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Paros, Naxos, Ios, OR Crete (Mykonos booked)

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With everything I read, I have a harder time committing to a plan/islands, it all seems amazing. First off, thank-you in advance for any help. I have racked up over 25 hours of research on the islands alone and still have to spend time planning for Italy and Spain. The more I learn, the more questions I have, and the more I doubt my initial ideas!

Initially I thought Santorini, Paros, Mykonos, Ios... but now Im reading about Crete, Rhodes, Naxos,....So, here is the deal. My mom (age 55) and I (female, age 29) arrive in Athens on June 23 after doing Paris and Rome over the course of a week. In Athens, we will meet up with my best friend Porter (male, age 30). Porter and I live at a ski resort in Breckenridge, Colorado, USA. He and I love festivals/concerts, rock climbing, biking, snowboarding, surfing, being outside, having fun (work hard, play hard mindset).

To begin with, we plan to tour Athens with my mom June 23-24 then depart to the islands on the 25th. (I know we should ideally do Athens in the end but my mom is leaving the islands before us, and I want to do this city with her). My Mom will be flying back to Athens on July 1 +/- a day (nothing booked yet, we want to tie everything in logistically). Porter and I plan to stay in the islands until we have to be back in Athens on July 12 for a 10:50 PM flight to Italy to begin the Cinque Tere. Only other obligation: From July 1-9 Porter and I have an amazing place in Mykonos on Paradise beach rented. This was over our budget but we wanted to treat ourselves. FYI: Greece budget is 90Euros per person per night, but can be more if it is really worth it, but less preferred :)

All in all, we want to be in a friendly and social atmosphere. Meeting people and Ideally having a short walk to the beach are top priority. Having town nearby would be nice too. We are single and want night life, somewhere for all ages while my mom is here as she is a social butterfly and loves partying and drinking as well. We also love the outdoors and having some day hikes accessible in some places would be nice too.

So here are the questions:
1) Where would you recommend June 26-July 1 for with Mom? I think it would be nice for her to see Santorini, but all three of us are on the same page with just wanting to "beach it" then go out at night. I know Santorini's beaches are limited, but I was still considering 1-2 nights here due to all the hype?! I was then thinking continuing on to Naxos or Paros, and then Mom can fly to Athens, we ferry to Mykonos to check in on July 1.
**From what Ive read, it seems we should ferry from Raffina (or should it be Pirraeus?) to the islands to get the experience and views. Is this true or should we fly? I definitely want the option to be outside on the deck of a ferry, but can't figure out which companies to use for this.
***I am totally open to flying somewhere from Athens that is further away (Crete, Rhodes,...) I just want to hit the right spot where we will all be stoked, then make it to Mykonos by July 1.

2) From July 9-12, Porter and I initially planned on partying in Ios. But, from what I'm reading, we may be too old for that scene now? We love to dance and party (Spending 4 days in Ibiza as well) but want to be around like minded people, not all spring breaker type young adults (Where should we spend these last few days before catching our 10:50 PM flight out of Athens on July 12?


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    I don't mean to be rude, but it's very late to be figuring this out. June- early September is prime time for Greece and and the islands, so many of the more reasonably priced hotels will be long gone.

    I think your best bet is to figure out ASAP which islands most interest you and get onto a booking engine to see what's available. Santorini-Paros-Naxos make a lot of sense because they are linked by the same ferry line.

    If you can find accommodations in Santorini for two days, do that, then go on from there to either Paros and/or Naxos, both of which fit your wish list.

    Parikia is the main port town in Paros. It has tons of bars, restaurants, and more night life available than Naoussa, which is where I like to stay. There are tons of beaches to explore, some of which you can get to by bus.

    In Naxos, look at the St. George area, which is close to the ancient chora ( old section of town) shopping, restaurants, and the Gate of Apollo at the harbor entrance.

    I prefer flying when possible to/from the islands, but at this point most flights may be sold out. If you're interested check ASAP on the AEGEAN/OLYMPIC website.

    Good luck!

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    You are going to have to do some gymnastics to make your trip revolve around your mother's needs and the 1-9 July booking on Mykonos. One solution would be for all three of you to go from Athens to Santorini on June 26th and stay in Kamari or Perissa, the black-sand beach resorts on the opposite side of the island from the caldera. You can still go by bus or car to the caldera side to take in the views, and it should be easier to find a good hotel in Kamari or Perissa at this late date.

    If you go to Santorini and want to be on the outside deck of a ferry, you need to take the 7:25am Blue Star from Piraeus. You may still be able to book a flight for your mother on July 1st from Santorini to Athens, but you will need to act quickly. If she leaves Athens on July 1st, think about putting her on a plane a day earlier so she can sty overnight in an Athens hotel.

    For the 9-12 July period, you should be somewhere from which it is easy to return to Athens. Both Rhodes and Crete would fit that criterion, but they are hard to reach from Mykonos, and neither would be worth it for only 3 days. You will probably need to return to Athens a day before your flight to Italy. My suggestion would be Paros, which is only 4 hours by Blue Star ferry to Piraeus.

    If all you need is a simple room, they are easy to find in June and early July, even if you show up on an island without a booking. If you want something more upmarket you will need to get busy. should help you find somewhere to stay.

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