Early Stages of Planning a Trip to Greece

hey hey exploratina
when are you planning this trip, how many people & ages, budget in euros?$$ if coming from USA?
when renting car, look at aaa.com/IDP if you will need an permit (translation of license), apply online or stop at an office. rental car desk may not ask but if stopped for whatever reason and asked for one without having will be a big buck penalty fee. read up on all road rules/laws. signage, needing a sticker in window or not, speed limits, tolls, parking. if stopping for photo-ops, walking around is luggage okay in car for safety reasons
since spending money for your trip so worth the $20-25 dollar to get same day. all divers need one and good for a year. many changes from years to years within different countries, keep up researching on all of them
many parts/towns/villages will be busy, some may close during parts of the years, cruise ships at many ports
cruisemapper.com
click ports, type which ones you're interested in, time/dates in port, scroll down to ship and see how many passengers & crew onboard, which adds thousands to visit islands.was not happy at santorini, had 6 ships in port day we there, packed worse than a can of sardines, grumpy/nasty people, taking cable car up or walking steps with donkyes & donkey poo with lines so long not wanting to miss ship. mykonos was just as busy with so many people, we zigged while others zagged and roamed different parts of residents homes. just be forewarned. keep asking questions, the forum will give you good bad & ugly. have fun and enjoy
aloha

Hello Princess Pupule,
Thank you for your informative reply! The trip is likely to take place sometime in late May or June next year, and it will be a solo venture (or just me and my buddy Rick, for those who ask along the way). I’m going to have to estimate the budget based on how the trip shapes up. For certain, will bring an international drivers permit and insurance.
I’ll definitely use the site you mentioned for trying to work around busier port days, if that’s possible, or at least to help me adjust my plans. It is sure sounding like the waves of cruise visitors can put a damper on the experience, and of those two islands in particular…Will definitely be posting questions regularly here…this community was so very helpful in helping to plan past trips!
Thanks!

Be careful not to try to visit everything the guidebooks suggest when planning your first trip to Greece. It will be impossible in just 15 days.

Regarding the islands, the RS guidebook isn't strictly speaking an island guide, but a summary of three of the more than 150 islands that can be visited.

Santorini and Mykonos are overpriced mass tourism destinations invaded by crowds from May to October and have nothing to do with authentic Greek islands. Mykonos has been a mecca for partygoers from all over Europe since the 1970s. Those who go to Mykonos knowingly go there to party and see celebrities. The others are either cruise passengers who only stay for a few hours or tourists misled by tourism marketing who haven't taken the time to do their research beforehand.

Instead of looking for ways to avoid the crowds, simply head to other islands where you'll find the true vibe and authentic landscapes that the Greek islands are famous for.

In the Cyclades, there are at least 15 other islands with the famous blue domes, whitewashed houses, and sandy beaches.

I put off visiting Greece for years because it was so overwhelming, but I finally got there and what made the trip a success was focusing on just one area and keeping the logistics simple (in our case, it was a ten-day drive through the Peloponnese; next time it will be just Crete, which is too big to add to most itineraries, or just northern Greece--I'll do the islands when I am retired and have more than two weeks at a time). Trying to fit in everything would have been a terrible time, hanging out in ferry ports and airports, so keep your plan in check and you'll be fine!

Hello JoLui and valadelphia, noted! I feel like island hopping is challenging and might end up being hard to add to the trip...unless i keep to maybe 1 or 2 and for a few nights each. In the past, I have found the pace of the RS itineraries to work well...but often I insert an extra night here or there at select locations...and it is always a good chance to slow down a bit or catch sights that I missed on the initial planned day for whatever reason, etc. like getting a flu or getting distracted by other sights.

I feel like Santorini is often unfairly maligned on this forum. We had a wonderful time there several years ago, staying in Perissa, which is a beautiful black sand beach in the south of the island. I think often what people are thinking of when they talk about Santorini is the main town of Fira (where the cruise ships dock, and it does get crowded during the day) or Oia (at the north of the island, where people crowd to watch the, admittedly spectacular, sunset). We did not find Perissa crowded at all- it was one of the most relaxing holidays we've had. There's also nearby Kamari, similarly quiet (at least when we went- which was in early September), and we did a really memorable boat trip to Nea Kameni and Thirasia, the two smaller islands nearby. If Santorini interests you, you can definitely visit and have a nice time! There is a good reason it is popular.

If you are looking for one island to base yourself on, rather than island hopping, I think Crete is the best- it's huge and there is so much to do. It's far from the mainland so I would fly to save time. But honestly, I think you could pick pretty much any island and have a wonderful time. Good luck deciding.

Our first trip to Greece was awesome and looked like this:

Arrive Athens, drive directly to Delphi (1n)
Visit Delphi, drive to Meteora (3n)
Drive back to Athens, ferry to Sifnos (3n)
Ferry to Milos (3n)
Fly back to Athens (3n)
Depart from Athens

Meteora and Sifnos were our favorites. Milos was nice but more touristy and less welcoming. Can’t speak to Crete…headed there in September.

Happy planning!

Just a few thoughts. You are going to be very tired after a long flight so renting a car and driving immediately on arrival is not a safe plan. Your best bet would be to get to your first island immediately on arrival in Athens. Getting over jet lag is way easier on an island. It is also important to realize that you need to be in Athens at least the day before your return flight.

We always fly to our first island. Generally you need 2 to 2.5 hours to make a connection. We always make time to visit Naxos. It is in the Cyclades where you see the white and blue buildings. It has a lovely old town area topped by a Venetian era Kastro with a good beach just a 15 minute stroll from the town. It has mountain villages to visit and lots of tourist infrastructure.

If you want a glimpse of Santorini or Mykonos there are daily boat trips to both islands from Naxos. You get the experience without having to pay the very high price of staying on either of these islands. We mostly visit Naxos in late May early June. These months are busy but not overcrowded as it will be in July and August.
Naxos needs a minimum of 4 days a week would be better. You can fly back to Athens and pick up a car at the airport for your Mainland exploration. Be sure you have GPS. By the way you do not need the IDP International Driving permit. It has not been been required for several years.

This is why you might want to visit Naxos
Naxos town 2024 https://www.flickr.com/photos/stanbr54/albums/72177720318203165/
Naxos town https://www.flickr.com/photos/stanbr54/albums/72157632094558042
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689

We have been to Greece twice and will actually be in Athens in a few weeks. This was our itinerary for our first trip which I was very happy with.

Santorini 3 nights
Naxos 4 nights
Nafplio 4 nights
Athens 3 nights

I know Rick Steve’s tours go to the Peloponnese. That is our next trip. We went to Crete, Delphi, and Meteora for our second trip.

We are here in Greece now . We left Vancouver May 27 and return June 28 !

We aren’t doing mainland - and we’ve been to Athens .

First what time of year are you going ?

Secondly - our fave islands so far ( and we’ve been to several of them 6-7 times lol ) are Naxos , Paros , And Syros

Least favourite is Mykonos.
And this trip we included Ios and frankly it wasn’t worth it .
If you do go to Ios , it’s tiny , you don’t need more than 2-3 days max - be mistakenly booked 5 .

We are on Crete now , in Heraklion- we booked 4 nights here and tomorrow go Chania for 7 . I wish I had given more time to Naxos and tried Milos ( haven’t been there yet ).

Hey Pat you are going to enjoy Chania old town and harbour. Have a great time.

Late May-early June is an excellent time to see Greece. That’s when we usually visit Greece as it’s the best time for us, although next year we’re planning on doing it in late September early October after making excellent friends and connections in Rhodes this past week and half. First of all, get your hands on the Rough Guide for the Greek islands. We took with us the last edition from 2022 and the newest one is supposed to come out some time this summer. We much preferred it to the LP guide. Buy your plane tickets early, first week of February is early enough as prices start to go up late February early March. Try to keep your island visits in one area of island’s such as the Dodecanese or Cycladic islands as travel between those is easier than travel between other areas such as Ionian etc. Depending on which islands you decide to visit renting a car or a scooter may be necessary but there are exceptions as some islands have better public transportation than others. For example, last year we stayed on Folegandros and Milos and even though both have buses, we found it easier and our hosts recommended we rent a car for ease of moving around, even on Folegandros, which is a small island and doesn’t have the same touristic services as others. This year we stayed on Rhodes and Symi. Rhodes for 2 nights then 4 nights in Symi and then two more nights on Rhodes before our flight back to Bergamo, Italy. We rented a car the last day and half on Rhodes and it was the best decision we made as we visited so many sites and villages that have limited bus service or are overlooked by tour buses, which we usually shun. On Symi we didn’t need a car as there’s only one main road and their buses run from 7 am-11pm every hour on the hour or half hour depending which direction one is heading. And most of the beaches on Symi are only accessible via sea and we used taxi boats the rest of the time. In four days we visited 6 beaches and each one was more beautiful than the other. One beach even had excellent WiFi (Agios Nikolaos-St Nicolas). It’s hotter on Symi than Rhodes by 3-5 degrees Celsius. The Cycladic islands are windier than those of the Dodecanese. I mention all of this just to give you an idea of what’s out there. Rhodes, obviously, being a fairly large island has a well functioning airport and has buses that go directly to old town and all of the resort areas.

Hello again!
Thank you Cat VH for the encouraging words. I think I’d like to see Santorini, even if it can be crowded. The busiest hours can be the best to just sit down, recharge, and journal or people watch. I’m making notes though about all of this and see what shapes up. Crete is sounding like somewhere that would be wonderful to go explore in and of itself…enticing but I think I’d end up feeling like I am shorting myself on experiencing it if only there for a couple days…
Thanks mml for mentioning your favourites…Sifnos keeps coming up! I get the sense that it is best to spend 3 nights per island visited, to get a few full days to explore.
Dually noted, stanbr, it makes sense to start with the islands first, and then tour around mainland. I think it would definitely be a bit stressful to envision several legs of travel in several modes just before needing to catch a flight home. I also find that I am often tired by the end of a trip and need a bit of a chance to get organized, and not feel rushed.
I also appreciate the mention of the possibility of boating in to Santorini and Mykonos instead of staying there. Having a home base can make it easier than having to pack up three or four times to see the same places! And good to know that an IDP is not needed, and thank you for the resource links introducing me to Naxos!
Thanks for sharing your itinerary BethFL! These island and city names are becoming themes!
Pat, I will be going likely Mid June for 3-3.5 weeks (at least that is the preliminary vision)…thanks for sharing your favourites!
Thanks for the book/guide suggestion, jonrossjan, and on the value of checking into what transport resources are available on whichever islands I end up on. I get anxious about transport…always worth a bit of research ahead of time. I appreciate you mentioning a car is worth it on Rhodes, but that there are main buses too. I suppose it depends on how much time one has on a given island.
More questions have come to mind…possibly silly ones…What is the situation with washrooms (are there generally public ones or does one need to find a café to buy a coffee for instance)? How is the parking on the islands and mainland (Athens vs other cities vs touristic sights)? Is it important to carry cash in Greece or can one reliable tap? Hands down favourite piece of clothing for hot days in Greece (is it humid, windy, dry sweltering heat, or other)?

You are at the start of a great adventure, with plenty of time -- don't try to get all questions answered at once -- it's like trying to get ta drink out of a Fire Hose. Go to your nearest public library, and take out an armful of travel guides. See which ones appeal. Xerox some useful pages. You might settle on one --- I have a looong shelf of them, but found the One BEST one to be ROUGH GUIDE to Greece. Overall, it has the most in-depth stutf on destinations, landmarks etc. It also has great sectitons on life-style, getting around - things like bathrooms, and how to order in restaurants. (Rick Steves is really good on Athens and pretty good on the Peloponnese, but barely-there on Islands... maybe because his in-person trips don't do the isles)

When you buy, tho, a warning. The NEWEST Editions may not serve you best. Why? Because -- to compete with Internet, Guides began prioritizing the Wrong Things. They devote Too much space to color pix -- when internet does those better. They also cram pages with transportation info, Hotel & restaurant lists --- and those also, you always seek the most up-to-date info online. And to make room for those, the guides slashed and cut out the precious CONTEXT -- the descriptions & details that show WHY you want to visit that magical destination in the first place. The story of a village, the beauty of that secret statue, the reasons the fort is there --that's what counts. So -- check online book sources, get an edition from 2012 or 2014, rich in insights an "hidden gems" ... and use this to choose your destinations & "rough out" an itinerary. To book your logistics, nearer to the time, use the internet and forums like these for latest hotel & dining ideas and 2026 bus & ferry facts,.

As Janet said, you have plenty of time to plan your trip.

Don't worry about details like restrooms, parking, or whatever else. Greece welcomes over 30 million visitors from all over the world every year and is inhabited by humans just like you: people who go to the bathroom, work, watch TV, shop, eat out and have drinks in cafes, raise children who go to school, etc.

You're not going to another planet!

Get guidebooks, real ones, not travel stories on social media, which is the worst mistake you can make. And be careful: while it's easy to go from "Santorini" to "Rhodes" by reading a travel guide or watching YouTube videos, it's difficult, if not impossible, to do so in real life unless you stay at least a month.

So if you choose Santorini, forget Rhodes or Corfu or any other island outside the Cyclades. The other basic method is to look at a map.

Don't focus on "must sees" and "best places" either, this will make planning even more complicated. Choose the one or ones that interest you in the same area.

To answer some of your queries:

What is the situation with washrooms (are there generally public ones or does one need to find a café to buy a coffee for instance)?
I have not come across many public washrooms in towns. On beaches, the busier ones tend to have them- often they are part of a snack bar/small taverna so if you are patronising that business you can use it. Sometimes there are also small basic facilities on their own- sometimes free and sometimes paid. I prefer "organised" beaches (with food, bathrooms, and sunbeds) so I check on Google maps and Trip Advisor first to see what the facilities are.

How is the parking on the islands and mainland (Athens vs other cities vs touristic sights)?
I haven't driven in Greece but they do have a very good bus system (KTEL) on many islands, and of course the metro in Athens.

Is it important to carry cash in Greece or can one reliable tap?
Every time we visit we use less and less cash. We always try to have a small amount just in case. It can also depend where you are going.

Hands down favourite piece of clothing for hot days in Greece (is it humid, windy, dry sweltering heat, or other)?
Visiting Greece is pretty much the only time of year I wear dresses- I like long ones so you are protected from the sun but you still get the breeze. Depending when you go it may be very windy. You can check monthly averages for temperature, wind, etc for any location on https://www.holiday-weather.com/.

Good luck as you continue planning!

Hi Janet and thanks for your response! Great analogy…the early stages of planning and gathering information really can feel like trying to drink from a fire hose! I know I’ll get good use out of the RS guide, but have indeed been a bit antsy to get guide on the islands so I can select a few in a cluster to visit. I picked up a Lonely Planet guide for Greek Islands, and a Rough Guide to Greece, which can supplement the RS guide. The Rough Guide has a good 80 or so pages on the Cyclades, which is where I think I’ll be focused for the islands (incidentally the Rough Guide to Greek Islands has about the same page count for these…so likely lots of the same information). I appreciate the comments around changes in guide content! I don’t usually care much for listed hotels, and go with comparing a few sites instead, and am especially keen on the one you pay slightly more to be able to cancel (not because I plan to cancel the trip but because being myself, I do things like accidentally book for the wrong year and can then fix these things when I have had a strong cup of coffee). Anyways, I very much value the contextual information around the history of locations and sights. Thank you!
JoLui, you clearly have a great reputation on here so thanks for your input! Yes, I am starting early this year as it will be a budget friendly summer for me this time around, so why not enjoy the planning stages while I can. I feel like it’s quite a bit of work but so much fun and learning! As for the washrooms, I do get the sense that Greece is very comfortable to be in…but I have had some rather “memorable” washroom moments during some trips…I suppose carrying a she-wee around is always a good idea, and who doesn’t need good reason to pop into a café anyways?
Thanks for pointing out that is easy to make quick connections between some destinations that might not work so well in a fluid itinerary. I am getting the sense that Crete, Rhodes, and maybe Turkey would be something to contemplate for a return trip sometime. I will keep a map open when reading about the islands, and just pick a small collection in proximity of each other to explore.
When you say to avoid selecting islands based on their having been flagged as “must see”, etc. I realize too that in asking friends or colleagues about their visits to Greece, everyone will be biased to recommend the best of the sample they explored…so going with what draws me in more directly, based on curiosity or what I am partial to find most interesting, might be the best bet!
Thanks Cat VH for helping with some of the answers! I always worry about washrooms…and this might sound funny but knowing where they are makes the goal of staying hydrated less of a worry. Using google maps to check out the basics of any site is good practice.
I’m thinking I’ll only be driving for the mainland portion of the trip…with a small chance of renting a car for a day on an island if it seems necessary to really get to the sights. It sounds like some of the main islands are very easy to see via public transit. Maybe not Crete but as mentioned, that is probably for another time!
For cash, it sounds like having a bit as a contingency plan is a good idea. By a small amount I assume we’re talking about having a few hundred in case it’s handy for meals or transport, etc.
And as for clothing, it sounds like dresses are the wise choice for summer. Thank you for the link to the site for checking weather patterns!
Thanks all for the encouragement and very useful guidance! I’m sure more questions will surface as a “draft” itinerary starts to come together. This forum is such a rich source of support in making any trip happen, and wading forward through the worries that can surface during planning!

Since the Cyclades will be your destination, and to complete your brand-new travel guides, you can consult the official Greek tourism website for these 23 visitable Cyclades islands.

https://www.visitgreece.gr/islands/cyclades/

Even if someone tells you (including me) "We went to this island, it's wonderful, go there too," or "We were very disappointed, don't go there," there is no island better than another; it's just a matter of perspective and what you're looking for.

I've visited a little over half of the Cyclades islands, and I wouldn't be able to rank them, or if I did, it wouldn't match anyone else's ranking. I don't like "best of" lists anyway. :)

That's why Janet and I recommend doing your own research.

However, there are a few basic principles to know.

• In about a week, don't expect to be able to visit more than two islands.

• Even within this group of Cyclades islands, there are islands that aren't directly connected to each other by ferries. There are even plenty of situations where it's not possible to go from one island to another.

• Another example is that going from one Cyclades island to Rhodes in the Dodecanese is impossible unless you go back through Athens or spend more than 14 hours on a ferry, which only operates this route once or twice a week.

For the mainland, it's pretty much the same. Even with a rental car, you won't be able to see all of these "must-see" sites unless you have at least two weeks.

So: Keep it simple and reasonable!

And since you like details:

Due to the narrow pipes, you can't flush toilet paper in Greece; there are trash cans reserved for this purpose.

You'll have to deal with two things in Greece that you can't avoid: wind and cats.

Although the weather is unpredictable more than 72 hours in advance, my only source for weather information is here:

https://meteo.gr/index-en.cfm

There is no website for cat encounter forecasts. LOL. But I do like cats, even if they can be a bit intrusive sometimes.

https://photos.app.goo.gl/vYSBA8wfHFsZHdbz5

https://photos.app.goo.gl/BHtXDNpoVijjGRdKA

Although it is theoretically mandatory to accept credit card payments, the Greeks have a long-standing culture, almost a tradition, of cash transactions to avoid reporting them to the tax authorities. Sometimes this allows you to get a discount.
I've often paid for a rental car in cash (for example, almost €200 just last month on an island).

That said, normally, a few dozen euros in cash and a credit card is enough to survive, eat, drink, and sleep.

Note that ATMs charge a flat fee of around €2 for each withdrawal. So, if you need to withdraw money, avoid making small withdrawals. Be careful with Euronet ATMs, they will charge much more than the €2 flat rate at bank ATMs.

@Princess Purple- if OP has an American drivers license Greece does not require the IDP. The laws changed a few years ago. I’ve rented cars in Greece in 2023, 2024 and this year so I’m well acquainted with their laws. It’s required in other EU countries, such as Italy, however. No need to give inaccurate advice.

Sounds very good, Tina! It seems you have a realistic view of what you can accomplish in 2 weeks, and are the kind of solo traveler I love... advance reading is part of the fun! Mid-May on is perfect timing, and if you can Squinge 1 extra day off work, and take tha Thursday night non-stop and fly home on the 3rd Sunday, you'd have 15.5 days actually IN Greece... a decent first-trip length. Here's a basic itinerary i've recommended for numerous first-timers who liked it a lot: It involves a lightning-fast visit to Santorini on the Weekend - when cruise ships are much less:

• DAY 1 FRIDAY - Arrive before noon; get 2pm flight to SANTORINI for max 36 hours; stay in FIROSTEPHANI get caldera views walkinig rim-path to/from FIRA; DAY 2 8 am - taxi to "famous" OIA village 8 am to beat tour-group invasion @10 am DAY 3 - take either 11 AM fast ferry w open back deck, or 3:15 Large ferry, to 2nd Island (I favor NAXOS -- largest, greenest, best beaches)
• DAY 3 - 8? 9? - Explore island & fascnating port town -- Then FLY to ATH in AM, rent car leave by noon for Nafplio in (Argolid area of Peloponnese (if non stop, an easy 2-hr drive on modern roads -- or you can take bus & just rent car for a day, locally.
• DAY 8or9 - DAY 12?- Optional sites - Corinth Canal - ANcient Nemea - Mycenae - Epidaurus ... AND Nafplio, considered THE most beautiful Old Town in all of GReece
• DAY 12- 15 - AM return to ATH; 3+ days for world-famous landmarks & Museums

You are very welcome- I'm the same as you, I like to always know the washroom situation in advance. It's true that you can't put any paper in toilets in Greece, it may seem a little strange at first if you've never travelled to somewhere with that restriction before, but if you're staying at a hotel they do empty the bin for you each day. Honestly I think whatever locations you wind up choosing you will have a wonderful time, it's just such a magical place.

Thanks for the link to the tourism website to learn more about the Cyclades islands, JoLui! It can often feel like it is necessary to add destinations or sights due to fear of missing out, but I realize everyone has only their own reference points available in their recommendations…and it’s results in even me withholding the “you have to see…” statements. You’re right…go with one’s interests! I feel like between the guide books, trends in commentary on the forum, and the site you provided, I should be able to identify a few islands I’d like to get to…and recognize it’s critical to keep how much time I have to be realistic in planning it out! I greatly appreciate you pointing out that connecting Rhodes to the rest of the Cyclades would just not be practical, and that at most, only a few can be covered in a week. I’m going to need to factor in transport and connections at the beginning of my planning, rather than just looking it up post-hoc. Sorry, Rhodes…maybe another time! For the main land, I think I’ll have 2 weeks or just over, for arrival and departure buffers. While I follow the RS guides quite closely, I’ll often an extra night here or there to allow for a bit of pause, especially after bigger transitions or travels stretches, in case things took longer than planned or there were unforeseen setbacks, and ensuring the rest of the schedule can be picked up from there (oh, you know, little towns or castles that just have to be seen up close, or I don’t know…interesting issues on Belgian trains that turn a 3 hr ride into an all-day “field” trip getting to know locals and fellow tourists in the car).
Yes! JoLui and Cat VH, I appreciate getting a bit of foresight on the details…just so I know what to expect. The matter of paper and pipes is good to know! Not an issue but just good to know! The cats? Really!? Note to self to pack extra allergy medication! On past trips, I have to say, there is something very sweet about sharing a bench or chair with a neighbourhood cat. Wind? Also good to know! Living in the Pacific North West…even on the hottest days…it can get so very cold and windy overnight. Is it the same in Greece or does the temperature remain warmer overnight? Is there a need to bring a jacket at all in the summer? It sounds like carrying a bit of cash is a good idea.
Jonrossian, and Princess Purple, I tend to bring an IDP with me, just in case…as they are very inexpensive to get and last a good year.
As for direct flights…it looks like that won’t be an option from Vancouver? I think this trip might work best if it includes a short stay on the East coast before finishing the journey out. Montreal or Halifax? Is this another reason to go through Paris? Hahaha. Janet, thank you for a quick visit itinerary to see Santorini and Naxos. I wonder which island works best for day-tripping to nearby connected islands, or if it is best to stay a night or more on an island and simply move on to another?
A quick question on luggage. No judgement please…slow learning curve here. My first couple trips to Europe involved a medium sized checked bag. That was stupid. I had a car once, and even then…it’s awkward. The time without a car was brutal, especially as one of the wheels got smashed on the flight out. The next time, I had a great carry on back pack, and a tote, but brought a bit too much, and probably most problematic, accumulated too much chocolate etc. along the way. Oh I worked it off, don’t doubt it! Should I go with the backpack again, or find something of similar carry one size that I can just wheel around? I like the backpack as I don’t have to care about cobblestone or stairs, but it can start to get heavy. A small wheeled bag seems like it might work well too, and I can carry a small cross body bag with that. What’s your preferred approach to lugging around your basics somewhere like Greece in particular?

As for direct flights…it seems like it won't be an option from
Vancouver? I think this trip might work best if it includes a short
stay on the East Coast before finishing the journey out. Montreal or
Halifax?

I don't know if this will be useful to you, but for what it's worth, I saw that this year the airline Norse Atlantic began operating direct flights to Athens from several US cities.
I checked the fares, and some days there are direct flights from Los Angeles or NYC to Athens for less than US$250 with carry-on and checked baggage (it's cheaper than some France-Athens flights!)

Note that this is a "low-cost" airline with probably minimal comfort, just like the price.

I wonder which island works best for day-tripping to nearby connected
islands.

Basically, there are no better islands for day-tripping to another island, even a neighboring one. Ferry lines and schedules are not designed for this type of activity, but for the needs of islanders and the supply of goods between the mainland and the islands.

And most of the time, this is not a common way to visit the islands. What is practiced is "island hopping." which means spending a few days on one island and then take a ferry to spend some other days on another island.

There are a few exceptions, such for example Paros-Antiparos or Milos-Kimolos, with dedicated ferries that shuttle between them several times a day in less than 30 minutes. But even with these island pairs, you could easily spend a week on one island and another week on the other.

What's your preferred approach to lugging around your basics somewhere
like Greece in particular?

Personally, I never think about it, and I admit it's the least of my worries.
In my early days as a traveler, I had a backpack. In Greece, I got around with it on a scooter, very convenient! But the years go by...

Now I have a piece of luggage that isn't very big, but big enough to not fit in the cabin.

So that's what I take. I book a ticket with checked baggage, and it's fine for 2 or 3 weeks, especially since there are very few occasions when I have to lug it around while walking.

Thinking about it, I could probably manage with a carry-on bag since we always rent appartments or houses with a washing machine, but the problem is that I always end up with a lot more stuff because, among other things, I have a few favorite clothing stores in Athens that I can't miss. :)

.

Thanks for the response JoLui!
I generally avoid flying south before flying oversees, as the time and exchange related costs can end up negating any savings…with family in the middle of Canada, I can likely incorporate a short visit on my way out…though NY would sure make for a fun route to start!
As for day tripping across islands, that is good to know…as it will likely make more sense to just stick to a few then and transition to them, perhaps starting with the furthest out and making my way back to Athens by visiting another or two at most, before touring mainland.
For the luggage…I suppose the duration of the visit and how many times I move around will need to be factored in...the carrying will mostly be happening during visits to islands, but there will be a car for the mainland. I know the issue of having space that quickly fills up…but for this I think I’ll bring a folded tote that can be checked in on the return. For some reason, I tend to bring back even practical items like cooler bags and cheap hats!

I'm going through a slow down phase in planning...a bit of nerves I think! But surely will have more questions!

Go to Hydra
You won’t get lost - no cars, just walkable cobbled streets and then dirt roads
Our son was able to run 4 miles and back
Our daughter collected data on her own for her NASA internship visiting the monasteries and parts in between
Beach boats from 1100, 1200, or 1300
I would recommend Bisti beach

Yes YVR-YYZ-ATH
Or YUL
But also look into SEA-IST-ATH
Turkish airlines airlines is good