Advice needed for a 3 weeks in Greece

Just a few basic remarks.

3 nights on an island is only 2 full days; plan for at least 4 nights, and even in 3 full days you won't be able to see everything the island has to offer. For Naxos, you can plan 6 nights.

Crete is huge, if you can visit part of it in a week, you certainly won't be able to see everything, even in 2 weeks.

An important logistical detail:

Milos is in the Western Cyclades, as soon as you want to reach an island that is not part of this subgroup, you risk facing difficulties or being unable to get to that other island.
For example, while Milos and Naxos are very close geographically, you could spend hours getting to Naxos from Milos because it is only possible via small island-hopping catamaran ferries (which are not pleasant at all). It's the same thing in the Naxos-Milos direction.

So if you want to visit 2 islands including Milos choose another island in the Western Cyclades. Sifnos could be the one you would like the most. Since Sifnos does not have an airport, you will have to take a ferry to get there and leave.

We are thinking of visiting Hydra the day the tour ends as a day trip.
Then going to Crete the next day.

Avoid planning such travel sequences, there can be unforeseen issues with ferries (bad weather, strikes, breakdowns).
Always have a safety margin. This approach is obviously essential if you have to take a flight to return home, do not plan a ferry journey right before your flight on the same day.

Since you didn't specify the exact date in May, I would just like to add that Orthodox Easter celebrations in 2027 will take place between Good Friday (April 30) and Easter Monday (May 3).

It is a very busy time, a lot of sites and museums close, and ferries and flights are packed.

As Always, Jo-Lui brings Great information promptly, which reminds all of us how vital it is to research Key factors. Hoping your RS tour is May 17 - 30, but Probably May 10-25, which means u arrive Easter MONDAY, May3. If so... plan way ahead! Book a flight to your chosen Island many months ahead of time, and allow at least 3 hours layover, because airport will be super-busy & the new European check-in/out system takes extra time. Now, about choosing destinations --

Advise to skip Hydra ... over-promoted by R Steves because his tours dont do islands, and it's a one-day add-on so people can tell friends "I went to a Greek island." Lovely harbor, but better beaches are hard to reach ... a lot of rich elites have stayed here, have pvt homes, movies made here, partly why the hype. But it's not handy for your purposes.

Also suggest skipping Milos, tho I've had good visits in past. Problems: now over-discovered, bad construction underway, spendy crowds. Also - experience in Milos is a sailboat trip around (or half-around) the rim of the island... and September being about THE windiest month in Greece, and sailboats wont go.

ARRIVAL - MY Vote : catch onward flight ( 2 or 3pm) to NAXOS... it's ideal time of year for this green & fertile isle, for exploring its dramatic inland terrain, gorgeous sandy beaches, fascinating port town... and tho it's been "discovered" (alas) not overrun by cruise mobs (port cant take megaships) or huge tours (airport only takes modern turboprops, not jets).. Five days is barely enough to experience this largest Cycladic isle but I envy you!. Fly back on Sunday -- or consider a 6 hr "mini-cruise" (9:45- 3pm to Piraeus) on large open-deck BLUE STAR ferry.. like a small ocean liner). Sit outside & gaze at sea, then go indoors to leanback comfy seats to read & doze. You'll be rested AND energized AND Greece-savvy, checking in hotel for your RS pre-tour dinner. After u have your itinerary decided, we can advice many good-value hotels/pensions with seaview balconies.

POST-TOUR - My Vote: fly into CHANA Crete, and use it as base for your stay ... if its no more than 5 days or so. There's SO much to experience in Western Crete surrounding Chania (coastal area E of Heraklion is heavily 'tourist-holiday" country). After RS tour you may have had enough of museums/ancient sites ... if so, you could just enjoy nature, then fly to London from Chania. If not, on last day, an easy drive or express bus E along coastal highway 2 hours to Heraklion. Main goal = see its fine Museum (BEST array of Minoan treasures!) and perhaps go 30 mins out to famous Knossos... dine & spend night in Heraklion - fly out next AM to London.

II've been to more than 25 Greek islands since 1999, but these 2 are my top favorites, where I return again & again... each time making new discoveries. Its the same for Longtime RS contributor and ACE photo "stanbr" & spouse for more than 20 years in love with those 2 places, and have stunning photo Albums to show why. I'll link just 2 as a start:

Back to Naxos 2022 - https://www.flickr.com/photos/stanbr54/albums/72177720299940917/with/52156669601
Back to Chania 2022 - https://www.flickr.com/photos/stanbr54/albums/72177720299646015/with/52779937148

We are going to sandwich in the Rick Steves 8 day Athens / Nafplio tour in the middle of the trip.

Those start on Sun May 2 or May 16.

Greek Orthodox Easter is May 2

My guess is OP arrives Greece on May 10, so Easter Season should not affect their trip.

If you plan to visit other islands, doing a day trip to Hydra is probably redundant and a lot of bother for minimal return.on the time investment.

You are right Joe... I was looking at the wrong 2027 RS Tour, the longer one. That's a relief, not coping with Orth. Easter weekend.

Hello,
Yes we are arriving in Athens on the 10th with the tour starting Sunday night on May 16th. Easter shouldn't be an issue.
I thought the same thing about Milos and Nexos not being easy to travel to by ferry.
There is a ferry from Milos to four other islands including Sifnos. Should we think of visiting those islands and skip Nexos? Or skip Milos and concentrate on Nexos and islands that the ferry system connects directly with Nexos?. Would you risk going back to Athens by ferry the day the tour starts with just a few hours before the tour starts on Sunday? Could it be too windy in May where a ferry may be canceled. We would rather spend the night on an island instead of Athens.
So it looks like we should skip Santorini and spend our extra days in Crete and fly out from there. This will give us a full seven days Crete.
Skip the day trip to Hydra,
One reason I'm asking fo advice is this may be our only trip to Greece for sometime. There are many other countries on our wish list that we would like to visit so we are trying to get a good Greek experience in our three weeks.
Thanks again for the advice. It really helps.

The ferry route through the Western Cyclades starts in Piraeus and usually runs all the way to Santorini, stopping at Kythnos, Serifos, Sifnos, and sometimes Kimolos, followed by Milos, Folegandros, and Sikinos.

This is a subsidized route that operates year-round, though not necessarily every day outside the peak season.
So, if you choose one island from this list, it makes sense to pick another from the same list if you want to visit a second island—though you should still check the ferry schedules.

I admit that, like Janet, I’m not a huge fan of Milos compared to the other islands on this list that I’ve visited, but that’s just my personal opinion.

The advantage of Naxos is that it’s a 45 min ferry ride from Paros (from where you can also visit Antiparos), and it’s within easy reach of the Small Cyclades islands: Iraklia, Schinoussa and Koufonissia which are connected to Naxos daily by the Skopelitis (Small Cyclades Lines). You can even go as far as Amorgos, the "Big Blue" island.

Could it be too windy in May, leading to ferry cancellations?

Yes it happens at any time of year, ferries stop running when winds reach 8 Bf or higher.

It happened for 2 consecutive days in May 2025, also for 2 consecutive days in May 2024, though not this year in May.

In June 2022, we were stuck on Tinos for a day. In September 2019 we were on Amorgos and there were 3 consecutive days without ferries. I once missed a return flight because I was stuck on Sifnos due to bad weather (I hadn't followed my own advice, my own fault).

That said, the risk is low, though unpredictable. So it's up to you,

If you absolutely want to minimize the risk, fly to Crete. But remember: good times make good memories but bad times make the best stories. :-)

Thank you for the information.
I am leaning towards Naxos instead of Milos now. You mentioned there are smaller islands that one can reach from Naxos. Would day trips to other islands near Naxos be better then moving motels and islands?
We are used to leaving early in the morning and not returning to our room until late in the day or early evening. Would it be worth a ferry run, then rent a car then return later in the evening to our base island. Would it be much different going to see another island or should we just concentrate on sites in Naxos?
So I'm thinking of flying to Naxos in the afternoon on Monday May 10th. That will be the end of almost 24 hour trip for us from the West Coast. So day 1 in Naxos will be Tuesday and a kick back day with minimal travel or site seeing to get over jet lag. That gives us Wednesday, Thursday and Friday. I will leave Saturday open to take a ferry back to Athens in case the weather is questionable. If the forecast looks good we will travel back on Sunday before the tour starts.
Then with the RS tour ending on Sunday that gives us seven full days in Crete with us flying to London the following Monday.
So we want to stay Chania to do the Samaria Gorge hike and the beaches on the west side. I also want to see the historical sites like Knossoʻs in Central Crete. Should we fly into central Crete stay two nights there then move up to Chania? If we do that can I rent a car from one airport and return it at a different airport. Or do we just base camp in Chania and day trip to the museums? They say it can take a couple hours to drive there. But perhaps that drive is nice so a two hour drive there and back could be an enjoyable experience but does that give us enough time to see the sites?
So the general attitude of the group is spend a week on one island instead of island hopping with three nights on each island? Thats the way I'm leaning right now.
I envy you guys that have been to twenty plus islands. Thanks again.

Yes it happens at any time of year, ferries stop running when winds reach 8 Bf or higher.

What does the number of boyfriends have to do with ferry sailings?

Or is that board feet of lumber?

Beaufort is the boyfriend's name.

Haha, it's true that the term "Bf" can be confusing if you've never sailed. It's even more so in French, because it combines the words "beau" (handsome) and "fort" (strong), terms that might (or might not) apply to one's boyfriend. :-)

See, for example, the weather forecast for Naxos with the predicted wind (Bf) and gusts for the next few days:

https://meteo.gr/cf-en.cfm?city_id=17

That being said, don't let paranoia stop you from traveling. Millions of travelers go island hopping in Greece every year without any issue with the ferries (Greek taxis seem to be a bigger concern!).

To get back to mbosteder's questions, I'd say you do whatever you want once you're on an island. Some people prefer staying in a "downtown" hotel, having walkable access to shops and a beach, and dedicating a day or two to exploring the island by bus and maybe taking a boat day trip.

As for us, after spending months on the islands, we pretty much know how we operate: we always rent houses or apartments with a kitchen, ideally away from towns and shops. We rent a car for the entire stay, usually near a beach but not necessarily since we spend more time exploring the island by car or hiking rather than hanging out at the beach. We never take organized boat or island tours because we plan everything ourselves, but we might sign up for a water sport activity that requires special equipment. We do our grocery shopping at mini-markets or from local producers of wine, cheese, or other local specialties.

So it's a different style that maybe requires a bit more research (I spend weeks, or even months, researching). Once we're on the island, it's day-to-day improvisation. I always make a map. For Naxos, it looks like this:

https://www.google.com/maps/d/edit?mid=1d7GZMjFODUlB8lf7EPSXQRwu-YXaKxw&usp=sharing

We've met Americans and Australians who chose to rent a studio on an island for about two weeks and take the ferry to other islands for 2 or 3 days. Which means budgeting for two accommodations, one of which remains partially unused.

We also recently met a retired American guy (from New Jersey) traveling solo who was visiting islands at random without booking anything, just catching whatever ferries were available. He had even lost his phone and didn't seem to care at all.... :-)

From Naxos, you can find tons of organized day trips either by bus on the island or by boat around the island with stops at secluded coves and a picnic, or visiting Delos for the day. Most of which you can also organize on your own. You can also rent a car for just part of your stay to visit places inaccessible by bus...

So there are all these approaches and all kinds of ways to stay on an island; it depends on you and the time you have available.

I don't have any recent experience with Crete (my last visit was over 25 years ago), but the principle remains the same.

Regarding car rental, many car rental companies allow you to pick up the car at one location (such as the airport or port) and drop it off at another. You just need to check their websites and run some booking simulations. Try to prioritize Greek rental companies over major international ones like Hertz or Avis. They are usually cheaper, more flexible, and less fussy about the car's condition upon return.

However, be aware that, just as anywhere else in the world, a rental company that is significantly cheaper than the others isn't always the best choice.

"it's true that the term "Bf" can be confusing if you've never sailed. " The standard abbreviation for Beaufort (at least in English) is Bft, not Bf. That way no confusion with BF :-)

That's right; I didn't add the 'T' because it could be interpreted as "Boyfriend in Trouble." :-)

Meteo.gr uses the term Bf in reference to Beaufort wind speed.

"Meteo.gr uses the term Bf in reference to Beaufort wind speed." I think that this is because of a(n) (auto) translation error from the Greek Μπφ which is the Greek abbreviation for Beaufort

We have been to both Naxos and Crete but on different trips.

We spent four nights in Naxos after Santorini (so no jet lag). We spent 4 nights there and really wished for at least five.

My suggestions would be:

1. book a flight on Sunday morning so you don't have to consider whether a ferry would be cancelled. That would reliably get you to Athens for your tour.
2. You could easily occupy yourself for the whole time (five days) on Naxos. Delos is a day trip some people have done. Paros is close by and could be done as a day trip, although I don't know how worthwhile that would be. I haven't been to Paros but my impression is the best places are not not where the ferry comes in. If I were to do a day trip, I would go to Delos because it can only be visited as a day trip.
3. We spent 11 nights in Crete. We flew into Chania and out of Heraklion. That is what I would do (or in reverse if Chania is better to get back to London) if you want to go to Knossos. I would spend five nights in Chania and 2 in Heraklion. We had a car but you would not necessarily need it for this itinerary. We stayed in a small town outside of Heraklion and drove to Knossos but took the bus into Heraklion to visit the archeological museum and the historical center. It is very easy to do (we had tired of driving so left our car in the parking lot at Knossos).
   
4. There are trips you can book from Chania to the beaches and to the Samarian Gorge.
5. I do not know how good of shape you are in but I would watch some videos on the Samarian Gorge trail. It is a very steep decline that is hard on your knees. You can not turn around easily if it gets to be too much. My husband had torn his ACL a year earlier and we elected to do the hike from the bottom. We took a bus to the coast and then a ferry and hiked up to the town of Samaria and then turned around. The length was about the same but we skipped the difficult steep section. We were in our early 60s.
   

Here are the trip reports I wrote. This may help you figure out how much you can do.

https://community.ricksteves.com/travel-forum/trip-reports/back-from-2-week-trip-to-greece-3f99d9bb-9215-4eb2-9081-dc48c0535dd0

https://community.ricksteves.com/travel-forum/trip-reports/report-on-trip-to-crete-delphi-and-meteora

Thank you Jo and Beth. Jo for the map where I saw the seven village hike and Beth for your trip post. Tell your son not to feel bad about the ATV, sh** happens. I hit a bridge two blocks away from the rental car agency in Dublin which caused a couple thousand $.
Beth, thanks for the advice on the gorge hike. My wife and I just completed the Camino Portuguese this past spring so we think we can make it. Especially being mostly downhill. We may skip Mt Zues hike because it's all uphill. LOL.

I am sure you will be fine on the Samarian gorge trail if you are really hikers. I have a friend whose companion barely made it down in time for last ferry. She should not have been doing it.

Mt zas is not that hard. My son did it with his injured leg. But perhaps going between villages would be more rewarding. It is well marked which is one reason we did it. But I didn’t have a map like you now have!

Enjoy! You will love Greece.

But I didn’t have a map like you now have!

It's still probably better to get a real map you can crumple up and scribble on, like this one for example:

https://nostromoweb.fr/en/hiking-trekking-2/naxos-311-terrain-hiking-map/

You can find them on Naxos. It"s useful even if you aren’t hiking.