Accommodations and Tours - Naxos and Santorini

It's true, finding something in Imerovigli in August and September for $200 is very unlikely. Expect to pay between $240 and $300 per night. Check Pearl on the Cliff Hotel & Suites, Andromeda Villas and Abelonas Retreat. For wine tours check Santorini Wine Adventure Tours and Santorini Wine Tours. Also have a look here: https://www.viator.com/Santorini-tours/Wine-Tasting-and-Winery-Tours/d959-g6-c21

I recommend Venetsanos Winery to you for sunset watching while enjoying a tasting of their wines with some snacks.

We loved the Hotel Aethrio in Oia (https://www.aethrio.gr/). Best sunset view from the private veranda our room had. It looks west to the sunset, much better than the high priced caldera views which look south. It has a pool, breakfast, and is right across from our favourite restaurant in Oia, Candouni.

In that price range, I doubt you will find anything with a caldera view in Santorini.

We were very pleased with Spiridakos Sailing Cruises. We opted for their premium daytime cruise and found it well worth our time and money. https://www.santorini-yachts.com/ We also loved everything about our stay at Lithies Traditional Homes in Santorini, however it does not fit your requirements. As for Naxos, I would suggest that you check out Naxos Discovery Tours. Nicolas is fantastic and one of the best guides we have ever hired. Worth every penny. https://www.naxosdiscovery.net/

I am not sure that staying at Ag Prokopious on Naxos is the best choice particularly if you will not have a car. While there is good bus service to Naxos town during high season we have seen the bus drive right past the crowd at the bus stop because it is full from pick ups at Plaka beach.

Have you considered St George beach. Its part of Naxos town just a 10 minute stroll along the waterfront headland to Naxos town waterfront promenade. Naxos town is the centre of the islands transportation hub including ferries and the KTEL bus system.
You get a quiet beach vacation with all the attraction of the town with its maze of back alleys all topped of the walled Venetian era Kastro.

From there you can take the bus to the west cost beaches, mountain villages and the tour companies. KTEL offers a round the island tour that is fairly inexpensive. We have never taken it but have heard its a good one. We did chance to arrive at one of the Kourous statue sites at the same time as this tour and listened in to the guide. I thought the presentation was well done informative but not boring long.
For an outstanding tour consider Philema tours. We took the cheese making tour which included a stop at a country farm where we got to feed the goats, then a sit down meal in the farmhouse with traditional Greet food and home made barrel wine. By the way we finally figured out how to stop a Greek host from refilling your glass of wine. If you empty the glass hospitality insists that it be refilled. That will go on all until you stop drinking and leave a full glass. Then we got to make goat milk cheese. It turns out this farmer supplies the local products store where we buy all our cheese in Naxos town. The cheese we made, would be on the shelves in 4 months.
The second shop was at a local winery where we had very generous tastes of 5 different wines.

For fun this is what Naxos is like

Naxos town https://www.flickr.com/photos/stanbr54/albums/72157632094558042
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689

Naxos 2019 https://www.flickr.com/photos/stanbr54/albums/72157711294807761

Images of the Philema tour are in the 2019 images.

We rented a car on Naxos for the 4 days we were there and loved the flexibility it gave us to explore. Initially we intended to take the bus from Place (where we stayed) to Naxos town but decided ultimately to rent bc it was inexpensive and gave us the opportunity to be spontaneous. I decided on Plaka because I did not want the crowds of St George or Agios Prokopios. There are plenty of people and services at Plaka, but it is big enough to feel spread out. Sounds like, if the bus is full of people from Plaka as Stan mentioned, it could work for bus-reliance as well....

If you choose to stay on one of the west coast beaches then I am with Jessica Plaka is our favourite beaches. While there is no village the area is serviced by a string of hotels and tavernas just across the dirt road from the beach.
Look at three brothers it is a taverna and hotel. We have stayed there several times, most rooms have a sea view. We will be booking there again next year.

We just returned from two weeks in Naxos and Santorini. We did AirBnB in Santorini (the great cave house II) which was fabulous and about 250/ night.
In Naxos we stayed in Agios Prokopios at the Hotel Katerina. It's lovely, a 2 min walk to the beach and the owner George is super kind and helpful. Not sure of August prices but we paid 112$/night for the family room which included 2 rooms and kitchenette. Breakfast was 6E extra but I think it's included in some room prices. We rented a car (25E/day) when we wanted to see more of the island but had no issues with the bus to/from Hora/Naxos town or to the airport when we left.
We did a wonderful 3 hour walking tour with Vassiliki who can be found at naxosprivatetours. com.

We just got back from Santorini and Naxos.

Loved, loved, loved Hotel Grotta in Naxos. Family ran hotel with the best breakfast I have ever had in my 25 years of touring Europe. Great friendly staff makes you feel like family. Very clean. Fantastic location. Can walk to town in 5-10 mins. We had a car because we wanted to explore the island and not take the bus. Glad we had a car for all 4 days, but I think a lot of people just rent a car for a day or 2.

We stayed in Fira in Santorini because we didn't have a car and just wanted to walk around (get over jet lag). We stayed at Scirocco Apartments in Fira. Great location, sea views, sunset views and pool. Family ran hotel. Again, great service- highly recommend.

Santorini Dave was a great resource because Rick Steves doesn't say a lot about the islands.......We were very happy with his restaurant recommendations. Hotel Grotta was a Santorini Dave recommendation and Scirocco apartments was recommended from this forum.
Got covid tested in Naxos on Friday for our return flight on Monday. Got PCR results within 5- 6hours of being tested.

Grotto is great if you rent a car for the whole time ... otherwise it's a lot lot of walking. Ive stayed there & in the Place next to it, Iliada Studios, so I know. The nearest Sand beach is St. George and that's a looong walk. By the time u'd get back to Hotel after a swim, y ou'd be all sweaty again. You can take a bus to the other beaches... outbound the beach bus goes uphill near the Grotta and u could flag it on the road --- but at the time YOU are gong, that bus would be full, and would pass yu by. To get a seat, you'd have to wlk down to the end of the ferry pier, where all busses start from. Sure, the Grotta host is very friendly -- but so are hosts all over Naxos... because most of the good places are family-owned, family-run, and for them hospitality is a given. Every place I've stayed in Naxos (& that's 14 times) has been sparkly clean, welcoming hosts, and, at those places that provide breakfast, a delicious meal. So, what it's about is Location.

I second the suggestion of Stanbr ... Plaka is the longest beach so that even int late-august, early September, there's room to spread out. Plenty of sunbrellas & sunbeds if u want them, but long empty stretches in between. I cannot imagine why you want a pool, when the most glorious water in the world stretches for miles, clear as crystal, no tide, you step into it and within 10 feet it's deep. If you INSIST on a pool, Plaka has a lovely place called Aegean Land with a huge pool, cafe, changing places, long beachfront of sunbrellas. I don't stay there, but take the bus out there, use its facilities, no charge when ou buy a snack or drink on beach.