3 week Greece itinerary in May

1/ You can keep your original plan with the 5 nights in Naxos. But it all depends on what you intend to do there. If you rent a car, you'll have plenty to keep you busy for 4 days (I spent a total of 15 days in Naxos and I didn't see everything).

2/ It's always difficult to recommend places to visit in the Peloponnese. Especially since in 4 days you'll have to make some choices.
The best thing would be for you to do some research and see what interests you. Don't try to see too much, travel times in the Peloponnese are much longer than you might think from looking at Google Maps.

Another option would be to dedicate these 4 days to visiting Meteora and Delphi. It's up to you.

3/ On the Greek islands, I always rent from local car rental companies. I don't have any particular preferences except that I prefer rental companies that don't require prepayment through an online booking system.

Try Google Maps, center the view, and zoom in on Naxos Town (where the port is) and search for "Rent a Car".

Then you just have to choose based on rates, car types, reviews, etc.

The vast majority of rental companies can arrange a pick-up and drop-off of the car wherever you want, whether it's the airport, the port, or sometimes even your hotel. Sometimes all it takes is sending an email asking about prices and availability. No formalities are needed; you can often pay in cash when you pick up the car, this is quite common in Greece.

4/ Same principle as for Naxos. If you want to rent a car at the port of Piraeus, zoom in on the port with Google Maps and search for "Rent a Car".

If you're returning to Athens by ferry and want to head straight to Nafplio, the best option is to rent a car at the port of Piraeus.
From the port of Piraeus, the airport is in the opposite direction from Nafplio and about an hour away. Renting a car at the airport adds at least 2 hours to your trip to Nafplio.

Alternatively, in Athens, all the car rental companies are located on Siggrou Avenue in the city center. Some have an office at the airport. I sometimes rent cars from Athens, either in the city or at the airport, using the same principle: no prepayment through an online booking system. This provides some flexibility for last-minute cancellations.

Siggrou Avenue is located here:

https://maps.app.goo.gl/yEV5KeTKjX2mvXEf7

5/ In Naxos you will find all kinds of excursion and daytrips options at local travel agencies. You can take a look in advance at some travel agencies that have websites. One agency established for years in Naxos is Zas Tour, but you'll find others there. They have signs in front of their shops showing the tours they offer.

Since boat trips depend mainly on the weather, there is no point in booking in advance without knowing what the weather is going to be like.

https://zastours.com/naxos

JoLui, I am grateful for your response. Excellent information and suggestions!
I have struggled with what I (and family) would like to see after Nafplio that doesn't involve a lot of driving, and I am now rethinking my itinerary. I am considering adding another island and am wondering what you think of these two possibilities.

(1) - add Crete:

• Monday, May 4, fly to Chania, Crete - arrive Tuesday, May 5: (4 nights in Crete). We would stay in Chania and visit Balos Lagoon, Elafonissi Beach, and focus on the region not too far from Chania.
• Saturday, May 9: Ferry to Santorini (3 nights Santorini).
• Tuesday, May 12: Ferry to Naxos (5 nights Naxos).
• Sunday, May 17: Ferry to Athens - rent a car and drive to Nafplio (4 nights Nafplio).
• Thursday, May 21: Drive to Athens, return car rental (3 nights Athens).
• Sunday, May 24: fly home.

(2) - similar to original itinerary but add Milos:

• Monday, May 4: Arrive in Athens (3 nights Athens)
• Thursday, May 7: Fly to Santorini (3 nights Santorini)
• Sunday, May 10: Ferry to Milos or Naxos (have to look into which is the most logical route). Either 4 nights Milos or 5 nights Naxos.
• May 14 or 15: Ferry to Milos or Naxos (Either 4 nights Milos or 5 nights Naxos).
• Tuesday, May 19: Ferry to Athens - rent car and drive to Nafplio (4 nights Nafplio).
• Saturday, May 23: Athens
• Sunday May 24: fly home.

I have to admit I haven't researched Crete or Milos much. I know Crete is huge so perhaps going there for 4 nights doesn't make sense?

Thank you for your help!

There is an issue with your plans to leave Crete. There is no ferry from Chania to Santorini or for that matter Naxos. There is two ferries a week from Rethmnon to Santorini. All the rest of the ferries are from Heraklion which is a couple of hours drive from Chania.
I might respectfully suggest you fly from Athens To Chania and spend as much time as possible exploring West Crete. Honestly you need a minimum of two weeks to experience west Crete.

Every change of location you do will eat up a minimum of the morning. Fewer hops gives you more time to experience where you are.
If you decide not to do Crete then you might want to consider 3 nights on Santorini and 5 in Naxos. They are good companion islands, all the great views in Santorini and the authentic Greek experience on Naxos. Naxos needs a week to fully explore if you have the time.
Do less and experience Greece slowly.

Here is a taste of Naxos.
https://www.flickr.com/photos/stanbr54/albums/72177720329571437/

I forgot to post my Chania images.
https://www.flickr.com/photos/stanbr54/albums/72177720318408008/

Thanks stanbr! Assuming Crete is out of the question, what about adding 4 nights Milos or Paros either before or after Naxos?

I really do not think Crete is out of the question. Its a great destination with so much to see and do.

You have certainly done you research and have chosen really good destinations . What you have to decide is what do you want to do most and eliminate the other enticing options. Greece is best explored slowly. Fewer island hops make for a more satisfying experience.

Thanks stanbr - I just noticed that you’re in BC …so are we! (Vancouver).

Given that Crete is so large and has much to see, I think that’s best for another trip where we can focus on that.

I completely appreciate your suggestion to not do to much island hopping as it takes up a lot of valuable time - unfortunately, I am in the challenging position of trying to strike a balance between going “slower”while ensuring that my 19 and 22 year old daughters don’t get too twitchy.

Does the itinerary below seem too rushed?:
3 nights Athens
3 nights Santorini (flight from Athens)
5 nights Naxos
4 nights Milos
4 nights Nafplio

Also, in Naxos, my intention (and preference) is to find a single accommodation and rent a car to do day trips. Is this advisable. Or is it better to stay in two villages to reduce the driving?

Thank you so much!

As stanbr pointed out, any island hopping takes at least half a day. This means:

On island A, pack your bags - check out of the hotel - transfer to the port - wait for the ferry - take the ferry - arrive on island B, transfer to the hotel - check in - unpack.

The more island hopping you do, the more time you waste that could be spent visiting fewer islands.

Also, without wanting to discourage you from going to Milos, there are several things I'd like to clarify.

Milos is in the western Cyclades and doesn't rely on the same ferry routes as Naxos and Paros. This means that to get from Milos to Naxos or vice versa, you'll have to take a small Seajets catamaran ferry (Superjet or Superjet2) which operates the Cyclades island circuit from April to October. It will take a considerable amount of time. Not to mention that these catamarans are very uncomfortable.
For example the route of these ferries from Naxos to Milos is as follows:
Naxos-Koufonissia-Amorgos-Santorini-Folegandors-Milos.

That's almost 5 hours by ferry (and a nightmare if the sea is rough) instead of about 1 hour if the route were direct.

I would add that about 50% of Milos is a Natura 2000 protected area, almost entirely uninhabited (where driving is prohibited without a 4WD vehicle), and unlike Naxos or Paros, Milos has very few villages (3 or 4) in the non-Natura 2000 zone.

Having visited most of the Cyclades islands, Milos is one of my least favorites, but that's just a personal opinion. If you absolutely want visit another island, you should check out Amorgos, the island of the deep blue, located between Santorini and Naxos.
It's one of the most beautiful islands in the Cyclades and still relatively untouched by the mass tourism of the islands with airports.

https://amorgos.gr/

From Santorini to Amorgos, it's about a 1-hour ferry ride (daily), and there are many ferry options from Amorgos to Naxos.

There's no need to have two bases in Naxos.

Some videos:

Amorgos:

https://photos.app.goo.gl/FpmYyDGaCx42R4Z29

Naxos:

https://photos.app.goo.gl/CQD3YJ2niF2Egyda6

I was also going to suggest Amorgos for a third island.

The thing that is hard to grasp at first is how much you have to plan your trip around ferry routes. My first trip to Greece I initially wanted to visit islands in three different island groups. Once I understood the ferry routes better, I ditched that plan.

We have been flying to Greece from the west coast for years. One of the things that we have realized that getting over jet lag in Athens is a double whammy, you are in a foreign country with different character so you do not understand what is going on and your brain is not fully functioning.
You will regret spending only 5 nights in Naxos, It takes a minimum of a week to do it justice. 10 days would be better.

You probably should find a hotel near or in Naxos town. That gives you a really good town beach St George just a 10 minute stroll along the headland and all the activities and sites of Naxos town.
We always get a hotel at St George.

When you decide to explore Naxos interior thats when you should rent the car. If you want to visit west coast beaches you do not need a car the bus service is good and inexpensive.

My suggestion would be to Immediately fly to Santorini the day you arrive in Greece. Connection time needs about 2 hours for a flight to Santorini. Santorini while very busy and expensive is amazing and your fuzzy head will perk up.

Naxos and Santorini are good companion islands to pair. Rather than doing additional island hops take advantage of the excursion boats that goes to other islands and archaeological sites.

Return to the mainland from Naxos and do Nafplio and end your trip in Athens.

Here are some more images of Naxos.
https://www.flickr.com/photos/stanbr54/albums/72157634605629689/
https://www.flickr.com/photos/stanbr54/albums/72157656336387898/

Hey stanbr:

I know Naxos is a favorite of yours so can understand your recommending it.

i was there way back in early October 2013 and at the time it was great, far less tourists and Naxos Town was pleasantly busy without crowds. The rest of the island was very quiet and enjoyable with numerous villages, mountain roads, coast and beaches and so much more.

I know Naxos has become very popular and attracts more people so hopefully it still retains a good Greek "vibe"

Are those videos on Google Photos yours or stock videos?

I have a Google Account for photos so a bit curious if you can upload videos.

JoLui, thank you for enlightening me about the ferry system and Naxos-Milos! That has saved me a ton on time and heartache!

After reading all of your comments and others in is forum, I’m thinking I should just add the extra days onto Naxos. That way we will have time to spend time at the beach and explore, and do a daytime watercraft trip. Should I add all 4 nights to Naxos or add 3 to Naxos and another to Nafplio (ie. increase it to 5 nights from 4).

I’m so grateful for everyone’s time and suggestions!

I’ll consider flying directly into Santorini - will look into that as well.

Thank you so much!!

make it 4 nights (Minimum!) in Naxos. Tho Nafplio is full of interests, its compact so can be appreicated in 3 FULL days. I hope when you say "extra days" you are dropping the (bad) idea of cramming Milos into your trip. Sometimes more is NOT more ... less is more.

I hope you have listened to the Vets, and put Athens at the LAST, where it will be most appreciated ... if you see its famous landmarks and museum treasures when you're fresh off a looong international journey, everything will be a blur. Also, unless you are a massive ancient-history buff, a lot of it will pass you by. But being in Crete, Naxos, and Nafplio... seeing ruins, vistas, famous sites there, the Athens wonders will resonate much more. BTW, if you visit Athens' Ancient Agora, just west of Acropolis, download the FREE Rick Steves Audio tour... really adds to the experience.

Hi Janet!
Yes I’m definitely listening to the vets!

Currently I have:
3 nights Athens
3 nights Santorini
9 nights Naxos
4 nights Nafplio
1 night Athens

I’ll look into getting a connection to Santorini and do Athens last. That would mean Santorini would not overlap a weekend at all so more busy there, and our flight logistics might be an issue but I’ll definitely look into it. Since it has been recommended many times on this forum it sounds like good advice.

Thank you!

Please do consider the Fly on Arrival approach... Yes this means Santorini on a Tuesday maybe, and there WILL be cruise ships -- but we have a strategy for that, Too! You DONT stay in crowded costly OIA... look at FIROSTEPHANI .. just on the north fringe of Fira Town, walkable to shops & clubs there, but away from the hubbub -- and many hotels with gorgeous cliffside balcony views at 1/3 or 1/2 the cost of Oia similar. Best-buy nominees -- Hotel Mylos, Sunset Hotel, Agdanema Apts.

OIA STRATEGY -- book taxi for 7:45 arrive 8 am - have 2 hours to stroll, take pix, enjoy beauty, before huge cruise airmies invade and jampack lanes at 10 AM ... then take but to FIRA, see small good museum, maybe bus/taxi up to High Anient Thira on bluff, 360° view.
Save swms for Naxos - santorini beaches are black grit.

FERRIES -- Best AM ferry, is CHAMPION JET - , small rear platform open for 20 mins to see cliffs on departure .. arrives Naxos about noon, Resrved inside seats so no rush, but costs €€€. the BIG B lue Star Ferry leaves 3:15 - arr 5:15 -- has 2 upper back-decks for seating, enjoying the seascape. Economy seats v reasonable but outside seating 1st come 1st served. Best Srategy: arrive dock by 2:30, get in line near exit door. When exit opens there's a rush up ramp. Strategy -- teens rush up steps & snag good deck seats, adults stash big bags on racks on main (vehicle deck). That's what kids are for!!

Thanks Janet that’s great advice! My family is concerned that 9 nights in Naxos is too long. Better to do 9 nights Naxos or 5 Naxos, 4 Paros?

Thank you!🙏🏼

If you're taking a flight from Athens to Santorini, I strongly advise against flying with Ryanair, the Irish low-cost carrier. While they may seem cheap, they'll charge you so many extras that you'll end up paying two or three times the advertised price. Instead, fly with Aegean or Sky Express, two excellent Greek airlines with fair and honest pricing. You'll have at least a dozen flights a day with these two companies

Regarding the Santorini-Naxos ferry in May 2026, it will be the Superrunner Jet, not the Champion Jet that Seajets is planning to operate. It normally departs at 9:50 AM. It also has a sun deck at the stern, but it's not designed for lounging for hours. Anyway you wouldn't tolerate the wind for very long (nor the sun, as you'll be facing due south).

My family is concerned that 9 nights in Naxos is too long. Better to
do 9 nights Naxos or 5 Naxos, 4 Paros?

As for whether to shorten your time in Naxos and go to Paros... that's the eternal dilemma for everyone going to Greece for the first time: wanting to see as much as possible.

In your case, it's true that 9 nights in Naxos might seem too long. But it depends on what you usually do on vacation.
If you spend most of your time in Naxos Town and Saint George Beach, taking a drive or two around the island, then 4 nights will be enough. That said, keep in mind that staying on the beach and swimming in May might not be your main activity.

We never go to Naxos Town except to arrive and depart by ferry because we prefer quieter places, and there are plenty of them on Naxos. Further south on the west coast, there are some huge beaches with no paid sunbeds.

In any case, the beach only represents a small part of our activities on the islands; we spend more time wandering around villages, monasteries, farms, wineries, or going hiking or boat trips.
We never stay in hotels but rent apartments or houses with kitchens, which gives us more independence and freedom.
If you're more into that style, there's enough to keep you busy for 9 nights.

If you're short on ideas, here are a few:

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

Otherwise, why not go to Paros? It's not even an hour away by ferry (and I love Paros, except for the village of Naoussa).

It's up to you, depending on your preferences.

Hey Tommy good to hear from you. Those photos are all mine.

Thank you all so much, your help and advice is invaluable!

I have decided to add 4 nights in Paros, out of concern that my family will feel like 9 nights is too long in one place (as lovely as Naxos is described, I’d rather have everyone leave on a high note, yearning for more, than feeling restless).

I’ve also changed our flights to we have a connection with flight to Santorini:

Arrive May 5 Santorini (3 nights)
Naxos 5 nights
Paros 4 nights
Nafplio 4 nights
Athens 3 nights

We will rent a car on Naxos and Paros.

Thank you all so much for your time - it really is special what you’re doing, to help people get the most out of a destination you hold dear to your hearts🙏🏼😁

This looks like a wonderful trip. You aren’t rushing but have good variety. We loved Naxos but would have also opted for another island with the time you have.

For your daughter who wants a boat trip — One of my favorite excursions in Paros was “A Lazy Day with Captain Ben.” It’s full day boat trip around the nearby island of Antiparos, which is where he’s based, but he does swing over and pick up people in Paros. There’s food and drink and music — he makes a couple of stops to swim off the boat & he stops on a beach for lunch.

You might even consider staying on Antiparos instead of Paros. It’s a tiny island with not a lot to do — there’s one deep cave with stalactites & stalagmites, lots of beaches, a cute little town. There are frequent (hourly?) boats between Antiparos & Paros so you can easily stay on one & visit the other. It might be a nice change of pace from the bigger, busier places.

I'm a big fan of staying on Antiparos, and hopping over to PAROS (2 ferries,one is just 10 minutes , run continually, one until 1 am) to sightsee, and even enjoy clubbing there... but staying in a charming village and -- importantly, either on, or 5 min walk to lovely beaches. R Steves top contributor & photo Ace "Stanbr" has an album of Antiparos scenes ... at night its wandering Agora (main shopping & cafe lane) is lantern-lit and magical. https://www.flickr.com/photos/stanbr54/sets/72157632126687570/

The place I'd stay, if you are lucky enough to book it, is Thalasea (that's Greek for Sea) - http://www.thalasea.gr/ walkable in 10 mins from ferry, It's family-run, top reviews ... has apts for 4, lovely views downhill 100 yards to amazing NOn-commercial beach (sunbeds but no noisy tavernas) -- lovely in May ... here's a photo: https://antiparos.com/explore/psaraliki-beach/

Paros' port town, Parikia, isn't as dramatic as Naxos Town, but has many interesting historic facets and (unlike Prettified Naoussa) is a real town -- but its nearest beach is just, meh. Better beaches require bus rides -- or special boats tht don't start til high season. So it's fun to go sight-see, then swim, sun & wander in Antiparos. Here's a photo-journal of how to do it -- https://agreekoddity.com/monday-24th-june-2013-a-day-trip-to-paros/

BTW, I also thnk Lazy Day w Capn Ben is Great choice for your daughter who likes the combo of boat excursion & beautiful beach... choose this rather the costly & less satisfactory Santorini Caldera cruises, where you just climb on lava rocks and sometmes swim in supposed "warm springs" with water coloration that can wreck a swimsut,

Thanks again everyone for the fantastic suggestions for outings etc!

I thought I had all my questions answered, but now realize that a have a few more.

In terms of booking ferries, and car rentals on Naxos, Paros and Athens:

1) As foot passengers, are advance reservations recommended in May? Just wondering as, obviously, we have changed our itinerary quite a bit and although it seems like a great one, I don’t know for certain that we will not make future changes. The flexible/refundable fares are quite a bit more expensive of course, so I’d prefer to book them closer to the date. Just wondering if fares/availability are an issue if you hold off on booking foot passenger tickets.

2) it would be difficult to book car rentals without knowing the ferry bookings as you have to indicate a pick up/drop off time. Anyone have any tips to best manage this, other than cancelling and rebooking car rentals if plans change? My experience with a lot of car rental companies is that if you want to change a reservation you often have to rebook and cancel the old one, which can mean getting paying a lot more for the car rental. Not sure how things work in Greece, but usually they will only hold your reservation for an hour past the designated pick up time.

On Naxos we have an accommodation booked in the St George beach area, and on Paros I am considering an accommodation close to the beach in Parasporos. Since I think our Paros accommodation is about a 30 min walk from ferry terminal would it be wise to get car rental immediately, or are taxis abundant and reasonably inexpensive? Or is it better to get a place closer to the ferry terminal?

Would prefer to be close to amenities but not part of the party/nightlife action.

Thank you!

It's your choice, but personally I wouldn't recommend Parasporos if you want to be able to walk to places like restaurants, bars, bakeries, or mini-markets.
Parasporos is primarily a residential area along the road leading south on the island; it's not a village or a place for strolling.
If you want to be close to the sea, consider Aliki or Drios.

Aliki:

https://maps.app.goo.gl/VLoXiubKBAesUEby9

Drios:

https://maps.app.goo.gl/qvDSrytwDNo2D4Tm6

It's far too early to book accommodations. You have plenty of time, many owners are on vacation, and some haven't even set their 2026 rates yet. When I go to the islands in May, I don't worry about bookings until March, and the average advance booking lead time, according to Greek tourism statistics, is 50 days.

Your concern about refundable tickets is irrelevant since you have absolutely no need to book the ferry in advance.
Buy your Santorini-Naxos tickets once you arrive in Santorini. Do the same for the rest of your trip. Buy your tickets as you go. Go to a ferry ticket agency or book them online on the ferry companies' websites.

Check the ferry schedules on Ferryhopper. This will give you an idea of ​​your arrival time so you can rent a car. Here's what's currently scheduled for May 8th from Santorini to Naxos:

https://www.ferryhopper.com/en/booking/results?itinerary=JTR00%2CJNX&dates=20260508&passengers=1&vehicles=0&pets=0

Regarding car rental, don't worry too much about knowing the exact schedules, the Greek way of life isn't the North American way. There's a lot of flexibility in terms of scheduled times. In Paros, unless you have accommodation in Parikia, rent a car and pick it up at the port when you arrive by ferry. Return it to the port as well if you're departing by ferry.
I've been to Paros many times and I always do it this way.

Ultimately, I realize I'm just reassuring you about almost all your questions and concerns. This will simplify things for you, and I hope it's helpful. :)

Thank you everyone for tips on boat cruise and ferry bookings etc!

I’m looking into us staying in Antiparos - we usually stay in Airbnbs so we can have two bedrooms rather than use sofa beds or book two separate hotel rooms (family of 4), but they are not very plentiful on Antiparos and are quite expensive for what you get. I’ve enquired with Thalasea about their 4 person accommodation. Sounds like Antiparos is beautiful, and we can take a day trip to Paris from there.

Really appreciate all the great feedback, thank you!!

Personally, I find Antiparos nice, but not nice enough to stay more than two nights compared to Paros.

It's true that Antiparos is relatively expensive, offers far less variety in things to see and do, and fewer choices of places to stay, than Paros. Furthermore, if you have a car, it will be largely useless in Antiparos, where there's almost nothing to explore by car compared to Paros.

The map speaks for itself.

https://www.google.com/maps/d/edit?mid=1z9zcPtVkkjzEwrXDj6XUG_5n_jcNaYZb&usp=sharing

Thalasea overlooks the island's only road, and although the traffic is fairly light, it's not exactly what you'd call a quiet place.

And we can take a day trip to Paros from there.

When it comes to day trips... The day trip is from Paros to Antiparos, not the other way around, which is illogical.

Thanks, JoLui! However intrigued by the lovely beaches on Antiparos, I admittedly was a bit worried about my daughters finding it a bit too "boring" (for lack of a better word), and now knowing that day trips are the other way around I will book accommodations on Paros. We will definitely do a Lazy Day boat cruise and perhaps take a day trip there if we feel like we've run out of things to do in Paros.

Just so you know — formal day trip tours may only go from Paros to Antiparos, but there are boats running all day long between the two islands. From Antiparos to the port of Pounda on Paros (and then the reverse) takes about 15 minutes.