As a starter to explore ferry services, go to the Ferryhopper.com and punch in your route searches. Note: air travel between islands is not generally good. Air travel is normally only feasible between Athens (or other mainland destinations) and the island in question. Some exceptions do exist – Rhodes Kastellorizo, Kos-Leros-Astypalaia, Thessaloniki-Limnos-Ikaria etc. but again you will need bookings weeks in advance.
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.
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.
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.

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.
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.
Located on the eastern coast of Malaysia, the Perhentians consist of two islands. Both are stunningly covered with a lot of palm trees, wide beaches, and crystal blue water. There’s not much to do here, and visitors typically lay on the beach all day, resting from last night’s drinking. It’s the perfect place to put up a hammock. A strong monsoon season limits when to go to between March and October. During the other times, it’s best to head to Thailand, where the weather is nicer.
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.
Hi Dave, going to Greece in September from the 3rd to 18th. Paros and Milos are pretty much decided but we are not sure about adding a 3rd island. We arrive in Athens early in the day from an overnight flight so will be jetlagged. My husband is staying on for an additional week near Thessaloniki. We have already visited Athens, Aegina, Crete, Santorini, Mykonos, Paros, and Rhodes. My husband isn’t really a beach person and I love the beach so we do need a mix of things to do. We are pretty fit and enjoy being Active. Great restaurants are a must. Any suggestions?

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.


It’s rare to have a sizeable international airport just minutes from the main attractions of a place, but Las Vegas has always been a place to break the rules. Its airport handles flights from all over the world, and it’s just 2 miles from the Strip. Free shuttle services and an onslaught of taxis await to whisk you to your hotel. Minutes later, when you’re out exploring, there are numerous ways to get around. It can often be quicker to walk between casinos especially when the traffic’s gridlocked, but taxis and buses ply the Strip and surrounding areas too.
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Nine weeks in Greece is a dream itinerary it certainly gives you lots of flexibility. As you seem to have Athens and the Peloponnese sorted, you just need to sort out your five weeks on the islands. What you need to realize, however, is that the islands are not all mutually interconnected, but rather they are ‘grouped’ – both administratively and from the point of view of transport routes. Here are the main groups.
Question: Is it worth taking the evening ferry on the 4th Sep to Crete (Heraklion) from Santorini, then the bus onto Chania so that we can do the Samaria Gorge on the 5th? Spending the full day in Chania on the 6th and taking the last flight out of Chania that night back to Athens? (or do you think this is trying to squeeze in too much in too little time)?
Close to this island is a little island that provides excellent snorkeling opportunities. You may even spot a few reef sharks. Bathtub-warm water and fine sand beaches kept me here for over three weeks. It will do the same for you. Visit between November and March for the best weather and the fewest people. May through October sees a harsh monsoon season that shuts the island down. The best way to get there is by boat from Pak Bara.

Unlike its luxurious Caribbean neighbors, here you’ll only find more budget-friendly hotels and guesthouses. Everything needs to come by ship or airplane, so it’s not super cheap. However, since no non-natives can own property there is no influx of overdevelopment, keeping the island simple but beautiful. For a more rustic, non-touristy getaway, this might be the island for you!
I think Naxos would be the best island for you: incredible beaches, wonderful villages, great restaurants, and some very good hotels (though I don’t think I’d go so far as to call them hip – but nice, for sure). The farther south you go from Naxos Town the quieter the beaches get – so keep going to find the balance you prefer. If you want an island with a little more hip but beaches not quite as perfect then try Paros. If you want to err on the quieter and idyllic side then Antiparos or Ikaria.
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Considering your interests (great food, hiking, beaches, nightlife unimportant) then Naxos should definitely be your other island. (And Naxos has many daily ferry connections with both Santorini and Athens.) Also, Athens needs at least one full day to explore so you should drop any thoughts about Delphi or Nafplio. Also, I would look into flights from Athens to Santorini on your night of arrival. If you could get to Santorini that night (and move your day in Athens to the end of your trip) you’d almost gain an entire day and could spend two nights on Naxos.
These little coral islands are surrounded by excellent diving, snorkeling, and white sand beaches, and are filled with friendly locals. Private resorts litter the islands, and a vacation here is also very pricey. Luckily, Bangkok Airways offers cheap flights to and from Thailand. The best time to go to the Maldives is from November to May, when the weather is cool and dry. June through October sees wetter and hotter weather due to the monsoon season.
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