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9 Nights in the Cyclades - Santorini and Paros/Milos/Both?

9 Nights in the Cyclades - Santorini and Paros/Milos/Both?

Old Jul 30th, 2022, 10:20 AM
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9 Nights in the Cyclades - Santorini and Paros/Milos/Both?

Hi all,

I'm taking a slightly last minute trip to Greece in early September (Aug 31 - Sept 9). This forum has been very helpful, but I am still a bit torn on where to go and what makes sense from a practicality and interests combination. I've been to Greece before (Athens, Peloponnese, and Ionian islands) and absolutely loved my time, and even though I have shorter on the ground time I really wanted to visit the Cyclades. I'm planning this trip solo, although a friend may join me for some part. Here's my itinerary now:

Wed Aug 31 - land Santorini at 4:15 PM, night Santorini
Thurs Sept 1 - night Santorini
Fri Sept 2 - night Santorini
Sat Sept 3 - ferry to Paros/Milos
Sun Sept 4 - Paros/Milos
Mon Sept 5 - Paros/Milos
Tue Sept 6 - Paros/Milos
Wed Sept 7 - Paros/Milos
Thur Sept 8 - Paros/Milos, ferry back to Santorini, night Santorini
Fri Sept 9 - depart Santorini at 3:20 PM, fly back to USA via LHR

Key questions I have for this group:

1) Do I need to travel back to Santorini the day before my flight home? Or could I at this time of year feel confident there would be a morning ferry from Paros or Milos to Santorini on Friday morning, so I can add the night to that island?

2) If I can ferry the day of flight safely, should I split 3 nights in Milos and 3 nights in Paros? I love the idea of Milos and the wild beaches and getting on a boat to see all the inlets, but it also seems like Paros maybe has a wider variety of activities and places to eat/drink, and maybe nightlife (although it's not a high priority to me at all it could be interesting).

3) Should I only spend 2 nights in Santorini? My main goals there are to do the hike between the towns and soak up the views, so I feel as though maybe the 3rd night I could add to Paros or Milos, especially if I try to do both? I am a slow to medium paced traveler generally; last summer I spent 9 nights in Mallorca with 3 in the hills in Solar and 6 in Palma heading to various beaches and other areas and that was an idyllic trip. Based on my interests (a little hiking, water based activities, different beaches and beach scenes, good quality food more leaning toward taverna and mid range restaurants rather than super fancy meals) and being a solo traveler, it seems like 9 nights in Santorini would be too much, but maybe a 2/4/3 or 3/3/3 between three islands is too much, so that's why I initially thought 3/4 nights in Santorini and 5/6 nights in Paros OR Milos was the best fit.

4) How much would it complicate things to add Mykonos? It doesn't really seem like it's the right fit for me and it seems to add logistical challenges, although I'd guess early September is a little less crazy, but my friend loves clubs (although not beaches, pool person) so figured I would ask.

5) I know I don't need / shouldn't rent a car in Santorini; I would also not rent a car in Paros and/or Milos: any reason I should reconsider?

Thank you for reading and your feedback!
rndtraveler12 is offline  
Old Jul 30th, 2022, 12:08 PM
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Cannot comment on Paros or Milos. But we spent 3 nights on Santorini this past May.

I would spend 3 nights on Santorini. If you feel comfortable driving, I recommend renting a car for a day to see the rest of Santorini. That's what we did, and it was a fascinating day. So glad we saw more than just the spectacular caldera views. We visited the Akrotiri archaeological site, the Akrotiri lighthouse, red sand beach where you can take a short hike to see the red cliffs, and had drinks and snacks on black sand beach in Perissa. We stayed at Blue Dolphins Apartments in Firostefani, which is quieter than Oia. I wouldn't spend 9 nights on Santorini - too expensive. It was easy driving on Santorini, although my husband does all the driving when we are in foreign countries. But it was easy/peasy.

We visited Naxos instead of Paros and also rented a car for a day on Naxos. Again, very easy driving. So I assume it would be easy driving on Paros, too. A rental car allows you the luxury of exploring the island at your own pace.

Although I am not a Greek expert, I think it might be risky taking the ferry back to Santorini on the same day your flight departs. From my research, the seas could be rough and the ferry could be cancelled. Then you would miss your flight. I think you should return to Santorini the night before.

KarenWoo is online now  
Old Jul 30th, 2022, 12:40 PM
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KarenWoo thank you so much, that is very helpful! This is making me think I should see if I can rearrange things and put my time in Santorini at the end. I fly in late in the day so would spend my first night there, but probably start with the other island(s) and then leave 3 nights for Santorini last and can easily fly home without ferry connection worries.

Wed Aug 31 - land Santorini at 4:15 PM, night Santorini
Thurs Sept 1 - Mon Sept 5 - travel to Paros/Milos, 5 nights
Tue Sept 6 - Fri Sept 9 - Santorini 3 nights, Friday afternoon depart Santorini

I'm really not a driver at all though I have a license, so I'd prefer to walk/scooter/bike/boat/taxi/bus around rather than go by car. I appreciate the freedom a car gives someone, but I've usually found myself able to see everything and not be blocked from things without one, so unless it's really necessary I will probably not rent my own.
rndtraveler12 is offline  
Old Jul 30th, 2022, 01:19 PM
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I see you also posted this question on TripAdvisor. Yes, leaving Santorini until the end sounds like a better plan.

As for Paros vs Milos, each island has its own advocates, but you have a better choice of ferries to/from Paros, including the superb Blue Star Ferries every day. This is the main ferry route between Piraeus (Athens) and Santorini with stops at Paros and Naxos. The ferries between Santorini and Paros are all large car carrying vessels.

Santorini to Milos is a cross-route, served in summer by tiny Sea Jets catamarans, Superjet or SeaJet 2, notorious for making their passengers seasick when the sea is rough. They are the first to be cancelled in high winds, so not to be depended upon when you have a flight home. There are also a couple of conventional ferries between Santorini and Milos, but not every day.

I have been going to Paros and Antiparos for many years, and those are my favourite islands. For nightlife on Paros, Naoussa would be the best place to stay, and there are some hotels with pools. Personally, though, the sea around Paros is crystal clear, and as warm as it will ever be in September. I prefer salt water to chlorine.
Heimdall is online now  
Old Aug 1st, 2022, 02:55 PM
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Thanks, Heimdall! This is very helpful, and good to know about the ferry comparison between Santorini-Paros and Santorini-Milos.
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