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Initial Planning Stages of month long trip to Greece

Thank you to everyone for your posts that I have already read!

My wife and I are heading to Greece for a month long trip 30 days +/- depending actual flights I can book with United reward miles. We are leaving in June most likely the last week no exact date as of yet. We are budget travelers. We are both 50 years old and enjoy exploring new areas. We prefer to stay in one spot to get to know the local area then move on. We went to Costa Rica for 21 days and enjoyed four locations as we were driving the drives were an enjoyable part of the adventure. We enjoy the outdoors, beaches, seeing old towns, hiking, being on the water/boating, drinking wine and eating all types of food. Not into party scenes but don't mind being out late with good conversation.

First question:
We are departing out of Boston Massachusetts. My initial foray to look at booking reward miles is that it is quickest/easiest to fly into Athens THEN fly to our next destination vs. Flying into Crete and returning from Athens. Has this been the experience of others using United or United partner airlines to fly? I saw 14 or 15 hours of travel time into Athens. When I looked at flying directly into Crete it was 27-30 hours. OR am I looking too early? I want to book the flights for the trip so I can start to look at the traveling between for flights/ferries and once this is deteremined finally book our lodging.

Second question is Itinerary based...
1st day Arrive Athens and transfer to a plane to Crete (then per Stanbr and Janet's advice leave to first stop)
2-8 Crete
9 travel to Cyclades Islands
10-16 (undecided which Island)
17 travel to (stay in Cyclades or travel to Dodecanese Islands or the island of Lesvos)
18-24 (undecided which island)
25 Travel to Athens
26 -29 Athens
30 Return Flight

YES lots to unpack there...
Crete is on our must do list. It seems to have a little bit of everything we want. We are considering adding a day or two to Crete and reducing others. I am thinking the flight out of Athens to Chania is the way to go... thoughts on this?

For our second stop we are looking to explore the Cyclades let me say we will not be going to Santorini or Mykonos on this trip. We are looking for less crowds (ok so I know it will be July and it will be crowded but we would like to minimize this aspect). The island of Naxos/Paros/Ios/Sifnos ALL seem to be a favorite among many... We are open to suggestions for this second stage! staying in one or one island would be great Thoughts....?

I realize staying in the same island chain maximizes our time in each location BUT since we are here for a month and not traveling to 15 spots -- What is the advice of going to a different island chain for a week?? The island of Lesvos seems to be another great option as well. THE issue is getting there and time... I am thinking of this as almost 4 vacations linked together. Am I being too ambitious in my thoughts of getting to a different chain or a different spot... IF this is too ambitious... should we shake it up a bit. A different route perhaps? Flying from Athens to Lesvos to start... working our way south (flying as ferry would be too long?) ending in Crete. Then flying back to Athens for the last stop??

4 days in Athens seems to be right for us. We prefer to go at our own pace and see things... if we don't see it "all" we are ok with that. The travel days we see as bonus evenings in our locations and are part of the adventure. ANY and ALL thoughts/comments are greatly appreciated... I will post individual questions on islands etc... once we get the rough outline figured out.
Thank you!

Posted by
2950 posts

Your plan seems workable to me. One thing to keep in mind when you're thinking about travel between island groups, especially those groups that are far apart, is how you move around efficiently. Ferries are great as long as you don't choose islands that are too remote or not popular enough to justify frequent passage between them. For example, getting from the Cyclades to Lesvos will limit you to a few islands from which you can make that connection. Obviously this dictates your choices for you. Of course, if you can afford to fly then it's not an issue, but if you're on a tight budget you need to do as much research as possible to figure out where to go. This ferry route map is not 100% current but it's the best one I've found so far. Add to it that you can get to Lesvos from Mykonos and to Rhodes/Kos from Santorini.)

As an exercise to help you figure out a route and travel times use and once you have some islands in mind, and with a little patience, you can backtrack to this last June/July to plot a course and see which islands are the best fit.

Good luck!!

Posted by
6 posts

Thank you for the map! I have been piecing together information unsuccessfully.

The first island we visit we will be flying too. Then we are looking at ferries or flights -- whichever makes the best sense both monetarily or time or if it is even possible!

We keep flip flopping on just staying with Crete and the Cyclades or adding another island chain...
Thank you,

Posted by
2898 posts

Congratulations on your dream month! Since you're in your 50s & taking a month, I'm guessing you must be educators... so you cannot leave in May, and you think late june would be easiest to manage. I'd like to convince you to crunch your time, organize yourself, and leave as early in June as you can -- All schools & colleges these days are over by June 12 -- at least in VA. Why not aim for take-off on June 13?? I say this because of Global Warming... this past year I was in GReece May 31 - June 18... and this period was always wonderful, mid-80s typical. 2019 was the HOTTEST June in Greece as well as USA; duing our stay we had 2 stretches of 3 days of 94-95° weather. That really knocks out noon - 6 pm for anything but a beach... and I think you want to explore & discover. Please, if you can, push it back to June 15.

Itinerary --
Matt, don't be greedy -- one chain per trip, usually. Sometimes you can do a ferry link, between chain,s if you're lucky. ANd don't try to do anything much else if you go to a N.E. Aegean Island ... they're the hardest to link up with. For instance, on my trip #3, in May, we flew staight to SAMOS. It proved to be a good "springboard" to 3 other destinations in less than a week. Sayed in a cute hotel edge of port VATHY, did Day trips to Ephesus (on TUrkey coast) and PATMOS, and a 36-hour ferry/car visit to CHIOS -- a remarkable island! It's now been "discovered" and may change a lot. In Samos, without a car, we just explored around Vathy -- with car hire, Western Samos is a wonderland! The year we went, there was then a great link direct from Samos to Naxos... now I think a ferry link from N E. Aegean goes only 1-2 x a week to the Cyclades, stopping at Mykonos & Syros. And Lesvos is not well-connected to anything; you'd pretty much have to fly back to Athens then out again. Look at GREAT website Rome to Rio and you'll see. On one trip, my companion & I flew straight to Rhodes for 3 days (great!), then wanted to get to Samos -- but it took a Loooong ferry ride to Patmos at midnight, then a next day ferry to Samos. Lesbos would have taken another ferry & a full day to reach. Big lesson -- almost No flights from Island to island.

If Crete is a must-do, then follow strategy Stanbr & I always end up advising... fly to Chania, a couple days at least for the lovely town & nearby, then rent a car... drive south? Imbros Gorge? Sougia? THen back up to N? Or just down to Matala, then N. E. to Heraklion area. Ferry goes only to Santorini, but you can use it as a "switchboard" and go to Milos. From Milos, easy to Folegandros, SIfnos Serifos, then to Mainland.

For Crete, remember, it's a country. You can only sample it in one visit. I've been there ?5 times, 5 days or so per time and stanbr many more. And still, I haven't been farther East than Palace at Malia...

Posted by
1117 posts

You are aware or course that each change of location will take you pretty much one full travel day, which is o.k. IMO if you want about four locations and have 30 days. However, if you choose different chains of island, you may have to make that two travel days between islands, depending on ferry connections.

We are looking for less crowds (ok so I know it will be July and it will be crowded but we would like to minimize this aspect).

If this is an important aspect for you, here's my recommendation: Choose islands that don't have an airport.

Most tourists choose the convenient and fast way to get to an island, which obviously is by air. So, since you do have a pretty long vacation and thus can risk going a bit slower, I'd recommend finding islands that are slightly off the average tourist radar. The Western Cyclades might be an idea. Or something as off the beaten track as Amorgos. The Dodecanese Islands also have some cute little islands that are inaccessible by air. Or consider the Sporades Islands (except Skiathos).

If you decide to choose islands that are slightly off the beaten tourist track, it might be a wise decision to stay within one island chain so travel days will not get too much. But you'll just have to set your own priorities there.

Posted by
6 posts

Than you Janet and Anna for your replies!

Janet - Yes my wife teaches. Her last scheduled day is the 17th but we will inevitably have snow days. How many is the question! Her last day this year was June 25th! We are booking and have to book safely for this reason.... Predicting last day is very rough. The weather is our ongoing concern for exploring as well when we arrive.

The rome to rio site is great and is a valuable asset for planning. First I have heard or seen it! thank you.

Since we are ending in Athens is it better to go to a closer Island work down toward Crete... Then fly from Crete back to athens to finish? Two thoughts - get to a closer island faster and beat some heat... end in Crete where it is larger and can get away from the as crowded areas easier with a car rental?

Crete is huge so we expect to have only a small sampling of its wonders. our itinerary for Crete or any stop is not set yet as we want the outline of the trip first then plan from that point.

This is not a I haven't done any research question it is a I have done too much reading online question! Does each island truly have its own feel? For example, someone visiting New Hampshire USA then traveling to Vermont USA would say there was a small difference in culture. Mind you if you live here you would say there was a huge difference! This is one of our thoughts for traveling to a different island chain to get a drastically different Greece in each of our stops. But the logistics are quite costly in either time or money.

Anna - I agree avoid the airports islands to minimize the crowds which is our thought on avoiding the more advertised islands that have the larger draws. I understand we may miss some great spots but that is a very acceptable trade off for us. This may mean some complicated transfers which is our concern that the timetables will not line up OR it lines up on paper but not in reality.

Thanks for more help and focussing our efforts.

Posted by
2280 posts

I have never been to Greece so I can’t offer you much help. However, I did have one comment. I dislike ending my vacation in a large, bustling city, particularly if I have been traveling in rural, scenic areas or small quiet towns. I find it very jarring and sometimes tiring. I think I would do better in Athens at the beginning of a trip. You might be completely different and be energized by the hustle and bustle of a large city, but I wanted to give you something to think about.

Sounds like a fabulous trip, whatever you decide!

Posted by
1117 posts

@Carroll: I agree perfectly about how you feel!

However, there is a very good reason for ending the trip with several days in Athens. All kinds of things can go wrong. Connecting flights from the islands can be cancelled. Ferries might be delayed due to weather conditions at all times of year. We've had all that happen.

Now guess what happens if you have scheduled your return trip to Athens with the last connecting flight or ferry? Well, there goes your return flight home - without you.

Posted by
1016 posts

Hello virginia/beth/matt. Whatever you choose to do you are going to have an amazing time.
We have been to Greece severl times and our experiences have provided us with a plan to maximize the experience.
Get out to your first Island as soon as you can make a connection. Of course you can do Athens first but Athens is hot dusty busy traffic is unbelievable and it is definitely a foreign city. I can assure you that getting over jet lag on an Island is the right choice. By doing Athens last you give yourselves time to adjust to being in Greece. How things work, how people interact and how long it takes to get from one place to another.

Crete is a great choice for your first island. Over the years we have spent a minimum of 10 days in Crete and a maximum of three weeks. We continue to find new places and experiences. While I am not suggesting you spend your whole time in Crete I can assure you that you will not be bored and you will save a lot of time on ferries if you make that choice. Having said that I would consider adding at least a few days to Crete.

Yes Chania is our favourite city and getting over jet lag in Chania is a perfect introduction to Greece. It will take you 2 days just to explore the Venetian harbour and back alleys of Chania. Chania is well situated as a base for day trips.
Theotokopoulou St area

You can visit Rethymnon ( similar to Chania) but with a different vibe. Visit Ancient Aptera and some nearby villages as well as the Agia Triada Monestary. Further west you can do the day boat excursion to Gramovossa and Balos lagoon which I heartily recommend. You can go to the far west coast at Falasarna where there are good beaches and an archeological site.
Gramovossa, Balos and Elafonissi

Ancient Aptera, Melidoni Cave and village.

Now go head south to the Libyan Sea villages of Paleochora or Sougia. This coast is rough and beautiful with remarkable mountain and sea views.
You can take the ferry trip along the coast hopping from village to village. The last time we did this trip we simply took the bus to Sougia and then hopped the coast by ferry all they way to Chora Sfakion. We stayed a minimum of two nights in each village. Very relaxing and simply not crowded at all. You can easily to 10 days to 2 weeks just experiencing the west and south villages.
Ferry trip Libyan Sea
Crete Libyan Sea villages

You can change your base to Rethymnon or Heraklion for the central area. While Heraklion is a very busy chaotic city it actually has several interesting things to see including Knossos, the archeological museum, The Venetian harbour and the castello.

Head south to visit Phastos another Minoen Palace like Knossos but it is not had any reconstruction. Our absolutely favorite ruin is at Gortyz/Gorten/Gortinya. It was once the roman capital of Crete and there is a gated ruin there but when you walk out of the parking lot and wander through the nearby olive groves you will discover a partially buried Roman city. You will have that site all to yourselves. Its as if you discovered this treasure all by yourselves. Another south coast village Matala is a great location. It still clings to its hippy culture and is a bit of a unique experience.
Remember this plan has not yet even touched the East section of the island.
Knossos, Phastos and Gortyz

I have run out of room.

Posted by
2898 posts

Matt, listen to my friend Stanbr -- he is THE Crete expert on this forum. Only problem is, he's been SO many times, maybe 10-12 in past 20 years, he's discovered too many fascinating destinations there! I suggest limiting Crete to 10 days ... and not necessary to rent car whole time, certainly not in days exploring Chania, then you could do that bus thing south, w. ferry along shore & back North. After that, rent car to drive down thru Spili to PHaistos, Matala (I have ONE place i recommend in latter - Dimitris Villas, lovely & serene away from the busy beach-row), then drive N.E. with stop @ Gortyn (EARLY in day; july heat!). In Heraklion, I vote for seafront Kronos hotel if u can get front balcony -- easy walk to museum, fortezza (good meze restaurants there); for Knossos either bypass Heraklion on highwy & see it first -- or turn in car & use local bus to see it.

And NO -- don't hop outward & fly back from Crete. Why? Because it's more efficient the other way. Fly into Chania, end up at Heraklion. Why? Because almost only ferry service to other islands. Take Heraklion daily 9:45 to Santorini -- stay Minimum time because of jampacked situation (I know a tiny rimside hotel away from crowds); after 24-36 hours, ferry onward: Santorini is a great "switchboard" port to get elsewhere in Cyclades... over to West chain, or down to Naxos-Paros (from these 2 u can daytrip to Mykonos/Delos if latter's sacred-isle ruins appeal). In this area I tend to favor Naxos (good local busses, in high season one can stay out at Plaka beach), and Antiparos (small and magical, tiny port is walkable to several fine beaches... no group tours or cruise crowds). From these closer isles, you can either fly or ferry to mainland.

You admit some of your confusion is due to overdose of ONline. Right! Realize that many online sites are promotional -- they give only plusses & highlights, never warn of drawbacks. Their goal = maximize tourism, never mind facts. Your wife is a teacher; she should prod you to Real Research. You have plenty of time -- Hie thee to a Library! Boston has splendid ones(next to Philadelphia of course). Browse the guides, borrow 3 -4 and compare. Advantage of Guides - they must give more candid/realistic info on plusses/minuses, or they won't maintain sales. Don't just choose newest editions -- hotel/restaurant/transport specifics may change but you get these on internet anyway; major sites, history, cultural backgrounds do not. Comparisons -- R STEVES GUide is v. good on Athens for newbies & Pelopponnese; almost zero on islands. ROUGH GUIDE best overall, but I'm not fond of newest edition, LONELY PLANET heavy on logistics. FODORS good for mid-level travelers, limited # of islands. CADOGAN Guide Greek Isles; dated on logistics, wonderful on contexts. BLUE GUIDES - the Gold Standard for ancient sites, history. EYEWITNESS - Good photo/graphic overview, no details.

Posted by
847 posts

I know everyone suggests flying to the island on the arrival day in Athens and it makes sense in a lot of ways. But to someone who is risk averse like me, I usually can't do that, what if the flight to Athens is delayed and you miss the flight to the island. If you leave loads of time between them you minimize the risk but then are stuck with hours in the airport if the flight is on time. And if it's delayed enough you'd still miss it. I'd much rather 'waste' a night in Athens and take a flight the next day. But another option is to reverse the itinerary and start with an island only a few hour ferry ride from Athens, one which has multiple ferries per day. Then work your way to Crete. Then you would end in Crete and fly back to Athens from there.

I would stick to the Cyclaldes. There are more islands to choose from than you will want to visit so no need to work with complicated ferry schedules to go to another island group. You could do Paros, Naxos, Santoroini, Crete. Or Sifnos, Milos, Santorini, Crete. Lots of possibilities but stick to the Cyclades and Crete. I think Crete deserves 8 days (or more) but each of the smaller islands can be enjoyed in 3-4 days. If all you are doing on the mainland is Athens then 3 days is enough.

Here's my photos of all the places I've mentioned:
Here are my trip reports:
(Santorini, Milos, Sifnos, Fologandros)

Crete -

Santorini, Naxos, Paros, Athens -

Posted by
1016 posts

As I mentioned I ran out of room so here is part two of my thoughts.
Every island hop eats up a minimum of half a day. Even the short one hour hop from Paros to Naxos with a 9:30 check out of the hotel plus the ferry trip we did not get out of our Naxos hotel until 3.
The point is that the less ferry hops you do the more time you have on the islands you visit. It is also important to plan to stay in the same island group which adds efficiency to your hops. The Cyclades islands make a lot of sense for you after Crete.
While the ferry schedules and routes are expanding with more choices essentially the ferry routes go from Heraklion to Santorini then you can connect for Milos, Ios, Naxos Paros and Mykonos plus several smaller islands. At the end of the route the ferries turn around and do the same route in reverse. As someone mentioned you can start your Cyclades Island routes by starting at the closest Island to Athens and work you way to Crete. However that decision puts you on the afternoon routes with the ferries arriving Crete Heraklion around 7:30 in the afternoon. That pretty much means you will have to overnight in Heraklion. We do Heraklion to Santorini to Naxos and are on the beach in Naxos around 1 in the afternoon. Thats 6 and a half hours either on the ferry or enjoying your first afternoon/ evening in Naxos.

You asked about similarities of Greek islands. Crete is very large. It has great beaches, mountains, villages, ruins and 4 cities. The people are full of hospitality and are very happy that you have chosen their island. Crete is pretty unique. The closest comparable island would be Naxos. It has the feel of Crete with everything I mentioned except it only has Naxos town with no cities. Naxos has a permanent population so it will give you an authentic Greek experience. It is also much smaller than Crete but it will still take you a minimum of 4 to 7 days to give you enough time to visit most of the island.

Naxos and Paros are very similar and are close by. From Naxos the sun sets over Paros. Both are delightful islands and either one would be a good choice for the Cyclades. Even though they are similar there are always arguments about which one is the best. I would say, virtually everyone will like either island but there is a saying" you are either a Naxos person or a Paros person." You really can't go wrong choosing either. We have made our choice.
Naxos Town
Trip around Naxos

Mykons is similar to Paros and Naxos with the same white and blue buildings, beaches and a pretty main town. Mykonos though has branded itself as a high end island. So everything is at least twice as expensive than Naxos more like Santorini without the view.
Milos and Santorini are both Volcanic Islands so have amazing landscape formations, both are different though. Santorini is packed with tourists and amazing views. Milos is totally laid back with just enough tourist infrastructure and sunset views that easily compare with Santorini sunsets,

Hope this helps in your planning.

Posted by
7990 posts

We spent two weeks in Crete staying in and near beautiful Chania. Greek friends advised us to concentrate on western Crete except for a day trip to Heraklion to visit Knossos and the Archeological Museum. We enjoyed driving to Chora Skafion and taking a ferry to Loutro on the south coast where we stayed a few days. We drove all over western Crete, beaches, monasteries.
We enjoyed staying on Paros after getting away from Santorini. Paros was so Greek in feeling after the crowds of non- Greeks on Santorini.
We stayed in Naoussa and would return there. Mountain villages and rides all around the island were wonderful.
We have been on the Dodecanese too, very interesting islands , but different. Save those islands for another trip.
The one thing that jumps out at me about your itinerary is that you are not including Napflio. I urge you to consider it, only a two hour drive from Athens on good roads. We were told that Greece’s two most beautiful towns are Napflio (on the Peloponnese) and Chania( Crete.)

Posted by
1117 posts

A word of caution since Virginia, Beth & Matt are going to be traveling in high season:

We have stayed in Naoussa in high season before, and we found it to be extremely touristy. It is by no means the quiet authentic Greek fishing village it is described as in some older travel guides. Our stay in Imerovigli on Santorini on that same trip was nothing in terms of crowds compared to Naoussa.

That said, our stay in Naoussa was very enjoyable nonetheless, and the town had the advantage of having a great and very punctual bus hub, but if you are looking for peace and quiet and less crowds, it might not be such a good choice.

As a general rule, on most islands it's going to get more crowded the closer you get to the sea. If you want more Greek life and less crowds, go inland.

Santorini is a different matter. You have to get out of the way of the cruise ship crowds there, so avoid the crater side of Fira for hotels, restaurants, and shops. Oia of course is terribly touristy too, but there are some smaller towns along the crater rim (Firostefani, Imerovigli, Megalochori) that cruise ship tourists are unlikely to find within their limited time.

I just see that you are not going to Santorini - oh well, I'll just leave this in here anyway.

Posted by
2898 posts

Isabel's jitters about plane delay arriving in ATH and thus missing the connection make some sense if the OP is bargain-hunting flights, and chooses one that connects in Europe -- THAT is where delays occur. If you fly in to London, Frankfurt, C DeGaulle, etc and connect to a noonish flight... bigger chance for delay in take-off. IF you bite the bullet and pay a higher price for a nonstop from N. America -- Air Canada, Delta/JFK, AMerican/PHL, and UAE or United/Newark -- these all take off late afternoon fly overnight, arrive ATH at times spaced out from 9 - 10:30. Even if one of these is delayed as much as 90 minutes or more in take off, they have that looooong stretch over the Atlantic to make it up. In the 10 nonstops I've taken, every one has landed on time or early.

Posted by
6 posts

WOW - Thank you all. I have a lot to digest.

I understand the jitters about a connecting flight. We had a flight to London from Boston MA a few years back... A tornado of all things happened in MA. Long story short we arrived in London 15 hours later than expected! So I understand the jitters. We are flying with United air reward miles so it will be a "discount" type ticket but I am trying to find flights without any connections in Europe -- We will have a connection in the states or Canada..

Yes to everyone. Crete does seem to deserve more time. We tossed ideas around and ran out of days quite quickly! Thank you all for the tips you have passed along so far!

StanBr -- the coastal village ferry hopping you mention on the south coast this sounds like a truly unique experience and deserves more.

Janet -- yes we are going to the guides books (live in New Hampshire fly out of Boston -- so our town library is small but we can always head to other towns nearby!)

Anna --

Our new thought with all of your kind advice -- your timely responses and sharing of your knowledge is truly appreciated! It is always better to hear from an actual traveler!

1 Arrive Athens/Depart for Crete
2-13 Crete
14 Ferry to Cyclades (still undecided which is fine for this stage)
15-19 1st island
20 Ferry to second island
21-24 2nd island
25 travel to athens
26-29 Athens perhaps 26-30
30 or 31 departure

This plan is still rough but seems like a better smoother less confusing trip without any unnecessary confusing ferry issues. (I agree with one of our responders about this). But we are not booking or committing to anything yet for our Cyclades destinations. We want a working outline to book our flights -- which we do have now.

Thank you-- after we book our flights and have done more research -- is it better to follow upon this thread or create a new one for more specific questions?

Posted by
2898 posts

I would think it's a good idea to start a new thread -- but with a beginning paragraph of recap just like the one you gave above... but saying y our first thread was (give title-- so people can look it up) and you got helpful advice to guide your research and choices, on tweaking your itinerary. Give your EXACT dates (and explain that education job prevents going earlier), and THEN proceed to your new tentative itinerary.

Posted by
2898 posts

Good luck on library guidebooks ... remember most libraries have an Interlibrary Loan Program with vans trundling back & forth to trade books; ask your local about it.

Posted by
847 posts

Janet, you have a good point about nonstop flights, but it's not a cost issue for many people, it's an availability issue. Like the OP, I fly out of Boston - no non stops flights to Athens. My daughter flies out of San Francisco - also none. My sister out of Charlotte - also none. And connecting in the US doesn't eliminate the risk. Just saying, have a solid Plan B. Will you be able to get another flight to the destination that same day? If so, then most people would risk it. But if flights are sold out well in advance then what. I've had this problem lots of places besides Greece and would love a good solution. But so far the only thing I've figured out is to have an itinerary that either keeps me in the first city for several days - so if I would just miss one day of sightseeing and not the domino effect of screwing up the whole itinerary. Or to have an itinerary where there are alternate modes of transport like a train, car or ferry.

Actually the last couple times I've been to Greece (and other places as well) what I've done is fly non stop to London (lots of options, Norwegian is super cheap) and spend a couple/three days there, then fly to where ever. You can get flights from London to just about anywhere. This of course means you have to want a few days in London but I always do. If you are more limited by time than money this isn't a good solution, but if you have more time than money you can put together some very economical itineraries and get a few 'bonus' days in London.

Posted by
1940 posts

We have flown into Athens on United miles many times, through several different airports (coming from Colorado) -- and we have never missed our separately-booked flight out to an island. If you're worried about this, Aegean Airlines has Flex fares that cost a little more but allow you to re-book with no fee. But if you allow a couple of hours between arriving and departing flights, it shouldn't be a problem.

I applaud your decision to go slowly. You might even consider spending your whole time (minus your ending days in Athens) on the island of Crete. Change locations every 5-6 days, and you will feel like you're on a totally different island, without the hassle of ferries or airplanes. We did this once on the island of Lesvos and it was one of our best trips ever. Sunrises on one side of the island, sunsets on the other.

Save the Cyclades islands for another trip. And then island-hop through the Dodecanese for yet another amazing adventure.