The four of us are going to Greece for the first time in early June and plan 3 nights on Santorini. Should I book an Airbnb in Fira or within walking distance or in another town and get a car rental. Is parking in Fira a nightmare? Will Fira be super busy and noisy the first week of June?
By early June Fira will be VERY busy and parking will be a challenge but not totally impossible. You might just have to walk a bit from where you park to where your hotel is located. It just depends. Even though Oia also gets really busy it's where I always choose to stay, but if you want easy walking-distance access to lots of nightlife focus your search on Fira and Firostefani. A rental car is a great way to explore the island. I always recommend Vazeos in Oia, Tony's in Firostefani, Spiridakos in Fira and at the ferry port, and Motor Inn in Kamari Beach. All of these will arrange to drop off a car for you at your hotel, the port or the airport.
Not interested in nightlife. Should we stay in Oia? Would it be difficult to get to the airport from there as we depart at 5am and would need to get a taxi around 2am? (maybe later). It definitely looks less congested. Can we walk to restaurants from there? We also want to book a sunset cruise. Would it be a hassle to get to their departure site from Oia or do you think they would pick us up? Any info is appreciated. I feel I need to book fast as places are filling up.
I wouldn't make any decisions based on how to get to the airport. We are talking about a difference of maybe twenty minutes by taxi, so o.k., you may have to get up a bit earlier if based in Oia. But that really shouldn't be the decisive factor for you.
It's not going to make much of a difference in terms of crowds and noise either. Both towns are the busiest and most crowded ones on the island.
About a rental car, well, it depends. We rarely book one because most Greek islands have a fantastic and inexpensive bus system. Fira is going to be the hub, so you'll get everywhere from there.
Remember that this is the rim of the caldera we're talking about. Large parts of Fira and Oia - especially the more picturesque areas - are not accessible by car anyway. You may have to park some walking distance away from your lodgings.
The taxis and shuttle services are used to the need for early pickups for that 5am flight. No problem there as long as you don't mind a pickup around 3am if you're in Oia. It takes around 40 minutes to get to the airport but only 15 minutes if you're staying in Fira. For that first flight all you need is an hour or so at the airport, especially if you've downloaded your boarding passes already.
There are lots of shops, galleries, cafes, and restaurants in Oia as well as a few mellow bars. Some of the sunset cruises actually originate in Amoudi Bay below Oia, so all you have to do is walk down the steps to get there if they don't offer a free pickup.