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Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel plates with no visible seams, the polished surfaces of this 33-foot-tall sculpture reflect infinite variations of the Chicago skyline. The work’s design was chosen from among more than 30 others commissioned by the city, and it was inspired by liquid mercury.

Dive deep into island lassitude with afternoon tea at the Moana Surfrider, the Victorian-era hotel nicknamed “The First Lady of Waikīkī.” Grab an open-air table and sample one of six locally crafted teas, ranging from Lemon Rooibos to Moana Sunset, a mix of sweet mango and tangy ohelo berries. The $45 classic service includes savories like duck prosciutto, “furikake” salmon, and a caramel cream puff with black sea salt. Not to mention green tea sorbet and a curd made from lilikoi (passionfruit) and Devonshire cream. Kick things up a bit with a nonalcoholic pomegranate fizz or a Poema sparkling brut rosé!

Dornier’s modern cellar and production facility is quite different from the traditional 18th- and 19th-century buildings you’ll see in the winelands. For example, a pool above the cellar regulates the temperature of the wines in an eco-friendly way. Its reflective surface also helps keep the entire subterranean building cool. The cellar’s overall design pays homage to the Dornier family’s history in the aviation industry. Contact the winery in advance to arrange a tour of the facility, then enjoy a tasting of award-winning wines like the Dornier Donatus White (a blend of chenin blanc and rich sémillon), the Dornier Merlot (with hints of plum, mint, and roasted nuts), and the Cocoa Hill Sauvignon Blanc (featuring notes of mulberry, roasted oak, vanilla, and spice).

A breezy little beach hotel filled with rough wood, natural linen, and flea market finds, the Rose seems, to the uninitiated, like a pure product of quirky Venice’s hipsterfication. In fact, the historic, wood-and-stucco building was built by the beach town’s founder, Abbot Kinney, in the early days of the 20th century; rumor says it was his private brothel, frequented by such friends as Charlie Chaplin. By the 1970s, at the height of Venice’s drug culture, the building had become a flophouse of sorts, and neighbor Dennis Hopper was known to drop by. Before two British photographers discovered it, the house had turned into a mural-covered crash-pad for surfers, yogis, and beach bums of all kinds.

Looking at the low-key Rose now—the town’s first true boutique hotel, barely half a block from the beach—one would hardly know that the entire history of Venice had passed through it. The rooms are spare but stylish, with large windows, art photography, and vintage furniture. Some rooms are large enough to live in, whereas others share a hallway bathroom. Amenities are minimal—Stumptown coffee, bicycle rentals—but a relaxed beach house that attracts artists and creatives looking to delve into Venice’s eclectic, vibrant culture doesn’t need to try too hard to be cool.

Among Playa Avellana’s numerous pleasures, the small-town, almost-no-cars vibe sets the scene for true relaxation—as well as fun. Look for Lola’s—perhaps the hippest spot in town—in the tiny business district and try out fresh, locally sourced pizzas, mahi-mahi tacos, and veggie burgers; smoothie lovers will go nuts. Locals and visitors pack in under the almond trees late mornings after surf excursions and other adventures. Be on the lookout for Lolita, the piglet daughter of the original Lola (sadly no longer with us) as she frolics in the sand or ranges across the property.

A massive stretch of soft white sand calls you to the Caribbean at Cancún’s largest public beach, a quiet spot amid Hotel Zone resorts. The waves can be a bit rougher than elsewhere, so it may not be great for swimming, but the strand is one of the city’s few surfing spots. Playa Delfines also goes by the name El Mirador, thanks to its spacious hilltop deck overlooking the ocean and hotel skyline and its large, colorful “Cancún” sign that’s perfect for photo ops. Among the other welcome amenities: restrooms, a playground, small shady palapas, and an outdoor gym.

If you’re looking for the prefect French vacation destination, the picturesque city of Pau, in Southwest France, may just have it all. Its location is perfect, almost equidistant from the stunning Pyrenees Mountains, for hiking and skiing, and the seaside, for enjoying the sun and surf. It is surrounded by rolling hills covered in vineyards, producing sweet white jurancon, and rich fruity red wines. The bustling city market is one of the nicest I’ve visited in France and the restaurant offerings are varied and of excellent caliber. Throw in a photogenic chateau, friendly locals and proximity to international airports and you have the perfect holiday spot. The only problem is, (like me) you may not want to leave.

On the Dominican Republic’s northern coast, near the tip of the Samaná Peninsula, this unpopulated Atlantic beach stretches three miles from Cape Samaná to the cliffs of Cape Cabrón. To get here, you’ll need to take a four-wheel-drive vehicle or a boat charter from the small fishing village of Las Galeras, but once you arrive, you’ll find a nearly empty stretch of sand. The west end of the beach features calm waters ideal for swimming and snorkeling, while the east end has great waves for surfing. You’ll also find spots to rent kayaks, snorkeling gear, chairs, and umbrellas, as well as a few food vendors serving rice, beans, and seafood cooked over an open-hearth fire. This is the place to go when you want to get away from the crowds.

Catching the sunrise at Pandawa Beach, also known as the “Secret Beach” in South Bali, was an adventure from beginning to end. After learning about it from Rob, the owner of Suara Ombak Cottages (www.wavevoice.com) where we stayed during our SURF LIFE retreat, we woke up before the sun, hopped on our motorbikes and headed for the unknown paradise. Once there, we first stopped to admire the massive sculptures being carved out of the cliffs along the path to the beach. Then, down on the sand, as we waited and appreciated the natural beauty around us with only us three and some local fisherman, we witnessed the most magnificent sunrise that looked as if the sky was lit on fire. Riding our motorbikes to catch the sunrise at Pandawa Beach was spontaneous, powerful, unforgettable, and felt like our own treasured secret adventure.

Coco frios are sold on every corner during the high season (fall and winter) in Puerto Rico. Cold, fresh coconut water is the lifeblood of island living. Literally, if you were ever stranded on an island, you could sustain yourself on what’s inside a coconut (just ask Les Stroud). There is a difference between coconut water and coconut milk. Coconut water is clear to translucent and not as sweet—you harvest this from a fresh green coconut that has just fallen, or is ready to fall from the tree. It might taste unusual at first if you have never tried it, but this is actually the best form of natural electrolytes to replenish yourself after a workout or surf session. Watch the roadsides for the carts and folks with machetes—because this is your hint that coco frios await you!

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

While scouting out the remaining lighthouses left standing on the Oregon coast, I was lucky enough time my visit with two gray whales. There’s a vintage whale watching station just across the parking lot at the Umpqua River Lighthouse and with a few quarters, I was able to see the action. By flipping through my guidebooks, I learned that morning is the best time to scout for the views of the mighty whales, that like to hang out at the mouth of the Umpqua River where it empties into the ocean. In the morning light, the sun is at your back at the viewing station, meaning you can spot the whitecaps that the whales create (instead of the ones that the wind and waves create later in the day). At the station, you’ll find a sign with a few helpful suggestions to spot these magnificent creatures. You’re instructed to look for puffs of vapor that seem to hang in the air, just above the water. Those spouts usually rise twelve to fifteen feet into the air and when you spot one, you’re bound to see several in the same area. Soon, you’ll be able to observe the head, back and flukes as the whales roll on the surface.

Usually I take a train across the Øresund Bridge, an engineering marvel that connects Malmo, Sweden, to Copenhagen, Denmark. Unfortunately, the train travels below the vehicle deck, which means you can’t actually see the bridge. And this is a bridge worth seeing. The crossing itself is about 10 miles. Coming from the Swedish side, the first five miles of your trip is over a bridge that floats 187 feet above the water before briefly landing on an island and then diving into a tunnel beneath the sea. The girder and cable-stayed bridge section has two pairs of free-standing cable-support towers that seem to grow in height as you approach . . . until they disappear into the sky. Even on a road that is more than 200 feet above the surface of the water, the tops of those towers are still almost another 400 feet above. Rent a car and take a trip across (either Copenhagen or Malmo makes a good day trip), but be prepared to pay a hefty fee for the privilege. The toll is roughly $60 U.S. each way. Øresund Bridge English-language web page has current toll information: http://uk.oresundsbron.com/page/1087

I was in the Ribeira district of Oporto. I wanted to see the Gothic and Baroque Church of Sao Francisco. So I wandered into the church that was listed as one of the most important and beautiful churches of Oporto. It was said to be very ornate. I was mesmerized by the beauty of this huge edifice with the elaborately decorated interior said to have more than 300 kilos of gold dust covering altars and other decorative surfaces. I stood there and tried to think of the work involved in completing this church. It must have been a huge undertaking ( as were so many of the monuments the world over). The church was built originally as a small building in 1245 by the Franciscan friars in honor of Saint Francis of Assisi. In 1383, a much larger church was built.It was finished about 1425. The structure is a basic Gothic church with the large rose window. In the 17th and 18th centuries, Baroque architecture was added. The Franciscan friars were buried in the catacombs which you can visit. There is also an ossuary with thousands of human bones. The interior is very large and you need at least an hour to peruse this monument. This is an attraction that you should not miss while in Oporto.

Lake Matheson is a magical little spot near Fox Glacier. It’s a great place to take a walk at sunset, before enjoying dinner and some local wine at the Matheson Cafe. On a clear day, the reflection in the lake proudly displays all the reasons to be in love with the Westland National Park region of New Zealand, while the rugged peaks of Mount Tasman and Mount Cook rise out of the mountain range. This is glacier country at its best. The lack of wind—the lake is set within the dense rain forest—means Lake Matheson’s surface is calm and still. The reflection photo opportunities have made this lake the most photographed body of water in New Zealand (and that is saying something). The walk around the lake takes about an hour and a half, and you have three viewing platforms offering exceptional perspectives along the way. Hit the trail just before sunset and have a glass of Otago Pinot Noir at the cafe while you watch the sun set over those mountains. The cafe opens at 5:30 p.m. and I’d suggest the mushroom risotto.