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Last April, I spent a morning hiking along the San Pedro River, just NW of Bisbee, AZ; the caterpillars were astoundingly abundant. When I stopped, I could hear them munching on leaves all around--a surround-sound of crunching, the aural fecundity of spring. Between Sierra Vista and Bisbee, the high grassland highway slowly slopes down to this cottonwood-lined river--one of the few free-flowing rivers left in the Desert Southwest. This ribbon of forest stretches from the Mexican border up towards the lower-elevation desert, providing a flyway for migrating birds and even habitat for the occasional jaguar (very rare). In the late 1980’s, this area was made a National Conservation Area, and it’s a nice shady walk in what can often be sun-blasted country.

One of the iconic sights of the American Southwest, Taos Pueblo has been inhabited for at least a thousand years. The adobe architecture seems to spring, organic, from the earth at the foot of Taos Mountain. It’s a UNESCO World Heritage site, but a living community, not a museum. San Geronimo church, at the center of the pueblo, is a relative newcomer here--built in the mid-19th century to replace the Spanish mission that was destroyed in 1847, when U.S. troops bombarded it as part of a campaign to quell a rebellion. Its history has been turbulent, but the setting is beautiful, and Taos Pueblo welcomes respectful visitors today. Before exploring on your own, take the time to listen to one of its college-student docents on a brief guided walk. They’ll be telling you about their families...

Arriving to Getaria can be done by bus, but one of the most unforgettable parts of visiting this village is approaching (or exiting) it by the sidewalk that winds along the sea. Depending on the time of year, you will have endless views of a calm sea or rough waves that remind you of the power of nature and make you admire the Basque people’s hardiness. It’s about a 40-minute walk from Zarautz to Getaria, on a flat sidewalk. There’s even a bathroom halfway. No excuses.

The Sanctuary of the Madonna di San Luca has a commanding presence in the landscape overlooking Bologna. We arrived knowing that it was connected to town by a 2.5 mile portico some say can be seen from space. We dropped our bags at the hotel, grabbed some water and headed for the hills. No map, no directions. There are signs that guide you, eventually. Get a map. The streets and neighborhoods heading up to this massive, covered staircase are wonderful to get lost in, which we easily did. Finding the entrance, we began our pilgrimage to the church at the top of the stairs. There are 15 chapels celebrating the Mysteries of the Rosary, kind of like the stations of the cross for any of the Catholics in the audience. We hike/jogged up to the top, stopping along the way to enjoy the view and the artwork. The 18th century Sanctuary at the top provides spectacular views of the Emilia/Romagna countryside and of Bologna in the valley below. It was hot and sunny on our visit, but one of the locals told us it snows up on the hill during the winter. We had a quick decent, then out to happy hour where the specialty is the appertivo bar. For the cost of a glass of wine or cocktail, many of Bologna’s restaurants invite you to graze gratis at the traditional piccoli morsi trays laid out across the bar. It’s easy to make an evening out of nibbling on a variety of meats, cheeses, pastas, pizzetes and deserts at any number of stops. After a long, inspiring walk; my kind of tradition.

I’m not sure any other city epitomizes the California dream as well as the surf-centric college town of Santa Cruz. The Dream Inn is the perfect base for exploring and has affordable rooms, a retro-chic design, and a beachfront location within walking distance of the famous boardwalk. The hotel can arrange surf or SUP lessons (you’ll want to rent a wetsuit, even in the summer!). For those who’d rather take in the action from the shore, rent a bike from nearby Pacific Ave Cycles and peddle along West Cliff Drive until you reach the famous surf break, Steamer’s Lane. You’ll be able to watch talented surfers (and ambitious novices) surf some serious waves. A short drive away you’ll find Henry Cowell Redwoods State Park. From the parking lot, take the Meadow Trail to the Loop Trail to Pipeline Road. Follow the road along the river and turn left at the Ridge Fire Road and follow it to the Observation Deck. You’ll be rewarded with spectacular views of the Santa Cruz Mountains. For an even greater reward, grab a seat at the Dream Inn’s new Jack O’ Neill lounge and try one of the great cocktails (the Old Timer is a mix of Knob Creek, lavender sweet tea, and muddled fruit) and if you’re lucky, there might even be a live band.

Catch the train from Genova Brignole station to Santa Margherita Ligure (about a 30-minute ride, leaving every ~30 minutes) and walk down to the large dockside pedestrian area. You will see the bike rental station just a few steps away from the bus ticket kiosk. For ~5 euros, you can have a bike for the whole day—a perfect option for exploring the fantastic surroundings! While the roads are all paved, they are incredibly narrow, and cars tend to drive quickly. Just be aware and stay very close to the edge for your own safety. Portofino (a 15-minute ride) is a gorgeous town frequented by international tourists and stunning yachts in the summer months. Originally named for the schools of dolphins (Port’Delfino) that often pass this cove, the landscape around the village is breathtaking. If you come in the spring, you can ditch your bike to spend the day hiking the paths up to the perched fort and church, or simply enjoy a gelato while gazing at the quaint fishing boats in the marina.

Want hot chiles? mild peppers? powder? paste? Across from the old Spanish mission in Tumacácori, you’ll find it. For decades, family-owned and family-run Santa Cruz Chili & Spice Co. has been providing flavors in Southern Arizona. There’s even a mini Western Museum...and of course, you can sample the sauces and salsas... The Santa Cruz valley, between Tucson and Nogales, is one of the oldest continually-farmed regions in the U.S.; for four thousand years, native peppers, beans, squash, cactus and corn have been cultivated, even here in the desert. Then, beginning in the 17th century, Spaniards introduced Mediterranean plants: grapes, figs, pomegranates, figs, quince...and cattle ranching. A small garden on the grounds of the Tumacácori mission across the road from the Santa Cruz Chili Co. still grows some of these heirloom crops. A visit to the mission and spice market make for a great afternoon or day trip from Tucson. Go south from Tucson on I-19 for about an hour. (Note: I-19 is marked in kilometers, not miles; quirky.) Take Exit 29, turn left, then turn north on the old highway, and you’ll see the big chile-pepper sign on the left, just before you get to Tumacácori mission National Historical Park. The store is closed on Sundays.

This three-mile beach, located near Frederiksted at the southwest end of St. Croix, is the longest in the U.S. Virgin Islands. Part of the 380-acre Sandy Point Wildlife Preserve, the beach is an important nesting area for the endangered leatherback turtle. Beach access is via a dirt road, open Saturdays and Sundays. The beach may be closed during turtle-nesting season, from March to August, so check with your hotel before you make the trek.

Santa Monica is officially on the map with this spectacular property, the second hotel for the Proper brand after its debut in San Francisco in 2017. Like at the first location, celebrity interior designer Kelly Wearstler heads up interiors and has produced an absolute stunner, drawing inspiration from her own Malibu home as well as the hotel’s circa-1928 Spanish Colonial Revival building. (The property actually straddles two buildings; the other half is a sleek new construction, connected by a courtyard and sky bridge to the historic part.) The 271 pet-friendly rooms feature original Kelly Wearstler wallpaper, vintage lamps and tables, and custom-made sunburst headboards that remind you you’re near the beach. Guests can also look forward to roomy bathrooms, complete with travertine marble, full-size Aesop bath products, and super-soft Parachute for Kelly Wearstler robes.

Around 700 people live in the only permanent settlement in the Juan Fernández Archipelago, San Juan Bautista on Isla Robinson Crusoe. Although no longer as isolated as it was when Alexander Selkirk, the likely inspiration for Robinson Crusoe, was a castaway in the archipelago, the village is still remote. It can take up to two days to make the sea crossing from the Chilean mainland (but less than two hours by plane). While most of San Juan Bautista’s residents rely on catching crab, fish and lobsters for their incomes, tourism during the summer season is an increasingly important part of the local economy.

The former Colegio de San Ildefonso is a magnificent colonial structure set around several imposing, multistoried arcades with halls now decorated by some of Mexico’s most spectacular murals. Even better, it serves as one of the city’s most ambitious and engaging art museums, with an edgy, wide-ranging focus that never fails to surprise. Recent years’ exhibitions have featured avant-garde foreign artists like Vik Muniz and Ron Meuck; homegrown blockbusters like Javier Marín; Candida Höfer’s striking architectural photography; and Marilyn Manson’s macabre visual works. Try to get a peek into the Colegio’s old amphitheater, where one of Diego Rivera’s first major commissions looks better than ever.

Two of Manila’s most famous churches can be found in close proximity to each other within the historic walled city of Intramuros. The 16th-century San Agustin Church, a UNESCO World Heritage Site, is the oldest church in the Philippines and was the only building in Intramuros to survive heavy bombing in World War II. It boasts an impressive interior with trompe l’oeil effects, a Baroque pulpit and a majestic pipe organ, and the museum houses treasures of Old Manila. A few blocks away, the Manila Cathedral, restored many times since the original version was built 450 years ago, hosts religious artworks and sacred relics and was visited by Pope Francis in 2015.

Sanur is a beautiful and quaint part of Bali with hotels along the boardwalk that lines the beach. The boardwalk really makes Sanur special, as walking in Bali can be treacherous in most of the towns with narrow streets and tiny sidewalks, but this paved path in Sanur is great for biking and long walks along the beach. Walk to the south end of the boardwalk for a great view of the sunset and find a nice little cafe to have a Bintang (beer) or a Bali kopi (coffee).

This arsenal of apps will upgrade any road trip. Easily find hotels, restaurants, secret swimming holes, day spas, restrooms, and gas stations so you can fully enjoy the freedom of the open road.

Route 66 opened November 11, 1926, and as it celebrates its centennial in 2026, we’re helping travelers prepare for the ultimate road trip—on the ultimate highway. Here are the can’t-miss trips, stops, and stories to explore along the way.