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Thoughts on 2+ week Greece/Island Itinerary

I love this sight! so helpful, thank you in advance.
My wife and I (60+) are planning a 25th Anniversary trip for Oct 2025. We want a good mix of sights, food, history and culture, we are not partyers. Thinking Athens (3), Peloponnese/Olympia (1), Corfu (3), fly to Santorini (2or3), Naxos (4). Was also interested in Rhodes and/or Crete but want this to be relaxing and not cram too much in. Thoughts?

Posted by
2693 posts

You're being fooled by the tourist brochures. It's impossible to see all these places in such a short time.

Corfu is in the Ionian Islands, Rhodes in the Dodecanese Islands, Santorini and Naxos in the Cyclades, Crete in another location, Olympia is in the Peloponnese at the other end of Greece, an 8-hour round trip from Athens.

There are no flights between the islands, you'll have to go back via Athens.

Except for a few rare exceptions involving overnight ferries, there are no ferries between the different island groups.

The maximum you can see in 12 days (not including arrival and departure days) with a fairly busy schedule, being optimistic and optimizing your itinerary is, for example: Athens + One site in the Peloponnese + One island in the Cyclades (or Crete).

Posted by
3467 posts

Jo-Lui (as usual) is so perceptive ... please take her advice! (BTW, you get best advice when you say (1) WHERE you're coming from -- from Western US or Canada, it's much longer/more exhausting journey and (2) WHEN in October -- 1st 2 weeks vs last 2 can vary a lot for weather & "open" island facilities). Besides the limits she mentioned, ferry skeds in Cycladic islands v limited AND fast-ferries often affected by rough seas (either cancellations or seasickness). BTW your 1-day allotment for Peloponnese means you have yet to look at a map.

IF you say "2+" I take that to mean involving 3 weekends -- i.e. landing by noon on a saturday, and 2 weeks later, leaving Sunday AM. This gives you 14.5 days. -- and I recommend Oct 4-19. Here are 2 feasible itineraries to research:
(1) Day 1 FLY afternoon to CHANIA Crete for 5-6 days; from HERAKLION fly FRI am to ATH, Rent car, Drive to NAFPLIO in Pelops for 4-5 nights... Return Car to Airport, final 4 nights in ATHENS
(2) DAY 1 Fly Afternoon To SANTORINI for 2 nights - Large BLUE STAR ferry (2 hrs) to NAXOS (4 nights) Fly AM to ATH, rent car drive to NAFPLIO for 4 nights, return car to airport, final 4 nights in Athens
I've done a version of each, with newcomers, and it can be enjoyable & unrushed, IF there's good planning; if you're not up for details, consider using an Athens-based travel agency (Fantasy travel and Dolphin Hellas are often recommended on these travel forums). They are used to dealing entirely online with N. American travelers. They can handle the logistics of transport & hotels for an independent-travel visit for you ... leaving you the pleasant job of deciding on activities and dining.