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Escapes of a Lifetime

U.S. News & World Report

Escapes of a Lifetime

If you’re like many boomers, you now have the time and money to visit those places you’ve always wanted to see. But sifting through the subjective opinions of friends and travel writers can be a challenge. U.S. News has partnered with TripAdvisor, a popular travel website, to identify the places that most spark wanderlust among middle- and retirement-age Americans. We surveyed more than 1,200 TripAdvisor travelers, asking them to rank in various categories the destinations they most like to visit. (More than 70 percent of the respondents were 45 or older.) Here are their top picks—and a look at the unique qualities of each locale.

Laura Powell, a veteran travel pundit and creator of the Daily Suitcase

blog, thinks she understands why Australia’s largest city has become the favorite destination of Americans: “The thing about Sydney is it’s viewed as exotic because of its distance,” she says, “but yet it’s familiar.” And, of course, language is not a problem.

Kulbir Harnal, a retired commercial pilot from Reston, Va., who’s visited twice, notes that distance is less of a concern to the newly retired. “If you’re working, the leave you get is hardly two weeks, and that’s not enough to go to Sydney. The flying time itself is three days,” he says. Retirees, however, can “take a month off.”

Travelers may want to use some of that time to visit the eastern beaches around Sydney like Bondi, Manly, Bronte, and Coogee. “The Blue Mountains begin 90 minutes west of the city and are fantastic for a day trip or a longer stay,” says Nick Dent, the editor of Time Out Sydney magazine. “The Hunter Valley, starting 90 minutes north,” he adds, is a “picturesque wine region famed for Shiraz and Semillon.”

Powell notes that the city combines sophistication with a “laid-back” atmosphere. It may also seem particularly welcoming, Dent says, as the people “tend to find Americans charming and will happily talk to them.” You’ll likely find opportunities to chat with locals by going to plays—check out the schedule at the Sydney Theatre Company—or shopping around Oxford Street in Paddington. (Dent suggests that anybody looking for a quiet evening avoid lower Oxford Street in the Darlinghurst neighborhood, with its high concentration of pubs.) You don’t need a ticket to appreciate the famous opera house; instead it can be enjoyed from atop the equally iconic Sydney Harbour Bridge. “The three-hour tour and climb can be expensive,” Dent acknowledges, but “the views are terrific.”

Sydney is also known for its food. Head to Chinatown for the best Cantonese, Szechuan, and Thai meals. For a light snack and some coffee, try a café in the southeast section of Surry Hills.

For lodging, most of our travelers agree that the central business district offers the best rates while keeping you in the heart of town. The Kings Cross neighborhood often has particularly good deals. Both Powell and Harnal recommend vacationing in October or November, when you can experience the Australian spring with smaller crowds and potentially find better deals. Hotels also slash prices from May to August. “With enough planning,” Harnal says, “I would say $100 per day is more than enough for two people who are staying and eating and moving around that area.” 

Sightseeing remains the bread and butter of tourism in the nation’s capital, which can boast of some of the country’s most recognizable landmarks. These include the White House, the Capitol, the 19 museums of the Smithsonian Institution, and various monuments that are clustered largely around the National Mall—and offer free admission.

Longtime residents suggest you explore lesser-known sites as well. Julia Taylor, who has lived in the District for 13 years and works in the nonprofit healthcare field, recommends visiting the Southwest waterfront to see the Titanic Memorial, where each April 14 (the anniversary of the liner’s collision with an iceberg) a group of men “come down at midnight in black tie and tails with champagne” to toast those who perished with the ship.

Freelance writer Tara Tag­hizadeh, who has lived in the Washington area for two decades, mentions another hidden gem: the Hillwood Estate of cereal heiress Marjorie Merriweather Post in the Van Ness area of the city. “It’s perfect in the summer and the spring,” she says, because you can walk around and see the “beautiful gardens.”

The city’s Georgetown section is always a draw, with its boutiques, restaurants, historic homes, and cobblestone streets leading up to Georgetown University. Walking through the neighborhood “reminds me of Europe,” Taghizadeh says. 

When you do venture to the Mall, consider trying Taylor’s favorite spot: the steps of the Lincoln Memorial at dawn. “You’re facing east, with the sun rising, with the backdrop of the U.S. Capitol dome, the Washington Monument, [and] the World War II Memorial. It can simply be breathtaking.”

For accommodations, you can often find lower rates just across the Potomac River in Rosslyn, Va. The Metro rail system will take you to the Smithsonian station in about 10 minutes. There also can be good weekend rates at the major chain hotels in the city center, which will put you equally close to the major sights. Walking, biking, or taking the Metro are the best ways to see the city. As Taylor notes, “Parking in D.C. is not inexpensive.”

Hotel rates are generally at their lowest in the winter, but the weather can be an issue. Your best bet is to visit the city in late fall or in the spring, when you can catch the famous cherry blossoms around the Tidal Basin.

“The great thing about dining in Florence is you can have a great piece of pizza or a great gelato, and you don’t have to spend a fortune,” says the Daily Suitcase’s Powell, who has visited the city five times. You can plan your meals around visits to some of the city’s best-loved attractions, like the Uffizi Gallery or the Duomo. There’s great bistecca alla fiorentina (thick Chianina steak) in trattorias along Via dei Leoni, or flatbread pizza around Piazza San Marco. “It’s a long-standing fast-food tradition locally to grab a tripe sandwich” from a street vendor, says Robert Reid, a frequent visitor and U.S. travel editor for Lonely Planet. Local opinions differ on which handmade gelato makers are best, he says, but he casts his vote for a white chocolate gelato with strawberries or pepper from a gelaterie called Vestri on Borgo degli Albizi. 

And since Florence lies amid the vineyards of Tuscany, you might not want to leave without a case of red wine. Reid likes to visit the southern Chianti hills not far from the city. “You can arrange to tour the 11th-century cellars once used by monks at Badia di Passignano,” he says. 

Barrie Seidenberg, CEO and president of the tour booking company, also recommends taking small-group cooking classes that include a tour of the San Lorenzo market. “You’ll get the opportunity to really understand more about the ingredients in this region,” she explains.

In early spring, the brisk temperatures are ideal for walking around. Keep in mind that room rates drop the farther you stay from the city center. Reid says he splits his vacations in the region, staying at houses on working farms (agriturismo) and at family-run bed and breakfasts.

This Shangri-La at the tip of the boot in southern Italy combines the casual atmosphere of a coastal town with the look of a medieval city. Reggio di Calabria was a metropolis and important port during both the Roman Republic and the Byzantine Empire. City attractions include the Cathedral of Reggio Calabria and the Riace bronzes of Greek warriors, which are on display while being restored at the town’s Palazzo Campanella.

The Lungomare, a seaside promenade, offers a delightful stroll. “In the nighttime there are bars and restaurants, and you can go for a long walk. It’s beautiful,” says Maria Tuttocuore, an analyst for the travel market research company PhoCusWright and a native of Sicily’s Messina province, across the strait from Reggio di Calabria.

One of her favorite local dishes is the grilled swordfish roll, filled with breading, pine nuts, Parmesan cheese, and parsley. Round out your meal with a granita, a popular shaved-ice dessert made in lemon and coffee flavors, among others.

Tuttocuore recommends making a day trip to the city from Sicily. “If you take the plane from Rome one way, it could cost 100 euros, but if you’re taking the bus or boat from Sicily it might be just 10 to 20 euros.”

Avoid the town in the late spring or early fall—that’s when most vacationers seek out the idyllic off-the-sea breeze. Summer offers nice discounts, along with sweltering temperatures. But if you come for the sights and not to swim, consider visiting around November.

The Masai Mara offers a spectacular variety of wildlife. Sam Kigongo, a former East African tour guide now living in Phoenix, says visitors can observe giraffes, crocodiles, rhinos, and zebras. “If you want to see lions you have to get up early in the morning,” he explains, “because when the sun comes out, they hide in the bushes.”

Consider hiring a guide to show you the premier spots for wildlife. Among these are the campgrounds near the Mara River, where hippos and crocodiles congregate. If you’re lucky, you might see a rare black rhino near the Ngama Hills.

Kigongo recommends staying inside the park, calling it “much safer” than surrounding areas, which are cheaper but leave travelers more vulnerable to crime. The State Department has issued advisories concerning theft and kidnappings in Kenya, and urges travelers to register with it before leaving home.

The dry season (December to March) tends to attract the most tourists and so is the most expensive time to visit. The best rates are available in late March to May and in October and November, when the weather is rainy and visibility can be limited. Kigongo says the reserve offers a great experience any time of year except July and August, because these months “are very dry and animals cross into Tanzania or vice versa.” Still, even this season is an attraction, as many travelers enjoy witnessing the annual wildebeest migration.

“Wailea’s fantastic,” especially the shores of Ulua and Mokapu, Lonely Planet’s Reid says of this coastal town in southern Maui with a reputation for luxury. “I guess the one thing about Hawaii in general and certainly with Maui is that most of the resorts are very full-featured, with plenty of things to do right at the hotel,” Seidenberg of says in agreement.

More adventurous vacationers will have many options, like taking a snorkeling cruise around Five Caves or a bike ride down the dormant volcano Haleakala to view the sunrise. “You have to get up in the middle of the night,” Seidenberg says, as most tours leave the area hotels around 3 a.m. Because the biking is downhill, the journey is not strenuous, she adds, calling the view “unbelievable.”

In the evening, visitors can enjoy the amethyst-hued sunsets while taking a leisurely stroll along the 1.3-mile path that connects the Wailea beaches to the resorts. “You can spot humpback whales offshore,” Reid notes.

Maui hums year-round, but the peak travel season coincides with the rainy season of mid-December to mid-April. To save money, tough out the winter at home, so you can head to paradise in late spring or early fall.

Bora Bora, one of the Leeward Islands in the South Pacific, offers luxurious accommodations ranging from floating, thatch-roofed bungalows to dedicated spa suites. Filmmaker Letia Clouston and her husband, Matt, who live in Los Angeles, have stayed at the all-inclusive, no-hassle Le Méridien Bora Bora, which boasts its own sea turtle conservation lagoon, where guests can swim with the turtles. “There are rooms with glass floors that are located over the ocean,” says Clouston. “It’s unbelievably beautiful.”

Clouston also recommends taking an ocean excursion to snorkel with black-tipped sharks and stingrays. But visitors can also hike up 2,400-foot Mount Otemanu or take 4x4 safari tours on the island’s interior roads. For more leisurely touring, Bora Bora offers sunset catamaran cruises (“the most peaceful moment in our lives,” Clouston says), walking Matira Beach, or exploring the town of Vaitape for a few souvenirs, such as black pearls and wood carvings.

You can also enjoy the warm friendliness of Bora Bora’s residents. “I came down with a sinus infection and a complete stranger drove us to a pharmacy,” Clouston says. (Non-French speakers should invest in a phrasebook, though, as not many islanders speak English.)

Airfare to Bora Bora and lodging on the island are quite expensive. The summer months (November to April) are humid with lots of rain, greater hotel discounts, and fewer visitors. But if you’re coming all this way, you might want to splurge for the idyllic weather of the peak season (May to October). “We were there in July, and the weather was perfect,” says Clouston. “Warm sun, ocean breezes, and very little rain.”

This resort area on the southern side of Kauai has long been popular with newlyweds, as it tends not to attract noisy young families or spring breakers, and leisure activities are endless, says Lonely Planet’s Robert Reid.

“A couple day hikes take in Hawaii at its most unreal,” he explains. “The coastal Mahaulepu Heritage Trail goes by ancient sand dunes, overlooking pounding surf, and the relatively flat four-mile round-trip hike to Hanakapi’ai Falls gets the payoff of a gentle swimming hole below a 100-foot waterfall.”

“The helicopter tours are always spectacular,” notes’s Seidenberg, because “you can see the coastline and volcanoes, and the weather and water are so beautiful.” Most of the excursions will take you around the stunningly rugged and virtually inaccessible Na Pali Coast on Kauai’s northwest side.

If you want a more intimate view, you can sign up for a kayaking or snorkeling expedition around the area. For ultra-romance, Seidenberg says, couples can enjoy one of several sunset cruises, which offer champagne and, in the winter, whale watching.

For the best discounts, fall may be the season to make your romantic getaway.

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