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Spend the night nestled under the Golden Gate Bridge in the most dignified of accommodations: the former living quarters of high-ranking officers in the U.S. Army. Cavallo Point is the result of the luxurious reimagining of a cluster of military lodges located within the Golden Gate National Recreation Area, just over the bridge in Marin County. Today, the 142-room hotel serves as a retreat for in-the-know travelers and locals looking for an easy, elevated escape from everyday city life. Original brick fireplaces and beamed ceilings mingle with modern finishes and furnishings, such as butter-soft leather sofas and whitewashed Adirondack chairs. The expansive grounds are meant to be explored on foot or bicycle. The Wellness Weekend package includes all meals, prepared with an emphasis on health at Murray Circle restaurant, morning yoga classes, guided hikes, a spa treatment, nightly wine receptions, and plenty of free moments to soak in the serene meditation pool—the very best kind of boot camp.

If anything’s endemic to Orange County it’s surfing—there are 40 miles of coastline here, after all. It’s not hard to find passionate practitioners of the sport, but doing is one thing and teaching is very much another. For newbies or even intermediate surfers looking to get back on a board, La Vida Laguna’s approachable, confidence-boosting instructors are the surest way to success. In private and semi-private lessons, their goal is to ensure that their surf pupils—starting from age eight—stand up on a wave, of course, but they also want to create more ocean advocates in the process. Wave safety and selection plus etiquette training are part of the lessons, along with pop-up drills, positioning, and gentle pushes at Thalia Beach, which has consistently calm waves for beginners. Guides also lead stand-up paddleboard lessons, hikes, and kayak adventures (expect frequent sea life sightings), tailoring and combining experiences upon request. Appointments are necessary and can be made on the phone, online, or at the company’s historic Craftsman bungalow in downtown Laguna. Local tip: For fewer surfers in the water, book a couple lessons on weekdays during the winter season.

It’s one of the hardest reservations to score in the country, but not just because of its diminutive size (22 seats in all) or limited days of operation (Wednesday to Saturday; dinner only). For one, the Catbird Seat feels both intimate and exclusive: Guests are seated at a U-shaped counter that surrounds a central open kitchen. Then, there’s the thrill of the unknown.

Strategic Hospitality, the Nashville-based restaurant group started by homegrown entrepreneurs Ben and Max Goldberg, has hired a roster of notable chefs for extended stints, giving them carte blanche to create whatever inspires them during their tenure. Among them: Trevor Moran, an alumnus of Noma in Copenhagen. Since January 2016, Chicago-born chef Ryan Poli (another Noma vet, who also trained at the French Laundry) has held the reins, calling upon influences from his two-year stint working in kitchens around the world. A couple of recent hits: an umami-rich black truffle risotto made with sunflower seeds instead of rice, and noodles made with nori and spiked with zesty yuzu.

Though Barcelona is hardly the epicenter of paella (that would be to the south, in Valencia), this hands-on culinary workshop/dining experience offers a fine introduction to what’s arguably Spain’s most famous dish. Set in an appealingly hip Raval-area space featuring soaring ceilings, exposed brick walls, and industrial lighting, the class starts with a welcome glass of cava along with a brief overview of paella from founder Alex Betolaz and chef Alex Villar. Don an apron at your cooking station, but don’t expect anything too labor-intensive; ingredients are, for the most part, already prepared, though you will do a bit of chopping, pouring, and stirring. (You can book your paella preferences ahead of time, and vegetarian options are available.) Then you’ll gather around a long wood table and sample various Catalan specialties along with your paella (and there’s usually plenty of sharing going on). Choose from three different paella-making experiences, starting at €50/per person for two courses and going up to €85 for multiple courses plus unlimited wine.

The longest developed rail-trail in the country, Katy Trail State Park snakes across Missouri for 240 miles, from the western edge of the state to the St. Louis metro area. Built on the former corridor of the Missouri-Kansas-Texas Railroad, the well-maintained park closely follows the Missouri River, offering bikers, hikers, equestrians, and everyone in between a scenic way to see much of the state. The section between Cooper and St. Charles counties is an officially designated segment of the Lewis and Clark National Historic Trail, adding an educational aspect to any exploration. Most choose to bike a portion of the trail, though hiking, running, and horseback riding are also great ways to experience the park, all the while surrounded by forests, wetlands, prairies, and abundant wildlife. A favorite stop along the way is the charming town of Rocheport, where you can make a pit stop at the bluff-top Le Bourgeois Winery for fine wine and views of the Missouri River Valley.

What do you get when you mix a little Don Draper, a bit of Andy Warhol, a smidge of The Jetsons, and a touch of PeeWee’s Playhouse? The vision of two local architects, the cheerful Vintage Design Hotel Sax is a paean to post-war optimism in the Malá Strana neighborhood, where each of the 23 affordable accommodations are individually decorated with restored vintage furniture and artwork, colorful geometric wallpapers, and retro pieces. Rooms aren’t particularly spacious but are comfortable nonetheless and include amenities like smart TVs, free WiFi, and air conditioning. There isn’t an on-site restaurant, but the lobby bar sells salads and sandwiches throughout the day, and a space off the lobby stocks free coffee and tea, as well as wines and soft drinks for purchase. The complimentary breakfast, however, is served buffet style (you can pay to order à la carte items) and can be enjoyed from the hotel’s fourth-floor terrace overlooking Prague Castle and the Petřín Lookout Tower.

Caesarea, the city and harbor that Herod built, is now preserved as a national park. A walk along its pathways allows visitors to experience the city’s role as part of ancient Rome and its days during the Crusades in the Byzantine era. Check out a concert at the partially restored amphitheater, or dive in Caesarea’s sunken harbor and underwater archaelogical park. Ancient ruins, including the remains of Herod’s palace, sit along the coastline. A state-of-the-art visitor center offers a historical perspective, complete with famous figures presented as hologram tour guides: King Herod, Rabbi Akiva, the Apostle Paul, and Hannah Senesh. Right outside the park’s boundaries, find a modern city with restaurants, cafés, and some eclectic galleries selling wine, cheese, olive oil, and jewelry—plus a lovely stretch of Mediterranean beach.

Inspired by the famous Fox Theatre—the Moorish-style movie palace turned performance venue is just across the street—Hotel Indigo Atlanta Midtown strikes a musical note at every turn. The experience begins at reception, where the desk resembles a drum set and a collage of show tickets from the past 30 years decorates the wall behind it. Guest rooms riff on the theme with accent wall murals that make it look like you’re either attending a concert or starring on stage, but the overall vibe is playful comfort, with pops of green on the quilts, spa-like baths with Aveda products, flat-screen TVs, and free WiFi. If you find yourself hankering for soul food, the chicken and waffles at the on-site restaurant should do the trick, but don’t pass up a drink at the black-and-white bar counter, which looks like the keys of a piano and is backed by a wine display that evokes the inner workings of a jukebox.

Only a block from the waterfront, the Alexis Hotel is actually a complex of three buildings, all with a place on the National Registry of Historic Places. The oldest part of the hotel was built in 1901, the newest in 1908. Beautifully renovated and restored in 2007, the Alexis (part of the Kimpton Hotels brand) maintains much of its historic character with features like wood-burning fireplaces and exposed brick. Because the hotel is comprised of three different buildings, none of the rooms are the same and the features vary. Some rooms have balconies, some face the courtyard, and the fireplaces aren’t limited to the best-of-the-house suites. The rococo-meets-modern design scheme, a rotating art collection (to complement current showings at the nearby Seattle Art Museum), nightly wine reception (5–6 p.m.), and pet-friendly policy all add to the relaxed, residential atmosphere. And because the hotel is small and full of character, it’s a favorite for destination weddings.

About a two-and-a-half hour drive from Santiago (or 30 minutes by helicopter), Puma Lodge is located in the Andean foothills near the Argentine border. The lodge is part of the Chilean-owned Noi hotel group, which also has properties in Patagonia, Atacama, Santiago, and more. Opened in 2011, Puma Lodge has a ski chalet feel, with wooden interiors and a large fireplace in the middle of the bar and lounge area. The 24 rooms are all the same category, and the design is simple and comfortable with touches such as colorful throws and local artwork.

Many guests choose Puma Lodge for the heli-skiing, but there’s plenty on offer year-round and for the less intrepid traveler. Activities include hiking, horseback riding, or heading out for a picnic lunch by the river. There’s also an on-site spa, yoga studio, and wine cave. Outdoor hot tubs are great after skiing, and a swimming pool is a draw in the summer months.

Driving along the countryside in northern Portugal near Oporto I saw the spectacular hillside vines of the famous Douro Valley spread out in front of me for miles. The sight was breathtaking. I saw the steep hillsides with the vines on the terraces. The vines were loaded with grapes that in a couple of weeks would be ready for harvest. The vineyards were first established in the 12th century by Cistercian monks. There are numerous Cistercian monasteries in the area. UNESCO declared the Douro Valley a World Heritage Site in 2001. The Douro Valley produces the grapes for port, red, and white wines. Douro tours are available and run from a few hours to a few days. The cruises run from April to October. If you want to see the harvest picking of the grapes plan your tour for September. A drive through the Douro Valley or a cruise down the Douro River is an experience to savor. If you get to northern Portugal, look into a side trip to the Douro. You won’t be disappointed.

The Mayflower Inn & Spa in tony Washington, Connecticut, is the perfect place to spend a weekend if money is no object. Located in the heart of idyllic Litchfield County, the Maflower Inn & Spa is just a two-hour drive from Manhattan, but you’ll feel a world away from the hustle and bustle of the city as soon as you pull up to this rural gem. The owners decorated each of the inn’s 30 rooms differently - there’s nothing cookie cutter about this place - offering a unique experience every time you visit. And don’t forget dinner at the inn’s five-star restaurant, with a menu and wine list that rivals the best you’ll find anywhere. Complete your stay with a massage or facial at the inn’s magnificent spa for the ultimate luxury weekend. It’s not inexpensive, but if you want the height of luxury in the heart of bucolic Litchfield County, the Mayflower Inn & Spa is the place to stay.

Tucked on the corner of Hopkins Avenue and Monarch Street, White House Tavern occupies one of Aspen’s oldest buildings, a small Carpenter Gothic–style white house that was built in 1883. The offerings here don’t change from when the restaurant opens for lunch at 11 a.m. to when the sky darkens and the cocktails start flowing into the night. The menu is made up mostly of hearty salads (Thai steak and noodle, kale with rotisserie chicken) and tasty sandwiches, including an incredibly crispy chicken sandwich and a flavorful, perfectly cooked prime rib au jus piled high on a homemade roll. The cocktail list is short and tends toward the classics—negroni, margarita, martini—but the wine list is surprisingly ambitious.

A cooking school by day (Wednesdays and Sundays, to be specific), Black Sesame Kitchen hosts a 10-course family-style meal on Tuesday and Friday nights that allows visitors to sample Chinese dishes from a variety of regional cuisines. Most who arrive at Black Sesame Kitchen are strangers before the meal—but it isn’t uncommon to make friends over good food and generous pours of wine. ¥300 per person; advance bookings only.

For panoramic views of the entire city—for the price of a subway ride—take the Roosevelt Island Tram. As the suspended car runs parallel to the bridge, spanning the gap between Manhattan and Roosevelt Island, you’ll have unparalleled vistas of the New York syline and the East River below. There are few experiences as memorable or accessible, so be sure to ride the tram there and back—it’s particularly dramatic in the morning and evening.