Island suggestions after RS tour

I always recommend NAXOS, perfect for someone who wants historic/ancient sites, & scenery PLUS good food, friendly tavernas, great beauty. Here are a couple of Photo Albums to showcase its beauties -- not mine, they're by Naxophile "StanBR," most taken Late Spring but it's also lovely in Fall -- I've been there as late as Sept 25):
TEN DAYS in NAXOS - https://www.flickr.com/photos/stanbr54/albums/72157656336387898
TRIP around NAXOS - http://www.flickr.com/photos/stanbr54/sets/72157634605629689/
NAXOS TOWN - http://www.flickr.com/photos/stanbr54/sets/72157632094558042/

It's not clear if "I" is actually "we" or if you're going alone; I can say from experience that Naxos is just fine for a woman going solo -- it has a VERY good island bus tour (with a mid-day break for a swim), where invariably people meet other independent travelers & then meet up later for drinks or a meal. The best place to stay is at St. George beach directly adjacent to Naxos Town, easy10-minute stroll to town's cafes, tavernas, museum, shopping etc.

A ferry takes 5 hours, but a flight only 45 minutes. Theres a big Plus & a small drawback to flights: the Plus is that the airport is small, doesn't take big jets, so island isn't bombarded by tourist throngs. The drawback is only 2 flights per day in summer and 1 off-season, of a turboprop w. 40 seats -- so flights often sell out. But since you are looking faaar ahead and by knowing your dates, you can easily book a seat to and from. Furthermore if you sign up for an "account" at Aegean Air (that's really just getting on their list for e-mail alerts about special discount promotions) you can score a ticket for as little as €40 or so.. about = to conventional ferry, and less than fast-ferries. As always we vets suggest getting back to mainland the day or evening BEFORE a US flight out.

Haven't been to Corfu myself, not attracted despite all the Durrell books: several reasons -- you're going in October, Corfu is far northern isle, get cooler sooner, and rainy sooner. Also, its main shore towns can be somewhat UK "hives"; Corfu-lovers say you can avoid these package-tour havens by using car to drive to lesser-known spots ... but when I'm a solo traveler, I like to avoid the need for car rental... and Naxos has an excellent bus system that not only reaches outer beaches but all its inland villages.

BTW, in 2015, Trip Advisor issued a list of what it considers Ten Best Islands in the WORLD to Visit ... and in the whole of the Aegean - Mediterranean only listed ONE island. Not Corfu. Not Santorini. Not Capri. -- just NAXOS. See it before anything changes.

You may want to consider the island of Aegina just a short ferry ride from Piraeus. It's really a lovely island that is often overlooked because it's so close to Athens. However, it has one of the best preserved temples in Greece, even better than the Parthenon! There is an archeological site right in the main town with the remains of the Temple to Apollo. There is a centuries old abandoned Byzantine Village with lovely churches and fantastic murals. There is an ancient Olive Grove to explore, seaside villages, interior villages, great food and all within a short trip from the mainland.

The fact is, no Greek island is more than an hour's flying time from Athens, so that opens lots of possibilities. You may want to consider Rhodes, both for it's relatively warm October weather, and for it's historic sites.

Thank you for the suggestions of Aegina and Naxos. I'll look into both of them. I think I'll save Corfu for another time.

I would agree that Naxos is an excellent choice and if you have 2-3 days then that would be a good selection. Flights are available to Naxos but I believe are very expensive as compared to a ferry. You can do a test search for prices for this Fall on Aegean Airlines. If budget is not a concern then a flight will be your quickest means of transportation.

Naxos is one of Greece's nicest island with a good combination of Old & New World Greece!

We stayed at St. George Beach and loved it!

I would agree that Naxos is an excellent choice and if you have 2-3 days then that would be a good selection. Flights are available to Naxos but I believe are very expensive as compared to a ferry. You can do a test search for prices for this Fall on Aegean Airlines. If budget is not a concern then a flight will be your quickest means of transportation.

Naxos is one of Greece's nicest island with a good combination of Old & New World Greece!

We stayed at St. George Beach and loved it!

Either Aegina or Naxos would be fine.

Santorini is cliche/expensive, but does have the postcard views/sparkling white houses covered in bougainvillea in Oia, as well as amazing sunsets and a prehistoric site (you mention you like history). It has a volcano, hot springs, and wineries that you can tour, and is small enough that you can drive all around it on ATVs if that sort of thing is fun to you. Beaches didn't seem to be as nice as other islands in terms of the crystal-clear turquoise water, though we didn't visit every beach. I know Santorini gets a bad rap for being touristy, but honestly we had a lot of fun there. If I was only ever going to choose one Greek island to visit in life, I might pick one like Santorini - not necessarily because it is the best one, but because it has the postcard Greek Isles look that you always daydream about (we were going in with some specific expectations based on the photos we've always seen of the Greek Islands, and wanted to experience that in person. Walking around Oia early before the crowds arrived was almost like being in a storybook).

Naxos is much more low key than Santorini. This is good in some ways and not as good in other ways. The not as good part is that it's not quite as groomed and fixed up for tourism as Oia, Santorini, so at first we were a little disappointed with the dingier white buildings, dusty lots full of weeds, etc near our hotel in St. George. But then we discovered the main boulevard along the water as well as the old market area, both of which are very cute, so this island grew on us over time. It was much more relaxing (birds cooing in the morning and such), and had some beautiful turquoise water to swim in. It was fun to stroll at night, and was certainly less expensive. I believe there are some historic sites scattered here and there, though aside from the Portara, I'm not sure if there are any really huge ones. In the end, we wished we had another day there (particularly to drive around the island) and found ourselves feeling a bit nostalgic when it was time to leave. I'm not sure I would personally tell somebody to go to Naxos as their one and only Greek island, but it is certainly a nice pairing with one of the more touristy islands as long as you go with the right expectations. For reference, when you talk about scenery, we took several hundred photos in Santorini vs. maybe just 100 in Naxos, so that might give some reference for how photogenic each place is (both definitely have their beautiful portions for sure). That being said, most of our photos in Santorini were in Oia, which is so ridiculously crowded that it's not somewhere you'll want to spend most of your time...the other towns are probably not any prettier than what you'd find on Naxos. If you want "the quintessential look" and only have a couple days, then Santorini might be your place. If you want authentic in the sense of it being more Greek even at the slight expense of perfectly-whitewashed looks, or if you end up having longer to stay and want somewhere to relax/stroll/swim, then Naxos is your place.

We did stop by Mykonos for an afternoon, and I personally did not care for it at all. It seemed to be full of non-Greek stores (United Colors of Benneton, Louis Vuitton, etc). Everything seemed catered to English-speaking tourists (much more so than Santorini, in my opinion...at least most of the places we passed in Santorini still seemed to be Greek businesses and restaurants). But then again, my friend who recently went to Mykonos, Santorini, and Corfu said Mykonos was her favorite, so to each her own. In all fairness, we were only there a few hours and it was horrendously windy (meaning we were kind of just counting down the time till we could leave by the end), so perhaps we might have liked it better if we'd gotten the chance to move around outside of the main tourist center. But for me personally, I wouldn't have any desire to return there.

Hope you have fun!

PS, when you talk about reliable connections, I'm not sure whether there is more risk of cancellations with ferries or flights (leave yourself a good cushion either way, as weather does cause cancellations on occasion), but I think the main tip I'd have is if you do take a ferry, choose the slower Blue Star ferry. They are huge and minimally affected by weather, whereas the fast ferries like the one we took between Naxos and Mykonos get tossed to and fro when it is windy out, making for more of a white-knuckle experience (they were passing out barf bags) and a higher risk of cancellations. You mention not wanting to spend too much time on a ferry, so if you choose an island with an airport and don't mind a small plane (depending on the island), flying will definitely save you time. For reference, Athens to Santorni is 8 hrs by ferry (I believe) vs. only 45 minutes by plane. Also for reference, our plane tickets (we had to choose the flexible fare ones based on our itinerary, and also had to book at a peak time) were close to $200 per person whereas our ferry tickets were roughly $46 for a 6 hour ride. Might make the most sense to fly if you're only going for 2-3 days, since the ferry takes at least a half day each way to get to places like Naxos and Santorini.

(Sorry if that is a repeat of advice above...I only scanned).

Sky Express has just taken over the Athens - Naxos - Athens route (as of Oct 1st). Currently they are flying only 4 days/week to/from Naxos: http://www.skyexpress.gr/DESTINATIONS/Scheduledflights/tabid/132/articleType/ArticleView/articleId/376/language/en-US/Flights-from-Naxos-to-Athens.aspx

No telling what the schedule will be next fall, but without daily flights it would be risky to rely on Naxos for a 2 or 3 day break. Naxos gets very quiet after September, and that's why there is a reduced flight schedule. Another reason I suggested Rhodes is that it has a longer season, and takes only 15 minutes longer to reach by air. Other islands (to name a few) that will still be awake in October are Santorini, Corfu, and the Saronic Gulf islands that are quick to reach by ferry from Athens.

I'd expect Crete to have good transportation available, too, but I wouldn't go there for just 2 or 3 days.

We loved Naxos so much.. its a far more authentic experience.. people live and work there year round.. not like Mykonos and Santorini that rely mostly on the tourism business and much of the stores and many hotels close for winter ( owners often going back to mainland for winter)..
Naxos is so far our favorite island.

With the short time you have I was going to recommend Hydra but looks like you are going there as a part of the tour. So I concur with the others here (esp. Janet) who recommend Naxos. I have traveled to many Greek islands over the years and Naxos has a little of everything and would give you a great Greek island experience. Yes other islands are more scenic, more historic, quieter, louder, more beaches, etc. But Naxos has a little of all of that. PLUS it has this great Venetian history that you should do a little research about before you head out. The Venetian history in Greece is often overlooked but is fascinating.

Also try Naxos cheese - it is one of the best. If you are in Athens and Rick's tour takes you to the Psirri district behind Ermou street - most of the tavernas there are run by Naxians and the food is typical of what you get in Naxos. Going to Psirri and then visiting Naxos was really rewarding for me and my mom. We also happened to be on Naxos on Megali Oxi day (a national holiday marking the day when the Greek president refused to capitulate to Italy during WW2 - Megali Oxi means "the Big No") and there was a parade and huge celebration.

No matter what island you go to you will love it. each island has its own personality and you will enjoy finding your own special island. Have a great trip.

So I'm going to Naxos next time we travel to Greece, which will probably be next year as I am in love with Greece.

If you'd like an easy island to get to and visit historical sites.. look to Mykonos and take the day trip to Delos.. an UNESCO site and extremely interesting. We don't do the night life, but loved our 2 nights in Mykonos and find a tour around the island... get out of Mykonos city. Very interesting and diverse. This island is close and the ferry would not take that long. There is a restaurant that does exquisite grilled seafood and the city is empty when the cruise ships leave. I know that it is the party city, but we have no idea where that is. get a good hotel for sunsets and you will be happy. You will have the place to yourself in the fall.