Cyclades Island Hopping

I am not clear are you flying direct to Santorini from Europe or are you landing in Athens at 5pm and flying to Santorini the next day.

I am going to assume you are flying to Santorini from Athens. If that is incorrect take no notice of the next comment.

There will be at least three flights to Santorini after your flight to Greece arrives at 5pm. Experienced travelers find a connecting flight (you will need about 2 hours) although if you have flown to Greece from Europe you will already have done passport control so an hour and a half will be fine. Why waste time hanging around Athens for a few hours when you can be in Santorini on day of arrival.
Check Aegean airlines for those flights.

Once at Santorini I always suggest that you stretch your budget here and get a caldera view. It will be very expensive but worth every euro. Santorini will be very crowded in August so having your own balcony allows you to get all the views without being crushed by all the cruise ship people. My budget can only stand 3 nights in Santorini but fortunately thats enough time to see it pretty well. By the way Santorini beaches are pumice not sand and are very hot. One probably isn't looking for a great beach experience in Santorini.
Santorini http://www.flickr.com/photos/stanbr54/sets/72157632154800782/

Logical islands to go to next would be Milos which is ringed with really unique beaches. You need to rent a car to see Milos properly but it is a good choice. Its on a decent ferry route which can be a short trip back to Santorini for your flight out. Milos also has an airport so if you are flying back to Athens don't bother going back to Santoirni just fly from Milos.
Milos 2011 http://www.flickr.com/photos/stanbr54/sets/72157632109429236/
Milos 2013 http://www.flickr.com/photos/stanbr54/sets/72157634779985764/

My personal choice would be to head the other direction and take the ferry to Naxos and or Paros. Both are perfect companion islands to Santorini with the same white and blue buildings only everything will be at least half the cost of Santorini. They both have far superior beaches and Naxos in particular has many interior mountain villages to explore. Both are on direct ferry routs. Both have airports to fly back to Athens or alternatively they are a couple of hour ferry ride back to Santorini for your return flight.

Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/

You are going to have a great time.

Stanbr54, thanks for the advice and links to your photos, that is a lot of help. To clarify, we are flying from NYC to Santorini which means a layover in Europe so we were not planning on flying from Athens to Santorini.

Thanks for clarifying. It will be best if your second island is a close ferry hop back to Santorini for that return flight. The 3 islands i mentioned all qualify and are all very good.

Hello!

Such wonderful news, congrats on taking the next step! You are going to love Greece for sure.
Paros and Naxos are pretty close to Santorini. Do you need to go to only one island? Ios and Sifnos are beautiful too. Milos is also an excellent choice since it has more than 70 beaches! All of them of exquisite beauty. Milos is famed to be the "couple island"! If you are looking for something more alternative and raw you might want to check out Amorgos. The ferry schedules aren't set for the new summer season yet, but during the time you'll be in Greece I don't think you'll encounter any issues. The schedules usually come out around March. It is best to book your tickets as soon as possible since even the locals go on vacation in August. In case you need more tips on the above I'll be glad to help :)

I hope you'll have a summer to remember <3

Thanks for the advice! In the time we have, would you recommend visiting one more island in addition to Santorini or visiting two more islands? Would it be worth the extra travel time to visit two more islands?

Do you have to fly in and out of Santorini? If so, that means returning to Santorini for a final night before your flight home. I don’t think anyone would recommend taking a ferry from an island to Santorini to connect to an international flight on the same day. There are occasional ferry cancellations or breakdowns which could cause you to miss that flight.

Edit: I just noticed you have an early morning flight out of Santorini. So you will definitely stay there the final night.

Now you have your initial 3 nights on Santorini plus a final night there. That leaves 5 nights for another island. I would choose only one (probably Naxos with maybe a day trip to Delos or one of the Small Cyclades). Milos is beautiful but is a little harder to get to and to navigate once you are there.

Hi Ethan,

You can choose Paros or Naxos.
Paros is approximately 3 1/2 hours with Blue Star Ferries Line or 1 1/2 hour from Santorini with Hellenic Seaways Line

And although, it’s not so famous as Mykonos and Santorini, bus it has one big plus! It’s for everyone! It has beautiful beaches, sport activities, trendy bars and clubs, tasty food, wineries, traditional architecture, paths for trekking and hiking etc. The list as you might understand goes endless. It is the perfect destination for both families and adventurous travelers. That’s why if you go to Paros, you notice the variety of ages that visit it, from young people and students, to families and older couples. This creates an amazing mix that gives this island an extra dimension! Also have daily cruises to small Cyclades, Delos and Naxos too

https://polostoursparos.com/daily-cruises/

Since you can't count Day 10 (pure travel day), that will leave you with 9 days of "real" vacation. Travel pace may be a matter of taste, but since you're on your honeymoon, I would think you'll want to relax and enjoy and not only rush from place to place. So I'd make that four nights on Santorini at least, so you get at least three full days out of it.

Every change of location will basically cost you one day for traveling, so for a 9-day vacation, I'd add only one more island to that. Milos certainly is nice, but I wouldn't recommend any of the eastern Cyclades because, to the best of my knowledge, that will involve a change of ferries in Naxos. Since you are explicitly asking for "easily accessible to Santorini", that probably wouldn't be for you.

I'd vote for one of the islands along the ferry line to/from Santorini, like Naxos or Paros. From there, you can easily do day trips to neighboring islands like Tinos or Mykonos and Delos.

.. hiking, and exploring the islands like locals.

Well... if you want to "explore the islands like locals", don't even think of hiking. Get one of those mopeds, forget about using a helmet, and zip across the island and through the narrow town lanes, making as much noise as you possibly can. ;-)

Hey Ethan, there is an update on the Greek Island Hopping I told you about in my previous post. I saw they re-opened the island hopping pass you might want to check it out and see if the dates suit your planning. Until the time of your travel more shipping schedules are going to be added for sure. This pass works with the ferries that belong to Hellenic Seaways. I think that you will definitely have the time to see Paros and Naxos. Paros is a small island, in 2 days you'll see most of it. Naxos is just on the opposite side of Paros. You can see it without binoculars, they are that close! You can spend the rest of your days in Naxos or even head to Ios, which is at a close distance too. Regarding Santorini, 2-3 days will be fine.

If you want to take day trips this is also possible with the pass and you'll get to see Mykonos and Amorgos if you don't need to spend a night on another island, that is if you don't mind spending some time on the ferry. It might also help to check the distance between the islands and see in which order it will be best for you.