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This twin-peaked headland—and the ruins of the 18th-century Fort Shirley garrison—preside over Prince Rupert’s Bay, Dominica’s largest wetlands and a docking area for smaller cruise ships. An 1802 revolt here led to the British Empire abolishing all slave soldiers, making this Dominica’s most important historic destination—and now a worthy World Heritage site. A short climb leads to the restored buildings and a splendid viewpoint, complete with cannons. Longer trails spike out into the dry coastal woodlands, populated by crabs and grass snakes (Liophis juliae, known locally as kouwes).

Azul de Oaxaca Hotel + Galeria is among the numerous lodging options in the city’s colonial Centro neighborhood, but the aesthetic of this hotel tends more toward the contemporary, even though it is housed within one of the city’s typical 18th-century buildings. Respect for the centuries-old style is evident in the preservation of the building and courtyard. Rooms, though, are decorated with contemporary art and furnishings. Guests can enjoy a number of common areas, including a library, chapel, gallery and gift shop, patio lined with tall cacti, and rooftop terrace bar. On Sundays, guests are invited to enjoy local specialties, including quesadillas, at the on-site restaurant, which serves breakfast, lunch, and dinner seven days a week.

Set back in a leafy area behind Casino Square and facing the sea, the sprawling, elegant Hotel Hermitage is a slightly less ornate alternative to the glittery fussiness of Hôtel de Paris, though it’s equally steeped in neoclassic grandeur. Many of the rooms and suites feel more contemporary than the hotel’s hand-painted Belle Epoque frescoes and stained-glass winter garden lobby dome designed by Gustave Eiffel. Accommodations range from rooms with clean lines, soft colors, and walnut furnishings to the most sought-after suites, with private terraces and lovely sea views. Because of the hotel’s spaciousness, it’s particularly well suited to families who want a touch of nostalgic glamour along with high-tech plasma screens and other modern amenities. The hotel’s V.I.K. (very important kid) program offers everything from a game room with activities to access to the private beach and pool for children.

Le Petit Hotel is housed in a former leather merchant’s building that dates back to 1867 and boasts original stonework arches and pillars at its entrance. Truly a “petit” hotel, its 28 rooms are spread across four floors and divided into S, M, L, and XL. Although it’s small, the hotel packs a stylish punch, mixing century-old exposed brickwork and stone with funky hardwood floors and modern-day luxuries—from free Wi-Fi and iPod docks to platform beds and multi-jet massage showers. In the guest rooms, splashes of bold, sunny orange and black accents create a contrast to the fresh white walls. Situated in the heart of Montreal’s fashionable Old Port area, guests are just steps from much of the city’s best shopping, dining, and art.

Set in an 18th-century palazzo, once a former bank, the Park Hyatt Milan boasts interiors designed by American-born, Paris-based architect Edward Tuttle. It aims to wow from the outset. Guests are greeted by a lobby decorated with sophisticated materials such as warm travertine stone and alabaster, and topped with a 30-foot glass-domed cupola. There’s a discernibly modern aesthetic throughout the rest of the hotel, though, from the vibrant modern art scattered throughout the public areas to the contemporary color palettes (creams, beiges, and gentle grays). Rooms are correspondingly elegant, with high ceilings, expensive dark woods, rich wool carpets, and hand-selected furnishings (Murano light fixtures, Bang & Olufsen TVs). The bathrooms are especially impressive, not only because of their generous size and marbled interiors, but also thanks to the mirrored walls, double sinks, octagonal stone and glass showers, and Lauro Tonatto bath products.

The suburb of Rosebank has the best of both worlds: it’s home to major commercial hot spots, but it also boasts peaceful pockets of lush lanes. The understated Clico Boutique Hotel sits in one of the latter areas, but guests will be surprised to discover that it’s just a few minutes’ walk from some of the city’s liveliest eateries and shops.

It’s all about personalized attention at Clico, and the nine rooms make it easy for staff to attend to guests’ every whim. The chef can customize menus, and the staff will dote on guests with a smile—even making sure they toast the sunset with a glass of Veuve Clicquot in hand. When staying in a hotel named Clico, after all, one can rest assured champagne will be flowing freely.

The hippest kid on the block has risen from the most unlikely of origins: the Fenway Motor Hotel, a run-down mid-century relic that once housed all manner of misbehaving musicians. Today the hotel feels more like an of-the-moment Los Angeles enclave, with mid-century furnishings, floor-to-ceiling Mondrian stained-glass windows, and upscale bathrooms. Local music and pop-culture memorabilia decorate the rooms and foyers, from framed Boston Phoenix covers (the city’s now-defunct alt-weekly) to vintage speakers and ‘70s-era phones.

In keeping with the rock-and-roll theme, both the lobby and the outdoor pool area regularly host live music. Lansdowne Street, home to legendary clubs like House of Blues, is just steps away, and of course no visit to Boston is complete without a stop at next-door Fenway Park (tours of the ballpark are available daily and year-round).

Ace Hotels—whose growing brand epitomizes a cool, unfussy, überhip hotel stay—debuted at this site in 1999, and it has become a kind of template for the company’s trademark style. While offering the essentials (including serious coffee by Stumptown), the Seattle Ace Hotel is very much a budget property and doesn’t provide fancy amenities (in fact, standard rooms share a bathroom). But the minimalist guestrooms, with their vintage furnishings and original, Pop Art-esque artwork hanging on walls, are spotless and cozy, and the hotel does offer a comfortable, convivial stay in the supremely walkable neighborhood of Belltown. The brick building has high ceilings and hardwood floors, and a few of the rooms have partial water views. Common areas aren’t large, but they’re the kind of spaces that invite conversation with fellow travelers.

On the North Fork of Long Island, Shinn Estate Farmhouse Inn is tucked away on a peaceful vineyard. Rooms are in the estate’s historic 1880s homestead, and guests get to experience life on the vineyard—and taste the final product in the winery’s tasting rooms. There is also a lovely front porch and gazebo for kicking back with a glass of wine. A cozy wood-burning stove in the reception area is an ideal spot on a chilly day. Breakfast here is a slow and civilized affair, starting with hot coffee and finishing with a full farmhouse hot breakfast from chef David Page, made from farm-fresh ingredients. This is the pastoral North Fork at its best, designed for lazy afternoons, sleeping in, and one too many glasses of wine.

The largest of Tanzania’s state-administrated national parks, Ruaha is home to the Great Ruaha River, imposing baobab trees, and one of the greatest populations of elephants in any African park. It has few lodges and therefore few tourists. It is also wilder than its close neighbor, the Selous Game Reserve, and boasts a truly authentic safari experience. Night driving is not permitted, nor are walking safaris, generally, due to the large number of elephants here. But hidden away on the Jongomero River in the remote southern area of the park is the Jongomero Camp, which is both fantastically luxurious as well as truly one with its surroundings. It is possibly the best camp in the whole of Tanzania, and its guides are second to none. In addition to the breathtaking campsite itself, it offers “fly-camping” trips on which the adventurous traveler can spend the night under the stars.

The vast wilderness of Glacier 3000 continues to beguile visitors year after year. While you can ski here, most take a snow cat or dog sled across the plateau, or hike to the precipices and look down on the surrounding area. Glacier 3000 is also home to the world’s highest rollercoaster, which hurtles around corners and dips drastically, imitating the sensation of freefalling toward the ice at heart-racing speeds.

Located in Messinia’s Mediterranean area, this popular beach is most well-known for its distinct “omega” shape. Locals and visitors come here to lap up the waves, admire the dunes, sunbathe on soft sand, hike, and bird watch. Other attractions located above the beach include Nestor’s Cave, the ruins of Old Navarino Castle, and the tomb of Thrasymedes (Mycenaean period). As you climb, you’ll enjoy aerial views of the Divari Lagoon of Gialova, Navarino Bay, and the olive tree-littered Peloponnesian Hills. Interestingly, Voidokilia Beach is believed to be the place mentioned in Homer’s Odyssey, where Telemachus (son of Odysseus and Penelope in Greek mythology) was greeted by King Nestor—who is thought to have used the beach as a port during ancient times—when searching for his father. For a guided experience, Navarino Outdoors offers a bike tour of the beautiful Voidokilia, with time to swim and enjoy views of Gialova Lagoon.

While it’s located mere minutes from Tel Aviv’s trademark beaches, the Brown TLV Urban Hotel is decidedly city-centric. Not coincidentally, it’s also in the center of town, surrounded by an array of distinctive neighborhoods like the UNESCO World Heritage-designated “White City,” the old Yemenite area of Kerem HaTeimanim, and the seemingly endless street market that is Nachalat Binyamin. Beyond being a strategically positioned home base, however, the hotel makes for a great escape. Once you’ve explored the city on a free loaner bike, you can retreat to the rooftop hot tub, the indoor-outdoor Garden Bar, the den-like living room, or—if you’ve booked one of the Zen-inducing Relax Rooms—your private balcony, ideally after an en suite spa treatment.

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.

Glockenbachviertel, one of Munich‘s prettiest neighborhoods, is located south of the city center and next to the Isar River. Formerly home to the city’s Jewish community and millworkers, Glockenbachviertel was the center of Munich’s gay and lesbian community in the 1980s. In recent years, rapid gentrification has morphed this area into Munich’s most luxurious neighborhood. Quiet streets are lined with beautiful residential buildings and there are plenty of beautiful bars, restaurants, and shops. Take a stroll in the evening or do some shopping before dinner. Don’t miss Hans-Sachs-Straße and its fun boutiques, cafes, and bistros with outdoor seating. One of my favorite meals during my trip was at Das Kranz, a stylish restaurant that focuses on organic produce. The menu changes weekly to take advantage of seasonal, local ingredients. The flavors are fresh and the presentation is beautiful. The fun, relaxed atmosphere (with outdoor seating in summer) further adds to an enjoyable meal.