These groups are generally better connected among themselves than with other groups, so you are probably better advised to target them on this basis. As it’s your first time to Greece, you may want the full-on Greek island experience and you could easily fill your five weeks flitting from one island to the other in the Cyclades. You could start in Kea and work your way down to Milos via Kythnos, Serifos and Sifnos then segue to Paros and Naxos. Dip down to Santorini, up to Mykonos and back to Piraeus. The map will also show plenty of other Cyclades islands to pick and choose from such as Ios, Sikinos, Folegandros, Amorgos, Syros, Tinos and Andros – yes! too many choices, but you will find that sticking to one group it will be easier to get between them. Realistically for a period of five weeks you will not want to be doing more than 6-8 islands.

Hi! I have fallen in love with the cyklades and have visited Santorini, Ios, Naxos and Folegandros in late june. Folegandros was the best, a fantastic island. We are now thinking about going to Paros the last week in September. Naoussa seem to be a great place. What’s the weather like in late September? Is it still quite warm? I also wonder about the sea conditions. May the sea be rough at that time of the year? I don’t like wavy ferry rides 😨 Thank you for a good sight!
Beach Day: Spend a day on one of many beautiful small beaches and bays, including pebble and sand beaches. Beaches to check out are Pocukmarak (the biggest beach on the south side, which also happens to contain a stone sarcophagus and two covers in the water that are around 1500 years old), Tratica, Carpusina and Sotorisce (the biggest and the most popular beach on Silba).

Congress passed the Air Transportation Safety and System Stabilization Act (P.L. 107-42) in response to a severe liquidity crisis facing the already-troubled airline industry in the aftermath of the September 11th terrorist attacks. Through the ATSB Congress sought to provide cash infusions to carriers for both the cost of the four-day federal shutdown of the airlines and the incremental losses incurred through December 31, 2001, as a result of the terrorist attacks. This resulted in the first government bailout of the 21st century.[44] Between 2000 and 2005 US airlines lost $30 billion with wage cuts of over $15 billion and 100,000 employees laid off.[45] 

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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.
Fabulous site Dave! I am taking my daughter to Greece for 12 days in late May 2017 as a grad gift (yeah I know…, I think my Dad gave me a Timex watch, but I digress) and we are flying into Santorini expecting to spend 5-6 days there then ferrying over to Mykonos (not really sure why?) for a couple days. A couple days there and then flying into Athens for 2-2.5 days to inject some culture into what is otherwise somewhat hedonistic trip. I was wondering, after reading about other islands whether it is worth going to Mykonos. I’d love to go to Crete but it seems to be tough to squeeze that in. The original plan was to go to Istanbul for a couple days but it seems really sketchy right now. So is Naxos a better idea than Mykonos? Should we stay longer in Santorini? Is 2.5 days too much for Athens? Any and all info is appreciated.
Take everything you want Greece to be — olive groves and tavernas, fishermen and bakers leading quiet village lives, stone villas and cypress trees and brilliant bougainvillea — and put it on a tiny, Ionian island only reachable by boat: That’s Paxos. On the western coast, sheer cliffs, rock arches and 40 sea caves put on a stunning show. Daytrip to the neighboring island of Antipaxos for powder sand and water so aqua, it rivals the Caribbean Sea.
Folegandros – which means ‘iron hard’ in ancient Greek – is as barren as its name suggests. Fruit trees are protected from fierce winds by rings of stones. You won’t find sandy beaches lined with sunbeds; only limpid, pebbly coves, such as Katergo, Ambeli and Livadaki. Water taxis service some beaches in high season; otherwise you’ll have to scramble down rocky footpaths to cool off. On your way home, stop at Synantisi in Ano Meria for the island speciality of matsata (goat or rabbit stew with hand-made pasta).

Hi Dave! I’m planning my honeymoon for early September, starting from Santorini. I’d like to hit Naxos, Paros and finally Milos before returning to Athens. Is this order of islands doable? I’m most concerned about ferries being available to each of the islands, especially Paros to Milos. Are ferries routinely available daily in September? Also, for all these islands would three full days each be too much or not enough? My wife and I aren’t into nightlife, just looking for relaxation, great beaches, beautiful water and amazing food! Thanks!
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.)

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Blaca Hermitage in the south of the island is a must-visit, as well as Vidova Gora Mountain, which is the highest peak on the island, offering you stunning views across the Adriatic and to neighboring islands on a clear day. Brač is also where you’ll find the famous Zlatni Rat Beach, one of the absolute best Croatia beaches (and even in all of Europe) and a wonderful place to spend a day. This all makes Brač one of the best islands near Split, a perfect day trip from Croatia’s second-largest city.
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It’s a tough call. The good news is that whatever you decide, it will feel like the right thing after you’ve done it. You’ll almost certainly say to yourself, “I’m so glad we saw both islands” or “I’m so glad we had 6 full days on Santorini.” In deciding I would ask whether a return trip to Greece is likely or possible in the next couple of years. If so, then spend your 6 days on Santorini and explore that island, then return to Crete at some time in the future for a deserving 7 to 10 days. But if this is a one-time deal for the foreseeable future then do 3 days on Santorini and 3 days in Crete. (Whatever you decide don’t do a day trip to the other island as it’s not worth the time and effort.)
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The Ionian Islands are a quite different entity to the more familiar Aegean islands. There are in effect only seven of them plus a sprinkling of satellite islands that make for a very enjoyable package. They are different from the point of view of flora – they are greener and less barren than their Aegean cousins and they share a different history to the rest of Greece and the other islands, having absorbed much Venetian and Italian influences over the years. This is particularly apparent in the Old Town of Corfu where you could be forgiven for thinking you might be somewhere in Italy.
The sleeper hit of the Cyclades, Serifos is the summer retreat of interior designers and architects who prefer to keep the sandy beaches to themselves. (One French home-owner is so protective of her hideaway that she tells all her friends she summers on nearby Sifnos.) Even in August, you’ll find coves where you can skinny dip in blissful solitude. That’s because the best beaches (Kalo Ambeli, Vagia, Skala) are only accessible via bone-rattling dirt roads or donkey tracks. Better still, rent a motor boat from the laidback harbour, Livada. Make sure to moor outside Anna’s taverna on Sikamia beach for freshly caught fish and garden-grown salads.
Hi Dave! Your website is so detailed and helpful! I’m starting to plan a trip for late May-early June. We were interested in visiting Santorini, Naxos (we opted for Naxos instead of party-filled Mykonos) and Milos. Our main airport of arrival is Athens. What order should we visit all three islands (in terms of convenience of ferry/flight availability) and how many nights do you recommend allotting to each? Thanks in advance for your time!

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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. 

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