A complicating factor is that of origin-destination control ("O&D control"). Someone purchasing a ticket from Melbourne to Sydney (as an example) for A$200 is competing with someone else who wants to fly Melbourne to Los Angeles through Sydney on the same flight, and who is willing to pay A$1400. Should the airline prefer the $1400 passenger, or the $200 passenger plus a possible Sydney-Los Angeles passenger willing to pay $1300? Airlines have to make hundreds of thousands of similar pricing decisions daily.
Chania is a great choice. A wonderful charming town. Elounda is great for a quiet laid back stop, Agios Nikolaos has a more interesting vibe and is more of a real town. Also very charming. I prefer Ag Nik but Elounda has more luxurious hotels. (Crete hotels.) Naxos has lots to see in the interior so if you didn’t explore then certainly consider that. Folegandros and Milos are both incredible. Folegandros is more suited to walking and relaxing (and has some top notch restaurants and hotels). On Milos you need to do a tour and get out and actively explore to do it justice. Geologically Milos is stunning. A little like Santorini but with better beaches.
While technically a subtropical island, the Azores make for a great getaway if you’re looking for something beyond the standard resort getaway. The islands boast tons of hiking and beautiful nature. Rent a car and explore the winding roads of the main island, São Miguel Island, taking it secluded beaches and picturesque waterfalls. Best of all, it’s close to both Europe and North America and makes for a great stopover point if you’re traveling between the two.

Islets of Proizd and Ošjak: Visit the islets of Proizd (a famous beach in the area) and Ošjak – two of the most visited destinations in the area. Proizd is a small island that can be reached by a small excursion boat featuring three beautiful beaches with turquoise waters, several walking trails and a small restaurant and cafe. A day trip to this island is highly recommended. Ošjak is known as the Love island because of its beautiful nature, peaceful surrounding, and tranquillity. Enjoy swimming in unspoiled waters, walking through a dense pine forest and exploring an interesting cave. 

Sarah-Jane — Thanks for another helpful article (this one on planning an island-hopping trip). Chasingthedonkey.com is a great website and my first go-to place for information on Croatia. I have scheduled my third 3-month-long stay and still have so much to do and see in Croatia. Personally, my favorite times to visit are in the “shoulder” seasons …. September-November and March-May.
To island-hop some of the most beautiful havens in the world, book a trip to Asia, which lays claim to six of this year’s top 15 destinations. But if you only have a week, you’ll hardly suffer. Each of the islands on this list is worth a visit on its own, from the perennial World’s Best list-makers Maui and the Galápagos to Portugal’s rising star, the Azores, with its friendly locals and awe-inspiring landscapes.
Since airline reservation requests are often made by city-pair (such as "show me flights from Chicago to Düsseldorf"), an airline that can codeshare with another airline for a variety of routes might be able to be listed as indeed offering a Chicago–Düsseldorf flight. The passenger is advised however, that airline no. 1 operates the flight from say Chicago to Amsterdam, and airline no. 2 operates the continuing flight (on a different airplane, sometimes from another terminal) to Düsseldorf. Thus the primary rationale for code sharing is to expand one's service offerings in city-pair terms to increase sales.
The 1978 U.S. airline industry deregulation lowered federally controlled barriers for new airlines just as a downturn in the nation's economy occurred. New start-ups entered during the downturn, during which time they found aircraft and funding, contracted hangar and maintenance services, trained new employees, and recruited laid-off staff from other airlines.
Kefallonia was severely shaken by an earthquake in 1953 and thereafter lost its quaint gloss. The picturesque northern port of Fiskardo however, escaped much of the destruction and remains to this day one of the main focal points for visitors to the island, so is a good spot for a stay of 2-3 days. Pretty, waterfront cafés and restaurants and a cosy, folksy feel predominate. Asos, between Fiskardo and Argostoli is a west coast ‘resort’ village that pulls in its fair share of visitors and the view down to Asos from the main island road is one of the most photographed spots on Kefallonia.

Ferries are not really cheap any more – certainly not like they used to be – but the vessel fleet is better, safer and faster than in previous years so the cost is justified. You can get exceptionally cheap deals on longer-haul routes if you are prepared to forego a booked seat: €14 v €40 on a run to a mid-distant island, but it’s probably wise to consider taking fast catamarans to get to core islands (Mykonos, Santorini, Paros etc.) and even then, go the extra 10/15% for Business or even VIP class for the extra comfort. On longer hauls it can be cheaper to fly if you seek out flights online and book beforehand.
Ferries between Naxos and Milos don’t start until June 7th (one each way, every day after that). Ferries between Santorini and Milos start April 28th and there is one every day in each direction. And there are always ferries between Naxos and Santorini. So if the dates work I would fly to Santorini (the longest leg) then ferry to Milos then Naxos and back to Athens. But if you need to travel between Naxos and Milos before the 7th then ferry Athens to Milos to Santorini to Naxos and back to Athens.
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.
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Fiji is poised for a comeback after 2016’s Tropical Cyclone Winston, the most severe on record. The quintessential Fijian Jean-Michel Cousteau Resort on Savusavu Bay reopened in September with 25 newly thatched houses known as bures. For total seclusion, guests are ferried via seaplane to the remote Kokomo Island, a new collection of 21 bures and five villas on uninhabited Yaukuve Island.
What’s most stunning in Bali — dazzling beaches like Nusa Dua, Seminyak and Jimbaran Bay? Ubud’s terraced rice fields, sacred forest and ancient monuments? Or the island’s 10,000 intricate temples, including Pura Empul (the one you bathe in) and Uluwatu sea temple? Experience all of the above and decide for yourself. The Land of the Gods also boasts a loveliness that is more than skin-deep, thanks to its warm people and ubiquitous, inclusive spirituality.
Hi Dave! One more question, do you know of any resorts with heated pools or private jacuzzis/pools in the room that are heated on islands other than Santorini and Mykonos? Looking for something above 26/27 degrees and can’t seem to find any! Elounda Beach resort said they could heat the private pool but it costs 45 EUR per degree! Hoping you know of another option that would allow us to swim comfortably in Early June. Thank you!!
Zakynthos, or Zante, has shrugged off its reputation as a destination for lads on tour (as long as you avoid Lagana and the built-up south coast) by rebranding itself as Greece's greenest island. It's not just the emerald hills sliding into the electric blue Ionian: much of the south coast is a nature reserve where endangered loggerhead turtles hatch in the sand. The turtle beaches are off limits, but there are countless coves in every hue of green and blue. Favourites are tiny Xigia, with its bubbling underwater springs, and craggy Porto Limnionas, with sunbeds wedged between the rocks and palm-frond umbrellas positioned between the pine trees. Skinari is the starting point for boat trips to the most famous landmarks, the Blue Caves and Shipwreck Beach, where a rusting liner leans into the chalky cliffs. From Keri, you can cast away for Marathonisi island, another turtle sanctuary.
Where to stay in Andros: Food stylist Allegra Pomilio hosts intimate cooking retreats at Melisses, her family’s elegant villa overlooking the submerged ancient city of Paleopolis. Ktima Lemonies, an elegant estate surrounded by lemon and olive groves, is less than a mile from Hora but feels light years away. At Onar, an organic farm with a smattering of cottages overlooking Achla beach, you really are miles from anywhere.
Krk is a large island and it has many towns and villages to explore, as well as fun campgrounds and resorts to stay at. Connected to the Croatian mainland by a bridge, this is a very accessible island. Krk has varying landscapes, with an arid feel to the north, a lush green side to the south, full of bays and beaches, and the interior is hilly and rocky. If you want to enjoy wildlife then head into the woods on one of the many walking trails and see what you can spot!
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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