Greek island hopping itinerary

Greek island hopping itinerary: Guide to Greece

I am so blessed to come from a close and loving family who love to travel. We recently had a family destination wedding in Sifnos, Greece and this meant we had the opportunity to explore Greece with my parents and brother who flew out from South Africa. We were so fortunate to also have some of our best friends from home join us in Santorini and Mykonos. I’ve put together this Greek island hopping itinerary for some guidelines to experiencing some of the most beautiful islands of the Mediterranean. Then get booking because Greece is a magical place and not one you want to miss out on!

“It takes a lifetime for someone to discover Greece but it only takes an instant to fall in love with her”


A small island in the cyclade island group and so beautiful you would think you were dreaming, Sifnos is the perfect balance of stunning beaches, low key nightlife and peace and tranquillity. With many tourists oblivious to its existence you can enjoy the beauty of Greece without all the crowds and non-stop buzzing of the more popular cyclade islands; Santorini and Mykonos. We were in Sifnos for a family wedding and were lucky enough to experience a traditional Greek wedding ceremony which took place in a Greek orthodox church and was performed in ancient Greek

Where to stay

We stayed at Virginia studios in Vathi and although it was a fairly basic self-catering apartment it’s the best accommodation we have ever stayed at thanks to the location. The sea was literally only footsteps from our front door.

Greece island hopping itinerary

If you are after more luxurious accommodation there is also a 5 star hotel, Elies Resort also located on the beachfront in Vathi.

Greek island hopping itinerary: What to do in Sifnos

1. We spent some time visiting the capital, Apollonia, where most of the nightlife’ takes place. There are bars, cafes, boutiques and restaurants along a main street that is too small for any vehicle except a slow moving motorcycle. Apollonia is the most central point and from here all buses pass by connecting it with the rest of the settlements and the beaches.


2. Be sure to take a trip down to Faros, a picturesque seaside village at the south east of Sifnos. We enjoyed a leisurely lunch here, where we were seated at our table just metres from the sea. A Greece dream!

3. If you are in Sifnos you must have an evening cocktail at Dolci café. This is a beautiful setting with an amazing view and exquisite interior décor. It is especially beautiful when lit up at night time.



  • There are multiple options on how you wish to move around Sifnos. You can either hire a car, scooter, or quad bike, or alternatively use the public transport facilities (bus). The bus is however not very frequent and if you want to explore the island more freely, we strongly recommend hiring a car. During peak season 35-45 Euros per day is reasonable for a small car
  • One of the best things about Sifnos is that there is no airport (less tourists), therefore you will need to fly into Athens and take a ferry to Sifnos. It is advisable to purchase your ferry ticket upfront
  • Although we stayed in Vathi and would highly recommend it there are obviously also other options for your Greek island hopping itinerary. It is logistically convenient to stay in Kamares which is the port town. Faros, Kastro and Platys Gialos are also good areas to look for accommodation.
  • Sifnos is small – the one circle road around the island is 37 miles. You can easily take a trip around the island in a day stopping off for lunch and exploring the many little villages.

Greece island hopping itinerary

“Sifnos: One of the dots in the ocean that can be hardly detected on the map. However, if you visit it, you will feel that there is no other place on Earth like this “- National Geographic


Our next stop in our Greek island hopping itinerary was Santorini. Known for its exquisite panoramas, multi-coloured cliffs, romantic sunsets and volcanic-sand beaches, Santorini is like a painting come to life. This is one of the few places that I have been to that is truly more magical and more beautiful than any postcard or photo I have ever seen. This is the heart of Greece!

Greek island hopping itinerary

Where to stay

We stayed at a lovely little hotel, just minutes’ walk from the amazing caldera views in a quiet and relaxing location but close enough to the centre of all the action in Fira; Loizos stylish residences.

Greek island hopping itinerary

Filled with all kind of shops, cafes, bars and night clubs, Fira is the capital and the most cosmopolitan settlement of Santorini. If you want to experience natural beauty, amazing views, lively nightlife and feel the liveliness of the island then Fira is the place to stay. If you want more info on hotels, you can check out this great guide from It’s all bee for the best hotels in Santorini.

What to do

1. When in Santorini we would highly recommend taking the boat tour out to the Volcano. Here you will have the chance to explore it, see its crater, touch the lava rocks and feel the steaming volcano underneath your feet. You will also get the chance to swim in the hot springs, known in Greece for their beneficial and therapeutic effects. The boat tours depart either from the port of Athinios or from the old port in Fira and while there are a variety of tour packages available we chose the short excursion which cost us only 20 EUR each.

2. We added the cable car to our Greek island hopping itinerary. The Fira cable car is a popular attraction in Greece probably because most people do not want to have to trek the 588 stairs between the Old port and Fira. We opted to walk down the spiralling path to reach the port for our boat trip and we used the cable car to get back up. If you are walking up the steps be prepared as it is quite a hike. The cable car option is a very quick trip up and the views are amazing. It costs 6 EUR each way. There is sadly also an option to ride a donkey for 5 EUR, either up or down the pathway. There has been much concern about the treatment of the donkeys and mules used as a taxi service up and down the steps.


3. We also made sure to visit the famous black beach and red beach of Santorini. The red beach is the most famous among tourists and you will need to climb a small hill, and walk a seaside path along the mountain to reach it. Truthfully, we were not all that impressed with the red beach, probably because I may be a little naive and was expecting soft red sand. In reality you will find a unique landscape of red and black volcanic rocks, red tainted pebbles and course sand. However it’s still a must see when in Santorini. The black beaches would be better for a ‘beach day’ as they are filled with lots of places to eat and drink, beach bars, umbrella’s and lounges.

4. It goes without saying that when in Santorini the number one attraction on your agenda is to embrace a magnificent sunset. We made sure to catch the sunset every evening. Fira and Oia are both great places to watch the sunset. Although I don’t think there is a bad sunset view in Santorini. Our advice is to get to one of the many cliff-clinging bars and restaurants along the cliff edge in Fira early enough to ensure yourselves a seat and perfect view. You can enjoy a few sundowners while staring in awe at one of the most beautiful sunsets you will ever see. Santorini will not disappoint!

There is another great guide published on From East to West with RMS, with so many ideas of things to do in Santorini.



  • Santorini legs are a real thing. We walked so much in Santorini we were physically sore, the hills and slopes of the island don’t help. It is however a great way to work off the delicious Greek food that you won’t be able to get enough of.
  • Where to stay: Fira, Oia, Imerovigli, and Firostafani that are located along the caldera cliff are the best locations when looking for accommodation. Fira is the capital and has stunning views of the caldera. Firostefani is a short 10 minute walk from Fira. If you want to be close to the action of Fira but don’t want the crowds then Firostefani is great. Oia is the most romantic town and is famous for its fabulous sunset views. Imerovigli is Santorini’s quietest town and is a 20-30 minute walk from Fira.
  • There is an airport in Santorini which has year-round flight connections with Athens and summertime European connections. Alternatively you can fly into Athens and take the Ferry from Pireus port
  • It’s not necessary to hire a car as the bus service works well. Santorini is small and getting from one town or beach to the next is quick and easy so you don’t have to feel limited by the place you pick. (It’s less than 30 minutes from Fira to the beaches by bus or taxi and 20 minutes longer from Oia to the beaches).
  • Santorini is not known for its beaches. As we quickly discovered Santorini beaches are composed of volcanic sand and pebbles. Very unique and beautiful to look at but they’re not the idyllic golden sand beaches that are found elsewhere in Greece.


Greek island hopping itinerary

Mykonos, famous for its summertime party scene and beautiful beaches it’s one of the most popular islands of the Mediterranean. We had to include her in our Greek island hopping itinerary. It’s all about the energy and attracts many celebrities from P Diddy to Bon Jovi. But it’s not just about the nightlife as many people may think. Mykonos is perfect for walks along the narrow streets of Chora, watching the sunset from Little Venice, staying in luxurious hotels and swimming at exotic beaches.

Where to stay

We stayed at Damianos Hotel which is situated only 500 metres from the centre of the island and a 14 minute walk from the famous Mykonos windmills. This is without a doubt the best and most warm hospitality that we have ever received. We cannot recommend this hotel enough. This is a family run business where Thanos (the owner) and his mother attend to each guest with the utmost care and make you feel as though you are part of the family. The location is amazing, the hotel is beautiful, spacious and clean, there’s a pool and a great view. The price to quality ratio is excellent!

What to do

1. ATV’s are a great way to get around Mykonos. We had so much fun exploring the island on ATV’s, making our way from the centre town to super paradise beach to paradise beach and stopping off at many local spots along the way. However be sensible as they are very dangerous! The Mykonos roads are narrow and windy and ATV accidents occur almost daily during the peak season. We used them during our day activities but opted for a taxi service for the late night party scene. You know what they say – rather be safe than sorry!


2. Have a sundowner in Little Venice. Alefkántra better known as “Little Venice” is a maze of tiny streets. It offers a myriad of bars and restaurants for you to choose from for the best sunset setting in Mykonos. From the harbour area it rises up towards the windmills. It’s perfect during the evening just before the sun goes down. It is however quite overpriced and you can find lovely dinner spots a bit further into town for a much better price.


3. Party at Paradise beach: There is something so exhilarating about beach clubs! Sipping on cocktails with salt in the air, the sea breeze blowing through your hair, sand in your toes and good music! Who doesn’t love a beach party? In Mykonos the beach clubs turn into night clubs and the party never stops! The paradise beach experience is incredible!


  • Where to stay: If you want to be close to the centre of the island you should definitely stay at Damianos hotel! However if you are looking for a beach area Platis Gialos and Ornos are good choices. They have a great selection of restaurants and shops meaning that you wouldn’t have to travel too far. Elia, Kalafatis and Kalo Livadi are also beach area’s but they are a bit far out from Town. As a result they have very limited night-time dining.
  • As with Santorini there is also an airport in Mykonos meaning you have the option to take a flight. Alternatively you can use the boat. Research your options depending on your departure and destination point. We used the ferry from Santorini to Mykonos but it was quite a bit cheaper to take a flight from Mykonos to Athens when departing.
  • Transport: Many hotels offer a taxi service to get you between the port/airport and hotel. However if not it is advisable to pre-book a taxi especially during peak season
  • Mykonos is known to be quite expensive. However if you look around you will find places that are a lot more budget friendly.


The heart of ancient Greece and the capital of one of the most iconic destinations in the world. Athens is a cultural playground buzzing with a combination of history and the new modern era. We only spent 2 nights in Athens but it was enough to experience the heart of this ancient city!

What to do

1. The Acropolis: This is one of the historical sites that you cannot miss when in Greece! It’s truly awe-inspiring to see what man created with no technology. As a bonus there is a stunning view of Athens from the top! Tickets will cost you 20 EUR and it’s open daily from 08:00 – 19:30pm. It’s advisable to go either early morning or late afternoon during summer. It can be quite unpleasant and affect visibility during the heat of the day


2. The Acropolis museum: We weren’t impressed but it costs only 5 EUR and many people love it. So if you have some time before the Acropolis you should check it out for yourself.

3. The Plaka: This area is the oldest section of Athens and an area surrounded with cobblestone streets, restaurants, Jewellery stores, tourist shops, and cafes. Situated under the slopes of the Acropolis, Plaka is one of the most attractive districts of Athens. It’s a beautiful area and offers an abundance of restaurants to dine at or bars to catch a drink at.


  • The food in Athens was beyond AMAZING! It was the better than any of the Greek food we had at the Greek isands. It was also so much cheaper.
  • Great news: Athens is cheap! Especially compared to the more touristy islands. So if you want to purchase any gifts, momentous or go on a shopping spree then do it in Athens!
  • Two nights in Athens was more than enough time to explore the main attractions. But we hear that the coastal side of the city is beautiful. If time is on your side check out the less touristy side of Athens too.

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This is a great primer for what can seem like an overwhelming number of island and possibilities! Hopefully I can return and see some more for myself.


Greece is on top of my bucket list and i really found your blog very useful and informative. Thanks so much for sharing. I never knew about Sifnos so now i can add it to my list too


Beautiful pictures. Very nicely described.