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Cyclades Itinerary Thoughts - June travel w young adults

We are heading to Greece with our 18 and 20-year-old kids (their first time, our first in 30+ years!), in celebration of the younger one's high school graduation. After much discussion and research, we've landed on this as an itinerary, but there are a few elements we're debating tweaking.


June 9-12 (3 nights) Santorini - staying in Firostephani (fly there directly after landing in Athens)

June 12 - ferry to Paros to meet captain of charter sailboat

June 12-16 (4 nights) sailing, finish in Milos. Depending on wind/weather, will visit Paros, Sifnos, small Cyclades, etc.

June 16-22 (6 nights) Milos - staying in Pollonia w rental car

June 22-Fly to Athens, rent car and drive to Delphi (around 2.5 hours drive)

June 22-23 (1 night) Delphi

June 23 Drive back to Athens (return car)

June 23-25 Athens (2 nights)

June 25 Fly home.

The potential tweaks:

1) Is 6 days too long on Milos, or to put it differently, should we spend a few nights on a different island instead to see more/do more? We are travelers who like a mix of activities and chill time...we will hike, swim, snorkel, wander through towns, take photographs, eat good food, but also sit with a book in the shade or nap on a beach. Too much moving around tends to create cranky dynamics, but at the same time, we want to see a good range.

2) Is Pollonia too quiet for the young adults, who may want to head out in the evenings? This isn't a major party trip, but it would be fun for them to grab a drink and meet other younger travelers passing through...not sure if there's any of that in Pollonia. Seeking a compromise, since the real adults (who are paying) also don't want to sleep next to a disco!

3) On any of these locations, are there any "totally worth the money" excursions or private tours or activities that you recommend? We will definitely be sailing around Milos, and I think will also take a sail in Santorini. But beyond that, curious what folks - especially those who traveled with older kids - considered the top highlights worth splurging on!

Posted by
237 posts

In addition to a sailing day, I really enjoyed the hike from Oia to Fira in Santorini. I also loved the wine tour and tasting at Santo Winery; noting that the young adults are below the drinking age in the US, do they have any interest in wine and wine-making?

Going down to Ammoudi Bay might be fun. There are lots of young adults swimming and jumping off tall rocks. Just make sure to bring water shoes/sandals of some kind as the rocks are fairly sharp when climbing in and out. I will warn that it’s kind of a nightmare to get down/back up - long steps covered in donkey poo, or a trafficky cab ride. But lovely once you’re down there!

Posted by
3333 posts

Your itinerary sounds wonderful! RIght sequence, good amount of time (as long as you are well-organized for Athens sightseeing -- there's SOO much!). A few comments:

DOMESTIC FLIGHTS -- book NOW... these are filling up fast; you might be in time to catch a "promotional price" -especially the MILOS Flight - not as many per day

CAR RENTAL -- ALso check NOW because both Athens & Islands are short of cars, don't want too wait & hear "sold out" on the size u need (if u can drive stick, bettere supplies).

MILOS -- GLAd u are thinking about that ... Yes, Milos is a dilemma ... the Port town of Adamas has a less-than-mediocre beach ... I have stayed both there an in Pollonia. HOwever, I believe you should re-think and look fr smething on edge of ADamas. Why?
•  Pollonia has only 3 - 4 places to eat, and will be VERY Quiet in June.. we were there early june and boy, nada at night
• Adamas, yes, has the most restaurants, bars, and maybe even a club or 2 ... but if you stay in Pollonia & drive iin for dinner and a glass 'o wine or 3... then there's the long lonely drive back on windy UNLit road. We did this but we had a stalwart teetotal driver.
• DOn't worry about noisy disco disrupting your sleep. June is NOT PArty time in Milos
• With your car, you can get to all the island's great beaches ...
• DO take a round-island sail (I prefer half-round, more time for skipper to stop at coves, & beach BBQs) -- I favor big catamarans vs small sloops, because even if windy cats can stay undersail, while small boats reef & go 100% motor, no fun. Check weather forecast before u commit... boats line up in harbor 6 pm & before dinner u can go aboard, talk to captains, maake your choice.
• Do Not miss the ancient ruins & the catacombs... Do NOT miss Mining Museum if only for it's unforgettable 30minute video.

APORTIONING STAYS - I would suggest taking 1 day of Milos and adding it to ATHENS ... then u could do justice to sights & activities - & your young adults will find pllenty to attract them

Posted by
87 posts

it's a nice trip.

About the 6 nights in Milos

In my opinion if you stay in Pollonia, the kids (and you) risk being a bit bored, especially in June.
Pollonia is a small village north of Milos with just a row of tourist bars and restaurants along the quays, and not much to do (not many beaches, and to my knowledge there is no disco!) .

What is good when you are in Pollonia is that you can go to Kimolos which is 30 minutes from Milos with a ferry that leaves from Pollonia and goes back and forth all day (The "Osia Methodia" / you can cross with the car) and is a much more authentic little island. But unfortunately for your children, without disco either!

If you want to find a little more "urban" animation in Milos you have to stay in Adamas, the capital.

Sifnos which is just north of Milos is a very beautiful island too (one of my favorites)
with traditional villages, beaches, walks to do and renowned gastronomy
The village of Kastro in Sifnoscan be compared to Oia in Santorini without the hordes of tourists and the souvenir shops. There are still donkeys but the inhabitants use them to transport goods because the streets are not accessible by car.

Anyway, I wish you an excellent trip!

Posted by
87 posts

It's a beautiful trip.

Regarding the 6 days in Milos.

If you stay in Pollonia you might get bored, especially in June. It is a village north of Milos with just a row of restaurants and bars along the quay.
The small beaches are without interest and there is no discotheque!

What you can do from Pollonia is to go to Kimolos by boat (The "Osia Methodia" / you can put the car in the boat) which goes back and forth all day in 30 minutes.
Kimolos won't have a nightclub either, but it's a very charming little traditional island (there are still bars, restaurants and accommodations)

In Milos the only place where you will find "urban" entertainment is Adamas.

Posted by
87 posts

About rental cars in the Cyclades.

With the exception of trips Paros-Antiparos and Milos-Kimolos. Not all rental companies accept that you take the car to other islands. Ask before renting
If they allow it there may be an insurance surcharge (due to the ferry).

In June you can easily find car rental companies in each island and you will not have to pay the ferry ticket for the car.

About hikes, walks in the villages, good food and reading on the beach in the shade of the tamarisks there is an island that is perfect for that, it is Sifnos.

The food is famous, there are many hiking trails, villages with quiet beaches: Platis Gialos, Vathi, Faros (you should not stay in Kamares, the port). Also a typical village called Kastro that could be compared to Oia in Santorini, without the hordes of tourists. The inhabitants still use donkeys to transport their goods because the "streets" of the village are not accessible by car.

Anyway, ask your captain for more details when you're there.

And above all, have a nice trip!

Posted by
16 posts

Thanks to all who have weighed in!

Does anyone have a place they love in Adamas? I will of course do my research but will be looking for either a 2 bedroom suite/apartment/space where there is enough room to spread out and find shady corners to relax. Budget is somewhat negligible, though not to the tune of many hundreds/night. (For comparison, the place we reserved in Pollonia, which is fully refundable, is around $250-300/night for a two bedroom apartment that included breakfast, a sitting area, and a small kitchen space).