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One of South Africa’s most famous sights, Robben Island is located four miles to the west of Cape Town. Its history as a prison is almost as old as the first Dutch settlement on the cape, dating all the way back to the 17th century. Today, the island is a UNESCO World Heritage site and museum, offering guided tours by former prisoners. After visiting the graveyard and maximum-security facility, guests can finish with a stop at the cell of the island’s most famous prisoner, Nelson Mandela. The half-hour ferry ride to Robben Island includes breathtaking views of Cape Town and Table Mountain. Just note that the ferry only runs three times a day in the low season; in the spring and summer, there’s an additional departure in the late afternoon. Book your tickets far in advance.

This hotel is on our list of The 11 Best Hotels in Chicago.

Set directly across from the Art Institute of Chicago, this former members-only men’s gymnasium is now the Chicago Athletic Association, which is part of Hyatt’s Unbound Collection. Enter at street level off Michigan Avenue and walk toward the back to find a staircase that leads to the old swimming pool, now a venue for parties and pop-up concepts. Take the nearby elevator to the restaurant, Cindy’s, easily the best rooftop scene in the city, with highly Instagrammable terrace views overlooking Millennium Park, the swooping Frank Gehry–designed bandshell, and Anish Kapoor’s Cloud Gate (aka the Bean).

Park yourself in the second-floor lobby and hang with locals as they tap away on their laptops and sip lattes by the two oversize fireplaces. Walk through that expansive by Roman & Williams–designed room, where light beams in through ornate stained-glass windows, and you enter a warren of table games and darts, all festive and typically open to the public. There’s also the secret six-seat bar, the Milk Room, a relic of Prohibition, and the James Beard Award–winning Cherry Circle Room—a sexy, dark restaurant with a circulating martini cart and a meat-centric menu.

Upstairs in the 1893 landmark, 240 guest rooms reflect the building’s former life, with gym horses as foot beds, working fireplaces in some rooms, plasterwork ceilings, ornate carved wood wainscotting, and a clubby vibe. Some of the rooms are rather small, but the location is hard to beat, and the cozy, wintry ambiance makes it a popular (and fun) place to spend a weekend. And because the CAA keeps an eye on its water conservation, sources its food locally, and adheres to strict recycling standards, eco-conscious travelers can feel good sleeping here.

The historic MV Liemba is the oldest functioning ferry in the world, and a voyage down Tanzania’s Lake Tanganyika on this landmark is a colorful experience. Your fellow passengers will include traders loading and unloading cargo (anything from pineapples to flip-flops) and locals using the ferry for transport. On the southbound journey, the boat departs from the town of Kigoma and travels 300 miles to Zambia, where its makes its first port of call on land. But in between those two stops, while still on the water, travelers can transfer to smaller ships in order to reach places like Lagosa (a jumping-off point for the Mahale Mountains National Park) or the peaceful beach area of Kipili.

Lovers of Vienna’s homegrown early-20th-century Wiener Werkstätte design style will want to visit the Café Schwarzenberg: It was the preferred haunt of Josef Hoffmann. The illustrious architect who cofounded the Werkstätte drafted many ideas there that came to fruition. Opened on the Ringstrasse in 1861, the café takes its name from the nearby square that is itself named for the Prince of Schwarzenberg, a prominent Austrian field marshal in the Napoleonic wars. Guests are treated to huge vaulted windows under high ceilings and those who sit outside on the terrace enjoy views of the illuminated Karlskirche dome while they sip their Einspänner coffee with its dab of whipped cream on top.

Inspired by a former Ford car dealership that once sat on the site in upscale Mission Hills, Fort Oak’s interior mixes old and new; hexagonal tiles and brass accents give the space a vintage feel, while a black oak communal table and plank flooring bring a modern industrial vibe. Executive Chef Brad Wise excels at wood-fired cuisine—the exhibition kitchen has a 7,000-pound grill and range where he fires up 45-day dry-aged ribeye and Australian wagyu beef—but what really sets Fort Oak apart is a raw bar serving seafood towers and buttery hamachi poke. For a decadent night out, slide into Fort Oak’s chef’s counter for a six-course tasting menu cooked by Wise (offered Wednesday and Thursday nights every other week; reserve ahead).

A larger, more luxurious alternative to an inn-style getaway, the ocean-facing Gurney’s Montauk Resort offers gorgeous views, plush accommodations, and top-notch amenities, including a whopping 2,000 feet of private sandy beach. The spa is the star attraction and includes a Finnish sauna, steam room, Roman bath, and saltwater swimming pool, all of which are only open to guests to maintain a quiet, exclusive ambience. Other property highlights include a salon, fitness center, and selection of restaurants, ranging from Scarpetta Beach (which serves Italian cuisine) to Tillies (a more casual bistro with hearty American fare and brunch specialties on weekends). Not surprisingly, the guest rooms and cottages are especially luxe, with lovely wooden floors, walk-in rain showers, and big windows with sweeping sea views.

Set in a historic building renovated by local architects Hild and K and Albert Weinzierl, Munich’s Louis Hotel has a prime location on the edge of the vibrant Viktualienmarkt. Stylistically, it mixes the Baroque with the contemporary, complementing detailed stucco, French balconies, and walnut bed frames with luxurious Italian fabrics, oiled oak floors, and designer furnishings. In addition to 72 chic rooms, guests can look forward to a lobby with a large fireplace, an in-house gym and sauna, a trendy Japanese restaurant, and a rooftop terrace with sweeping views over city landmarks like St. Peter’s Church.

One of the city’s top restaurants, Cicciolina offers Italian-style dishes with a Peruvian flair, such as quinoa-encrusted prawns and osso buco with pumpkin ravioli topped by local cheese and a touch of Andean mint. There’s plenty to choose from, including seafood, duck, beef, alpaca, chicken, and even a few vegetarian dishes, as well as perfectly done handmade pasta. You can pick from either the tapas or the full-restaurant menu in the bar area, but not the other way around, so you may want to go twice, as the tapas are fabulous, too. A great wine list and yummy desserts finish out options in a small, lovely venue. Reservations are a must.

Become a Paniolo (Hawaiian Cowboy) for a day and do an actual cattle drive while on the Big Island of Hawaii. Even though it was a rainy, moody day, it was the perfect unique experience to have in Hawaii. Hawaii is much more than beaches! More information about my experience at Dahana Ranch: http://www.ottsworld.com/blogs/cattle-herding-in-hawaii/ Dahana Ranch P.O. Box 1293 • Kamuela, HI 96743 • toll free: (888) 399-0057 • p (808) 885-0057 • f (808) 885-7833 • [email protected]

The beach may be the magnet that draws crowds to Trancoso but its the Quadrado that is the heart of the town. The town square sits atop a hilltop offering stunning views of the mangrove forest and sea below. The 1,050-feet-long green park is anchored by the town’s iconic white church and bordered by 50 or so Crayola-colored old fisherman houses. During the day most of the homes stay shuttered due to the heat. But by 5pm, particularly during the peak summer season, they open their doors to reveal chic boutiques and art galleries, restaurants, and pousadas like Uxua and El Gordo. At sunset wild horses graze in the square sometimes interrupt the local kids’ soccer game. The square is filled with crowds after sunset, and artists and artisans come out to sells their goods while musicians come to play music and capoiera dancers come entertain passersby.

So you want to drive through a tree? Well, you’ve got options. (At least for now. Since no new drive-through trees will be created any time soon, for obvious environmental reasons, the existing ones are maybe the last of their kind.) There are actually three trees in the vicinity of Redwood National and State Parks whose trunks are wide enough to accommodate a car. The Chandelier Tree, at the Drive-Thru Tree Park, may be the most well-known and most frequently photographed; pay your $5 and get behind the wheel. The Tour Thru Tree, near Klamath, is the other tree with a human-constructed tunnel. The only organically occurring drive-through tree in the area is the Shrine Tree in Myers Flat, on Avenue of the Giants. The opening in this tree was primarily nature-created—though at this point it’s held together with some human help. Shrine also has a fallen tree with a drive-up ramp, a stump you can walk through, and a couple of playhouses carved from redwoods.

Now this is truly a place you never want to leave. The infinity edge pool at the Marriott in Wailea, Maui. The pool reached right out to the Pacific Ocean, and you almost felt as if you were in the ocean itself. Grab an umbrella drink, swim over to the edge, and stay there for a couple hours to take it all in. The wonderful staff will also bring you the freshest fruit you have ever had too. And, as you watch the sun go down on the horizon from this exact spot, you can join the Luau by the beach below...or simply stay here all night.

Six out of what was once at least 16 Native American burial mounds remain preserved atop the bluffs overlooking St. Paul and the Mississippi River. These sites, 1,500–2,000 years old, are thought to have been built by the Hopewellians and then added to by the Dakotas. Upon excavation, archaeologists discovered a variety of offerings, such as mussel shells, arrowheads, copper ornaments, and bear teeth, as well as an unprecedented clay death mask with the imprint of the original face fully intact in the mold.

Once the center of commerce in Charleston, the City Market is now the heart of tourism. Although its location near the cruise terminal can make it feel like a kitschy open-air market in the Caribbean, the tackiness is part of its charm. Yes, you’ll find Christmas ornaments painted with Rainbow Row and enough cutely packaged pralines to give you a stomachache, but you’ll also see Gullah artisans weaving the finest examples of sweetgrass baskets available. Peak season brings 140 different merchants, and weekends include live music and food vendors. The market’s a requisite stop for any visitor and a one-stop gift shop for loved ones back home.

The oldest wooden home still standing in Nassau, Balcony House is named for the long, second-floor balcony that stretched across the front of the home. Historical maps suggest that the house could date as far back as the late 18th century, during an era called the Loyalist period, and in the mid-1800s, this house was the residence of Stephen Dillet, the Bahamas’ first-ever black member of the House of Assembly, as well as a justice of the peace and inspector of the Nassau Police. Today, Balcony House has been restored into a museum where guests can climb the beautiful mahogany staircase and explore the rooms decorated with period furnishings. Admission is free, and donations are accepted.