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Wobbly floors, a crooked staircase, dusty books, an old piano, and a few hundred years of character mix together in the beating heart of old Dublin, the Temple Bar. I spend more than half of every year on the road, calling in at one hotel and the next, and I’ve been lucky to have spent time at some fabulous hotels and holiday homes. This joint at No. 25 Eustace St. is near the top of the list. From the Irish Landmark Trust website: “The Irish Landmark Trust saves heritage buildings throughout the island of Ireland that are at risk of being lost through neglect or inappropriate use; conserving and restoring these buildings so they can be let as holiday homes.” The next time you’re in Dublin with your family or a large group, forget about calling in on modern digs, and check out No. 25, or one of the other heritage properties managed by the trust. It was a beautiful experience, and I can’t wait to check in again. Next time I plan to visit an old lighthouse, fort, or country home.

One of the more relaxing evenings away from home was spent at the Outrigger Hotel in Kailua-Kona on the Big Island of Hawaii. I checked in with no problems and was even upgraded to a partial ocean view room! I had enough time to mosey on through town to grab some dinner and watch the sun sink to the ocean (complete with a green flash). The hotel was comfortable and situated next to a beach filled with a all sorts of fish and sea turtles. Snorkeling at Kahaluu Bay Beach Park, right next door to the hotel in the morning was one of the best snorkeling experiences I have had in Hawaii. The water was clear and the marine life was over-abundant! Sitting at the beach bar in the evening with live music and the sound of the surf was enough to relax the body and soothe the soul for a great night of sleep! If you are local, make sure to book their Kamaaina rate. **Unfortunately, the Keauhou property has closed. However, the Outrigger has several other properties on the Big Island.

I think the most appealing aspect of Old San Juan is the architecture and design of the city. Residential apartment buildings have been converted to designer boutiques or little B&Bs, and interior courtyards invite hungry guests to relax and unwind in the shade.... I’ve been to this area multiple times and still I manage to find a street I’ve never wandered down. Some are more popular than others, in particular Calle San Sebastian, which hosts eateries, bars, and shops, and Calle San Francisco. At the corner of this street is my particular favorite, Franky’s antiques. It’s in a four-story building, loaded with vintage goodies. There’s so much to see, one trip is not enough. If you want to shop, consider wandering all morning and into the early afternoon. You’ll be delighted by all the unique shops. Then, take a break at my favorite restaurant, Triana, for Spanish-style tapas and their famous sangria. It’s a must-stop place any time I’m in the old city. You don’t need a car to get around. Just park at one of the garages and explore by foot. There’s lots to see and do in Old San Juan.

“9 Streets” (De 9 Straatjes) is a charming, picturesque shopping area in the heart of Amsterdam‘s canal district. Located between Leidsestraat and Raadhuisstraat, this area is named after the nine side streets connecting the main 17th-century canals in the stylish Jordaan neighborhood. Spend a leisurely day browsing in the artisan boutiques, local designer shops, art galleries, cafes, canal-side restaurants, bars and more. You’ll be intrigued by all of the unique, beautiful objects for sale.

Chania is one of the most beautiful cities of the island of Crete. One of the most beautiful corners of the city is the harbour. It was built on the Venetian era. Visitors will find there monuments of both the Venetian and the Ottoman history. The harbor was constructed by the Venetians at around 1350. Apart from the monuments to be seen by visiting the Venetian Harbour in Chania, you will find along many restaurants, cafes and bars. The area is very lively and crowded day and night.

Across the river from the Badung Market—Bali’s largest traditional produce and meat market—is the Kumbasari Market (also called Pasar Seni Kumbasari), where you can find craftspeople hawking their wares. Wander among stalls selling batiks, wood carvings, jewelry, paintings, and souvenirs.

Nestled within a landscape of moss and lava less than an hour from Reykjavik, the Ion Adventure Hotel is one of the few true luxury hotels outside of Iceland’s capital. Under the careful eye of owner Sigurlaug Sverrisdóttir, a no-frills barracks for geothermal power plant workers was transformed into a concrete-and-glass Nordic-modern showpiece that wears its reverence for the natural setting on its sleeve. Sverrisdóttir is committed to using local products—everything from the artwork to the bath products to the food are sourced from the area—and the hotel’s sustainable materials and practices, like using geothermal cooling for power, have earned it a number of awards. Plus, all 45 of the sleek but comfortable rooms feature fair-trade organic linens and floor-to-ceiling views of Lake Thingvellir or Mount Hengill, an active volcano. The glass Northern Lights Bar juts out toward the horizon, providing a perfect viewing spot when the aurora borealis appears; beneath it sits a large rectangular hot tub adjacent to the spa. As for adventure, the hotel is happy to arrange any number of excursions, including fly-fishing, horseback riding, kayaking and, for the truly bold, snorkeling in the Silfra fissure.

Every afternoon about 5:30 PM, islanders and connoisseurs of sunsets arrange themselves at their favorite beach side vantage point on the west and south shores of Oahu for a chance to see the legendary “green flash”. In all of my years of living in Hawaii, I have only seen it twice, but sometimes I think it was a result of a very strong Mai Tai and staring at the sun too long. If you’d like to try for a glimpse of this phenomenon, you might as well be sitting in a comfortable spot with a great drink in hand. SWIM is a poolside bar with views over the statue of Duke Kahanamoku out to Waikiki beach. On an upper deck of The Hyatt Regency Waikiki, you are above street level so nice treetop and beach views are yours. I recommend the Lychee Martini ( pictured). The pupus are really good here too and if you plan it right, might serve as dinner. If not, hop over to SHOR American Seafood Grill. Visible across the pool with indoor or outdoor seating, start with amazing Baby Kona Abalone with garlic herbed butter, the tremendous seafood tower or the catch of the day you pair with a sauce you select from the list like Pineapple Shiso Relish, Hamakua Mushroom, Soy Radish etc. Insider Tip : Valet your car gratis with purchase – so get your ticket stamped and tip your valet.

If you’re in Madrid and in the mood for tapas, you might not know exactly where to go or what to taste. The Mercado San Miguel (metro Sol) takes away all that decision-making by providing you with a taste experience all under one roof. The old, derelict market was renovated just a few years ago and turned into an upmarket culinary emporium of sorts. It has more than 30 food stalls, each selling something different. My favorite is the bellota ham sold at Carrasco, but there is plenty more. You can sample sherries and Rioja wines at the wine bar, or do as Spaniards do and pick away at tapas as you make your way through the market. I highly recommend the croquettes, or croquetas, in one of the outside alleys: they have ham, chicken, shrimp, cheese and a variety of others. The more standard tapas area easy to find, like tortilla, and seafood is beautifully laid out for you to pick and choose. Right in the middle is my top-rated tapa place. I couldn’t find a name for it but it’s the largest counter, shaped like a U, and has everything from potatoes aioli to steamed razor clams, with everything in-between.

Hailed as one of the country’s first true boutique hotels, Hotel San José started its life as a 1930s tourist court and became a 1950s roadside motel before falling into disrepair in a bad part of town. In the mid-1990s, Liz Lambert bought it and transformed it into a minimalist, mid-century–inspired hot spot, the first of her distinctive Bunkhouse hotels, and the South Congress neighborhood changed with it. Although it’s now a must-visit for out-of-town hipsters (and its bar a hangout for trendy locals), the hotel stays true to its roots; a majority of the furniture was made by local artisans from reclaimed wood and Texas leather, the three most affordable rooms have a shared bath, and Lambert’s experience renovating the hotel and contributing to the neighborhood’s gentrification prompted her to make the documentary The Last Days of the San Jose.

Nowadays, SoCo is Austin’s hottest neighborhood, and Hotel San José is in the heart of the action, hosting local and touring bands in its courtyard and parking lot, and offering some of the city’s best coffee at Jo’s, its affiliated café. Plan to spend at least one evening making new friends over Shiner Bocks at the long tables in the courtyard lounge.

Expat owned and run, this spot brings California-style burritos to Mexico. The tiny outdoor restaurant—featuring only three long tables—routinely fills with an eclectic mix of locals, foreign residents, and tourists in search of a casual spot for laid-back socializing. The hole-in-the-wall chic surfer vibe pairs well with made-to-order burritos and tacos with several kinds of seafood and tortillas; you’ll also find umbrella drinks, traditional Mexican micheladas (beers served with ingredients like lime juice, chili powder, and Worcestershire sauce), burgers, and ceviches. Best of all, it’s open round the clock, making it an easy option for wee-hour snacking when Party Center clubs let out.

Why we love it: An intimate retreat with an attentive staff that guarantees fuss-free tranquility

The Highlights:
- Personalized attention from a small, dedicated staff
- Guestrooms filled with Mexican antiques
- The all-day, oceanfront restaurant that serves local cuisine

The Review:
With just 12 guest rooms and a staff that’s smaller than a football team, NEST is more private home than resort. Owned by former music industry executive James Chippendale, the intimate property features simple, subdued rooms, individually appointed with antique and artisan furnishings sourced from San Miguel de Allende and throughout the Yucatán, as well as king-size beds, locally made bath products, and handcrafted French doors that fling open to welcome warm ocean breezes. Start your day with a probiotic smoothie and huevos rancheros at the beachside restaurant, then secure your spot on a palm-fringed daybed overlooking the powdery shoreline and azure waves. Your biggest decision may well be whether to watch the sun dip below the horizon from your plush perch or head back for complimentary happy hour at the bar.

Why we love it: A historic property with style to spare

The Highlights:
- Historic details like the marble lobby
- Thoughtful amenities like microfiber bathrobes, complimentary newspapers, and Gilchrist & Soames bath products
- A sophisticated on-site restaurant

The Review:
Housed in a former bank building from the 1920s, the Ambassador Hotel in downtown Kansas City is listed on the National Register of Historic Places. Today, the neoclassical property is updated with thoroughly modern amenities, but still features historic details like a showstopping lobby with marble columns, soaring ceilings, and sparkling chandeliers. Guest rooms are equally stylish, with custom furnishings, private label linens, and marble bathrooms with oversize walk-in showers, but for the ultimate luxury, book the 753-square-foot Loft Suite, which features two floors, one-and-a-half bathrooms, a wet bar, a living area, and original windows that bring in loads of natural light. When hunger strikes, head to the on-site Reserve Restaurant, where executive chef Jeremiah Lyman serves contemporary American cuisine and top-notch cocktails.

Built in 1934 from a couple hundred pine boards, the Dürkheimer Fass is the world’s largest wine barrel, and often described as the heart of the German Wine Route. Constructed by barrel maker and vintner Fritz Keller, it could feasibly hold 449,092 gallons of wine, but has never actually contained any liquid. Instead, it functions as a unique wine bar and restaurant, conveniently located on Bad Dürkheim’s main square.

Surrounded by vineyards, the small town of Bad Dürkheim is of course famous for wine, but it’s also known for its annual sausage festival, which takes place over two long weekends in September and is said to be the largest wine-related festival in the world. Additionally, the “Bad” in the town’s name indicates local wellness facilities, including thermal baths, a spa park, and the old Kurhaus, a former sanatorium that now houses a hotel. If you’re feeling energetic, you can hike up to Limburg Monastery, which was built in the 11th century and today hosts concerts and theater performances.

Set at the end of Duval Street, near Sunset Pier and Mallory Square, Pier House takes advantage of its waterfront address with three tiers of balconies and a pocket-sized stretch of private beach. Its location means guests are within walking distance of all of Old Town’s highlights, from the Clinton Square Market to the Harry S. Truman Little White House. Many come to follow in the footsteps of the mayor of Margaritaville himself, Jimmy Buffet, who played his first gig in town in the hotel’s now infamous Chart Room Bar. Order a rum runner, then head to the heated outdoor pool; though it’s on the small side, it has sweet views to Key West Bight. After an adventure-packed day, the rooms and suites offer low-key comfort, decorated with traditional furniture and local art and overlooking the ocean or tropical gardens and koi ponds. Equally serene is the full-service spa, one of the few on Key West.