Greek Islands itinerary advice, please!

Personally, I find Santorini to be too touristy and soooooo over-rated! OK if you like mingling with the hordes descending off cruise ships each day. It was so much nicer 10 years ago.

You don't say when you are visiting. I would recommend either the Pelion area, which isn't an island, but has the feel of an island - gorgeous scenery and small villages without being over-run with tourists (they all speak English) OR Skopelos plus Alonnisos (linked via a ferry). Skopelos is the more bustling, but with monasteries tucked away in the hills, which makes a good day's walk and Alonnisos is probably what Santorini was 40 years ago. Alternatively, just visit Crete - enough history and walks here to occupy you for a month or more!

Hydra is fine. It's upscale but still has a lot of Greek left to it. The best thing is there are no motorized vehicles allowed on the island. All transportation is done by donkey giving you an impression of the "Old" Greece. It's mostly a hang-out island with no beaches to speak of, no archeological sites, lots tavernas, shopping, and one of Greece's nicest waterfronts and lovely houses up and away from the waterfront. It does offer great hiking if you want to get away from people. It's good for a two night stay. Santorini on the other hand is one of the most heavily touristed islands in Greece. Lots of crowds, large cruise ships lying off the island, high prices, but spectacular scenery. If you like that it will be fine. However, there are a number of other islands that will give you a real Greek feeling, some even have airports which makes traveling to them easy: Astypalea, Naxos, Paros, Milos, Limnos, Skyros, Kythira and a few others. After Hydra you take the ferry/high speed boat back to Athens then get to the airport and fly to an island of your choice. It may be a little difficult for logistics to time the flight, though.

Actually, I think Hydra and Santorini make for a very interesting combination of attractions. You won't be sorry if you visit these two. There are some excellent hiking trails on Santorini as well as 2 archaeological sites, museums, and of course, "That View!" Flying there from Athens is a good use of your time. If you plan it right you can take the Airport Express Bus X96 right from the ferry port to the airport when you return from Hydra. The bus leaves Piraeus every 30-40 minutes.

The only reason I would go to Santorini would be for it's World-Class Archeological Sites. The views would be secondary. However, the crowds and costs keep me from doing so.

The hardest part of a Hydra-Santorini trip would be coordinating how to get from Hydra to Piraeus then to the Airport then to Santorini. It would have to be timed very carefully and in Greece that could be a problem! You could miss connections, you could have a very long wait at the airport or numerous other things that could throw timing off.

A lovely and overlooked island is Aegina just a short boat ride from Piraeus. It would be a lot easier than Hydra-Santorini because all you have to do is get back to Piraeus from Hydra then time the ferry ride to Aegina. Aegina has one of the best preserved temples in Greece, archeological ruins just outside the main town which is lovely, several fishing villages, an abandoned Byzantine Village, ancient olive trees, hiking, lots of neo-classical buildings and great tavernas and so much more and best of all still is Greek.

Consider substituting Paros or Naxos for Hydra. This would simplify your logistics ... ferry to Paros/Naxos, ferry to Santorini, fly back to Athens.

If you're interested in archeology/Greek mythology, you can take a day trip to the sacred island of Delos from either Paros or Naxos. If you choose to do this, you'd probably subtract a night or two from Santorini and add it to Paros/Naxos.

Making connections between Hydra and Piraeus in time for a plane to Santorini shouldn't pose any real problem. Even now, in the off-season, there are 3 ferries/day on that route. During the summer months there are up to 6 ferries per day, and they only take 1-2 hours. There are as many as 4 flights/day from Athens to Santorini during the summer months. The bus from Piraeus to ATH takes 75 minutes, so work that into your timing. Ferry schedules here: http://www.gtp.gr

We did the RS Athens and the Heart of Greece tour this past summer. You can easily travel between Hydra and Athens by catching the hi-speed ferry. You really only need 2 nights on Hydra and 2 nights on Santorini. Hydra is good for relaxing meals and a nice hike to the beach (water taxi back). On Santorini the traffic is crazy so plan for public transportation. We spent 3 nights on Naxos (very lovely beaches) and took the regular ferry to Santorini. We stayed in Oia and spent the first night/next day exploring that side of the island. The day we left (8pm flight) was spent on a tour of the island with Costas (#1 on Trip Advisor), who took us all over the island and dropped us a the airport. In hindsight, we wish would have stayed on the south side of the island to avoid the crowds and for the breathing space. You may want to consider just a few nights on Santorini and adding in 3 nights on another island. We really loved the relaxed feeling of Naxos and how easy it was to get around town, although our purpose on Naxos was to lay on the beach and not move, which is why we did not get around the whole island, just to the Plaka. You will LOVE your trip, I know I did!

Hydra and Santorini would be a great combination (IMO), and as pointed out by others the transportation logistics shouldn't be overly difficult.

You didn't say when this trip would be taking place, but in terms of "crowds" at Santorini the island is large enough that you can usually find some free space. For example, I wandered around the village of Prygos for part of an afternoon and didn't notice any other tourists. On the same day, I had lunch at a small roadside Taverna and again no other tourists there (but of course at the same time, FIra and Oia were swarming with tourists).

One tip though - plan on buying bottled water in both locations. Be sure to try Mastika (I should have brought a couple of bottles home, as I can't find it here).

I am just going by your expressed interests (sightseeing, r & r, good food, culture/history AND hiking), and based on this, I'd second Charlene's & Julie's advice -- NAXOS. Not only is it an easier connect than Hydra, it has more of what you say you want. (Hydra for some reason, is almost the only isle beside Santorini that Rick promotes). Not much culture/history to check out in Hydra, the main deal seems to be, no-car ruling, so only donkeys -- but in other less-touristic isles once u go inland a bit, back roads are rustic, little traffic, even sheep flocks. If you are interested in swims, better look at alternatives.

I'd suggest fly to Santorini for 2 nights/3 days, then at 3:30 pm, take BLUE STAR ferry to Naxos. It has best beaches in Cyclades (about 15 miles golden sand, in a string, either stay right on a beach or take a frequent bus for 15 mins or so). Also best hiking in Cyclades; see this expert http://www.cycladen.be/NaxosEng.htm The port town is fascinating, a maze of lanes, history galore, forts, castles, ancient ruins, and great shops (at 1/2 price of Santorini). NAXOS is largest, most fertile isle, go inland a few miles and farms, sheep, vineyards ... In the little groceries near tourist lodgings, you often see a basket of fresh-laid eggs on counter. Despite great amenities, not overwhelmed by tourism because port doesn't accommodate cruise ships, airport doesn't take big planes. We vets usually recommend doing your Athens 2 days last, unless the Rick thing starts with them. You can return to mainland via BlueStar ferry (2 sailings per day, the 6pm one gives u a final Naxos day), or flying (small jet 1x per day). Of course, also possible to reverse this --first Naxos, then ferry (2+ hrs) to Santorini, then flight back to ATH airport.

It would be easiest to recommend which, if we knew exactly what the Rick tour entailed (i.e. start in Athens hotel? End where?).

Thanks, fellow travelers! I think we will do Santorini and Naxos, for a total of 7 or 8 nights. We can't resist the beauty of Santorini, and Naxos seems like it meets all our needs. And we will be there in mid-late May so should beat the crowds--or we'll just deal with them 😊

Bakerdogs, you have chosen the PERFECT time, in my experience ... between May 15 - June 15 is ideal, weatherwise, the sea is just a little brisk for the first 30 seconds, then WONDERFUL ... and everything is open but nothing's crowded. Mornings, about 65-70 ... warmest time of day, 3-4 pm, 80-85 ... sunset is about 8:45 (!!) and it's back to about 70 (a sweater over the shoulders). And (as long as you don't leave the lights on in your room after dark) virtually no mosquitoes.