I think Greece would be a better option. 

Greece & Turkey's tourist season tends to end at the end of September although you can still visit, the smaller towns and resorts won't have much going on a lot of tavernas and restaurants will be closed. If you're aiming for capital cities then it shouldn't be a problem.

Us Brits would tend to head for Spain & the Canary Islands at that time of year for rest, relaxation and sunshine

Hi Rylee,

I have only been to Greece and Turkey in early Summer but I have often been to Italy and Andalucía in October and the weather was always sunny and warm.

You could go to Seville which is beautiful and visit places like Grenada Cordoba (Spain) and Ronda or you could  venture to the Tuscany region or Liguria and visit Florence Lucca Siena and / or the Cinque Terre 

Although you're not guaranteed hot sunshine the likelihood is that the weather won't let you down and the places certainly won't!

I would definitely opt for Greece, because Athens is still very much alive in the winter, and you'll be surrounded by mostly locals instead of tourists, plus the weather will be chilly but bearable (around 50 F). You can get to see a lot of the central sites like the Acropolis of Athens and Monastiraki without thousands of tourists around.

Explore neighborhoods like Gazi and Kifisias, which have great restaurants and nightlife around that time of the year, as does Kolonakiwith its incredible restaurants and bars.

Plus, you can venture to the town of Arachova, a stunningly scenic town and wonderful Greek ski destination just 1.5 hours outside of Athens, which will be full of warm tavernas and coffee shops.

I am Greek and i love both countries :)

Actually a lot of people prefer Greece and/or Turkey during winter since the weather is more bearable (in the summer it can get up to 40 degrees and a lot of people won't stand that).

That said, October could be a quite decent month temperature wise in both countries. 

So depending on what you want i would suggest:

a) Greek island hopping: combine Athens with some islands: Athens - poros - Hydra (Greece) - Aegina

If you want to see Athens and at the same time check out some islands then you could stay in Athens and take a day cruise from Athens to the fabulous Greek islands of Hydra, Poros and Aegina. See this tour: http://www.tourboks.com/en/product/cruise-to-poros-hydra-and-aegina.html - you will have all your transport to the islands, transfers and buffet lunch organized, you can sit back and enjoy your day cruise with free time on each island to explore.

b) Greece Mainland version 1: see some of the most interesting sites of Greece: Athens - Delphi - Meteora

You will see some of the most interesting sites in Greece: the archeological site of Delphi with Apollo temple and the Unesco World Heritage-listed rock-tower monasteries of Meteora.

See this tour starting from Athens including all the above:

http://www.tourboks.com/en/product/3-days-delphi--meteora--t-class.html

c) Greece Mainland version 2: most interesting archaeological sites: Athens - Epidaurus Theatre - Mycenae - Corinth (Greece) 

Spend your vacations in Athens and take a one day tour to the remains of the ancient city of Mycenae a major centre of Greek civilization from 1600BC to 1100BC and a world heritage monument and to Epidaurus ancient Theatre, reputed to be the birthplace of Apollo's son Asklepios, the healer. with this tour from Athens: http://www.tourboks.com/en/product/epidaurus--mycenae-one-day-tour.html you will also see Corinth Canal and Ναύπλιο the first capital of Greece

d) Crete and possibly combine it with Santorini

Go to Heraklion in Crete - plenty of things to do and see there! the food in Crete is simply AMAZING! and lots of nightlife too.

while in Heraklio i would totally recommend a visit to Knossos if you like history (check out this tour: http://www.tourboks.com/en/product/knossos-palace-city-tour-and-minoan-theater-from-heraklion.html ) or a Jeep safari tour if you prefer adventure! :) (check this one out: http://www.tourboks.com/en/product/land-rover-jeep-safari-tour-from-heraklion.html)

Finally from Heraklion you can go to Santorini for a day (there is a boat connection) - check this tour out for hassle free booking: http://www.tourboks.com/en/product/santorini-island-one-day-cruise-from-heraklion.html 

Santorini is the most famous Greek island so you will have two islands crossed out of "Your Greek vacations" list :) :

That's it - hope the above is helpful :)

Turkey is great though too... Istanbul is pretty amazing.. i could give recommendation for Turkey as well if needed :) let me know and whatever you decide HAVE FUN! 

Greek islands are a must visit but during the winter its hard to travel between islands so Your second option is better ( Turkey ) Istanbul, Cappadocia, Pamukkale, Ephesus and Troia would be great to  visit.

Have a good holiday

The weather is pretty good on both countries  because they are so close by after all! I am from Athens and can assure you that the weather is sunny and warm during daytime although it gets a bit chilly in the night. The sea is still warm to go for a dive too!

For Athens I've compiled a quick guide with things you can see and do which can be found here: http://aspectsofathens.com/2014/07/28/a-quick-guide-to-athens/

Here are some day trips around Athens http://aspectsofathens.com/2015/04/02/5-day-trips-around-athens/

I particularly like Ναύπλιο

which is a lesser known beautiful city (more deets here: http://aspectsofstyle.com/2015/07/30/nafplio/)

You could also go to Crete which is further south (and therefore warmer) and it has a LOT of things to see and do. City wise there is Heraklion, Rethimno and Chania. Culture wise you shouldn't miss Knossos. If you're into hiking then definitely visit Samaria Gorge. And as for beaches nothing beats Elafonisi

Here's a photo diary from Crete: http://aspectsofstyle.com/2013/09/17/crete/

from Heraklion: http://aspectsofstyle.com/2013/09/25/herakleion-crete/

from Rethymno: http://aspectsofstyle.com/2013/10/16/rethymno-crete/

If you decide on Greece let me know and I can give you more information!