A throwback to a gentler, slower, more elemental way of life, Astypalea is surprisingly easy to get to (daily one-hour flights from Athens). Every gap in the burnished hills frames a different view of Hora, cascading from the Venetian castle to seaside Skala. The scent of saffron biscuits wafts through the whitewashed lanes. Tucked beneath the battlements, Castro bar has a magical terrace that seems to float above the archipelago.


Once Greece’s ship-building centre, Syros still has a boatyard at Neorio. But the most splendid legacy of the shipping industry are the manor houses in Vaporia and Poseidonia. The beaches are slightly less splendid — with the exception of Delfini, Varvarousa, and Aetos in the wild north. But fabulous seaside tavernas abound: Ambela (ambela.gr) for fresh fish; Iliovassilema (chefbougiouris.gr) on Galissas beach for samphire and sea-urchin salad and rockfish soup; Allou Yallou (allouyialousyros.gr) for lobster with orzo. Perhaps the prettiest restaurant of all is Mazi (mazi-syros.com), a vine-covered courtyard festooned with bougainvillaea. Before you leave, stock up on loukoumi (rose-tinted Turkish delight) and San Michalis cheese from Prekas delicatessen (prekasyros.gr), and visit Zylo (zyloeyewear.com) for hand-made wooden sunglasses.
Where to stay in Crete: A 300-year-old hamlet surrounded by olive groves, Kapsaliana Village Hotel exudes peaceful authenticity. On a sandy bay just beyond Chania, Ammos Hotel smartly combines Scandi chic with a child-friendly vibe. Blue Palace Resort & Spa beats the (stiff) competition in Elounda with its spiral stone Isola Beach Club, thalassotherapy spa, and boat trips to Spinalonga island, a national monument just across Mirabello Bay.
The village square should be your first port of call on any Greek island: settle into your favourite café, pick up local gossip, and adjust to the languid pace of life. On Folegandros, this presents a challenge: the cliff-hanger capital, Chora, has not one but three squares, each brimming with a jumble of cafés, tavernas and dinky raki bars. We recommend Pounta (pounta.gr), where the Danish owner makes (and sells) the lopsided cups and bowls in which your coffee and Greek yogurt are served. From Chora, zigzagging steps lead up, up and away to the only real landmark, Panagia church; make the pilgrimage at sunrise (perhaps after an all-nighter at dimunitive Astarti bar).

Naxiots once made considerable fortunes exporting potatoes, cheese, marble and emery. Locals bequeathed undesirable seaside plots - useless for farming - to their laziest offspring. When tourists cottoned on to the island's scores of fabulous beaches, these wastrels found themselves sitting on gold mines. The west coast of Naxos is fringed with mile upon mile of powdery sands. Agios Prokopios and Agia Anna delight toddlers and teenagers alike with their shallow waters and beach bars. As you head south, the beaches get wilder: Plaka, where you can gallop across the dunes on horseback, Mikri Vigla for windsurfing and kitesurfing, and crystal-clear Kastraki.


Where to stay in Santorini: Trendier pretenders come and go, but Perivolas is still the most stylish and peaceful place to stay. If you have cash to splash, and can’t stand the crowds, take over Perivolas Hideaway, a waterfront villa on Santorini’s undiscovered offshoot, Thirassia, or Erosantorini, a stunning clifftop estate with a tiered pool plunging 1000 feet to the sea.
My boyfriend and I will be traveling to Greece on August 1-11th. We have 10 days. Is this a feasible itinerary for a couple in their early 30s who want beach, relaxation, good food, boating, and some history? Fly into Athens have one full day there then fly to Naxos for a day and a half, Milos for 3 nights, then Santorini for 3 nights, then back to Athens for our flight? We chose Milos over Naxos at first, but after reading your blog it seems the beaches in Naxos may be better?
Located in the Caribbean Sea, this Dutch-owned island is perfect. Voted one of the best in the Caribbean, Curacao is like being in tropical Holland. The town is built in the Dutch style, but the surrounding areas are all tropical. Hit the beaches, lay in the sun, and party the night away. This may not be Gilligan’s Island, but what it lacks in privacy, it makes up for in romance and fun.
Located in southern Thailand, this semi-off-the-map island is one of my favorites and the month I spent here remains one of my most fond memories. Here on Ko Lipe, the super-friendly locals bring in the daily catch for amazing seafood, as the island’s water is teeming with life. Accommodation is still basic, and most places turn off the electricity around midnight.
Unlike its luxurious Caribbean neighbors, here you’ll only find more budget-friendly hotels and guesthouses. Everything needs to come by ship or airplane, so it’s not super cheap. However, since no non-natives can own property there is no influx of overdevelopment, keeping the island simple but beautiful. For a more rustic, non-touristy getaway, this might be the island for you!

Located in southern Thailand, this semi-off-the-map island is one of my favorites and the month I spent here remains one of my most fond memories. Here on Ko Lipe, the super-friendly locals bring in the daily catch for amazing seafood, as the island’s water is teeming with life. Accommodation is still basic, and most places turn off the electricity around midnight.
The almighty church has kept nightlife in check. If you must see and be seen, head to quietly glamorous Astivi or Stoa bar, on miniature Agia Lesvias square, in Hora. Beach life is generally languid and low-key; Psili Ammos and Livadi Geranou are our favourite hideouts. Dinner reservations are essential at Benetos, for Med-Asian fusion on an organic farm, and Lambi for grilled fish on a purple pebble beach.
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