Where’s a fun place to stay and play? A promising residential destination for those looking to expand their property portfolios needs good airlift, security, sporting and recreational amenities, solid legal, financial and political frameworks, fine weather and fast broadband. Distance from metropolitan centres used to be an issue, but, post-Covid, digital nomads can work from anywhere. Naturally, it should also have that X-factor.

Many islands in the Caribbean tick all those boxes, so the region is currently seeing growth driven by North and South American as well as European buyers, who like the blend of work-life balance, dazzling maritime landscapes, constantly improving infrastructure and attractive tax regimes on offer.

The febrile political mood in the USA and violence in Mexico only increase the allure for North Americans of English-speaking havens a short-haul flight away. Traditional destinations such as St Barths, the Bahamas, Barbados and the Dominican Republic are well established. Others are now coming onto the radar. 

The British Overseas Territory of Anguilla has some of the best beaches in the Caribbean, a newly expanded airport with direct scheduled connections to a host of US cities, and an efficient FBO. By an amazing cyber fluke, it also has the hottest internet country code on the planet, namely .ai, which has raised multimillions for the local economy. In 2025, income derived from .ai domain-name registrations accounted for “about 47 per cent of the national budget”, according to José Vanterpool, Anguilla’s technology minister.

A private villa at Cap Juluca, on Anguilla (Image © Belmond)

The 26km-long island has some of the region’s most celebrated five-star hotels, which is the way most potential buyers first experience Anguilla. On a raised bluff above Meads Bay, Malliouhana has been a hospitality and culinary institution for a generation. Refurbished post-Hurricane Irma, it boasts an outstanding restaurant helmed by chef Kerth Gumbs, a full-service spa and access to the idyllic Turtle Cove.

A few kilometres south, the distinctive Greco-Moorish villas of Cap Juluca, its four eclectic restaurants and Guerlain spa are strung around the south-facing white-sand beach of Maunday’s Bay like exotic pearls on a Tiffany necklace. The Belmond property’s reputation for unrivalled service on a world-class beach attracts travellers from around the globe but particularly North America. And having experienced Anguilla’s charms, some now want a home on the island.

On a cove immediately to the west of Cap Juluca, Port Nimara is a brand-new nautical development due to open for the 2027/28 high season. At its heart will be a 118-berth marina able to accommodate 75m yachts, with a dedicated customs and immigration facility. The first 26 pontoons were installed in May. On shore, there will be 17 waterfront villas and eight condos in the first phase, as well as, in due course, a 62-key Equinox hotel, restaurants and bars.

A first look at Anguilla’s forthcoming Port Nimara development (Image @ Port Nimara) (Image © Beach Enclave)

“It’s a transformative project for Anguilla,” reckons local realtor Steve Haines of Trophy Properties. “Together with increased airlift – also a game-changer – Port Nimara is perfect for yachting types fed up with the prices on St Barths and gridlock on Sint Maarten. Anguilla has no franchised restaurants, no jet skis, no casinos and very little crime, and we have the ever-reliable English legal system. All in all, it’s a safe landing strip for Americans who make up 80 per cent of our clients.” Canadians, Brits and the Swiss, flying in through Sint Maarten, are in the market as well.

Beach Enclave on Rendezvous Bay, also being sold by Haines, is another scheme launching this year. Twenty-two homes, of which the pick is five oceanfront villas, are being built with luxe amenities that include a beach club and restaurant, wellness centre, racket club, dedicated concierge and private chefs. “Anguilla is on a roll – it’s an exciting time,” says Haines.

Other Caribbean projects that catch the eye include the 42 Mandarin Oriental Residences on Grand Cayman where completion and move-ins are expected in 2028; the Goldwynn Penthouses atop a 14-storey tower on Cable Beach, Nassau; and the Nevis Peak Residences being built beside the golf course at the Four Seasons on Nevis.

Indoor-outdoor living at one of Beach Enclave’s villas on Anguilla’s Rendezvous Bay

“Many factors are driving a lively Caribbean real-estate market, especially retiring baby boomers with available money,” suggests Suzanne Gordon of Sugar Mill Real Estate on Nevis. “Rather than moving to warmer climes in the southern USA, many Canadians as well as Americans are now choosing quieter places, like Nevis, away from the political fray, as their bolthole.”

The Abaco Club on Great Abaco in the Bahamas, originally founded by Peter de Savary, is another good example. This is today a mature 200ha private community with a magnificent new beach club on Winding Bay to go with new tennis, padel and pickleball courts, plus a spa on the way. The Cliff House continues to provide fine dining with lofty views out over Sean Connery’s favourite 18-hole tropical links.

The latest residential offerings include The Cays Reserve, 19 spacious beachfront residences of which 11 have already sold; The Green collection of turnkey cottages facing the golf course; and The Ridge Estates, eight premier homesites waiting for buyers to design and build their dream houses with views towards the Atlantic. Now under the Southworth umbrella, Abaco combines privacy with laid-back charm, set along three kilometres of pristine beaches. It all makes for a heady, rum-based cocktail. 

The oceanfront 17th hole at The Abaco Club (Image © The Abaco Club)

Elsewhere, at Jolly Harbour on the sheltered western side of Antigua, the chic daytime beach-club brand Nikki Beach – better known in St Barths, Ibiza and Saint-Tropez – is planning to build 127 residences in three four-storey apartment blocks, together with seven four-bedroom villas. The development, which also includes a hotel, is backed by Canadian-Antiguan businessman Calvin Ayre.

On a seven-hectare site between the marina and Jolly Beach, there’s a 50m-wide strip of public seashore separating the edge of the resort hotel from the ocean, so good security will be needed to maintain residents’ privacy. Jolly Harbour is rather run down, so the developer will also need the government to buy into the renovation of the area to attract the nautical nomads and investors making up their target market.

As with a number of other Caribbean islands, there’s an opportunity to acquire a local passport. These somewhat overhyped Citizenship by Investment schemes are generally disliked by immigration authorities in the USA, Canada and the EU, so although they do promote easy access to 150 or so other countries, their value is seen by many to be increasingly dubious.

One more notable proposition in the region is Emerald Caye, a private four-hectare island off the coast of Belize on which Six Senses are building 16 beachfront villas as part of a resort that features a signature spa, two restaurants and a kids’ club, all a 15-minute boat ride from the nightlife, shopping and airport at San Pedro on Ambergris Caye. Around the Caribbean, as elsewhere, the siren call of branded residences continues apace.

The arresting Caribbean view from an Emerald Caye villa, on the coast of Belize (Image © Six Senses)

European Momentum

The other beneficiary of global insecurity is southern Europe, from Greece in the east to Portugal in the west. On the Adriatic, Montenegro is in the queue to join the EU, possibly in 2028, and already uses the euro. It also has, in the beautiful Boka Bay around which towering green-clad hills tumble into Europe’s southernmost sea fjord, a perfect playground for sailors, which also happens to be a Unesco World Heritage site.

Porto Montenegro was the first, and is still the most prestigious, residential community on the bay, now with designer shopping, a jazz festival, a diverse range of restaurants and two five-star hotels overlooking a marina with more than 500 berths for yachts up to 250 metres. 

The latest residential phase to launch is Vero & Versa, a collection of just over 200 apartments, some of which have been bought by lifestyle investors, others by yacht skippers wanting a home base close to a good international school. The cream of the crop, with details still being finalised, is a 550sq m four-bedroom penthouse with a swimming pool on top of the Vero building.

A bird’s-eye view of the sprawling Porto Montenegro, on Boka Bay (Image © Porto Montenegro)

Airlift into Tivat Airport, about seven kilometres to the south, has expanded substantially in recent years, with scheduled flights arriving from all over Europe. The golf course at nearby Luštica Bay, when finished, will be the final piece in this already multihued Montenegrin jigsaw.

Of the Greek Cyclades islands, Mykonos has the best service infrastructure, nightclubs and choice of real estate. A-listers love renting private, gated estates and, after a slow 2025, Beauchamp Estates reports some are now buying. The agent has gone the extra mile in establishing its own concierge service on the island: if you want a Cohiba to smoke after dinner – it’ll find you one.

Beauchamp has a range of modish villas on its books both for rent and sale, of which Villa Kyanos, overlooking the sea in Houlakia, is a prime example. Seven en-suite bedrooms and a pool set into a sunset-facing terrace, a short drive from the clubs and restaurants of Mykonos Town, add up to a dream home with exceptional rental potential. A brand-new Four Seasons has just opened on the island, adding lustre to this ancient Aegean diamond.

Heading northwest, in the Venetian Lagoon, the 29ha private island of Santa Cristina, the domain of various Swarovski family members, is on the market for the first time in over 40 years. The main 860sq m villa sits in mature gardens with multiple terraces and organic orchards leading down to the dock and boathouse, while a farmhouse (or “casa colonica”) provides a further 565 square metres of air-conditioned living accommodation. This is a trophy residence on a truly grand scale.

Below: a glimpse inside Manifattura Tabacchi’s enticing Futura residences, not far from Florence’s historic centre (Image © Savills)

Also in Italy, for those who like a little culture with their pasta, Manifattura Tabacchi in Florence is a particularly exciting prospect. The city centre, however glorious its architecture, is overrun by tourists, so far better to live a 15-minute drive to the northwest where a 1930s-era cigar factory is being converted into a collection of apartments, ateliers, shops, restaurants and a fashion college reflecting the city’s creative DNA.

In the first phase, there are seven of 34 high-ceilinged Zenit apartments and 98 new Futura units left to sell. Some have ample roof terraces with views to the Arno river and Parco delle Cascine to the south, and the Duomo to the east. Conveniently situated on the way to the airport, this is an opportunity to buy into a vibrant, youthful community with an ambience similar to the King’s Cross regeneration scheme in London.

In Antibes, John Caudwell’s Le Provençal has now finished its major restoration, with 40 per cent of its 36 luxe apartments already sold. Once the Hôtel Provençal – in which the Duke of Windsor and Wallis Simpson, as well as Cy Twombly, Jean Cocteau and Pablo Picasso wined and dined – this grand projet is close to the Hôtel Belles Rives (decked out by Burberry this year) and across from the site of the annual Jazz à Juan festival.

Just launched, the five-bed Villa Jardin – which boasts more than 560 square metres of interior space – is a ground-floor home with about 925 square metres of private terraces and landscaped gardens enclosing an 11m private pool. A lucky buyer could move straight into this fully dressed, lavish turnkey home in the heart of the Côte d’Azur. It’s a seductive proposition.

Inside Villa Jardin, a five-bedroom hideaway near Cap d’Antibes (Image: Caudwell)

Overtaking the Algarve and Lisbon, the hip locale for buyers who like Portugal is now the Alentejo, with Comporta and Melides on the super-cool end of the scale. Excellent surf beaches, pine forests, eco-friendly houses and quiet neighbourhood restaurants are very much the vibe. Discovery Land’s CostaTerra is up and running with the Pine Barrens Villas, a collection of 30 turnkey homes inspired by traditional Alentejo farmhouse design, its latest offering.

Fresh on the market, Six Senses Residences Comporta has just been launched, next to a new 70-key hotel. Set within a protected nature reserve, 58 two- to five-bedroom residences – designed by Michaelis Boyd to reflect Comporta’s ethos of low-density, low-rise living – are due for completion in 2028.

Foreign investors put €3.9 billion into Portuguese real estate in 2025, up 10 per cent year on year, according to the Bank of Portugal. From being principally a retirement destination, the country is seen today as a much more dynamic lifestyle buy. In uncertain times, new finds and old favourites in southern Europe and the  Caribbean represent the crème de la crème for discerning global buyers.