Lefkada is the island that’s not an island. You can drive to it across the causeway from the mainland, but it feels every bit an island. Aristotle Onassis bought the satellite island of Skorpios here as his own bit of getaway paradise. Beaches, windsurfing, boat hire, good food and wine are all here and there are few built-up package resorts. The main tourist area is centred on Nydri.
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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.

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.

We would love your help, we are a party of four 50 plus adults from Australia and never have been too the Greek Island. We’re not sure whether we should be going to naxos or paros , we are there for 4 days and not sure whether just to stay on one island and ferry to the other and if you think possible even a day trip to santorini. Our priorities are culture and history, swimming in beautiful beaches, 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 will be our one big holiday this year as we will be celebrating my 50th birthday while there so want it too be special.
Hey, sailors: In May, the 35th annual America’s Cup heads to the pink-sand beaches of the Great Sound, a prime time for racing enthusiasts. The event’s official hotel partner, The Hamilton Princess & Beach Club, transformed its “pink palace” with new guests suites, exhale spa, a state-of-the-art marina and three new restaurants including celebrity chef Marcus Samuelsson’s new venue, Marcus’. The upcoming Ritz-Carlton Reserve hotel and branded residences plan to open a mega-yacht marina in time for the race, but keep this island on your long-term radar: Michael Douglas and Catherine Zeta Jones break ground on the redevelopment of the famed Ariel Sands resort in 2017.
Antigua is a small island that is often grouped with its nearby neighbor Barbuda. A popular gambling destination, Antigua has a good selection of casinos. It also has plenty of other exciting nightlife, including great restaurants, cafes and discos. The beaches are also spectacular, and you can find literally hundreds of them, with both white and pink sand.
Located in the middle of the Indian Ocean, the Maldives is a chain of 1,000 islands (200 are inhabited, and only 5 have any substantial population). The country is actually just a series of coral atolls that are barely above sea level. During the 2004 Tsunami, many of these islands were completely washed away. The government has built flood barriers to help lessen the impact of any future tsunamis.
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Hi, Dave! My husband and I will be going to Greece 8/26 – 9/4. We are flying into and out of Athens for cost efficiency. We really want to see Navagio Beach on Zakynthos for a day, and we realize this will likely be an overnight trip, or even 2 nights depending on the travel options. What is the best way to get from Athens to Zykanthos? What is the best way to get from Zakynthos to Santorini? Or is it best to just go from Zakynthos back to Athens and then to Santorini? We are trying to avoid additional flights but realize we may have to fly from Zakynthos to Santorini. 
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