The best of Santorini: an all inclusive guide for the first time visitor

Overview

Your annual leave is booked, flights to Greece are paid for and now there’s just the excitement and anticipation of waiting for your holiday of a lifetime! But what should you actually do in this island paradise that everyone raves about? Behind all of the fabulous photographs you’ve seen of Santorini, what are the best things to see, which town should you stay in and what activities should you prioritise? Well, keep reading for an all-inclusive guide to the absolute essentials in Santorini! I spent 5 nights in Santorini as a first time visitor and at every step, my mouth was absolutely wide open in absolute surprise and delight! So here is Santorini: the best of!

Santorini Island was the last destination of our 3 Week Trip to Greece, after completing an epic road trip around Greece mainland and then 2 nights on Naxos Island!

Where is Santorini?

Santorini is one of the Greek Cyclades islands in the Aegean Sea. A volcanic eruption in the 16th century BC shaped its rugged landscape and its caldera (crater) today is largely filled with water. Its famous clifftop towns are Fira, Imerovigli and Oia which lie on the west, overlooking the caldera. The eastern side of Santorini is much more flat, with beach side towns, such as Kamari, along the coastline.

Why the hype about Santorini?

Santorini is undoubtedly one of the most beautiful islands in the world, with its high mountain cliffs overlooking the caldera of an ancient volcano on one side, and its flat relaxed beaches on the other. It regularly features in magazines and social media posts. You’ve no doubt seen the bodily gymnastics of the lastest Instagram influencer precariously positioned on a white Santorini roof or a buffed gym bod posing next to a blue domed roof. It’s definitely showy and its small narrow roads are a hive of photographers all seeking to take a seemingly different angle on the same view.

If you can look past this facade of aesthetic fanaticism (granted, it can be difficult!) there is much more beneath the surface. The majority of the heaving crowds are centred in Oia, particularly around sunset. However, the remainder of the island is also home to stunning caldera views, ancient ruins, unique wineries, hikes with incredible views, multi-coloured beaches, lively towns and simply outstanding fresh seafood.

How do I get to Santorini?

Access to Santorini is by air (with an international airport) or by ferry, which docks at Fira. We came by ferry from Naxos Island.

Where Should I Stay?

Your accommodation selection will shape your entire experience in Santorini, so choose wisely! Despite its appearance on the map, it’s not a small island! Traversing the island can take 60-90 minutes by car. Consider what it is you’d like to see and visit on Santorini.

For classic caldera views on the cliff edge, I’d recommend Oia, Imerovigli or Fira.

Oia is well known for the ‘best views’ (both of the sunset and the classic blue-dome churches) but note that for direct sunset views, Imerovigli actually provides the most unobscured view. Never fear, you’ll get a great view from all 3 towns! Honeymooners tend to gravitate towards Oia, with traditional cave hotels being a popular choice. However, note that if you are seeking privacy and serenity, Oia is unlikely to fulfil this desire! Due to the terraced nature of the hotels, you will most likely have someone looking down on you from above. It is also the most expensive town on the island.

I’d recommend Imerovigli for those seeking a quieter, more intimate experience.

Fira is slightly larger and more energetic and is great for groups of friends, whilst Kamari has a relaxed ‘Bali-esque’ style beach atmosphere with promenade cafes and nightspots (albeit with no sunset).

Personal reflection:

Transport on Santorini Island

Accommodation location is vital because transport around Santorini is not straightforward. Options include: private car hire, ATV hire or organised group tour. There are only 25 taxis on the island and nigh impossible to secure. Whilst ATVs are popular, I wouldn’t recommend them for long distances because they can be quite unstable, especially when it’s windy. Being based in Oia, we arranged a few private half- and full-day tour options and were collected from a central meeting point in Oia. On one day we hired a Citroen C3 (any small compact car will do) in order to privately explorate the island, with a same day return option. This is because parking in Oia is a nightmare. The car hire was excellent and I’d definitely recommend this option to see other towns in Santorini.

Unmissable Highlights

1. Take in an unforgettable sunset at Oia Castle
2. Relax in your private spa overlooking the caldera
3. Descend the steps from Oia Castle to Ammoudi Port – or rent a donkey!
4. Indulge your tastebuds with fresh seafood at Ammoudi Port
5. Enjoy sunset drinks from a rooftop bar in Oia
6. Shop for locally made designer crafts, jewellery and clothes in Oia
7. Take a selfie amongst the famous Oia skyline
8. Get in line to photograph a blue domed church
9. Try the famous Assyrtiko varietal on an afternoon winery tour
10. Enjoy a sunset catamaran cruise
11. Explore the main city of Fira
12. Experience a meal in Fira with its caldera views
13. Hike from Fira to Imerovigli
14. Explore Imerovigli’s serene alleyways and unbeatable views
15. Hike to Skaros Rock
16. Have a romantic dinner or picnic in Imerovigli overlooking the sunset
17. Wind through the streets to the Akrotiri Venetian Castle ruins
18. Explore multicoloured beaches in Akrotiri Village – red, white and black!
19. Visit the preserved prehistoric village of Akrotiri – the ‘Greek Pompeii’!
20. Try not to get blown away at Akrotiri Lighthouse
21. Head to Akrotiri for the sunset
22. Ascend Messavouno mountain to visit the Ancient Thera ruins
23. Take a walk along the relaxed beach side town of Kamari
24. Experience a meal in a family run restaurant in Kamari
25. Enjoy the fun nightlife in Kamari
26. Watch a film at the Kamari Outdoor Cinema

1. Take in an unforgettable sunset at Oia Castle

There’s a reason I’ve listed this number one. It’s a quintessential bucket list item. Few dare to visit Santorini without venturing to Oia Castle on at least one evening!

It’s no understatement that the pathways and terraces in Oia are completely rammed a few hours before the sunset, all with the intention of securing a view of the horizon. It’s not the greatest social distancing advert but it’s definitely a cracking display of colour. The manner in which the fading day light dances across the buildings and hotels is probably more beautiful than its descent into the horizon itself!

2. Relax in your private spa overlooking the caldera

Privacy details aside, there is really nothing like enjoying a glass of wine in your private hot tub as the sun sets in Santorini. The splendid array of pinks, oranges and yellows outline yachts in the caldera whilst amplifying the intensity of the pink bougainvilleas that grow wildly along the narrow pathways interlinking hotels. For the early risers, it’s also a refreshing way to welcome a new day.

(Disclaimer: many of the ‘hot tubs’ listed on hotel websites in Oia are not all that hot in temperature!)

3. Descend the steps from Oia Castle to Ammoudi Port – or rent a donkey!

One of the only places to swim on the west side of the island is Ammoudi Bay. To reach that, you must descend the steps from Oia Castle to the quaint Ammoudi Port of which there are approximately 300. Near the castle are some of the most picturesque buildings and views of Oia.

A group of not-so-subtly-positioned donkeys create somewhat of a barrier on the descent from Oia Castle and if you’re not courageous enough to walk past their backsides, then you’ll have to either rent one or head back up. I decided to (nervously) risk it and the descent to Ammoudi Port was a treat for the eye. The white buildings of Ammoudi town nestle into the blood-red slope of the caldera cliff. (Note that if you secure a coveted taxi you can be driven to Venizelou Street, close to Ammoudi Port, but there is no parking here).

4. Indulge your tastebuds with fresh seafood at Ammoudi Port

At the base of the steps to Ammoudi Port are a few of the very best seafood restaurants you’ll ever visit.

Slightly further on from the cafes and around the headland track, is the perfect place for a cool-down swim, in Ammoudi Bay.

5. Enjoy sunset drinks from a rooftop bar in Oia

It goes without saying that this is one of the best things to do in Santorini. Try a glass of Assyrtiko, a wine varietal indigenous to the island of Santorini. For incredible views, Lotza Bar is unbeatable!

6. Shop for locally made designer crafts, jewellery and clothes in Oia

My favourite escape from the obscene vanity on every corner of Oia was simply to spend a morning shopping. During this time I chatted to local designers and shop owners to gain their perspective of life in Oia. It was completely grounding and centring and an interesting insight into island life. There are also some brilliant local designs in these stores which are authentic to Greece and worthy of support after the atrocities that the country has recently endured.

7. Take a selfie amongst the famous Oia skyline

I’m not sure I need to list this as I’m sure you’ll already have it covered on day 1! Be prepared to share your photo with many other people in the background. It’s quite rare to find a street in Oia that isn’t populated to the hilt.

8. Get in line to photograph a blue domed church

Another popular line-up affair is a photo with a blue domed church. Many tourists will literally have their photograph taken and then walk down some steps to take more of themselves, without consideration of others who are were patiently waiting behind them for a picture. This is the uglier side to Oia but it’s definitely still worth the patience for a snap or two.

9. Try the famous Assyrtiko varietal on an afternoon winery tour

One of my very favourite things to do in Santorini was an afternoon winery tour: truly the perfect afternoon! We had a private vehicle tour for this and were taken to 3 of the most incredible wineries on the island:

• Venetsanos Winery
• Argyros Estate
• Anhydrous Winery

Venetsanos has possibly the most stunning view across all 3 towns of Oia, Imerovigli and Fira. Our guide pointed out a circular barrier in the caldera which is the site of shipwreck.

At Venetsanos we were treated to their wines Santorini, Nykteri, Angallis, Mandilaria and Liastos.

Argyros Winery is a short drive past the town of Pyrgos and at 400 acres, is the largest privately owned vineyard on Santorini. It has more of an industrial-winery feel with an extremely modern cellar door and is nestled between scaling mountains and the flat plains leading to Kamari Beach.

Anyhydrous Winery has an inviting ‘backyard’ feel and without the landscape views of the previous two wineries but high in the quality of wine. We were served by a sommelier, offering assyrtiko, dolphins dry aged white, red wave Mandilaria and Islander sweet wine.

Each winery supplements its wines with a generous tasting board, all inclusive within the tour cost, which was €150pp.

If you have the time, then I’d highly recommend a visit to Santorini’s famous brewery: Yellow Donkey!

10. Enjoy a sunset catamaran cruise

Catamaran cruises are offered during the day, at dusk or in the evening. These are a popular choice which we signed up to on our last day. Alas the weather was too choppy to proceed.

11. Explore the main city of Fira

Fira (or confusingly sometimes listed as Thera) is the capital of Santorini and its biggest and most cosmopolitan settlement.

Fira is a non stop hub of activity! It’s natural beauty overlooking the caldera is a major drawcard and this is also where ferries come to dock. If you’re arriving to the dock, then you’ll either have to walk up, rent a donkey, have prearranged transport, catch the cable car (ski-lift) or try your luck at hailing one of the few taxis on the island.

During the day, Fira town is a pleasant place to spend a day shopping or winding in and out of cafes in the alleyways. It’s a great place to find a special keepsake of your time in Santorini, without the (obscene) price tag of Oia. There’s a greater variety of shops here too, so if you are staying elsewhere on the island, it’s a good place to stock up on any essentials. At night, Fira comes alive. It’s wealth of bars, restaurants, cafes and clubs spring into action and hundreds of tourists flock to them for a drink or a dance.

12. Experience a meal in Fira with its caldera views

You can’t visit Fira without having a meal in a restaurant with a caldera-view! It’s truly a sight to behold and the sheer drop in front of these high-rise eateries which gives way to the view beyond is simply indescribable!

I can highly recommend Restaurant Classico for their excellent cuisine and sensational complete caldera views from Akrotiri to Oia. Idol Bar is also amazing for chilled house tunes and a cheeky tipple.

13. Hike from Fira to Imerovigli

Many websites mention the hike from Fira to Oia (which is possible) but if you’re in Santorini in the middle of summer, you’ll likely want a slightly less taxing route. I’d say the most beautiful part of the walk is between Fira to Imerovigli and allows you to then enjoy dinner and a sunset in Imerovigli at its conclusion. The entire walk is 10km and from Fira to Imerovigli it is 2km. The walk takes you first through Firostefani, which is an extension of Fira so you may not realise you’ve entered a second village. It sits slightly higher than Fira however and after a small walk uphill, you’re rewarded with some incredible views.

Don’t miss Volkan on the rocks bar along the way! Their open terrace is the perfect place to rehydrate with a drink whilst overlooking its unique view of the caldera. It’s a little removed from the movement and busy-ness of Fira and it even has an outdoor cinema in the evenings! This friendly cafe serves the island’s local Volkan beer in various styles: Santorini blonde, black, red and grey!

Continue on the path to Imerovigli, drinking in the warm sunshine as it dances over the caldera beneath you!

14. Explore Imerovigli’s serene alleyways & unbeatable views

Sometimes the Santorini caldera is so striking that you forget to look at what’s directly in front of you! Allow some time to explore the quiet charm of Imerovigli town.

It’s a photographer’s dream: fewer people, unbeatable views and a peaceful environment. As mentioned, it’s also perfect for couples who want a romantic escape. However, don’t expect to find nearly the number of shops, restaurants and entertainment options in Imerovigli as you will in Oia and Fira.

15. Hike to Skaros Rock

You’ll notice a striking pillared rock formation jutting out into the ocean below the town of Imerovigli. This is Skaros Rock, a former fortress.

It’s possible to walk to after navigating down some steep steps in Imerovigli. If you’re taking the Fira to Imerovigli hiking trail, then allow another 30-60 minutes for this detour. There’s a small dainty whitewashed Church of Christ you’ll pass by. Be careful on windy days as it can be quite dangerous and forceful at this point.

As far as I’m aware there’s no pathway to climb to the top of Skaros Rock. We circled it and attempted to climb as far as possible but it seemed out of reach. At the base of the rock are the ruins of an old church, the Chapel of Panagia Theoskepasti. During the Byzantine era, this was part of a settlement of over 200 homes and several hundred inhabitants who lived around the rock promontory.

16. Have a romantic dinner or picnic in Imerovigli overlooking the sunset

I’d say that for sheer views, intimacy, remoteness and charm, Imerovigli is the most romantic town in Santorini. The streets are much more quiet and you’ll encounter less tourists, even in the peak of summer. The ones you’ll meet also seem to be more friendly and willing to engage in conversation.

When we first walked into Imerovigli (on the hike from Fira) I was astounded by the number of small boutique accommodations, most with private pools and spas seemingly perched right on the edge of the caldera. There was an instant calming feel here and a transcending serenity that I hadn’t encountered elsewhere in Santorini. For that reason, I’d recommend it to couples wanting a private retreat.

Imerovigli Restaurants

We decided to stay here for dinner and watch the sunset from this smaller town. There were some great options in Imerovigli but we did find it reasonably difficult to find at last minute. Remember to book ahead! We visited some roof tops bars and then ate some delicious stuffed squid with Aidani wine at Avocado Restaurant. Other recommended restaurants and bars are Le Moustache, The Athenian House, The Wine Bar and La Maison.

A Relaxed Picnic Option

Alternatively, why not pack a picnic and enjoy a simple evening in the open night air! Along the edge of the main road in Imerovigli are some park benches overlooking the caldera. There’s also a small corner store selling snacks, drinks and alcoholic options. We came here after dinner and enjoyed some beers with some other relaxed customers, while watching the sun set. It was one of my most memorable moments in Santorini.

17. Wind through the streets to the Akrotiri Venetian Castle ruins

Unfortunately the Akrotiri Venetian castle was badly damaged in an earthquake in the 1950s. Today it is little more than a few abandoned ruins which are not particularly well sign posted. There is a nice view from the top but it’s only something to do if you’re in the area. Sadly it is not a destination in itself any longer.

The small village of Akrotiri is worth a quick stop for its quaint homely cafes and boutique clothes and souvenir stores. There is also a beautiful blue domed chapel nearby.

18. Explore multicoloured beaches in Akrotiri Village – red, white and black!

Santorini’s incredible geology also extends to its beaches! It’s volcanic rock base gives way to some unusually coloured beaches. The most famous is Red Beach: its colour derived from the pulverised volcanic rock. Red Beach is located near the prehistoric village of Akrotiri. Watch out for its occasional landslides! The rocks feel like a gentle massage underfoot and it was quite busy the day we visited.

White Beach is nearby and named after the white cliffs that dominate its landscape. Adjacent White Beach is Black Beach, which is also home to Summer Beach Bar, a beach club with simple eats, drinks and day beds for hire. Note that the dirt road to these beaches is extremely rocky and littered with potholes. I found the rough black sea granules quite difficult to walk across personally! Other black sand beaches can be found at Perissa, Perivolos and Kamari.

19. Visit the preserved prehistoric village of Akrotiri

Akrotiri has been remarkably restored, a prehistoric settlement that dates back as early as the fifth millennium BC, when it was a small fishing and farming village. During the Bronze Age however, it was one of the most important Minoan urban centres and ports in the Aegean Sea. It had connections to mainland Greece and as far as Egypt and Syria. In the 17th century BC it was covered in volcanic ash and its preservation to this day is exceptional.

Today the site is covered by a bioclimatic roof and suspended walkways, which enable visitors to peer down at the archaeological remains from 2-3 storeys high. The settlement is estimated as being approximately 20 hectares, although not all of it has been uncovered.

20. Try not to get blown away at Akrotiri Lighthouse

This is another itinerary option for those in the area. The Akrotiri Lighthouse is perched amongst the strong winds on the southwestern tip of the Santorini crescent. It’s a rugged area, however its possible to see the entire caldera with Oia far off in the distance.

21. Head to Akrotiri for the sunset

For a wild and (very) windy sunset, head to the Akrotiri peninsula. The pinks and purples will light up the cliffs in front of you, a vision to behold.

22. Ascend Messavouno mountain to visit the Ancient Thera ruins

Sadly we did not venture inside the Ancient Thera ruins. Unfortunately much of the official online information regarding ancient Greek sites are incorrect and infrequently updated. Many of them close early in the afternoon as was the case with the Ancient Thera ruins. However we drove to the top of Messavouno Mountain which gave spectacular views across Kamari and the flat plains on the eastern side of Santorini.

23. Take a walk along the relaxed beach side town of Kamari

The peaceful breezy town of Kamari is the perfect antidote to the high flying Oia. It’s relaxed and calm, with streets being much wider and open. Here you’ll find some small cafes, fine dining restaurants and a mix of shops.

24. Experience a meal in a family run restaurant in Kamari

Along the waterfront promenade of Kamari is a series of upmarket and cosmopolitan cafes and restaurants. However, I’d recommend delving back into the smaller streets to find a cosy family-run eatery for your evening meal! There’s every chance you’ll find live music to accompany your meal, which will be sourced from local ingredients. It’s also worthwhile supporting these smaller cafes who have only just managed to survive their internal country crisis, as well as the Covid pandemic.

We first ate at Sellada, a homely inviting open air restaurant, who served us mouth-watering moussaka and meatballs. For dessert they brought out the most delicious grapes which were grown on the eaves of the building! We enjoyed Kamari so much that we returned for a second night, this time enjoying a huge platter of fresh seafood at Amalthia restaurant.

25. Enjoy the fun nightlife in Kamari

A clear favourite town for me was Kamari. The energy of this beachside town in the evenings was superb! It reminded me of coastal towns in Bali, where people come out in the evening to have fun enjoying music with a refreshing drink in hand. The fresh breeze off of the ocean was a salve to the peak summer heat of the day.

26. Watch a film at the Kamari Outdoor Cinema

You simply can not leave Santorini without experiencing the Kamari outdoor cinema! There is an old world charm about this venue from the moment one enters. Set amongst a backdrop of ferns and trees, with a superb selection of drinks at the bar, this is one of the most romantic things to do on Santorini. Entry is first come first served with no presale of tickets. I would suggest getting there early to join the queue as it sells out quickly!