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Perfect Holiday in Santorini, Greece – Itinerary and Travel Tips

Off Peak Holiday Santorini Itinerary Travel Tips Oia Blue Dome

Santorini is a must-go travel destination on every travellers list and its not hard to see why. The breathtaking view from the top of the caldera, the calm of the deep blue Aegean Sea, the joy of the blue sky, the impossibility of pinpointing where one charming hotel starts and another idyllic one ends as they drape over the cliffs makes this place seem unreal. It is a magical fairytale land, one of the most beautiful places on our little planet. Couple this with the produce fresh from the sea, wine from the fertile volcanic soil, juicy and sweet cherry tomatoes and white eggplants kissed by the sun, made into delicious dishes by some of the most passionate chefs, you should definitely mark this place in your travel calendar for this year. 

Off Peak Holiday Santorini Itinerary Travel Tips Santorini Map

Best time to go

April or October.

Best areas to stay

Search for your dream hotel in the towns of Fira or Oia. Both of these towns are equally amazing with as much to do and see and as many wonderful hotels as each other. We wouldn’t recommend staying outside of these two places as Santorini is best experienced through exploring the restaurants, bars, boutiques and art galleries which are mostly only situated in these two areas.

Getting there

It is easy to get to Santorini as there are direct flights from most major European cities. There are also ferry connections from Athens, as well as from the major Cyclades islands like Mykonos, Naxos, Ios, Milos, Crete, etc.

Perfect 4 Day Itinerary:

Day 1: Fall in love with Fira

The Arrival

Off Peak Holiday Santorini Itinerary Travel Tips Ferry Port

Our recommended journey starts with a morning ferry from Mykonos to get you to Santorini’s new Port, Athinios, at about noon. (Click here to read our itinerary for Mykonos)

As the ferry approaches, the sheer scale of the caldera cliff where the magical white and blue city seemingly floats on top of becomes clear and this is where the dream holiday starts…

Take your time to disembark from the ferry as most will rush out to get the bus or a taxi. Let the crowd disperse and pick up your pre-booked rental car from the row of shops facing the port. Its a short 15 min drive to Fira or 30 mins to Oia from the ferry port. Enjoy the magnificent view back to the Aegean Sea as you scale the winding road up the mountain/cliff from the port (but do keep your eyes on the road!).

A sip and a glass of local wine at noon

Perfect Holiday Santorini Itinerary Travel Tips Santo Wines
Perfect Holiday Santorini Itinerary Travel Tips Santo Wines

At the top of the cliff you will find Santo Wines ( A perfect place to start your discovery of Santorini as it blends good wine and food with unrivalled panoramic view of the Aegean Sea. Start with a pre-booked 30 min wine tasting tour, for €12 per person. Then sit down for lunch and be awed by the unbelievable view that will continually mesmerise you for the next 3 days.

Check-in to your dream hotel

After lunch, it is perfect timing to check-in to your hotel. We will leave it up to you if you can resist a quick dip in the jacuzzi pool in your cave hotel suite.

Explore and shop the streets

Off Peak Holiday Santorini Itinerary Travel Tips Fira

Head out onto the cobbled streets of Fira and discover handmade jewellery, art sculptures, paintings, unique printed t-shirts and other handicrafts, gifts and souvenirs. The shops/boutiques/galleries are along Ipapantis, Erithrou Stavrou and Dekigala between Orthodox Metropolitan Cathedral in the south and the cable car station in the north. Make sure to also cover off Marinatou, Mitropoleos street and Agiou Mina street as well. For such a touristic town, the quality of the products and shops far from what you will normally get in most tourist traps.

Step into the Santorini time capsule

Two hours before sitting down for your sunset appreciation, step into the Santorini time capsule at the Museum of Prehistoric Thera to discover the lesser known side of this unique island. Learn about the geological events that formed the unique landscape. Awe at the mind-boggling artefacts excavated from Greece’s Pompeii – a Bronze age thriving port city covered in volcanic ash 3,600 years ago. Relive the decadent life of these seafaring city-dwellers from a bygone era through the mesmerising blue monkeys wall art/mural/frescoes, potteries with swallows and dolphin paintings and the cute golden goat/ibex. Take the experience gained here and continue the discovery when you visit Akrotiri on Day 3.

Alternative Option: Down to the old port and ride a cheeky donkey

Off Peak Holiday Santorini Itinerary Travel Tips
Off Peak Holiday Santorini Itinerary Travel Tips Fira Old Port

If museums don’t do it for you, you can instead walk to the old port of Fira, Gialos. It is right below Fira town and you will have to walk 587 steps to go down over 200m to the sea-level. Marvel at the uninterrupted view of the Aegean Sea as you zig zag down.

Off Peak Holiday Santorini Itinerary Travel Tips Fira Old Port Thira
Zig-zag down from Fira town to the Old Port

The old port is normally quiet apart from when the giant cruise ships disembark or depart. Hence, this is a good place to come to for a little respite from the crowd if you are here during high season.

Off Peak Holiday Santorini Itinerary Travel Tips Fira Donkey Ride
Off Peak Holiday Santorini Itinerary Travel Tips Fira Old Port Donkey Ride

Afterwards you can take either a donkey ride or cable car to the top. However, please know that there have been recent reports of the donkeys suffering from spinal injuries, saddle sores and exhaustion. If you see signs of this or feel in anyway unsure, please opt for the cable car instead.

Romantic sunset over the Aegean

The sun sets at 7.45pm in April and 6.45pm in October. We would recommend enjoying it back on your hotel’s balcony or terrace with a chilled bottle of champagne. Alternatively, check out one of the tried and tested bars below. Advance reservation is a must.

Perfect Holiday Santorini Greece Itinerary Travel Tips PK Cocktail Sunset Bar
PK Cocktail Bar
Santorini Holiday Itinerary Travel Tips V Lounge Cafe Cocktail Bar Fira
V Lounge Cafe & Cocktail Bar

PK Cocktail Bar ( By far our favourite bar in Fira. Sipping a Metaxa 12 Star Greek brandy or an Earl Grey infused gin cocktail during sunset on this amazing terrace bar suspended on the cliff is a must do while in Santorini. They have a great selection of cocktails.

V Lounge Cafe & Cocktail Bar ( Just a stones-throw away from PK Cocktail Bar is this amazing lounge with first class view of the spectacle out on the horizon. This is as romantic as romance can get.

Feast as they do in “My Big Fat Greek Wedding”

After freshening up back at the hotel, put on your best outfit and head out for a culinary experience. There is a plethora of awesome restaurants and bars in Fira, as with the rest of Santorini. You will be spoilt for choice. Below are some of our recommendations. Do book in advance and ask for a table with a view.

Perfect Holiday Santorini Itinerary Travel Tips Naoussa Dinner Fira Homely
Perfect Holiday Santorini Itinerary Travel Tips Naoussa Dinner Fira
Seafood platter at Naoussa

Naoussa ( This is a true local Greek restaurant with a big heart. The home cooked dishes are delicious. The atmosphere is lively yet homely, buzzing with chitter chatter, live music and smashing of plates (yes, that’s right!). Be prepared for a wonderful time. Ask for a table upstairs on the terrace. Opa!

Argo Restaurant ( The best from the sea is what you will get here. Treat your tastebuds with fresh grilled squid, octopus, prawns or good old classics like deep fried calamari or seafood linguine. Book in advance to snatch a corner table on the upper terrace and feast on the beautiful view of the caldera.

Some suggestions for a holiday read

Before we continue on our itinerary, below are some suggestions for a holiday or pre-holiday read for you to fall further in love with Santorini.

Day 2: A walk to remember with blue domes and windmills

Pilgrimage to Imerovigli

Santorini Holiday Itinerary Travel Tips Imerovigli View
Bell Tower of Agios Anastasios Church in Imerovigli

After breakfast, the day’s itinerary starts with a 45 min trek across to Imerovigli, the highest town in Santorini. We highly recommend this as the walk is gentle and you will be rewarded with some of the most amazing views. But do wear proper sport shoes, sun protection and bring a bottle of water to stay hydrated.

Holiday Santorini Itinerary Travel Tips Skaros Imerovigli
Skaros Rock

Finish off your trek at Skaros Rock, which was once part of a fortress built by the Venetians. Although not very much of the mighty fortress structure still exists, it still worth the climb to admire the view from this unique vantage point. Do note that it is not easy to get to the top of the promontory.

Discover Oia

Off Peak Holiday Santorini Itinerary Travel Tips Oia

With an appetite worked up, a well-deserved lunch is in order. Walk back to Fira to pick up your car and set your GPS to Ammoudi Bay (map) in Oia. It is a 25 min drive and you might be able to park along the road down to the waterfront bay. If not, just drive back up to the parking space across the Oia Post Office (map). From there, it is a 15 min walk down about 300 steps passing by the Byzantine Castle Ruin to get to Ammoudi Bay.

Lunch from the Aegean Sea

Holiday Santorini Travel Tips Itinerary Ammoudi Bay Oia

Ammoudi Bay is a small picturesque port lined with some of the best no-frills seafood taverns against a backdrop of red cliffs. The scene is complete with colourful fishermen boats bobbing up and down by the jetty and holidaymakers joyfully swimming in the deep blue sea. A perfect spot to savour fresh seafood, chilled white wine to the tune of gentle lapping of the ocean waves. Below are two of our recommended taverns for this lunch from the Aegean Sea.

Holiday Santorini Itinerary Travel Tips Ammoudi Bay Seafood Restaurant
Dimitris Ammoudi Taverna

Taverna Katina Fish Tavern (taverna.katina) – Look for the bright orange wooden chairs and you will have found this food haven. Freshly grilled lobster, octopus, squid, fish and prawns. Don’t hold back and have the full house.

Dimitris Ammoudi Taverna ( – Right at the end of the stretch of taverns is this husband and wife run, homely, friendly tavern with freshly cooked seafood. Try the traditional Greek dishes like prawn saganaki, deep fried whitebait and grilled octopus drizzled with olive oil and lemon. Make sure you say hello to Captain Hook before you leave.

Explore what lies beyond the staircases

Off Peak Holiday Santorini Itinerary Travel Tips Oia Pathway

After lunch, spend some time wondering about this gorgeous town. Go wherever your feet take you. Make your way down the staircases, walk down that path and discover your own piece of Oia. There are amazing hotels to peep into, great views to admire. Don’t stop till you find the most photographed three blue dome church in Santorini. Take plenty of photos of the charming old windmills that look out onto the Aegean Sea.

Holiday Santorini Itinerary Travel Tips Oia Windmill View
Holiday Santorini Itinerary Travel Tips Oia Three Blue Dome

As with Fira, there are many boutiques and art galleries here to feast the eyes on. They are predominantly located on pedestrianised Nik Nomikou road which traverses across Oia town. You will find paintings, sculptures, art pieces as well as handmade jewellery, crafts and knick-knacks.

Off Peak Holiday Santorini Itinerary Travel Tips Blue Door
Off Peak Holiday Santorini Itinerary Travel Tips Streets

Another spectacular sunset

Due to it’s location on the island, Oia has the best sunset. The most popular place to catch the sunset is actually back at the Byzantine Castle ruin. But it is normally too crowded and more importantly you won’t have a cocktail or champagne or ice cold beer to hand. We would recommend making a reservation at Ochre Bistro ( or Sun Spirit. As sunset is such a big deal in Oia, you may have to combine dinner with sunset to guarantee a reservations.

A dinner to remember

What better way to cap off another day in this unique paradise than with some food and wine after sunset. There are plenty of restaurants on offer, but we would recommend one of the below for a truly once-in-a-lifetime experience. As always, please book them as much in advance as possible.

Holiday Santorini Itinerary Travel Tips Lycabettus View Best Dinner
Lycabettus – Best view in the world
Holiday Santorini Itinerary Travel Tips Lycabettus View Best Dinner
Lycabettus – a fairytail terrace

Lycabettus ( – probably the restaurant with the best view in the world. For the ultimate experience of Santorini, book yourself a romantic dinner on the terrace of this fine restaurant for sunset. They cook up some amazing Greek/Mediterranean seafood dishes to match the unforgettable view.

Holiday Santorini Itinerary Travel Tips Lefkes Oia View Best Dinner
Lefkes – Courtyard
Holiday Santorini Itinerary Travel Tips Lefkes Oia View Best Dinner
Lefkes – Entrance

Lefkes ( – If you are willing to trade-off the magnetising view from the cliff-side for the best and most salivating food, then jump into the car for a short drive to Lefkes in the village of Finikia. A world-class restaurant, beautifully laid out with awesome service, lively atmosphere and creative dishes. Make sure to try the moussaka croquettes with feta mousse and much-raved about slow-cooked lamb.

Holiday Santorini Itinerary Travel Tips Melitini View Best Dinner
Melitini – Entrance
Holiday Santorini Itinerary Travel Tips Melitini View Best Dinner
Melitini – Panoramic View

Melitini ( – this smart looking hidden gem has the best of both worlds. Delicious, fresh and tasty traditional Greek dishes with a decent view of the Aegean sea from their rooftop terrace. They serve tapas / meze portions so you can indulge in a variety of dishes. You can also catch the sunset from here.

Day 3: Taking in the view from breakfast to ancient civilisation to a red beach

A breakfast fit for the King & Queen

Off Peak Holiday Santorini Itinerary Travel Tips Enigma Breakfast
Breakfast on the balcony of Enigma Suites

Start the day with a leisurely breakfast on your hotel’s balcony or terrace. Take all the time you need to enjoy that magical view (again), you deserve it. But apart from the view, the greek honey, yogurt as well as freshly baked croissants are equally magical in Santorini. A morning of perfection.

A climb to an ancient Hellenistic civilisation with great views

Once you are ready to part with the forget-me-not view, get ready to explore the ruins of an ancient city once stood on the top of Mesa Vouno Mountain, known today as Ancient Thera. It is a 20 minute drive from Fira and up some narrow winding roads from Kamari town. Walk along the main cobbled road of this city and into the city’s market square (agora) and imagine what life would have been like from the limestone structures magnificently left behind. Admire the amphitheatre built on the slope of the mountain, where cultural performances entertained the citizen 2,500 years ago. The view of the Aegean Sea is breathless from here, it feels like you can almost touch the clouds from the top of the city. Spend about 1-2 hours taking in the history and the view.

Travel Tips: There is limited shelter from the sun as you explore the area, please bring water to stay hydrated. Depending on the time of the year, it can also get windy at the top. There is also no washroom in the area. Closed on Tuesdays.

Lunch at the black beach

At the foot of Mesa Vouno Mountain is Kamari town, known for the black pebble/sand beach of volcanic decent which seemingly stretches on forever. The colour of the beach plays on your mind as it is deeply black and so different from any other beaches that you might have seen. There is a wide selection of restaurants to choose from to refuel after a busy morning. Below are two of our recommended restaurants at the black beach.

Alismari – One of the many beach-front restaurants on the black beach of Kamari. This one has comfy deck chairs and umbrellas which you can sit on with no additional charge if taking lunch (as long as they are not too busy). Even if you didn’t, the alfresco seating under a leafy roof are comfy and great for people watching and taking in the beach view. The grilled squid, chicken, hallumi, burgers and pizzas are simple but delicious.

Captain’s Corner (@captainscornertaverna)- away from the beach promenade, you will find a gem of an authentic blue & white Greek taverna with big heart and mouth-watering fresh seafood. Savour the perfectly grilled giant squid, sumptuous lobster linguine, seafood risotto or succulent lamb while being waited on by friendly and warm staff.

Travel back in time to 1600 BC

After lunch, travel back to the Bronze age to Greek’s Pompeii. A 30 min drive south is the Prehistoric Town of Akrotiri, a Minoan thriving port city with trade connections with Athens as well as ancient Egypt. As with Pompeii, it all came to a sudden end in the 17th century BC, with an earthquake followed by the largest volcanic eruption in history covering the city in ash. That’s almost 4,000 years ago, mind boggling. Here you can visualise the wall paintings/frescoes seen at the Museum of Prehistoric Thira (Day 1) into their original surroundings. Be puzzled by the elaborate drainage system, sophisticated pottery as well as the seemingly “modern” multi-storey buildings with underfloor heating, hot and cold water and toilets. We highly recommend the guided tour to ensure you fully appreciate the history behind this amazing time capsule.

Red beach

Perfect Holiday Santorini Greece Itinerary Travel Tips Red Beach

Before heading to dinner, if you are in Akrotiri, drop by the Red beach – the only one in the world. It is a short drive and there is a car park that is a few minutes walk from the beach. It is a narrow strip of beach against a deep red mighty cliff with deep blue sea on the front.

The final supper

Holiday Santorini Travel Tip Itinerary Metaxi Mas Best Dinner Restaurant
Holiday Santorini Travel Tip Itinerary Metaxi Mas Best Dinner Restaurant

There is no better end to this perfect holiday than dinner at the Santorini dining institution of Metaxi Mas ( Their friendliness, warmth, fresh delicious food (Try the tasty broccoli soufflé and lamb shank with Santorini cherry tomatoes) and the panoramic terrace encompasses everything of the last 3 dreamy days. As the sun begins to set and as the fairytale holiday comes to an end, take a moment to absorb the feeling of living all the magical and unique moments, sights, views and experiences and as the moonlight takes over reflecting on the Aegean Sea, let that feeling and your your beautiful memories of Santorini live in you forever.

Travel Tips:

Driving Tips:

Rent a car for the duration of you stay. Although the island is not big, it will come in handy to travel in between Oia and Fira as well as tracking down places off the beaten track.

Do take a video of the inside and outside of your rental vehicle before you drive off. This will come in handy if there any disputes and unfortunately, there are high number of cases in Santorini.

There is ample parking around Fira and Oia town in April and October, though it is unlikely to be right outside your hotel. Get the location of the most convenient parking location from your head ahead of the journey. In most cases, parking is free.

Click here for google map location of the largest car parking space in Fira

Packing Tips:

Sun protection – Bring sunscreen, sunglasses and a hat to stay safe in the sun while in Santorini. As the building are low and plants tend to be low too, there are limited shade, especially when you are walking between Fira and Imerovigli or in Ancient Thira.

Travel power adapter – Greece uses type C & F power outlets and plugs (round, two pin plugs). Standard voltage is 230 V with a frequency of 50 Hz. Hence, don’t forget to pack a travel power adapter. Here is a link to one we have tried and tested.

Power extension – rather than buying a few travel power adapters, just pack one of your power extensions in your house to convert one power adapter to connect 3 or 4 plugs. Handy and practical.

Additional Reading:

For additional reading on this amazing island, you may want to check out our selection of top books on a perfect holiday in Santorini from our Amazon Associates links below.

Off Peak Holiday Santorini Itinerary Travel Tips Enigma Sunset
Sunset in Fira

Onwards to another Greek island:

If you have time, we would recommend to visit Mykonos, or another of the Greek Islands when you travel to Santorini. Below is our recommended itinerary and travel tips for Mykonos.

Off-peak Holiday in Mykonos – Itinerary & Travel Tips

We love Mykonos at the end of October, as the tourism industry gradually shuts down for winter on this beautiful Greek island. The famously hedonistic party season which usually draws in the hordes and packs out the island had clearly ended, so once more, it is a relaxed, peaceful, almost sleepy island paradise. The weather […]

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