We are planning a high school graduation trip for our younger son to Greece (seems many others are as well!). Based on feedback from many of the forums I have read we are going to just go to 2 islands, Santorini and Naxos, plus Athens so we don't waste as much time moving around and travelling to and from. We are looking for combination of outdoor activities - hiking, snorkeling, caves plus historical sites and relaxing. Also, want to stay in places where we can be within walking distance of restaurants etc so if the boys want to explore on their own at night they can. Am researching airbnbs and hotels. I am having difficulty finding accommodations in Santorini - many of the recommended places are already booked or only accommodate up to 3 adults or are more than we would like to spend (budget around $250 per night in Santorini. I know we can find better in Naxos and Athens).
Here's the proposed itinerary for a total of 11 nights.
Arrive Athens late night from USA early June
Spend 4 nights in Athens
Ferry to Santorini and stay 3 nights Santorini
Ferry to Naxos and stay 3 nights Naxos
Fly Naxos to Athens, spend the night near the airport as we have a 6 am flight back to USA the next morning
or reverse Santorini and Naxos and fly out of Santorini back to Athens as flights are cheaper
1. Where to stay in Santorini? Oia, Fira, imerovigli? Again, would like to be within walking distance of town and find someplace to accommodate 4 adults
2. Can we take buses around the island or at least from Oia to Fira. We will probably rent a car for a day or two.
3. Seems like many of the accommodations offer car rental. Is it best just to book through hotel?
4. Do we need to book ferry reservations in advance?
5. I have read that we need to allow plenty of time for getting back to Athens. If we take a 5 pm flight on the day before, would this be sufficient to take into account delays, strikes etc?
6. Are these airlines reliable flying from island to island? Olympic, Aegean?
7. Recommendations for boat tours in Naxos to see hidden beaches, snorkel etc?
8. Recommendations for a tour guide in Athens to give first day overview of the city and sights?
Little overwhelmed by all of the information so any details would be greatly appreciated.