This article covers Santorini, Naxos, Mykonos, Delos, and a couple of other islands from the 220-strong archipelago in the Aegean Sea that is home to some of the most popular destinations in Greece.
Santorini
Santorini ♥♥ (officially in Greek, Θήρα – Thira) is among the most coveted destinations for a large segment of casual travelers. Its blue-domed churches, frequently seen on the pages of travel magazines, exert a significant pull on a large number of people. Those who come will invariably appreciate, in addition to churches, the remarkable volcanic caldera, the distinct boxy-with-rounded-roof white-dominated architecture, and the impressive and comparatively barren landscape.
You also have to deal during the high season with crowds significant enough to diminish the appreciation a notch.
Oia ♥♥♥, at the northwest tip of the island, is a picture-perfect labyrinth of narrow walkways full of galleries and shops (jewelry is the prevalent product on offer, but there are also plenty of clothing stores, plus a very popular bookshop). Every corner of Oia is incredibly picturesque, and there are many beautiful vistas. At the height of the season, its central street may be challenging to navigate through the day, especially around sunset time.
Sunset viewing in Oia – a nearly “must” activity – is simply insane. The westernmost part of the village comes to a standstill with hundreds of people hanging on for the sun to disappear; the best positions are being occupied hours in advance. If the terrace of your hotel or apartment has a westward view, you are well advised to use that. Otherwise, book a restaurant with an elevated west-facing terrace and give yourself ample time to get there even if it feels that you only need 5 minutes.
There are several minor points of interest in Oia, but neither Maritime Museum nor Oia Museum seem to be open according to posted hours. If you possess the necessary energy, you can descend (and later ascend – which can be done via donkeys for an extra fee) to Ammoudi Bay, which is not strictly a point of interest, but rather a location for a couple of popular restaurants.
The ruins of the Byzantine castle are worth a quick stop, for the views.
Although Santorini is not a big island, you need a mode of transportation to get to villages other than the one you are based at. There are car services, and you can rent a car to drive yourself. A more fun activity is renting ATVs ♥ – there are many agencies offering them, and you don’t have to reserve far in advance. You can then get around the island pretty easily on your own, but it is not without drawbacks: cars get impatient with slower ATVs, which makes driving occasionally hazardous; the vehicles themselves are fairly easy to handle, but can present challenges to some; we personally had bad luck with one of the vehicles dying on us during the ride, which took some shine off. Keep in mind that you will be constantly in the sun – wear sunscreen, and reapply frequently!
You can also arrange for a guided tour of the island. We highly recommend Chara Abelioti ♥♥♥ (TripAdvisor link) who gave us a fantastic overview of what the island has to offer, bringing us to villages, local shops, majestic viewpoints, and keeping everyone engaged – adults and kids alike – throughout the tour.
Pyrgos ♥♥ (full name is Pyrgos Kallistis – Πύργος Καλλίστης) is a picturesque village that is nowhere as crowded as Oia. Climb up to its top for views and look into its churches.
Akrotiri archaeological site ♥♥♥ (Ακρωτήρι) is an impressive enclosed excavation of an ancient town, with entire buildings and many artifacts well-preserved. Our appreciation of it was greatly enhanced by Chara’s narration and usage of slides on a tablet, so consider visiting the place with a guide.
Faros Market ♥, close to the southwestern tip of the island, is a great stop to try local wines and produce. You can also visit local wineries, or at the very least, make a quick stop to admire the grapevine “baskets”.
Imerovigli ♥ (Ημεροβίγλι) is another pleasant village, although seemingly not as picturesque as Pyrgos. It has unparalleled caldera vistas, though, and Skaros Rock is a superbly scenic spot if you choose to walk to it.
The aforementioned ATV mechanical problem scuppered our plans to explore the main town of the island, Thira (or Thera, Θήρα – sometimes written in English as Fira). There are a couple of museums there, the Archaeological Museum of Thera and Museum of Prehistoric Thira, that may be worth visiting, as well as the Orthodox Metropolitan Cathedral.
The village of Megalochori (Μεγαλοχώρι) is another destination worth considering a visit.
Santorini is not known for many good beaches – the best ones are on the southern coast of the island. The closest to Oia is Katharos Beach, which still requires driving to and is not very inviting – rocky and rough. We did go to Perissa Beach ♥♥ during our guided tour – it is one of the best on the island. The beach and the sea floor are small black pebbles and sand; the waters are calm and warm; lounge chairs and sun umbrellas are paid for by ordering drinks from the nearest café.
If you decide to leave Santorini on a ferry, please be prepared to have your last impression of the island as barely organized chaos. The narrow set-up of the port causes huge people congestion and makes getting on a ferry a trying exercise. The only positive is a bunch of cafés to bide your time in.
Practicalities
Dining
As far as eating out is concerned, whether you reserve a table in advance based on online ratings or just pick a restaurant at random, it is hard to have a truly disappointing meal on Santorini. Worthy of specific recommendations in Oia are: Elinikon (at the western edge), a relatively small café with a great meze menu; and Kyprida (in the Maritime Museum vicinity), an upper-terrace restaurant with excellent sunset views when correct tables are reserved in advance. For breakfast, Vitrin (near the castle ruins) is a great crêpes choice with views.
Lodging
Accommodation-wise, if staying in Oia, in addition to the many resort-like hotels, a fun option could be an apartment made out of caves, but there will obviously be certain inconveniences related to the space.
Naxos
The island of Naxos ♥♥♥ (Νάξος) is the largest of all Cyclades but enjoys only a fraction of the popularity of some other islands in the archipelago. There is no international airport, which limits the number of foreigners coming here. There are no world-renowned sites that would attract highlight-seeking tourists. Those who come to Naxos are looking to experience the best of Greek hospitality and weather in a quieter setting.
We are completely in love with it.
Chora ♥♥♥ (the main old town) of Naxos is the kind of village I have always imagined Greek villages to be. Atmospheric town core on the hill, a labyrinth of narrow lanes, and picturesque corners at each step. Kastro ♥ district at the very top of the hill is almost entirely not commercial (although there are a few galleries and shops here or there) and has a few minor sights (such as the Archaeological Museum and a couple of churches). The lower levels of Chora comprise a delightful web of narrow passages full of boutiques and restaurants. There is also an Orthodox Cathedral ♥ at the northern edge of the old town.
The well-developed waterfront is more commercialized and gets very lively in the evenings, but it is expansive, open to the gorgeous marina, and definitely nowhere near as crowded as Santorini or Mykonos. A popular picturesque spot on the promontory at the entrance to the harbor is Portara ♥, a sole remaining fragment of an ancient fort. At sunset, hundreds of people come up here to photograph the sinking sun. At other times, the location provides great views over the port and the town.
If you happen to come across concerts at the Cultural Center in Kastro (daily programs run in the summer), it is highly recommended to go to at least one. A traditional bouzouki music concert ♥, with songs and dancing, is great entertainment lasting almost two hours; unlimited wine is part of the admission price.
St George Beach ♥ is about 10 minutes on foot from the port area. Sandy and very shallow, it is great for children. The biggest drawback is the virtual absence of any transportation options to get there, but if you stay in Naxos Town, you can definitely walk over.
Because the island is fairly sizeable, getting to other towns, beaches, or points of interest requires transportation. There are plenty of options to rent a car, as well as infrequent bus services between major points. Another option is hiring a private guide. Nicolas of Naxos Discovery (link) ♥♥♥ delivers a fantastic overview of the island, with stops at quaint towns, visits to Byzantine churches, interactions with local artisans, and plenty of information on the history, geography, and flora of Naxos; he always offers customization to your itinerary based on your specific interests.
Demeter Temple ♥♥, about 25 minutes drive southwest of Naxos Town, is a comparatively small but very impressive archaeological site – and free for entry, too. It may get crowded by mid-morning with bus excursions, so come either early or in the late afternoon.
There are over 40 Venetian towers on the island, remnants of the time when Venice ruled it. Many remain in private ownership, but some are open for visits. Bazeos Tower is among the most accessible.
The village of Halki ♥♥ (Χαλκί) is the historic capital of the island. Its pedestrian core is full of interesting galleries and local artisan shops. There is also a kitron distillery ♥ worth a visit. A few minutes walking off the edge of the village takes you to St-George Diasoritis ♥♥, an incredible Byzantine church (only open for visits a couple of months in the summer).
Another village definitely worth visiting is Apiranthos ♥♥ (Απείραθος), “the marble village” – and one of the highest on the island. Among future considerations are Filoti, Koronos, and Apollonas.
Another great way to explore the surroundings is a day of sailing. It will allow you to swim in hard-to-reach locations, set foot on other islands, and take a look at natural wonders such as Rhina cave ♥, all while passing the day in comparative leisure. (Itineraries vary.)
If you would like to take excursions to other islands while maintaining your base on Naxos, there are several day-cruise options. We took advantage of the Delos/Mykonos itinerary on MV/CAT Alexander – the ratio of sailing versus exploring is not that great in the end, but you still get about 3 hours in each location.
Practicalities
Lodging
In the “memorable stays” category, Grotta Hotel, at the northern edge of Chora, must be among the best family-owned hotel in the known Universe. Modern well-appointed cleanest rooms and public spaces, large bathrooms, nicest staff, all possible amenities (including a small pool with jacuzzi), great sea views… A fresh cake is left in the room after every cleaning. Breakfast is phenomenal, with so much choice of both homemade and standard items that you will struggle to maintain your waistline. The walk to the town center takes 5-7 minutes. The closest beach, unfortunately, is all large rocks – not exactly a safe swimming environment, so St George, which is mentioned above is the nearest workable option – about 20 minutes by foot.
The hotel offers a dinner menu, which is relatively not extensive and very good – mostly of simple traditional dishes; definitely a good choice for at least one of the nights of your stay.
Dining
As far as eating out is concerned, whether you reserve a table in advance based on online ratings or just pick a restaurant at random, it is hard to have a truly disappointing meal on Naxos. Worthy of specific recommendations are: Typografio (on the square at the southern edge of the main commercial path in the Chora), with the most amazing peaceful pedestrian village center setting and wonderful food; and Rotonda (on the approach road to Apiranthos), famous for its fantastic views for miles across the island, as well as pretty good food in generous portions.
Delos
Delos (Δήλος) was a sacred island in ancient times, and today the main and only reason to come here is for its huge archaeological site ♥♥♥. It is very impressive, with sections of remaining walls and preserved artifacts adding to the usual collection of free-standing columns. There is also a very nice display of artifacts at the compact museum. The lovers of ancient finds could easily spend a day here – 3 hours allocated by the day cruise schedule is the absolute minimum.
Mykonos
Mykonos (Μύκονος) is lively and colorful but feels a bit artificial in its prettiness. Many churches ♥ give it a bit of gravitas – and there are nice views along the bay, in addition to plentiful picturesque corners in town. Too many designer names on the commercialized streets correlate to crowds in town, but there are also fun galleries and atmospheric little streets. A few hours in Mykonos Town is on balance a fun experience. You are unlikely to miss the row of windmills ♥ or the area called Little Venice ♥; there are also several minor museums.
Koufonisia Islands
Our sailing trip took us to both the Upper and Lower Koufonisia islands, where we swam in coves and spent a little over an hour on the main beach of the larger of the two, called Finikos Beach ♥. You will unlikely to go there otherwise, but the secluded locations are as good a reason as any to work sailing to these islands into your itinerary around the Cyclades.
Paros
More of a hearsay of recommendation rather than something based on experience. While our day-cruise boat dropped anchor in Naousa port for a few minutes, we did not actually set foot on the island. The people who joined us on that cruise and were staying on Paros, painted a picture of an even less touristy quintessential Greek environment than Naxos, something that could be appealing to certain types of travelers.