Proposed early June itinerary to Greece with 2 college aged boys

Stay in Firostefani so you will have easy walking distance to everything Fira has to offer without being stuck in the middle of all the summer chaos. The island has an excellent bus system with the central terminal located in Fira. Rent a car from one of the reputable agencies. I always recommend Tony's in Firostefanni, Vazeos in Oia, Spiridakos in Fira and Motor Inn in Kamari Beach. They will bring a car to you at your hotel. If you live outside the EU be sure to bring an International Driving Permit from your local auto club office.
You can wait until you're on the island to book your ferry to Naxos. Domestic flights aren't normally caught up in all the airport issues which, by the way, should not be as bad as in the past since the new operators have made a lot of improvements. You can safely arrive an hour before departure. Aegean/Olympic are the same parent company and hold one of the highest Skytrax ratings for EU airlines. Snorkeling isn't very good there. Most of what you'll see is sea grass and algae-covered rocks. Instead, take a daytrip excursion from Naxos to the historical island of Delos which includes a stop on Mykonos for a couple of hours. Hopefully someone else will chime in about a tour guide in Athens.

Use the filter system at www.booking.com to search for the sort of accommodations you require.

I'll take a shot at answering points 2, 4, and 6.
Response to Question 2: I stayed in/near Fira when I was in Santorini and there are definitely buses there that you can take to Oia and various other spots on the island from Fira.

Response to Question4: I suggest making reservations because you are traveling during a busy time. It is anecdotal but I could not get tickets for the first two ferries that we wanted to take from Naxos to Mykonos because we waited until the day of travel to buy and the boats were sold out.

Response to Question 6: We flew from Athens to Naxos and from Crete to Athens without any issues. The hardest part was the check-in process in Athens which was let's just say not especially organized. You can check flightstats.com to see on-time arrival rates or flight cancellation rates because any experience discussed here will be anecdotal and not statistical.

When you say accommodate 4 adults, are you looking for one hotel room for four people, a rental, or two rooms? I found Santorini to be very expensive.

ITINERARY -- First of all --- do Athens LAST. You have so few days, every hour is precious! If you arrive late, stay nearby (Hotel AVRA has free shuttle to/from... or more budget-y, Hotel Peris also shuttles). Then u can zip back to airport AM of day #2, and fly to Santorini -- 50 minuts vs 8-9 hours on ferry... and a flight by 8 am will be a bargain, maybe same/less than ferry! Then at end of your island time, you can either fly back from Naxos or do the 6 pm BLUE STAR ferry (6 - midnight, but only about €43 for good reserved seating). You'll do all your sightseeing in Athens then ... and can choose whether to stay near airport or do a 3:30am taxi/car service. Doing Athens last lets u get over jet lag on an island. Plus: after being in Greece awhile, you'll be better equipped to handle a busy world capital ... and famous landmarks mean much more than if seen on day #2.

LODGINGS -- For best advice, be specific; tell us where online you are looking, and exact dates for each place... "june" has 30 days. Also, what websites are you looking at? I advise for fastest overview to go to booking.com and plug in your location, dates, 4 adults -- and up comes a list. But click the "Map view" in upper RH corner & you see google map with Blue balloons in exact locations for all their hotels, with price when u click on each (u can change currency on top bar). My recommendations:

• Santorini - FIROSTEPHANI -- its just on north fringe of Fira, walkable to Fira attraction but out of the hubbub, no need for car; u can bus to OIA (or taxi, early -early to beat Cruise mobs; do NOT drive up there, can't find parking); rent car if you want to go elsewhere on Island like (my scenic fave) Ancient Thira atop high bluff. Do not attempt OIA sunsets - a zoo...find a restaurant you like in Fira or Firostephani & you'll be happier.

• Naxos - ST. GEORGE BEACH or PLAKA -- St. George is directly adjacent to port town, yet is serene by night. in July=Aug, crowded, but in June is pleasantly populated. Shallow beach (wade out 100 yrds to swim) but fine water sports offered @ Flisvos sports center (kayaking windsurfing etc. Island has excellent bus service to all beaches...you could stay at PLAKA beach, busses run until 11 pm, taxis also available. In june many of us like staying in St. G, bussing out to far beaches, then having evenings in port town for dining, clubs, etc. NOTE: St. George has numerous places that would suit the 4 of you -- "1 BR studio units" that a have BR for 2, and main room with 2 daybeds, kitchenette ell, table & chairs, large balcony. SImilar on other beaches.

• Athens - CENTRAL... Look near Acropolis: this booking.com "filter Link" http://tinyurl.com/heq6edp shows places in those areas. There now are many pvt apts listed along with hotels, which would accommodate the 4 of you. Just be sure it works for when u arrive/leave, because there will be no central desk.

TOUR GUIDES - Athenswalkingtours is well established, but Athenswalks, a newer outfit is gettting gold stars, and I like some features better -- its Acropolis tours start earlier, to beat the crowd, AND it also has a late-day Acropolis tour (5 pm or so), when the crowds have left, and the light is great for photos.

Thank you all for your replies and suggestions. Most appreciated!

With 2 college aged kids, you will want to stay in Fira so that they can be where all the fun is and you will be walking distance to everything.

If you don't want to rent a car on Santorini, mopeds are available for rent everywhere and add to the adventure.

Totally agree with Janet's rec. to fly right to the islands and spend your time in Athens at the end of the trip. Not sure you need a tour guide while there as you will have time to spend in the different areas without worrying about logistics and transfers. Plaka/Acropolis; Archeological Museum/Palace; etc., can all be done on your own. Just prioritize what you want to see and study the RS book for advice.

You may be interested the custom hiking tours offered by Naxos Discovery Tours. Nicolas is a fabulous guide who would relate well to your teenagers. Our day with him was terrific! https://www.naxosdiscovery.net/highlights

when in Santorini, and you have time, do the Fira to Oia hike... We did Oia to Fira but it's the same thing. Get up early in the morning, 6am and start the hike.. it is about 3 to 3 1/2 hours, you can take the bus back. It is one of the best hikes I've done, it's beautiful. We were there in last August and stayed in Oia, Oia is much more expensive, but we loved it. The bus from Fira to Oia was packed to the last inch but it runs constantly. Take lots of water with you because the sun is really hot and make sure to wear a hat. Go to the black beach as well, it's really beautiful.

js4W -- have you had teenagers 18-19? They absolutely cannot get up by 6am, physically, it's a adolescent hormone thing! In my experience, it can be challenge enough to get them on an 8 am bus to OIA! At 10 or so, when the cruise-crush jampacks the Oia lanes, the group might consider doing part of that hike back towards Fira -- one could hike to Imervogli & get the bus, as one option. Then could do Ancient Thira next, directly above that black beach. Then you'd have hike & beach to contrast to same on Naxos, would be interested in post-trip comparisons.

Response to Question 4

I HIGHLY suggest doing this even 2 weeks in advance! Our itinerary included day trips from Athens to some of the islands. I was provided with information that we "would be fine" to purchased the ferry tickets once we got to Greece. The day we arrived and settled, I tried to book and they were filled up to 2 weeks from the date. We were stuck in Athens for 2 additional full days. We made the most of it and took the car out to some of the beaches and resorts but would have liked to have placed on one of the smaller islands. We went in mid-May.

Consider a great land trip combined with a Greek Island cruise. I have done both and the land trip allows your to absorb key places on the mainland, while the cruise allows you to visit several islands and not worry about transport and lodging.

Aegean airlines is having a 30% of sale for flights that originate/end in Athens. We just booked flights from Thessaloniki to Athens, Athens to Milos, and Mykonos to Athens for 29eu each for next summer.

https://en.aegeanair.com/?GS&gclid=EAIaIQobChMI1eKnhL2c5wIVEtvACh23kgi5EAAYASAAEgITSPD_BwE

Thanks for sharing this! Just booked our flight from Santorini back to Athens last night.

Are there any differences in the ferry companies? We are still looking at taking a ferry from ATH-Naxos June 7 even though a bit long but thought it would be part of the experience. Any thoughts on this?

You will be taking the ferry from Naxos to Santorini. Make that your Greek ferry experience. Why use up a half day of your time. Particularly with an Aegean seat sale now on.

We flew from Athens to Naxos. The time versus the ferry was just too great a difference. It was one of the most beautiful flights I have ever taken. Of course, the ferry is probably equally lovely but it's long. Plus, the airport at Naxos was like nothing I had ever seen. The only building is about the size of my garage. We saved our ferry trips for a Naxos to Crete and Crete to Santorini.

College age boys? They need pocket money and a moped. Don't make other plans, and don't expect them home early. Hope they don't bring home a souvenir that requires medical attention. Don't try to make plans around them, just tell them what you're doing and maybe they'll tag along.