This little island has always had an air of quiet glamour. And nothing has changed – all that’s different are the beautifully boho hotels and a fresh, Greek-isle twist on the pop-up culture, says Julian Allason

The fading signatures in the guest book of the Poseidonion Grand Hotel read like a roll call of 1960s glamour: Elizabeth Taylor, Bobby Kennedy, Marilyn Monroe, Ingrid Bergman. Now, like the century-old hotel itself, the island of Spetses has undergone a discreet refresh, regaining its lustre as a playground for smart Athenians and the global jet-ski set.

Spetses is only a scenic two-hour voyage by hydrofoil from the port of Piraeus, or a two-and-a-half hour drive from Athens International Airport along lovely corniche roads. But that hire car will have to stay on the mainland, as the four-mile-long island remains a 19th-century outpost, powered only by horse-drawn carriages and wooden caiques. Surprisingly little has changed since the flag of revolt was raised against Ottoman rule outside the church of Agios Nikolaos on 3 April 1821. After that things went a bit quiet, the Spetsiots being content to commemorate the glory of Laskarina Bouboulina, the world’s first female admiral. Her mansion (www.bouboulinamuseum-spetses.gr) is largely unaltered. They still hand-build ships here. Afroessa, the lateen-rigged caique of King Constantine of the Helenes, is often at anchor, especially during the Spetses Classic Yacht Race (www.classicyachtrace.com) in June, when 1930s J Class and vintage vessels compete. ‘It’s yachtie heaven with bikini bodies,’ says a seafaring friend.

With good swimming off three sandy beaches and plenty of watersports, the island provides enough nautical adventure (and old-money glamour) to challenge Portofino, Bodrum and the Costa Smeralda as a cruising port o’ call, with the added panache of being home to the superyachts of the Greek ship-owning oligarchy (the adjacent islet of Spetsopoula is still owned by the Niarchos family). The latest innovations on the island are summer pop-ups by fashionable restaurants from the capital, notably Freud Oriental (+30 22980 74553; about £75 for two) which serves sea-fresh sushi and sublime aji tataki sashimi of striped mackerel. Superchef Christoforos Peskias has introduced a Greek tapas tasting menu, using tsipouro and ouzo, in the bar and on the veranda of the Poseidonion (www.poseidonion.com; about £65 for two).

Such competition has provoked a mini maritime foodie war. Tavernas such as Patralis (+30 22980 75380; about £45 for two) on Kounoupitsa beach counterattack with live grey lobster and spaghetti. Not to be outdone in freshness, Tarsanas (+30 22980 74490; about £40 for two), on the Old Harbour, barbecues fish caught that morning and serves it with lashings of local gossip supplied by the owners. At sundown the good, the bad and the gorgeous make for Tôle (+30 22980 74110; about £95 for two), the club, restaurant and bar successor to Figaro, the disco where Jackie Kennedy was courted by Aristotle Onassis. My nephew, Tom, a serial tech entrepreneur, so enjoyed his evening here that he could recall nothing of it. Returning the following night, he was greeted by a round of applause from the staff. Spetses is like that: transgressions will happen wherever superyachties put in for shore leave.

As one strolls up winding streets past the fish market, the action moves away from boutiques such as On the Deck (+30 22980 773344), which stocks boatie fashion from Blumarine, to traditional shops such as Isola di Spezie (+30 22980 73982), which sells powerful pine- tree honey and aromatically spiced local olive oil. In this part of town, Nikos the barber still applies his cut-throat talents to well-lathered gigolos. Suddenly one is in the Greece of Patrick Leigh Fermor, and it seems not entirely improbable that an old sea dog will unscrew his peg leg to emphasise a point made over flaming glasses of ouzo.

Last autumn’s successful launch of Amanzoe (www.amanresorts.com; pavilions from £1,005), across the water on the Peloponnese mainland above Porto Heli, gave an unexpected boost to the Greek travel industry. The hotel, in essence a contemporary acropolis on a hilltop commanding the Argolic Gulf, has 38 exquisitely designed guest pavilions with private pools. And the restaurant (+30 275 4772 888; about £45 for two) does a light take on Peloponnesian cooking – with sensational views. Amanzoe is also introducing a new generation of monied visitors to Spetses, speeding them to the island on its fleet of powerboats. Next year, openings are scheduled in Porto Heli of a Chedi hotel, with the promise of impeccable service, and of a funky Nikki Beach club, suggesting the injection of non-stop dance music to the local mix.

None of the above is to imply that this sunlit corner of the Aegean is unaffordable. Prices are lower than in 2011, more so than might be accounted for by currency variations. The water-taxi fare for up to eight passengers to Spetses from Kosta on the mainland is £17, about a quarter  of what one might pay in Venice. A couple of drinks at the seafront Roussos café (where the people-watching is very convivial) came to under £6.

Spetses does both luxe and value places to stay, but with a dash of island boho. The upmarket option is the handsome, all-white bedroom decor of the aforementioned  Poseidonion Grand Hotel (doubles from £135) on the seafront, a 1914-vintage landmark which enjoyed a major refurbishment a few years ago. When I check in, the TV in my bedroom is showing the Greek Strictly Come Dancing, featuring men with Zorba moustaches in white tutus and tights. On the terrace, groups of beautiful young women are clinking glasses with distinguished men; later they return to gleaming, black yachts in the star-lit harbour.

One value-for-money hotel option on the island is Zoe’s Club (www.zoesclub.gr; doubles from £80), a romantic apartment-hotel with a pool in the old town. Another is the intriguingly named Orloff Resort (www.orloffresort.com; doubles from £100), which sounds like glitzski in Sochi, though there is no trace of Black Sea flash in this imaginatively designed compound of studios and apartments. Best of all is the hotel’s mansion, an atmospherically restored 19th- century sea captain’s house sleeping 10. Another large-party alternative is to rent a stylish villa through Five Star Greece (www.fivestargreece.com).

Spetses works from Easter until October, though my favourite time to visit is in early September for Armata, the annual re-enactment of the island’s greatest naval victory in 1822, when a two-week art festival culminates in a sea battle and the burning of an Ottoman warship to the backdrop of a spectacular firework display. ‘Money up in smoke,’ sighs my friend Katerina. ‘We Greeks do that better than anyone.’