Here is a lovely Santorini holiday for October (1-20th October) from London. It involves island hopping around Greece so it does involve a lot of travelling around - but for those that love to explore, it's definitely a trip worth doing. The flights are only with Easyjet so include hand luggage only, you are probably best sticking to compact hand luggage with the ferry and moving around a bit - so pack light!
You could do a shorter version of this easily enough, but if you are going to go to Greece and Santorini, this is a nice duration and not too rushed either.
Arriving on 1st October you will spend 1 night in Mykonos Town (you'll return later on in this trip to Mykonos). You will stay at the Dimitri Pension which is in a great location in Mykonos Town and ideally places you for catching the ferry the next day.
You will catch the ferry from Mykonos to Paros where you will spend 3 nights in Paros. Your accommodation is the Ampeli Apartments which has great reviews.
You will take the ferry from Paros to Naxos where you will spend 4 nights in Naxos. You will stay at the lovely Iliovasilema which again has great reviews and is centrally located.
You will take the ferry from Naxos to Ios where you will spend 4 nights at the Hermes Hotel. This is not far from the ferry port to so ideal location to explore.
You will take the short ferry from Ios to Santorini where you will spend 5 nights. This may be too long for people, but it's also a good opportunity to hire transport and get out and about in search of amazing sunsets. You could easily add time into one of the other islands instead and for some people Santorini and Oia is too touristy, but it's a good opportunity to enjoy the sea view and relax as the accommodation I've picked here is also a little more expensive than in the other places. The Kiklamino Studios has a sea view and I think is worth the extra cost compared to some cheaper options as it has brilliant reviews.
You'll end your trip by catching the ferry back from Santorini to Mykonos where you'll stay in the town for 2 nights
All the details:
Booking flights on https://www.easyjet.com
Book 1 night in Mykonos on https://www.ebookers.com
£27.96 using code AFFBOX
Ferry Mykonos to Paros Euro 72.60/£63.09 book on https://www.seajets.gr/en/
Book 3 nights in Paros on https://www.ebookers.com
£54.56 using code AFFBOX
Ferry from Paros to Naxos book on https://www.bluestarferries.com/en/
Book 4 nights in Naxos £87.24 https://www.ebookers.com
using code AFFBOX
Ferry Naxos to Ios Euro 33.80/£29.37 book on https://www.seajets.gr/en/
Book 4 nights in Ios https://www.ebookers.com
using code AFFBOX £62.57
Ferry Ios to Santorini Euro 31.80/£27.63 book on https://www.seajets.gr/en/
5 nights in Santorini https://www.ebookers.com
using code AFFBOX £225.43
Ferry from Santorini to Mykonos Euro 66.80/£58.05 book on https://www.seajets.gr/en/
2 nights in Mykonos £52.53 https://www.ebookers.com
using code AFFBOX