe, overlooking Grand Lake, embodies Afton’s old-fashioned feeling with a soda fountain, ice cream bar, and crawfish boils.

Shops: Shop a pecan grove at Afton’s Miller Pecan Company. Bet you’ve never had blackstrap molasses or Scuppernog jelly before.

Stay: Stay in the Elvis Room with its shiny purple comforters at the Route 66 Motel; it’s far from fancy, but each room has a different, fun theme.

Breakfast: Green Country Cafe is a sweet, small-town restaurant with excellent pie, but classic breakfast won’t disappoint either. Order a slice of pie to go for a midday snack.

Town: Springfield, Missouri, has the Route 66 Visitor Center and the well-preserved Rock Fountain Court Historic District, a group of stone cabins facing the historic route that used to be public lodging.

Eat & Drink: Springfield has more than 1,000 restaurants to pick from, but one that stands out (for its quirkiness, not local significance) is the London Calling Pasty Company, where you can eat British food in a double-decker red bus converted into a restaurant.

Nature: The Springfield area has more than 100 parks and is known for its trails — a good excuse to get out and stretch your legs.

Do: Route 66 runs right through St. Louis, Missouri, where you can visit the historic landmark, the Chain of Rocks Bridge. While in the area, see a true natural wonder, the Meramec Caverns, “Missouri’s buried treasure.”

Eat & Drink: While St. Louis has a vast dining scene, from elegant to budget-friendly, a one-of-a-kind, relaxed option is Crown Candy Kitchen in downtown, which makes its own candy and is decorated in 1930s style.

Stay: Treat yourself to an elegant night at the four-star Fleur-de-Lys Mansion, a B&B in a 1913 home with a garden.

Breakfast: Gourmet breakfast is included in your stay, all made from scratch. Even the bread, baked daily from a sourdough starter.

Town: You visited Springfield, Missouri, so why not Springfield, Illinois? Check out the self-guided Living Legends Tour, where you can learn about (and maybe meet) Route 66 via Springfield’s local entrepreneurs.

Eat & Drink: Have a hot dog on a stick for lunch at the Cozy Dog Drive In, opened in 1949 on Route 66. The current casual eatery is located next door to the original site, a historic landmark.

Do: Visitors love to see Chicago from above in the famous 110-story Willis Tower (formerly the Sears Tower) — and test their courage by stepping out onto the Skydeck, a glass deck 103 stories above the city.

Eat & Drink: Head to Pizzeria Uno, where Chicago-style deep-dish pizza was founded in the ’40s.

Stay: The Hotel Intercontinental Magnificent Mile blends elegance with history; the 1920s building used to be an athletic club and its indoor pool is a work of art, with Spanish hand-painted tiles, stained-glass windows, pillars, and fountain. Or for a slower option outside of the big city, book a night at the Route 66 Hotel and Conference Center back in Springfield.

Breakfast: Swing by Manny’s Coffee Shop and Deli for some innovative breakfast dishes, from a Breakfast Reuben sandwich to fried matzo scrambled and served with corned beef to French toast piled high with meats.

Town: Iowa City is a good half-way point. If you want to stop and see the sites, a fave is the Coralville Lake and Devonian Fossil Gorge, where you can see 375-million-year-old fossils on the former ocean floor. You can stop and camp here if you want to break up the drive.

Eat & Drink: Do brunch on the rooftop with views of the city at Vue, on the 12th floor of the Hilton Garden Inn Iowa City.

Do: The capital of Iowa is small enough to be stress-free but big enough to offer quality museums, like the Des Moines Art Center, as well as parks (a highlight: the Gray’s Lake Park), a zoo, and charming historic districts.

Eat & Drink: If you’re still craving nostalgia, you’ll love the ’50s-style Drake Diner. Breakfast for dinner, anyone?

Stay: Find lodging with personality (and a rose garden, pool, pond, and trails) at the Butler House B&B across from the Des Moines Art Center and Greenwood Park. Note: This former bed-and-breakfast is an AirBNB today.

Breakfast: Mullet’s serves fun breakfast with a multi-level patio and sweet views. Try the Wake N’ Bake Pizza.

Town: Check another capital city off your list in Lincoln, Nebraska. Get fresh air in the Sunken Gardens (built in the 1930s) as you stroll past ponds and sculptures.

Eat & Drink: Find the best burgers in town at Honest Abe’s Burgers & Freedom (there are four different locations). We’re always surprised by the Burger of the Week, like an Asian-style burger piled with chow mein noodles and cabbage.

Do: Get outside in Grand Island and visit the butterfly garden, or hike around the Crane Trust Nature and Visitor Center. If the timing is right (late February to early April), this is the best place in the world to see sandhill cranes. More than 80 percent of the world’s population migrates to the Platte River.

Eat & Drink: Get a taste of Grand Island at the Kinkaider Brewing Company. Wash down some hand-crafted Nebraskan beer with a Kinkaider Cheese Flatbread or a juicy steak in a stunning, century-old former theater.

Stay: Go camping at Mormon Island State Recreation Area, where you can enjoy fishing, swimming, a river, and some open space.

Breakfast: Family-run Tommy’s Restaurant is a local institution for traditional breakfast, including killer steak and eggs.

Town: Tiny Julesburg, Colorado lies right at the border after leaving Nebraska, but don’t be fooled by the town’s size. Julesburg, an ex-Pony Express stop, used to be called “the wickedest city in the West” and “sin city” for its proliferation of gamblers, con artists, saloons, horse thieves, and wild dance halls.

Eat & Drink: The food selection is limited, but a local hot spot is D&J Cafe, with quick and inexpensive American food, like a BLT sandwich and fries.

Do: After that long drive, you may enjoy staying a few days in Denver, if time allows. Walk around the 16th Street Mall or the Golden Triangle Art District. For a mini-vacation, make Union Station your home base, a gorgeous 1914 train station renovated to now house 10 restaurants and bars, shops, and even a hotel.

Eat & Drink: The sexy and modern Stoic & Genuine, located inside Union Station, specializes in fresh and creative seafood and oysters from both coasts — a benefit of Colorado’s location in between the two.

Stay: Complete your Union Station vacation by staying at the luxurious Crawford Hotel, where rooms creatively reflect different eras, from Victorian-modern to Art Deco-Pullman-style.

Breakfast: Order breakfast delivered from one of Colorado’s favorite breakfast spots, Snooze. Banana pancakes in bed are the only way to start the day in Denver.

Town: Stop at any of the ski towns along the way, from Vail to Aspen, or pick Glenwood Springs, Colorado, for a halfway break. Stay and play in Glenwood’s famous mineral hot springs, if you can.

Nature: Glenwood Springs boasts the world’s biggest hot springs pool, fed by naturally healing water that’s considered sacred by Native Americans.

Eat & Drink: For chef-driven steak and fish with a view of the Roaring Fork River, choose one of Glenwood’s finest establishments, Rivers Restaurant, for lunch or dinner.

Do: Outdoor wonders like Moab, Utah make the Route 66 loop its own worthwhile adventure. Explore the surreal red rock Arches National Park, named for its thousands of sandstone arches; you may want to stay here for a few days.

Eat & Drink: Desert Bistro is the place for a gourmet Southwestern dinner in Moab. You’ll find it, along with an impressive menu spanning gorgonzola-crusted beef tenderloin to a vegan quinoa pesto dish, in a small adobe house off Main Street.

Stay: Stay at the Sorrel River Ranch and Spa, a 240-acre luxury ranch on the river with custom-built cabins.

Breakfast: Although Sorrel River serves farm-to-table fare, a local love with tons of vintage character is the Moab Diner, with breakfast all day and an old-fashioned ice cream bar.

Town: Pause in Cedar City, Utah, home of the Utah Shakespeare Festival, plus nearby ski resorts, national parks, and a national forest.

Eat & Drink: Try a wood-fired, thin-crust pizza or old-world-style meatballs at hip and popular Centro, or get an arugula salad for a lighter lunch.

Do: You know Vegas for its debauchery, but this deep into a long road trip and you may want to explore the healthier side of Vegas. Book a treatment at one of the Strip’s 45 different spas, including many that are highly acclaimed.

Eat & Drink: You’ll love Harvest by Roy Ellamar at the Bellagio Hotel and Casino, a restaurant so fresh that herbs grow on the tables and walls throughout. Local and sustainable ingredients come together for a tasty, sophisticated dinner.

Stay: Treat yourself with a Stay Well room in one of the MGM Resorts. These health-centric rooms have air purifiers, aromatherapy with essential oils, white room lighting, a dawn simulator alarm clock, long-wave night lighting, vitamin C-infused showers, and more.

Breakfast: Veranda at the Four Seasons Hotel Las Vegas offers the best, healthy brunch, with revolving options that may include the likes of mango pineapple chia in coconut milk and breakfast salmon salad.

Town: Return to Barstow. This time, visit the oldest meteorite in the country and the famous Bottletree Ranch, an odd collection of metal trees and old glass bottles.

Eat & Drink: This one’s a chain, but a bucket-list item for many taco lovers. Barstow is home to the world’s oldest remaining Del Taco, dating back to 1964.

Nature: As you draw closer to LA, a quintessential Route 66 landmark is the Mormon Rocks, massive rocks right off the freeway. See them up close via a short trail starting at the Mormon Rocks Fire Station.

Do: Wrap up your Route 66 road trip by spending a day exploring the many historic sites in Los Angeles, including the Broadway Theater District and the Million Dollar Theater.

Eat & Drink: Finalize this history buff’s journey where the French dip sandwich is said to have been invented, at Philippe the Original.

Stay: End on a high note at the upscale and unique Calamigos Guest Ranch and Beach Club, outside of the busy city on 200 acres in the Santa Monica Mountains.