Greece Travel Planning Tips

Well, I survived the epic Kitchen De-popcorning of 2016 and am alive and well.  It was excruciatingly painful, but it’s done.  And that’s all I have to say about that.  Now I’m going to console myself by talking about a much more exciting topic.

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We traveled to Greece in September of 2015.  Prior to this, our only international experience was a tour package that we purchased to go to Italy.  We planned this trip “on our own”, meaning we didn’t use a predetermined tour package.  We booked all of our apartments and transportation ourselves.  We had considered doing this for our Italy trip, but we did a quick check of prices and realized we were getting a pretty good deal with our package (those group hotel rates must be bomb) and thought the ease of having it set for us would be good for first-timers.  However, for our second trip, we wanted to explore doing something on our own.

Itinerary Planning – Where to go?

We knew that we wanted to go to Greece, and I originally thought we might do Athens, Santorini, and Mykonos, only because those were the most popular islands that I knew.  As is our way, we started listening to the Rick Steves Greece related podcasts, and particularly enjoyed an episode on the Greek islands.

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This is what I think of when we are talking Greek islands

The podcast touched on SO many other islands, and basically blew our minds with how many Greek islands there actually are.  Once we realized the sheer number of islands to choose from, we hunkered down to do some more research and comparisons.

We read up on Mykonos and heard that it had more of a party/luxury vibe.  We tend towards wanting more history and unique experiences than a drunken, lazy, beach vacation (not that we are sticking our noses up at that, we would just go somewhere cheaper and closer to home.  Or to the Caymans on a whim.).  Also we are not fancy/luxury people (HA), so we decided to rule out Mykonos.

We limited a lot of our reading to Top 10 lists and the like, here are some of my favorite articles that we found:

  • Trip Advisor (is anyone surprised?)
  • Touropia – I liked the descriptions and quick hit list of “things to do” for each place
  • CNN  – I liked how this list was chosen with individual criteria (Best views, best food, etc)
  • Rick Steves Island Hopping Basics – Not a top 10 list but a lot of great information and helps to categorize all of the islands

Based on these lists, some other islands in the running were Crete, Naxos, Paros, Chios and Rhodes.  We ruled out Crete because it was so big, and probably deserving of it’s own separate vacation.  We had only about 2.5 days to play with, so we knew we would have to keep it to a smaller island.

Shopping inside the castle walls

Rhodes caught our attention almost right from the beginning.  It has a lot of medieval history and we loved the thought of being able to see the walled city and the castle.  It was also closer to Turkey and had ties from Venice and other places that we thought would give it a different vibe than Santorini.  We decided that we would wanted to visit islands with distinctly different cultures/architecture/etc. to really get the most out of our trip, and confirmed Rhodes into our third slot.

The castle in Rhodes


Now….how the hell do you get to all of these places?

You can take ferries from some of the islands, but Santorini and Rhodes are fairly far apart and a ferry would have been 4+ hours.  There also aren’t a lot of direct ferries (and in fact, a lot of days had no direct ferry option at all), and having layovers in different islands would add a lot to our travel time.

We realized we could catch a flight on the Aegean Airline and our total travel time would only be 3ish hours.  The price wasn’t bad either at €70.  This seemed like a no-brainer to us and we booked our flight.

In retrospect, the flights were pretty early for me and having multiple flights and connections all throughout were more stressful than I anticipated.  Our neighbors in Santorini used the ferries and said they were decent.  Not super comfortable or super efficient, but got you from point A to point B.  They did say you mostly had to stay in your seat and didn’t get to stand outside and enjoy the water views (which was the only big pro I could come up with for the ferry).  So…I really don’t know that there is a great option for island hopping transportation.  If I were to do it again, maybe I would choose islands that are closer together?  And do the ferries with shorter travel times.


A friend tipped me off on AirBnB (<- referral link with a $20 credit), which you have probably heard of.  On the off chance that you haven’t, it’s a website where people can list couches/rooms/entire apartments for rent all over the world.  There are a lot of advantages, you get to have a more local and personal experience over a traditional hotel.  You also get to stay in unique accommodations and in places closer to the actual sites you are visiting.

In our case, we were going to be traveling with four, so the price of a two-bedroom AirBnb was much less than the price of two separate hotel rooms.  Having the whole apartment offered other advantages as well, such as having a kitchen and a common space to hang out when you went home at night, and of course, the patios.

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Patio in Rhodes

Searching for the apartments was super easy , AirBnB has great search and filter options.  In most cases we wanted to be close to interesting sites (in the medieval walls in Rhodes and next to the Acropolis in Athens), so I would just zoom the map in to those areas and further filter the selections from there.  I would say I had the hardest time finding a place in Santorini, and really that’s only because I went in wanting something with complete sunset views (which is a tough request).  The place we ended up with had partial sunset views (a neighboring cliff cut off the last part for us), but it was still amazing and was the most beautiful patio I’ve ever had the honor of sitting and drinking a beer on.

Santorini patio

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Two out of our three AirBnB hosts offered to set up transportation for us from the hotel, and that worked out so amazingly well.  It really makes your arrival so seamless when someone is holding up your name and you just hop in their cab and they know exactly where to take you.  In Santorini, our hostess even set us up with a guy to meet us from our airport transport and carry our luggage down to the apartment.  The personalized service and flexibility on arrival times really set AirBnB apart from a standard hotel for us.  I also felt like we got more desirable locations for the same (and in most cases, less) money than we would have got with a hotel.  We had an amazing AirBnB experience, and have since used them to visit Asheville and just booked apartments for our Munich/Vienna/Budapest trip coming up this May.

Trip Preparation

We did a lot less preparation for this trip than we did for our Italy trip, mostly because a lot of it is one-time prep.  I already had a decent cross-body bag, and travel bag.

I did end up purchasing a multi-outlet converter because I didn’t have one that had the standard European configuration.  But if you travel a lot, you likely already have one.

The official language of Greece is Greek, which uses the Greek alphabet (you don’t say?), vs the standard Arabic alphabet.  Because of this, we found that most people don’t expect you to speak Greek and readily speak English.  Signs, menus, etc. were all posted in both Greek and English.


I ended up using a lot of the same apps that I already used in Italy, but just made sure to go in and download the Greece specific content.  This was the case for Rick Steves Audio Guide, Triposo, and  I did download three specific location apps that I found to be very valuable.  These apps are created by and have great categories for searching.

I specifically enjoyed the “Short Trips”, “Beaches and Beach Bars”, and “Itineraries” options.  Itineraries was great for suggestions and seeing how people recommended grouping activities.  Short Trips was perfect for situations where you found yourself with some extra time and wanted to explore an additional area that’s close to your home base.  And Beaches and Beach Bars is self explanatory 🙂


Packing for this trip was more complex than our Italy trip.  Because we would be visiting the islands and beaches I had to bring a lot of extra things like swimsuits, cover ups, extra underoos, beach bag, etc.  Luckily we live at the beach, so I already had all of those items.



I did buy a few extra casual dresses, and am so, so glad that I did.  Dresses are such an easy way to look put together with minimal effort and I found myself reaching for my dresses on most days.  I also packed a few pairs of colored shorts and tank tops and wore these on days where we were doing something more physical.  I didn’t want to be wearing a dress on top of a windy mountain in Delphi or while climbing all over the Lindos Acropolis.

It was a smidge windy
An easy dress for a mostly inside day

I bought a pair of comfortable sandals that I ended up wearing on most days.  I ended up deciding on the Born Eryka sandals (seen above), they were highly rated in comfort and I like the strappy style.  I was pretty picky about wanting something with a back strap, which I would definitely recommend with a lot of the rocky terrain that we ran into.

I also ended up buying a backpack for our hike in Santorini.  I just kept an eye on places like Marshall’s and TJ Maxx with a focus on something on the smaller side and with soft, comfortable straps.  I ended up using the backpack quite a bit, especially when we fit in some beach time and needed a change of clothes, and it was great to have on the plane (as unfashionable as it was).

So that was our planning process and some (hopefully) useful advice!  I’d love to hear about it if you are planning a Greek trip or have some additional tips!


This post is part of the Travel Tuesday link-up!  Thanks for hosting, Bonnie and Anna!



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