Planning Your First Greek Islands Vacation

With over 150 islands to choose from, planning your first Greek islands vacation could be overwhelming.  I planned our own first Greek islands vacation not too long ago and am happy to share the considerations that were part of our planning process.

When choosing the Greek islands for our first Greek islands vacation, I weighed the logistics of our 8.5-day trip against our interests and came up with the following Plan: Boston-Athens-Paros-Santorini-Boston.  We flew into Athens and then took a ferry to Paros where we stayed for a relaxing week and then finished our Greek Islands vacation by spending a busy weekend in Santorini. We flew home from Santorini (via London).

Here is how the planning unraveled:

Island Hopping Vs. Island Base

When planning Greek islands vacation, one of the first things to figure out is…the logistics of getting to the island(s) of your choice!   I have briefly considered choosing a “base” island to do day trips from,  but quickly realized (with the help of Fodor forum members) that with limited ferry schedules between the islands it is not practical.  There  are 7 main island groups and ferries typically do “linear” routes within the same “group”  before coming back to Athens same day (or next).  You can check out ferry line schedules via this link.    Note that schedules are seasonal and change every year.  Island groups with the most ferry connections are the Cyclades and Dodecanese, but even here there are typically only a couple of ferries offered each day  making a return back to your “base” at a desired time challenging. Instead, it is best to use the linear ferry “route” to your advantage by staying on an island for several  days and then island “hopping” to another island on the same route.  This way you will avoid paying for (and wasting time on) backtracking  and will be able to spend relaxing evenings exploring the islands (and hot summer mid-days – on the beach).  As an example, one popular ferry route in the Cyclades that we ended up using (offered by Blue Star Ferries) is Piraeus (Athens) – Paros – Naxos – Santorini-Naxos – Paros – Piraeus so you could easily island “hop” on this line.

Another transportation “tactic” is to FLY from Athens to a distant island, then hop by ferry from there. For instance, you could fly to Kos or Rhodes in the Dodecanese, then hop to smaller nearby islands.  Also important to consider when planning your island transportation is that some “bigger” islands offer direct flights to major European cities so you could fly home to/from there without coming back to Athens.

One exception to the “no island base” principal is taking a day “excursion” boats (not the regular ferries) to the nearby islands.  For example, in the Cyclades, from Naxos you could take day trip excursion to Paros (and vice versa) as well as to Delos and Mykonos.  These would probably offer limited island experience, but definitely something to consider if you prefer one island base but want to see other islands.  Some islands, such as Paros or Paxos offer “two islands” in one deal with nearby Antiparos and Antipaxos located only a couple of miles away from their namesakes (“anti”  means “opposite” in Greek).

Island Inspirations

In choosing the islands for your first Greek islands vacation, start by asking what are you looking for in your Greek island vacation experience: gorgeous beaches, picturesque fishing villages, busy party scene, historical ruins or something else? Or is there an island that simply calls your name? That happened with us and Santorini– it was simply calling our name.  For our second island for this trip we were looking for a relaxing place to stay for more than a couple of days and explore diverse beaches and picturesque little towns.

I was heavily perusing Greek Islands DK travel book looking for BEST beaches (Naxos and Paros were showing up a lot!) and most picturesque old towns.  This is how I chose Paros over Naxos for this trip: Paros has not one but three beautiful old towns – Naoussa, Parikia and Lefke  (and numerous villages).  In fact, Naoussa is considered one of the prettiest fishing villages on all of the Greek islands! Our trip was taking shape!

Our Trip

With only had 8.5 days on the ground in Greece  and a desire to see at least two islands we had to choose the islands that were within easy (quick) access from our arrival/departure points and each other.   This (coupled with the  diverse beaches and picturesque towns “inspirations”) worked well with the Cyclades island group.  We decided to spend 6 days on a an island of Paros -to form a more “intimate” and relaxing connection with one island and then a weekend on an island with a different – more bustling – “vibe” – such as Santorini.  (We also considered Mykonos which is in the same island group).

Paros and Santorini are in the Cyclades with good “linear connections” between them.  And – by leaving Greece from Santorini without coming back to Athens we were able to maximize our 8.5 days in Greece to the fullest!  

Starting (or finishing) in Athens

With only 8.5 days in Greece and two islands to explore- and considering it was a hot  and dusty August – we were tempted to skip spending any time in Athens and head to the ferry port straight from the airport.  We were so happy we have not skipped Athens!  We spent a crazy half day in Athens (started early in the morning to avoid the heat) with my high school friend and tour guide Svetlana exploring Acropolis complex.

We even squeezed time to swim in a relaxing pool in downtown Hilton.  We wish we had more time to explore the old town, but we did the best with the time we had.

High Speed vs Traditional Ferries

When looking at the Greek ferry schedules you will notice traditional ferries (e.g. Blue Star Ferries) and speed ferries (e.g. Seajets).  Speed ferries are smaller, cost more, and offer a bumpier ride in “rougher” seas.  Traditional ferries resemble “cruise” ships, and offer different styles/classes of seating, and even sleeping cabins.  Speed ferries typically save you 1-2 hours on a 4-5 hour journey.  For example, a Seajets ferry brought us from Athens to Paros in 3 hours while a Blue Star would have taken 4-5 hours depending on a route.  For a shorter journey from Paros to Santorini we decided to have a traditional Blue Star ferry experience (we pre-booked assigned “aircraft” style economy seats by paying a couple of extra euros- which I highly recommend in a busy summer season).  Note that delays are frequent on all Greek ferries.  We experienced about an hour delay on both of our ferry rides.

Useful resources to plan your Greek Islands Vacation:

1. Planning Greek Island ferries: we mapped out the ferry connections using https://www.gtp.gr/RoutesForm.asp then went directly on individual ferry sites to book. Note that there are 2 main ports in Athens: Piraeus (the largest) and a more compact Rafina (both have ferries going to the Cyclades).
2. Choosing accommodations: we used Booking.com to pick our hotels on Greek islands.   On Paros we stayed in Kalypso Apartments in a walking distance from Noussa and on Santorini we enjoyed the Ellinon Thea seaside accommodations in Firostefani.  I would be happy to answer any questions about these accommodations in the comments (they worked for us, but were by no means perfect!) I find the convenience of keeping all my reservations on booking platform and their online live chat help very helpful in planning and managing my reservations (I am also part of their Affiliate program which allows me to earn a small commission to support this website -if you book via the link I provide- at no extra cost to you!)