Finally, and this is perhaps the best tip of all – as it’s the old-style romantic one – book transport to and accommodation on one starter island (Paros is a good choice). Sail/fly there, sit down relax, pour cold drinks and eat healthy Greek foods for 4-5 days while working out where to go to next with your tablet under an umbrella on the beach. Book your next stop online and go there. Repeat the exercise. No hassles about being locked into a fixed itinerary and if you like a place, you stay longer. If not, you move on. You will generally find transport tickets for a day or three ahead and hotel owners often know someone on the next island who can fit you in. In Paros, Petres Hotel is a good starting point. Good luck and happy sailing!

Cooing American and Chinese honeymooners line up to take selfies as the sun sinks behind Santorini's caldera, the flooded volcanic crater. That view may be a romantic cliché, but it still takes your breath away. A volcanic explosion blew out Santorini's heart 3,500 years ago, leaving black-sand beaches, vertiginous cliffs in psychedelic hues, and swirling rumours about Atlantis in its wake. The eruption also preserved the ancient city of Akrotiri under layers of ash, and created fertile ground for exceptional Assyrtiko grapes and Vinsanto wines. (Sample them at Sigalas and Vassaltis wineries, paired with delicate dishes that let the grapes sing.)
You seem to have your heart set on Zakynthos but I have to say it’s not a good use of time for a sort-of overrated payoff. Your time is much better spent (in my opinion) seeing another Greek island in the cyclades (maybe taking a ferry to Naxos or Paros sitting outside on the deck drinking a bottle of wine) rather than taking a bus and connecting flights. Zakynthos and Santorini/Mykonos are on opposite sides of the country and the only way from one to the other is by flying (or some combination of bus and ferry). So, my recommendation is to consider spending those Zakynthos days in Naxos, Paros, Milos, or some other Cycladic island.
Thank you for putting together such a great site. My husband and I are planning a trip to the Islands in May – neither of us have been and, honestly, have no idea where to even start putting together an itinerary. We have at least 14 nights to spend there (and may be able to push that to 17). I’m in my early 30s, my husband’s in his early 40s. Our priorities are culture and history, swimming, beautiful views, nice towns, and food and drink. We’re not interested in clubbing at all, but more laid-back late night bars definitely appeal. This is probably our one big holiday this year so while the budget is more mid-range than sky-high, we can push it a bit for the right places or experiences. We’re happy to take in quite a few islands, or with a mix of longer and shorter stays.

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.

Dubbed the Isle of Flowers and crowned by 4,583-foot Mount Pelee, Martinique may just be the Caribbean’s best-kept secret. Some exploration is required to uncover the island’s treasures, like the Balata Gardens’ Treetop Trail of suspension bridges, Saint-Pierre’s 18th-century theater ruins, and the poignant Anse Cafard Slave Memorial. This overseas region of France is also considered the rum capital of the world; follow the Route des Rhums to tour esteemed distilleries like Clement and Rhum JM.
Hawaii’s biggest island has everything you could ever want to do and more. But what separates it from the other islands is Volcano National Park. Explore volcanoes, climb through old lava tubes, and watch as new lava oozes into the ocean. Then there are all the waterfalls on the island, too. Big Island has it all. I mean it’s Hawaii — how could you go wrong?!
With so much on offer, choosing where to go island hopping along the Adriatic Coast can be tough. Maybe you want gastronomic delights, perhaps you want to party all night long? Or it is that you simply want a sandy beach? Do you want to sail to the islands or ferry from mainland? The various and varied Croatia islands offer culture, nightlife, history and of course relaxation. Find out which one is perfect for you in this Croatian islands guide.
Everyone knows the Venus de Milo (which has stood in the Louvre since the 19th century). Until recently, very few had heard of Milos, the volcanic island where Aphrodite’s graceful likeness was discovered. Those in the know jealously guard their treasured island, and especially its 70 (or more) beaches — surely the most diverse and dramatic coastline of all the Greek Islands.

Christened the Garden Island, Kauai’s splendor extends from its vermillion Waimea Canyon, plunging down 3,600 feet, to its rugged Napali Cliffs, stretching up 4,000 feet. Often dotted with dozing monk seals, Kauai’s Poipu Beach has appeared on Dr. Beach’s esteemed list of America’s Best Beaches. Rivers, rainforests and waterfalls garnish the interior; don’t miss a photo op of Wailua Falls, famously featured in the opening credits of Fantasy Island, which aired from 1977 to 1984.


I need to finalize plans for a mid-June trip, looking to stay 9-10 nights. Traveling with my wife and two sons (24 and 16). Definitely want to go to Santorini, Mykonos and Athens. Was considering 3 nights at each, but after reading on your site, I am thinking about stealing a night from Athens and spending 2 nights at Naxos. We want to see the major sights in Athens, can we do that in a day? Any comments on the itinerary given our group is welcome.
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.
Thank you for putting together such a great site. My husband and I are planning a trip to the Islands in May – neither of us have been and, honestly, have no idea where to even start putting together an itinerary. We have at least 14 nights to spend there (and may be able to push that to 17). I’m in my early 30s, my husband’s in his early 40s. Our priorities are culture and history, swimming, beautiful views, nice towns, and food and drink. We’re not interested in clubbing at all, but more laid-back late night bars definitely appeal. This is probably our one big holiday this year so while the budget is more mid-range than sky-high, we can push it a bit for the right places or experiences. We’re happy to take in quite a few islands, or with a mix of longer and shorter stays.
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