My husband and I are planning a trip to Greece in May. We have already scheduled part of our trip which is a 6 day bike/hike/kayak excursion. This starts in Athens and goes to the Peloponnese peninsula. We have that scheduled for the end of our trip. We plan on flying into Athens and connecting on a flight to Santorini. We have 8 days to spend in the islands. We want to limit our travel to just 2 islands and think that Santorini and Naxos sound perfect for us. Should we split it equal, 4 nights on Santorini and 4 on Naxos, or 3 on Santorini and 5 on Naxos. We hope to so some hiking, enjoy beautiful views including spectacular sunsets, visit Akrotiri and visit small towns on the islands to get connected with the culture. I read that on Santorini the best place stay to be able to view the sun to stay is in Oia. Is that true or is there another location that is recommended? Any suggestions for where to stay on Naxos?

I'd recommend 3 nights for Santorini and 5 for Naxos. I must admit that I was underwhelmed (actually, put off) by Santorini, though Akrotiri is amazing and some of the ruins from Akrotiri in the museums in Fira are well worth seeing. In contrast, I loved Naxos. See if the Hotel Grotta on Naxos suits your interests. I thought it quite special.

You might find some useful information in my trip report. The relevant sections begin with post # 89.
With Gratitude for a Glorious Solo Month in Greece

Moved from Tech Support to the Europe Forum and tagged for Greece

Few places I reommend in Naxos are:

1. Agios Prokopios.
2. Plaka.
3. Hotel Grotta.

kja, thank you so much for your suggestions. I looked up the Hotel Grotta and wow it looks amazing! Definitely our style. I just booked us for 5 nights there and will go with 3 nights on Santorini.

Thank you for your suggestions. We've booked our room at Hotel Grotta and have put Agios Prokopios and Plaka on our list of places to visit.

Santorini is All About the Famous Caldera View ...so I'd advise you to cut back your stay to 2.nights (max 3) -- in that time you can appreciate the view, enjoy a couple of sunsets, see OIA while avoiding the mob scene (see below). skip the beaches (black grit) check out Akrotiri and then leave for Naxos, which has all the other things you say you want. You can do it easily, it's all in the timing & planning. Some tested tips (from my 13 trips & multiple visits to each island, with newcomers like you):

A SANTORINI STRATEGY - It's always helpful if you can give arrival/departure dates - so I must guess. Your 14-day total suggests you are still in work world, thus fly on Thurs or Fri, to enable 3 weekends. Am I right? That's good, because Santorini on weekend is less inundated by megacruise ships (So many that a limit of 10K cruise psgrs is now enforced! plus huge tour groups via jet plane & ferries). What many "vets" recommend
1) ATH arrival before noon on Fri or Sat; 2 hour layover - then 1 or 2 pm domestic flight to Santorini (book this NOW or in Jan, these sell out).
(2) do NOT stay in OIA (instead, Visit there, timed to avoid mobs & stay in FIROSTEPHANI, an ideal location ... many cliffside hotels w fab balcony views (way less $$ than OIA) bypassed by cruise crowd, just on N fringe of Fira town, walkable down the rimsiide path to its attractions but away from hubbub, no need for car rental. This map shows location - https://www.mapsof.net/santorini/thi...oogle_vignette This link is good for browsing hotel choices - https://www.booking.com/city/gr/firostefani.html HOtels w good caldera-view balconies include hotel Mylos (a BEst Buy) Sunset Hotel, Villa ILias, Blue Dolphins, Mill houses. PLUS for
(3) Tested Itinerary -- DAY 1, stroll rimside to Fira, then enjoy sunset dinner near hotel at Remvi Cafe - https://santorinidave.com/santorini-restaurant-remvi -- avoid OIa crowds/ripoff. Early night (jetlag) DAY 2 - Early! Arrange for 745 - 8 am TAXI (or rental car) - zip to OIA, to enjoy 2 hours strolling, picture taking in lanes viewpoints before tour-group Armies cram-jam lanes! When they come, you go...via rental or Bus, to FIRA... see small/excellent museum, have lunch & bus or car to Akrotiri (suggest guide unless ur r classics-expert). A winery-tour w caldera view gives you sunset without Oia's Mob Scene. DAY 3 - 10 am Champion jet2 Fast-Ferry, has small open-deck for departure view, gets you to NAXOS by 12: 15 ... with 5-6 days to explore the Largest Isle of the Cyclades, a treasure of landscapes, sunsets, beaches, hillside villages, ancient sites, hikes galore fascinating port town, and fab food.

NAXOS -- no time to outline itinerary today, but suggest for lodging you also look at places in St George (Ag Giorgios) beach, on south fringe of Port town. see this map: https://tinyurl.com/6n4bw3dp Hotel Grotta has lovely cliff views just up from Ferry pier, but not near any swimmable beach, you must drive or bus. At Ag Giorgios, many many family-owned hotels & pensions w seaview balconies walkable to all port-town attractions in 15-mins, along shorelilne. Check your options here: https://www.booking.com/district/gr/...giosbeach.html

Thank you for all the great suggestions and information!