My fiancee and I are heading to Greece in July. We’ve been to Naxos, Paros, Mykonos, and Santorini. This time we plan on being there July 1 to 23. We’re definitely including Milos, and one of Paros or Naxos. Any recommendations for other islands? Any particular ferry routes we should consider? Some “less touristy” islands are a must (for at least one island). We can be lively or very chilled. Thanks and best wishes!
My husband and I are heading to Greece in July this year. We fly into Athens and then are connecting to Samos where we are meeting up for a friend’s 50th birthday celebration. We have 4 nights here and then another week to explore some other islands. We would love to visit Santorini although I know it is not close to Samos so not sure if that is the best option? We thought about Paros or Naxos for 3nts, and then Santorini for another 3nts. Then fly back to Athens and spend a couple of days here before we head for Dubrovnik. Do you know if there are ferries between these Island points and would that be the best use of our time? I guess we don’t want to waste too much time travelling between points! We are just playing around with ideas at the moment as Samos is the only part set in stone. Open to any suggestions as this is my husband’s first trip to Greece and my last trip here was with my parents about 35 years ago!

We are having trouble deciding on another island to go to besides Santorini (we both want to go there). I was hoping you might be able to make a suggestion. We are not really into late night partying/night life. We LOVE good food..quite possibly the most important item on our list. We also like to hike, my husband is very into history, we love beer/wine, we could definitely be into in a less populated/touristy type spot. Gorgeous beaches and great views are also a plus.


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Hi Dave. Thank you for your amazing website! We (30’s / 40’s couple – no kids) used your recommendations last year in September and visited Santorini (7days), Milos (3days) and Crete (12days) before spending 3 days in Athens. The trip was amazing and Greece is calling us to go back again this year! We have a conundrum which we are hoping you can assist (well, many of them really!)
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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!!
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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.


I’m a little worried I’ll get bored in Milos. My husband likes to stay in one place, but I like exploring. We would have split our time more evenly but we want to stay on the caldera and it’s just too expensive to stay any longer than two or three nights. Alternatively, we could stay in Santorini for longer but move to a cheaper hotel. Perhaps Santorini 6 nights and Milos 6 nights?
I would recommend Naxos over Mykonos and with 12 days you could easily add Paros too. With Santorini, Paros, and Naxos you’ll get a good mix of different delights and some ferry island hopping too which is fun in itself. 1.5 days in Athens is perfect for most – 1 day for the Plaka, Parthenon, Acropolis Museum area; and a half-day to visit the Archaeological Museum which is a short drive or walk from the Plaka but hard to fit in one day along with the other sights.

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We are planning to come back at the start of September for 2 weeks to visit different islands for some beach and sun. To give you some background, we loved Santorini, Milos and the quieter / smaller places in Crete (Loutro, Falassarna, Samaria Gorge). We enjoy beach time, some hiking, site seeing, good wine / food and good / buzzy atmosphere at night for dinner / tavernas.
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.
Zakynthos is an island of certain extremes: beauty and crass, mass tourism of the worst sort. The islands – like all the Ionian islands is lush and verdant and boasts the now famous ‘shipwreck beach’ (Navagio) that many seek to travel to and swim at. Yes, it’s worth it and numerous excursion boats make the run from ports on the west side of the island. Environmentalists and capitalists clash daggers at Laganas where the mass tourism trade is carried out to the detriment of the Caretta Caretta, or loggerhead turtle that loves the beach as much as British tourists on a binge. Read this page for the background. There is an alternative scene to Laganas at Vasilikos over to the east, but it is much more low-key and less busy.
The other groups are best tackled individually. For example, the Ionians have no ferry connections to the rest of the Greek islands; the same story with the Sporades and the Argo-Saronics. The NE Aegean islands do have a link to the Dodecanese and the Cyclades but are probably best left for another trip once you have got the feel of the rhythm of the Greek islands.
Comfortable accommodation in May for 2 persons can be found for between €40 and €80 per night. A meal for two that includes a starter, two main meals, salad and a litre carafe of local wine will cost you around €25-35. This can vary widely depending of level of establishment you eat at. A cheap vegetarian dish (pulses or vegetable) will set you back by no more than €5-6 a plate. If you get your breakfast included at the hotel, that is good because breakfast can add another €15 for the two of you per day.
My husband and I are heading to Greece in July this year. We fly into Athens and then are connecting to Samos where we are meeting up for a friend’s 50th birthday celebration. We have 4 nights here and then another week to explore some other islands. We would love to visit Santorini although I know it is not close to Samos so not sure if that is the best option? We thought about Paros or Naxos for 3nts, and then Santorini for another 3nts. Then fly back to Athens and spend a couple of days here before we head for Dubrovnik. Do you know if there are ferries between these Island points and would that be the best use of our time? I guess we don’t want to waste too much time travelling between points! We are just playing around with ideas at the moment as Samos is the only part set in stone. Open to any suggestions as this is my husband’s first trip to Greece and my last trip here was with my parents about 35 years ago!
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!

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