Greece
Naxos has everything. A headland marked by a temple ruin greets you as your ferry arrives.(There is also a small airport.) The harbour lies directly below the Old Town (Kastro), a maze of narrow alleyways on a steep hill and, at its foot, the new town (Chora) with plenty of shops and tavernas and a lovely sandy beach just beyond.
No need to hire a car; the island can be explored by bus and on foot to reach various small archaeological sites. For a whole island of antiquity take the day trip to Delos (with Mykonos thrown in).
The able-bodied should stay in one of the small hotels such as Anixis in the picturesque Old Town: plenty of steps but no traffic, not even bicycles!
Google map: bit.ly/i62Qs9
www.hotel-anixis.gr/
Amfitritis Str, Old Town of Naxos, 84300 Naxos Island, Cyclades, Greece
+30 22850 22112
By far the best way to visit Greece is to take a flight only into Athens then take the one hour bus ride to the port Piraeus. Have a mental list of islands you wish to visit - use the many ticket agents to find a conveniently timed ferry. Outside the period mid-July to end of August finding accommodation is easy as people will meet incoming ferries. In Naxos I recommend Hotel Galini in Naxos Town. Other islands worth visiting, which can be reached easily from Naxos, are Syros, Amorgos, Folegandros and Donhoussa. Read a good travel book before you go!
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