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A buzz surrounds the Smyth, located smack in the heart of TriBeCa, with its recent reinvention: Chef Andrew Carmellini has revitalized the restaurant space, making it a destination for diners from across the city, and a redesign from Gachot Studios has brought a fresh feel to the decor. The new residential-feeling lobby is meant to be your TriBeCa living room, with all the neighborhood’s shopping, galleries, spas, Michelin-rated restaurants, and attractions right on the doorstep. One of downtown’s most poignant landmarks, the 9/11 Memorial, is a few short blocks away. Mirroring the neighborhood’s style, this hotel is understated and chic. Grab a stool next to TriBeCa’s designers, filmmakers, and photographers for a cocktail at the Evening Bar.

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.

Bermuda waited 45 years for a new-build hotel, but the Loren has proved worth it. Situated on eight acres fronting the turquoise sea near the center of the archipelago, the architecturally sleek luxury property eschews standard tropical patterns and pastel palettes in favor of warm modernism, with world-class art, floor-to-ceiling windows, and a sculptural glass staircase off the lobby. Each suite provides a plush landing thanks to marble baths with freestanding tubs and private terraces with ocean views, plus sumptuous Sferra towels and bath products by Malin + Goetz. For those who don’t want to drive the 20 minutes to Hamilton, the elegant seasonal cuisine at Marée (Bermudan baby greens with goat cheese croquettes and wild strawberries, local snapper with fava bean puree) exceeds expectations, and the botanical-infused treatments at the beachside spa will make the real world seem like a distant memory.

This abacus-inspired device tracks how many beers you take from the honor bar located next to the rooftop jacuzzi at Casa Tota (www.hotelcasatota.com). Located in the heart of Todos Santos, this new hotel is outrageously affordable (rooms start at around $85) and its restaurant serves a dangerously good margarita. Margaritas are on the house if you can out arm wrestle Casa Tota’s buff waiter, Raul.

One of the great pleasures of traveling in Mexico is visiting traditional local markets, which sell everything from produce and household goods to handcrafts and textiles. In San Jose del Cabo, the local artisans’ market, or Plaza Artesanos, is open daily. Vendors sell a variety of handmade goods, including rugs, pottery, clothing, and jewelry.

An institution throughout Mexico since the 1970s, this lively bar is especially popular with tourists. A non-stop party atmosphere includes waiters who spontaneously start singing or acting out in comical skits and instant conga lines. Menu items range from American to tacos and other Mexican fare. Drink offerings include basics such as beer, tequila and wine but can become “interesting” with the likes of the “Poison Kiss,” a potent blend of vodka, gin, brandy, red wine and amaretto mixed with orange and lemon juices.

Compared to other ancient pyramids in Mexico, the ruins at Xochitecatl draw relatively few visitors (we counted a dozen or so during our hour there). The Pyramid of Flowers and other pre-Columbian stone structures sprawl across 30 acres atop the dome of an extinct volcano. The 360-degree panorama takes in the entire Puebla-Tlaxcala Valley, with unobstructed views of the Popocatepetl, Iztaccihuatl, and La Malinche volcanoes, as well as nearby Cacaxtla, site of famous still-colorful Mayan-style murals painted 1,300 or more years ago.

On the non-descript, busy corner of Bucareli and Morelos streets in Mexico City is a café with a famous history: Fidel Castro and Che Guevarra met here at Café La Habana several times, chain smoking and drinking strong coffee, to plan the Cuban Revolution. Nowadays, you can still get excellent coffee—and pretty good food—while you plan something a little less dramatic (but more enjoyable), like your vacation itinerary. Old journalists and businessmen congregate here for hours on end while salt-of-the-earth, slightly surly waitresses take your order and bring you your food and drink. Come for breakfast and order their chilaquiles, motuleños, or molletes, and wash it down with an espresso or café americano.

The Darcy is high on style and also loaded with substance, thanks its eye-popping design, contemporary art collection, and free amenities that make every guest feel like a VIP. Kids can check out a Darcy Daypack full of items chosen to encourage a space or art-themed adventure in the city. Gentlemen can take advantage of the in-house haberdashery service to borrow or buy a pair of cufflinks or accessory, or have a whole suit custom-tailored in their room. A bike and scooter rental helps guests explore beyond the trendy Logan Circle neighborhood, while a nightly happy hour gives a taste of local grain-to-glass Green Hat gin. The swank captain’s quarters of Siren Restaurant serves a seasonal seafood menu, raw bar and caviar service, and craft cocktails, while the Lil’B Coffee Bar goes full Southern with a day menu of espresso drinks and New Orleans favorites.

Hello, rooftop pool! Leave it to Chicagoans to remain optimistic that summer will be amazing, even if winter lasts well into May. The rooftop pool (open to restaurant as well as hotel guests), occupies a prime spot on one corner of Six Points, that crazy intersection where three major shopping streets cross paths. That means the regulars are a mixed bag, but all come in for a good time, whether that means for brunch in the newly redesigned Café Robey street-level restaurant, to drink until dawn at the poolside Cabana Club bar, or to sneak up to its new sister, the Up Room, at the top of the deco tower.

This is where the cool kids (Uma Thurman, Led Zeppelin, Anthony Bourdain) lay their heads when they stop over in the Big Easy. The look is modern but not excessively so, location-appropriate, but not in an overly Fleur-de-Lys kind of way. Think: creamy hues, contemporary furnishings, and lofty ceilings paired with intricate woodwork, ornate chandeliers, and black-and-white photos of jazz greats. The former bank is also well positioned for late-night revelry, while still being far enough away from the French Quarter action—so you can get a good night’s sleep in one of the just-renovated king-size Apple rooms.

The Ritz-Carlton conjured true Viennese grandeur by occupying not one, but four former 19th-century palaces along the Ringstraße for its first Austrian location. Upon entering, guests will be suitably impressed by the beautifully ornate ceiling of the Melounge Lobby Lounge, where they can enjoy a light meal, tea, cocktails, and sweets. Rooms face either a courtyard or out to the city, and all offer plush beds and marble baths. All suites have a terrace or balcony from which to look out on this magical city. The extravagance reaches new heights with the incredible views from the Atmosphere Rooftop Bar, where stylish locals and visitors mingle. During the holiday season, it turns into the city’s most elevated and most exclusive Christmas market.

Union Station is as stunning as it is rich in history, and continues to be a vital hub for L.A. rail, metro, and bus transport. On the outside, the building resembles an art deco riff on the old California missions; inside, the inlaid travertine and terra-cotta floors show the sort of detail work so rare in modern depots. Local tip: Settle into one of the giant leather chairs in the cavernous waiting room and immerse yourself in the city’s seedy side with Chandler’s noir classic, The Big Sleep. (Without a ticket you can’t enter the waiting room, but you can at least enjoy the Navajo patterning on the station floors.)

The clothes at El Palacio de Hierro aren’t anything special, in the sense that they’re the same familiar brands and pieces you could probably find in your basic upscale department store at home. But if you open your suitcase and find that you’ve forgotten to pack some crucial piece of clothing or you need an extra pair of shoes, then El Palacio is a good place to find what you’re looking for. There are several of these stores around the city, and many of them also have a gourmet food court inside, so if you need a coffee or a snack, stop by for a tasty treat.

Decidedly more upscale and art-focused than other Kimpton properties, the La Peer takes fitting into its surrounding neighborhood very seriously. Located off Sunset Boulevard on the quiet and walkable La Peer Drive, the hotel is in the heart of West Hollywood’s design district, surrounded by galleries, boutiques, restaurants, and more. While there’s a separate entrance for celebrities, the property is actually quite welcoming to all. The lobby feels like your artist friend’s cozy but consciously designed living room, with little nooks for reading and working, as well as large-scale art pieces sprinkled throughout. Step out back to the indoor-outdoor bar, patio, and small but serviceable pool area to peep a piece by Retna and grab a drink and snack. For something more substantial, there’s also lobby restaurant Viale Dei Romani, an Italian trattoria that’s garnered critical approval for chef Casey Lane’s fine cooking.