Hello all! My wife and I are planning a trip to Dubrovnik, Croatia, and the Greek Islands next year and could use some help with overall itinerary planning. We want the total trip to be around 11–12 days (including travel days, so 9 or 10 full days in Europe). We are looking at going either in mid-May or mid-September because we want to avoid huge crowds, have warmer weather, and be able to enjoy the beach aspects of Greece while things aren’t at their most expensive. We definitely don’t have tons of money to spend, but we will be using points for the flights and aren’t necessarily on a tight budget when it comes to lodging or experiences.

We aren’t looking for a purely relaxing vacation, but we would prefer to move towns/islands only twice, which should give us about 3 nights in each location we stay at. The islands we want to visit are Skópelos, and potentially Naxos or Paros. My (very tentative) itinerary is below:

- Fly into Dubrovnik, Croatia, and stay there for 3 nights
- Fly to Skiathos via Athens and spend 3 nights on Skópelos
- Fly to either Naxos, Paros, or maybe a different island, and stay on that Island for 2 or 3 nights
- Fly out of either Mykonos or Athens back to the U.S. (if Athens, then we’ll arrive one day before the flight and spend the last night there)

Our interests:

- We absolutely love getting lost in different cities, towns, and roads, just wandering around to take photos, shop at small stores, or simply enjoy being outside in a new country.
- We aren’t looking for nightlife; instead, we’d prefer a more romantic, honeymoon-esque vibe.
- We appreciate seeing historical sites but aren’t necessarily big on museums.
- We love being outdoors and especially in the water.
- We absolutely want to go to Skópelos, but we aren’t completely set on another island yet.
- We don’t have much interest in Athens.

A few questions we’d love thoughts on:

- I know that September is much better for swimming and slightly warmer than May... but May has the flowers of spring and still brings early summer weather, though it’s often too cold to swim. Is this truly just an “it’s up to you and your interests” choice, or should we just go in September when we know we can comfortably swim?
- We desperately want to go to Skópelos (even though it’s a bit out of the way) and understand that to get to another island we’ll need to fly through Athens. With this in mind, does the general flow of the trip make sense (starting in Croatia and then moving on to the Greek Islands)? Or should we instead start with the Greek Islands, fly to Croatia, and then head home?
- Through our own research, we’ve set our sights on Naxos or Paros as the Cycladic islands we want to visit. But should we rethink this for another island? We know Santorini and Mykonos are very touristy, and while we’d be open to going there, we also know that all the Greek Islands have something to offer and can provide a great experience.

Any thoughts would be appreciated! We would love to be there for a month if we could, but financially and PTO-wise that isn’t an option (24-year-olds starting our careers, lol).

You posted a similar thread earlier this *year and received some valuable advice.

Personally, I'd choose either Croatia or Greece especially with such a short stint, not both. Keep in mind some flights might be seasonal, even in May or September.

What Travel_Nerd said! Here's your prior thread: Newlywed's first time to the Greek Islands and Croatia! Much advice needed

I'll repeat some of what I've said before, with attention to the revisions to your plans suggested by this current posting:

You are probably correct that you will need to fly through Athens for a number of these transitions, but I again encourage you not to force it: If that’s the routing that works best for you, fine, but start by simply entering your starting and ending points into flight search engines to see what comes up and what works. And I don’t understand why you would consider flying out of Mykonos to get to the U.S. if you are ending your trip in Naxos or Paros. Again, see what your options are. Just make sure that each transition, whatever the intermediate stop, is on the same ticket so it will be up to the airline to get you rebooked if something goes wrong.

I have to admit that I’m surprised that you are trying to include Dubrovnik in this trip. It’s well worth seeing – but there’s MUCH more to Croatia! And getting to Skopelos from Dubrovnik will, I think, take quite a large chunk of your limited time. Is there no where else in the Greek islands that appeals to you? Or would you not enjoy more time in the places you do visit? Remember: 3 nights really gives you only 2 days … much at all!

I loved Naxos; I’m sure I would enjoy Paros.

May vs Sept – your trip, your call! I loved the wildflowers in May, but then, I had no interest in swimming.

I agree that with so little time that you are spending too much time travelling from A to B compared with your time just enjoying yourselves. Getting to an airport and flying every few days is not my idea of a good holiday but I know that everyone is different. Both Croatia and Greece are better enjoyed at a more leisurely pace.

if you’re keen on Skopelos, then I would make your second island one of the Sporades ones and leave the Cyclades to another time. I’d also choose between Croatia and Greece. Both are worth more time for a better time.

To a certain extent it'll depend on the island(s) you pick but September isn't warm. It's still HOT.

Bouncing around is something to do if you have money and time to burn. You'll end up spending both just getting from A to B.

On swimming there are people who swim mid winter. No one here knows your personal cold tolerance. It'll also depend on the location. I remember one shallow bit off water off of Rhodes that felt like a hot tub early July. The water was so shallow it really heated up. Further out into deep water it was cooler.

Aegean Greece: the first haldf of September is still more or less summer, then it usually get's somewhat cooler and rainfall cannot be excluded.

Why just Dubrovnik? If you like walled medieval cities, go to Rhodos instead. It's logistically easier and the weather will be better (in both months, May and September).
For a less touristy Island than Naxos or Paros, you may check Skyros (can be reached from Skopelos via ferry - Mandoudi - bus - Chalkida - Paralia Kymi - ferry - Skyros)


Skyros

I agree with everyone else. It takes some effort to reach the Greek Islands so I too would limit your short trip to Greece. Spend less time moving and more time to experience your destinations