At a certain point in one’s life — involving financial security, luxurious tastes and the nearing of retirement age — avid travelers may want to choose vacation destinations with an eye toward relocation. You may be serious about the possibility, or it may just be a back-of-mind fantasy. But such trips could be life-changing.
“When retirees are in ‘splurge mode,’ I encourage them to be strategic about it: choose a blow-out trip in a place you could actually imagine living one day, then just enjoy it as a holiday,” counsels Federica Grazi, founder and managing director of Mitos Relocation Solutions, which focuses on retirement in Greece. “If the idea of staying longer keeps nudging you while you’re having your morning coffee or evening drink, that’s a powerful data point before you ever open a spreadsheet about taxes, visa or cost of living.”
Grazi says that a luxury stay is not about replicating your future retirement abroad; it’s about removing friction so you can really feel the country. “Great service, beautiful surroundings and no day-to-day stress give you a clear emotional signal: Do I feel at home here, or not?”
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However, she says, “The real risk with ultra-luxury is that you become too disconnected from the country you’re trying to ‘test’. If your goal is to explore a place as a potential retirement destination, the sweet spot is luxury that’s deeply rooted in the local territory — local food, local culture, local people — with five-star comfort layered on top.”
Here are some splurge experiences (both city hotels and self-contained resorts) that maybe, just maybe, turn into something more permanent.
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The ivy-covered Hotel Raphaël may not be the costliest place to stay in Rome’s historic center, but its location, just to the west of Piazza Navona, is incomparable.
It’s lovely, private and exclusive, to most travelers, a hidden treasure (check out the rooftop bar), but within walking distance to the Pantheon and the Trevi Fountain. Ristorante Santa Lucia, featured prominently in the film Eat, Pray, Love, is just steps away.
Price: When Romans flood back home after the boiling heat of summer, expect prices to spike to over $600/night in September at Hotel Raphaël.
Accessibility: Taxis can be difficult to flag down in the Eternal City, but the hotel’s staff will hook you up in no time.
Health Care: Hospitals in Rome are top-rated.
Safety: Rome is generally safe, but keep an eye out for pickpockets. Secure your valuables.
2. Antigua, Caribbean
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“In Antigua, the standout experience is Jumby Bay — a private island that has long been a favorite of high-profile guests for its exclusivity, arriving by private jet and private ferry,” says Joe Rice, head of citizenship programs at Global Citizen Solutions.
“For a paired experience, you can take a boat to Barbuda for a day at Nobu. From November to April, which is peak yacht season, rent a yacht in Barbuda for a few days on the water. Many travelers use local concierge services, such as CaribLife, to organize their time there.” Real estate options on Jumby Bay are expansive and diverse.
Price: A Jumby Bay cottage is $3,000+ in high season
Accessibility: Buggies and boats will take you anywhere you want to go.
Health Care: To seek medical care on the main island of Antigua, expats obtain travel insurance to access the private system.
Safety: Security is ultra-high on this private island.
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“Madeira is a favorite among affluent Portuguese families, especially over New Year’s Eve when the fireworks light up the entire bay,” enthuses Patricia Casaburi, CEO of Global Citizen Solutions. “It’s a beautiful and comfortable escape with mild weather all year and a relaxed pace, making it ideal for retirees looking for somewhere easy yet with impressive landscapes.”
Price: Reid’s Palace, A Belmond Hotel, an institution set on a seaside rock outcropping, offers rooms starting at around $850 during high season.
Accessibility: It’s probably best to rent a car for comfort and freedom to explore, but buses and taxis are available.
Health Care: The island’s Hospital Particular da Madeira is your best bet.
Safety: Rated extremely safe.
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“Swimmers and epicureans will swoon over the Belle Epoque Four Seasons Grand-Hôtel du Cap-Ferrat, situated on a hill that overlooks the Mediterranean on the French Riviera,” says luxury travel adviser Becca Hensley.
“Do laps in the oceanside pool where Picasso, Paul McCartney and Elton John — among others — jumped in, then eat a well-deserved dinner at Michelin-starred Le Cap. The property encompasses some 17 acres of gardens and epitomizes classic French glitz.”
Price: Over $3,000/night is a typical high-season rate, but you may be able to snag a $2,000 room in October, at the end of the season. Note that the hotel is closed for winter refurbishment until March 6, 2026
Accessibility: The French Riviera has all the conveniences of a highly developed area. There is ample train service on the coast and deeper into France.
Health Care: High-quality service, with a public option for residents and private insurance for better service.
Safety: The Riviera is generally safe, but as in all touristed areas, take precautions against pickpockets.
5. Vienna, Austria
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“For holiday stays for those with a sweet tooth, check into Vienna’s Hotel Sacher,” Hensley recommends. “Located next to the historic Vienna State Opera House on the renowned shopping street Kärntner Strasse, the lavish hotel is famous for its decadent chocolate Sacher Torte.
Don’t miss the Albertina Museum — and in season, enjoy the plethora of holiday markets located near the hotel.”
Price: Though the bare-bones rate may start at around $600, once spring hits, expect room rates of around $1,200. Prices can drop to around $700 in the summer, as people seek out beach destinations.
Accessibility: You name it in this walkable city: apps, buses, trams, trains, bike rentals.
Health Care: Vienna has all the hospital options of any major city in a highly developed country.
Safety: Vienna is an extremely safe city to visit and live in.
6. French Polynesia
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To hole up inside an overwater villa at The Four Seasons Bora Bora is to experience nirvana, and if you never want to leave the property, a small number of private homes is available for purchase ($5 million is a typical asking price).
Price: Per night, a $2,500 price tag is typical.
Accessibility: You can walk or request a golf cart ride all over this sprawling property. It takes roughly 45 minutes to fly to Tahiti (and a short ferry ride to nearby Moorea), where you should rent a car or hire a driver to see the sights.
Health Care: Hospitals are located in Tahiti, French Polynesia’s main island, and at the gateway to its international airport.
Safety: Not an issue at one of the world’s top private island resorts. Crime is low in Tahiti’s capital of Papeete.
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“For city lovers, a splurge stay in central Athens or on the Athenian Riviera — for example at a grande dame hotel near Syntagma or at the Four Seasons Astir Palace in Glyfada — lets you test a very different retirement model: museums, concerts, excellent healthcare and an international airport within easy reach, plus the islands just a ferry ride away,” Grazi says.
Price: At the start of the swim season in April, rooms at the Four Seasons fetch starting prices over $930.
Accessibility: The metro, buses and taxis are all readily available, and the city has made strides to make major landmarks more accessible.
Health Care: Athens has a plethora of high-quality hospitals, and Greece in general offers high-quality care. Health care is free or heavily subsidized, even for expats.
Safety: Violent crime is low in this generally safe capital.
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“In Cyprus, I’d send a retiree considering Paphos to somewhere like Anassa for their money-is-no-object trip,” Grazi advises. “You get a very soft landing: Mediterranean views, strong spa and wellness offerings, and easy day trips to the harbor, archaeological sites and nearby villages. If that combination of sea, climate and scale feels right, it’s worth exploring what a more everyday version of life there could look like.”
Price: Starting in high season in the last spring, expect pricing of $600-plus per night at Anassa.
Accessibility: Though there is a bus system, most visitors opt for taxis and car rentals.
Health Care: Cyprus boasts high-quality health care in a range of hospitals throughout the island.
Safety: Low crime rate and generally safe.
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The lush InterContinental Fiji Golf Resort & Spa provides a soft landing in this far-flung South Pacific archipelago. It’s located south of the major city of Nadi and is encircled by lovely beaches. Once you’re at the resort, everything is there, from spa to water sports to golf.
Price: Fiji’s dry season, from May to October, is the best time to visit, with rates ranging from $500 to $600 a night.
Accessibility: The hotel offers complimentary self-parking. A car is a good way to discover the island.
Health Care: Nadi’s Pacific Specialist Healthcare is highly regarded. International health insurance is recommended.
Safety: Fiji is a safe place; just take normal precautions with valuables.
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The one Latin American country that should be on every pre-retiree’s list is the land of “pura vida.” The still relatively undeveloped Papagayo Peninsula, located on the country’s west side (Atlantic coast), features top-tier hotel brands such as Andaz and Four Seasons. Water sports are plentiful, and inland trips to waterfalls and hot springs are readily available.
Price: Rates at the Andaz and the Four Seasons land at around $2,000 a night, give or take.
Accessibility: Cars are a necessity if you live off the peninsula (note that Papagayo offers increasingly interesting real estate options, with residents allowed access to the exquisite beach club). If you’re visiting, you can make do with hotel transport, but if you are moved to snap up a property, a car is a good idea.
Health Care: Esteemed hospitals, both public and private, are located in the capital of San Jose. The health care system is so respected that San Jose is known for its medical tourism.
Safety: Papagayo Peninsula is well-guarded and extremely safe; the country is also considered safe (outside of some dicey areas in San Jose).