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Island Hopping

We would like to spend four weeks island hopping in Greece. We have been to several islands as part of a cruise but now we would like to spend several days on the islands we will visit. We have recently retired so we are open to suggestions for any islands and times to visit. First, when is the best time to visit? We like to hike, spend time on the beaches, and just enjoy exploring the islands. We had been thinking of September. We also are planning on taking the ferries. We understand that we will be greeted at ferry docks with people with their three ring binders trying to entice us to stay at their place. We were thinking of doing that rather than make reservations In advance. Have any of you done that and how did it workout? Which islands would you consider a must see and which ones are lesser known gems? Is there anyplace you would avoid? Anything else that would be helpful as we start planning this trip? Thank you for any and all help!

Posted by
4171 posts

This September?

With four weeks, I'd definitely spend some time on Crete.

As for leaving places to stay to chance, I wouldn't do it. I've been working on a trip to Greece for October this year and it's amazing how many lodgings in our price range are already booked up and have been for awhile.

Keep in mind that September is still considered "high" season in most of Greece, so prices will reflect that. Weather will be warm, but being from Yakima, that shouldn't be an issue for you.

Posted by
2788 posts

You do not mention if you have a guide book yet. We took RS Greece tour last month and found his guide book tailored to mostly that tour. We also had a Lonely Planet guide book of Greece which covered the country much better. Both are available for purchase elsewhere on this web site. You might also want to click thru to RS Greece Tour to see where we went on that tour. Happy travels.

Posted by
3130 posts

The most comprehensive and informative publication regarding the islands is T. Cook's "Greek island Hopping".

Posted by
1396 posts


September is a great time to do the islands. Still warm but not baking, and the crowds are beginning to thin.

I would feel comfortable about just turning up and finding rooms on the day. Lo might be right that a lot of places which book on line are already booked, but the majority of rooms don't have online booking and just work on an ad hoc basis. I've never had a problem in September and, assuming you are happy with clean, comfortable but not over fancy accommodation I doubt you will either.

Have a great trip.


Posted by
3130 posts

If you do decide to show up somewhere without reservations be aware that sometimes the rooms that are offered at the ferry ports are not in the best of locations, so try to gather as much information as possible about the various villages on the islands you choose to visit. Find a map you can print out. The touts will give you a free ride to their rooms but are under no obligation to return you to the port or anywhere else, for that matter. Things to check: clean water, hot water, water pressure, electricty (24/7 or limited?), A/C (is there any and is it free?), sewer smells in bathroom, moldy shower, secure door locks.

Posted by
16894 posts

I have traveled this way several times in Greece and only ever made hotel reservations in Athens (to secure a low-budget option). Buying ferry tickets and finding rooms locally as you go is easy and always worked well for me in towns and islands of all sizes. It's much easier than trying to figure out ferry schedules ahead, and they often are subject to delay, anyway. People who show up at the dock or bus station have empty rooms and may be willing to deal, but the prices are usually low to start with. If they need to drive you to the room in their car, then that's especially a time to check where it is and how you can get back. Of course, I do travel with Rick's Greece book when visiting the regions it covers and use Lonely Planet for everything else. If you end up as far east as the Dodecanese chain, then I suggest the tiny islands of Lipsi and Agathonisi.

Posted by
2144 posts

Start by getting the Thomas Cook Greek Island Hopping book, as was previously suggested. It will give you a good idea of the ferry connections, both within each group and between groups. The exact ferry schedules listed in the guide may change from year to year, but it gives you a starting point. It gives suggested itineraries for each of the main island groups (the Cyclades, Dodecanese, Northern Aegean, etc.). And it has good little descriptions of each island.

Lonely Planet Greece guidebook also gives you some suggested itineraries. My book (7th edition) has a "Best of the Dodecanese" which we have done most of. A wonderful journey. We loved the Dodecanese. Gorgeous scenery, truly welcoming people, great food, low prices.

Island hopping works best when you stick to islands that have good ferry connections between them. That generally means they're in the same island group. The island of Paros is an exception .... it's a hub for ferries to/from several of the groups. What you DON'T want to do is pick out a half-dozen random islands you'd like to see, and try to figure out how to hop between them. If you try to combine, for example, Lipsi, Santorini, Crete, Lesvos, Corfu and Skopelos you would have a nightmare.

The big Blue Star ferries make regular, reliable runs through the islands. You could build an itinerary around Blue Star schedules (we did that once). Works very well. You can also check multiple ferry line schedules on

September is a wonderful time to travel. You may be met at the docks by people with rooms on larger islands, but not on the smaller ones. If no-one meets the boat, look for a travel agency (saying "Accommodations" or "Rooms") or a hotel near the dock. Or, what we usually do, is the night before we are leaving for an island we will call hotels on that island and check for availability. Take your Lonely Planet book with you, or an iPad. Then we don't have to wonder about where we'll be sleeping. Usually we'll rent a car for just a day on each island. Some islands we just spend 2 nights, some 6. Every island has ATMs and wifi. We personally prefer the smaller, less-touristed islands to the larger, more well-known ones. But that could just be us.

Let me know if you have any questions. I envy you!