14 Days Island Hopping in Greece
We had recently sold our home and quit our jobs to focus on traveling for a few months. We had just went to Iceland the month prior, and had no idea where to go next. While researching, we stumbled on some photos of Greece’s idyllic white-washed buildings and turquoise beaches. Iceland is one of the most expensive places in the world to travel, and although it was the most amazing place we had visited thus far, we were looking for something a bit more affordable. It was also October, and we were surprised to find out that it Greece was still sunny and warm. We did not have a lot of time to research anything, as we planned on going just a few weeks after we booked our flights. We had no idea what islands we would be visiting or where we would be staying. We figured this all out each day depending on the weather, the attractions each island had to offer, and how easily we could get around each island without having a vehicle (we had an issue getting an international driver’s license). Our extensive research of Athens and the islands led us to this 14 day itinerary of Greece.
Read Next: How to Visit Greece on a Budget
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Day 1
Athens
We arrived in Athens after a very long flight from the midwest, and immediately made our way to the Verifone kiosk in the airport to get our SIM cards (we made the mistake of using our cell phone international plans in Iceland). Although I am sure the SIM cards cost more at the airport, our plans lasted us the entire duration of our trip and we had pretty good reception everywhere we went. Our second task was finding a taxi to take us to the hotel. They charge flat rates to get you from the airport to downtown Athens or to the port to hop on a ferry, and this was posted outside near the taxi line. I had read that most tourists do not rent a car in Athens and instead walk, taxi, or take the bus. Ride share was not an option in Greece when we visited. Once we got into the cab and started zipping our way in and out of the traffic, we were really glad that we were not driving in mainland Greece. Our taxi dropped us off at our hotel, DAVE Red Athens, and we found that our room had been upgraded to one with a balcony.
After settling into our room, we checked out the tropical themed bar and the rooftop, before making our way to the historic sites. It was a 15 minute walk to the first site, Hadrian’s Library. You can purchase a ticket at any of the historical sites, or online. You can purchase a pass for a single site or one that includes entry into all of the ruins, including the Parthenon. Our next stop was the Temple of Olympian Zeus, which is currently under restoration.
After a short 5 minute walk, we arrived at Acropolis hill, where you can walk around to see many more historical sites including the Theatre of Dionysus, the Theatre of Herodes of Atticus, and the Parthenon. You will also be rewarded with amazing views of Athens from the top.
Before sunset we found a traditional Greek restaurant where we had dinner in the charming neighborhood of Plaka. We ended our evening by seeking out some nightlife downtown, and found the Juan Rodriguez Bar near our hotel. We absolutely loved this place for its amazing cocktails, ambiance, and music. We stayed for a couple of the best cocktails we have ever had before calling it a night.
Day 2
Athens
The next morning we woke up to it pouring outside. We ran out of the hotel in our rain coats and found a coffee shop nearby to hide out for as long as could. Coffee is a bit different in Greece than we are used to. The coffee shops mainly consisted of espresso and Freddo Cappuccinos, which are unique to Greece. This is an iced espresso beverage with frothed milk. This was also my first time trying a spinach pie (made of phyllo dough and stuffed with cooked spinach). Many cafes in Greece carried these, and they were often vegan friendly. It was forecasted to rain all day, so we had planned to visit the Acropolis Museum. You can purchase your ticket at the museum, but we ended up standing in a long line in the rain. Instead, I would recommend booking online. We spent around two hours in the museum which has several indoor levels and an outdoor exhibit underneath the museum, where the original village of Athens had been built.
We stopped for dinner nearby at Veganaki, a restaurant serving traditional Greek food that is vegan friendly. We had a wonderful meal of plant-based feta and pita, moussaka, and dessert. This is where we also tried the Greek alcohol Raki, which is made of fermented grapes. It is about 40% alcohol and best sipped over ice (and shared). It was still raining by the time we left to go back to our hotel, and the streets were flooding. We entered our hotel completely soaked (we forgot to bring an umbrella), and fell asleep around 8PM, due to the jet lag.
Day 3
Milos
We woke up super late the next day and it was still raining outside. We got a cab to the port in order to catch the next ferry to the island of Milos. We had decided on Milos because we wanted an island that was between mainland Greece and the island of Santorini, where we also planned on visiting. Another good choice would be the very popular island of Mykonos. It was a hard choice for us between these two islands, but we ultimately decided on Milos because of the unique coastline and the beaches. You can book your ferry online or in person in Greece (we found out that the rates are cheaper online) and you can choose between a slower ferry or pay extra for a speedier ferry, ran by SeaJets. We opted for this every time in Greece, as it shaves hours off of your trip and we found it well worth it, especially when the sea is rough. Due to the stormy weather Greece was having at the time, we encountered a turbulent voyage to Milos, and many seasick passengers. I am very prone to motion sickness myself, so I sat down, closed by eyes, and tried my best to sleep. If you are susceptible to seasickness, I would recommend taking some sort of medication before you board, as most of the ferry rides were at least two hours long. Because the ocean is unpredictable, the ferry rides can last longer than expected; by the time we arrived to Milos, it was dark. We had never been so relieved to be back on solid ground. Our wonderful hotel host was waiting for us with her vehicle and gave us a complimentary ride to our hotel. We arrived to one of the most beautiful hotels we had ever stayed at, with views of the sea, and a very friendly cat. We had purposely chose a hotel close to Sarakiniko Beach, one of the most unique looking beaches on the island, and close to the town of Adamas (the port town), and Plaka. After getting settled in our room, we set off down the road to the only nearby restaurant, an authentic Greek tavern just up the road.
Day 4
Milos
Our first morning in Milos was cloudy, but warm, and free of rain. We made our way on foot down to the beach (it was an eight minute walk from our hotel). Sarakiniko Beach was absolutely beautiful and this morning we practically had the place to ourselves. We explored the rock formations leading to the turquoise waters and wandered in the abandoned mining tunnels. Because it was only 70 degrees and cloudy, I felt it was a bit too cold to take a swim, so we instead we wandered to the nearby town of Plaka for the day.
It is about a half hour walk from the beach to Plaka and the road is not really friendly for walking, so it is best if you rent a vehicle of take a bus. Our hotel host told us that they had just stopped the buses for the season. Even so, when it is running, it only has stops in the most populated part of the island. Milos is an island where you would want to rent a vehicle (most people rent ATVs here). Unfortunately, because we had issues getting an international driver’s license (it is required in Greece), we were not able to get to the other part of the island, without spending a fortune on a taxi. Another option in Milos is renting a boat to travel around the entire island. On our way to Plaka, we stopped at the nearby grocery store to pick up some snacks for later. We found a traditional Greek restaurant where we had fava beans with bread, gemista, and drinks.
We had been told that Plaka is the best to place to go for sunset in Milos. Plaka is a very charming Greek town that really encapsulated everything we expected from Greece (white washed buildings, beautiful shops and alleys, and views of the sea).
The most famous sunset spot in Plaka is at Kastro, the Venetian Castle. There are signs in town that point to the walkway that leads up to the ruins of the castle and a Greek church. It is an easy hike and we had a beautiful view of the coast, the nearby village Chora, and a beach. We still had a couple of hours before sunset, so we decided to go back and explore the rest of the town. Many of the shops were closed for the season, but we did find a bakery, where I had the best watermelon sorbet. Gelato and sorbet is very popular in Greece, and we found it everywhere we went. The sorbet is much more gelato like than the sorbet I’ve had in the United States, and I had it almost every evening, trying all of the flavors.
We still had plenty of time before sunset, so we walked back to Sarakiniko Beach, and arrived just in time. Although we only encountered a handful of people that morning at the beach, it was now pretty busy. After sunset we spent time in our hotel, booking our ferry for the next day. If you rent a vehicle, you could easily spend another day in Milos, exploring the other side of the island.
Day 5
Santorini
We found an early ferry to Santorini the next morning. The ferries run at less frequent times during the shoulder season, and depending on the island you are leaving and the island that you are planning to visit, there may not be a ferry going out more than once a day. SeaJets also have a different schedule than the slower ferries, and we had to take this into account each time we booked. It was a pretty short ferry ride to Santorini from Milos, and we arrived with plenty of time in the day before sunset. Santorini is a very popular island, and we were surprised by just how many people were visiting, compared to Milos. Santorini has a pretty good bus system, so you could easily take the bus from the port to Oia or Fira (the most popular cities). Because we did not know the bus schedules, we had already arranged transportation from the port to our hotel in Oia. Many of the hotels will offer this for a fee (it was not cheap). We arrived in the city of Oia at our beautiful hotel, The Museum Project Oia, located off of the main walkway near all of the shops, restaurants, and the famous sunset spot.
After checking into our hotel, we spent the evening walking around the main pathway before finding a restaurant overlooking the caldera. Most of the restaurants in Oia are traditional Greek or seafood restaurants. We made it out of the restaurant in time to start our way toward the sunset point at Oia Castle. Everyone knows to go here so it was packed by the time we arrived, and there was nowhere to stand at the castle. People get here very early to claim their spot for sunset. We found a place to get a few photos nearby, and then went back to our hotel for a quick nap (the jet lag was still getting to me). We woke up around midnight and set out to check out the nightlife in Oia. It was eerily quiet as we stepped out of our room and onto the main walkway. We had read that there is not much nightlife in Oia, and most people go to Fira if they are looking for night clubs or bars. We found one bar open, but it was packed, so we spent the evening walking through the city and going to the castle at night for stunning view. It was actually one of the most memorable nights we had in Greece, as Oia is loud and busy during the day.
Day 6
Santorini
We woke up the next day to do the very popular hike from Oia to Fira. Most people walk from Fira to Oia as more people are staying in Fira (it is the capital) and it is more downhill to hike in that direction. I recommend doing this hike early in the day, for the best lighting and before it becomes too crowded. You will be rewarded with beautiful views of the caldera on this hike. You will also hike through the town of Imerovigli (about halfway through) and pass a stand along the way that sells fresh squeezed orange juice, which was wonderful to quench our thirst during the hike. The hike from Oia to Fira is around 6 miles long and takes anywhere from 2-3 hours, depending on how often you stop for the views.
Fira was much busier than Oia, being the capital of Santorini, and is full of restaurants and shops. There is a large bus depot in Fira with buses going to all of the most popular destinations on the island. The bus schedule is posted at the booth and you pay for your ticket as you board the bus. Each destination has a different cost, and it is cash only. We really liked taking the bus in Santorini as it was very affordable and easiy to navigate. We decided to go to the Red Beach (Kokkini), due to its unique color. Once we arrived at the bus stop, it was about a 10 minute walk to the beach, where you can purchase alcohol or smoothies from a canteen to sip while relaxing on the beach. It was difficult to lay on this beach, as most of it was covered in a type of mulch. Although it did make for striking scenery, this was not our favorite beach in Greece, due to the popularity of the beach and lack of sand. This was also the bus stop for the archeological site of Akrotiri, which is a short walk in the opposite direction of the beach. The water was pretty cold here in October, but we swam for a bit before boarding the next bus to Fira, and then from there a bus to Oia. We walked around until we found a traditional Greek restaurant with live music while we ate.
Day 7
Santorini
On our last full day in Santorini, we decided to spend it with views of the caldera, relaxing in the sun. It is cheaper to book a cliff hotel with views of the caldera in Fira than it is in Oia. Another option would be staying in the town between Oia and Fira, Imerovigli (although there is not a bus stop there). We took the bus from Oia to Fira and arrived before check-in, so we decided to get lunch. I found a delightful vegetarian/vegan friendly restaurant, Falafeland, and had a delicious volcano falafel wrap. After lunch we made our way back to our hotel and checked into our cave room with a balcony overlooking the caldera. We spent the rest of the day sipping drinks and sunbathing while watching the sunset. That evening we walked around the town of Fira, tracking down more sorbet.
Day 8
Santorini - Crete
We had decided to spend the most time in Crete, as it is the largest island in Greece. We booked a ferry for that afternoon, as the only other option was 6AM. Another option is flying to Crete as it will save time and you can fly directly to the airport in Chania (a city in Crete). The downside is that is does cost a bit more, especially if you are checking bags. There is not a direct ferry from Santorini to Chania (where we wanted to go). Instead, we had to ferry into the town of Agios Nikolaos, which was the closest option we could find. Our ferry arrived there pretty late in the evening, and it was too late to catch the bus, so we stayed in town for the evening. We found a hotel just a few blocks from the port. Our hotel host was extremely kind and helpful, giving us a list of popular destinations and restaurants in the area. Being a port town, most of the restaurants are seafood based. We ended up going to a delightful little pizza shop for pizza and beer for dinner. On the walk back to our hotel room, we saw a rooftop bar, so we stopped on by to have a cocktail with views of the city.
Day 9
Crete - Chania
We had to wake up very early the next morning to catch the bus to Chania. Instead of going straight to Chania, you can opt to stop at Crete’s capital, Heraklion, where you can tour the Minoan Palace of Knossos. It was about a five hour bus ride to Chania. The bus system is wonderful on Crete, which we were so grateful for, since we did not rent a car. We chose to stay in the middle of the city at Central City Hotel, and were only a few minutes from the central bus station. We absolutely loved our room, the location, and the hospitality we experienced at this hotel. Were were able to check into our hotel room as soon as we arrived and, after settling in, we went to get lunch. I ended up at Falavela, the most delightful vegan friendly falafel restaurant. We were both blown away by the falafel here, and I continued to come back during our stay in Chania.
The coast is only a 15 minute walk from where we were staying, and after lunch, we decided to walk the coast all of the way to Agii Apostoli beach for sunset. The water was surprisingly warm for October and many people were swimming. On our way back to our hotel, we stopped at a grocery store for some fresh fruit and snacks for the week.
Day 10
Crete - Elafonissi Beach
After checking out the bus schedules online, we decided to take the bus the next morning to Elafonissi Beach, a popular beach in Greece, known for its pink sand. I’m not sure about the rest of the year, but during October the bus only goes out in the morning and then picks you back up in the afternoon. Of course if you rent a vehicle, you will not have to worry about this. The beach has two cantinas for drinks and snacks, and you can rent beach chairs and umbrellas. It was really windy the day we arrived and we were told by a local that the weather is unpredictable here this time of year. Although we did not swim, the water was shallow and warm enough to wade in. The bus picked us up back up at 4PM and it was a 2 hour ride back to Chania. For dinner that evening, I tried the vegan restaurant, Pulse Vegan, and ordered a giant mezze platter with samplings from the menu. It was easily large enough for two. Pulse Vegan is located in the Old Town district in Chania, which is an adorable little area to walk around in and have a drink.
Day 11
Crete - Balos Beach
The next day we went to Balos Beach near Kissamos. This beach is the most popular beach in Crete, and was probably our favorite single destination of the trip. There are a few ways to get here. One of the most popular ways for tourists to visit is by booking an excursion by boat from Kissamos, which also stops at Gramvousa island. Another option is to drive yourself, but we read that the road is pretty rough and a 4WD is recommended. However, we saw many 2WD vehicles on the road, they were just going much slower. Since we did not have a vehicle, we opted for a 4WD bus excursion instead, that only went to Balos Beach. We chose this option, as we did not really care to go to Gramvousa island (people visit this island mainly to see the ruins of the Gramvousa fortress), and we wanted to have more time at the beach. The boat excursion splits the time between the island and beach, and left earlier than we wanted. We took the bus from Chania to Kissamos and arrived in time to get a cup of coffee before starting the excursion. We did not purchase a return bus ticket, as we were not sure exactly when we would arrive back to Kissamos. We arrived at Balos fairly early, before it got too crowed from the ships, and stopped by the cantina for a drink before choosing a spot on the beach. Most of Balos is very shallow and you can sunbathe in the shallow waters without being completely submerged. We had five hours at the beach (we wished we could have stayed for sunset), before we had to walk up the hill to our bus. This 20 minute uphill hike is one of reasons a lot of people prefer the boat excursion, rather than driving to Balos. After arriving back to Kissamos we ran to the bus stop, and purchased a bus ticket about 10 minutes before our bus left back to Chania. We arrived back in time for dinner at Laganon Fresh Pasta, a restaurant our hotel concierge recommended, and went to bed early. We had an excursion booked for the next day, and our pickup time was 6:15AM.
Day 12
Crete - Samaria Gorge
The next day we woke up while it was still pitch dark to board the bus to Samaria Gorge in Crete. The bus picked us a block away, and we were the last stop before we made our way to the gorge. We decided on the excursion because most people hike one way through the gorge and then ferry out from the other side. If you decide to tackle this on your own, you will need to figure out bus schedules and ferry schedules. Samaria Gorge is in a national park, and we got there just as the gates opened for the day. It was nice being the first group inside, and we were able to see the sun come up as we hiked down the gorge. The ferry did not go out until several hours later, so we had plenty of time to make the hike down which is pretty steep at first, going through a forest with views of the mountains, and then eventually through some the ruins of Somalia village and then through the gorge at the end. The 8.9 mile path had mile markers along the way, and it was pretty easy to find the path the entire time. We arrived in Agia Roumeli village in about 4 hours time, with several hours to kill before the ferry left. We stopped for beer (which was wonderful after the hike) at a tavern and then at a restaurant overlooking the sea for lunch. There are several little restaurants here to get something to eat and drink while you wait. We went to the beach to relax in the sun and I ended up taking a nap. We boarded the ferry around 5PM and from there ferried back to Sougia, where our bus was waiting for us. Our guide continuously told us that our bus driver was one of the best around and we were in good hands. We didn’t think much of it until we started driving through the mountains at horrifying speeds on cliffs overlooking deadly drop offs. I quickly closed my eyes and tried to sleep, so I did not have to see us careening toward our deaths. It was about 1.5 hours from there back to Chania, so it was quite late when we arrived at our hotel. We found a Greek fast food spot to get a quick dinner, before going back to our hotel room for the night.
Day 13
Crete - Chania
We had two days left in Greece, so we decided to spend some time around the city. If you want to spend less time in Crete and see an additional island instead, you could choose to add another island near Santorini or Milos (perhaps adding in Mykonos), but it makes for lots of traveling in a two week span. We were pretty sick of ferrying and taking buses by the time we were ready to leave Greece. Also, the only ferry leaving Chania is back to Athens. We spent our 13th day in Greece wandering through the various neighborhoods of Chania (we really enjoyed Old Town and Kastelli). We started off the day with a pour over coffee at a cafe and then made our way to the nearby hospital to get our Covid test, as this was required to fly back to the United States. It was really affordable (only 10 euros), and we were in and out; the results were emailed to us by the next day.
We spent some time at the Venetian Harbor, which is full of touristy shops and restaurants that look out at the lighthouse. It was windy that evening and the waves were coming up over the sidewalks and soaking everyone as they walked. We visited some of the shops where you can buy anything from handmade ceramics, to fine art and jewelry, to bowls and utensils made from olive trees. We ended our evening in Old Town at a traditional Greek restaurant with live music.
Day 14
Chania - Stravos to Monastery Katholiko
For our final day in Greece, we found a nearby hike that started from the town of Stravos and ended at the ruins of Monastery Katholiko, dating back to the 1600s. I could not find a bus that went anywhere near there, but did find one that went to Stravos. If you have a vehicle, I would just suggest parking at the nearby monastery, Gouverneto Monastery, and walking from there (a much shorter hike) to Monastery Katholiko. It was a two hour hike from the town of Stravos, but it was worth it once we arrived, as the ruins were beautiful. If you continue straight down the path, you will reach Katholiko Beach. Because it was already getting dark, we hiked uphill instead to view the ruins. We explored the two caves here as well. The cave of St. John the Hermit is very deep and has a rope that leads you all the way back. It gets very dark and if you do not have a flashlight, it could be quite dangerous. I recommend brining a headlamp if you have one. We went almost to the end of the cave but stopped as bats started flying at our heads, and that was enough for me. Once we exited the cave we continued uphill toward Gouverneto Monastery, where we encountered more ruins and another cave. Once we reached Gouverneto Monastery, it was dark outside. Just be aware that this is an active monastery that has rules regarding dress (shorts are not allowed), noise, and swimming at the beach. In order to get back (without walking in the dark), we had to call a cab. We were picked up in 10 minutes and were dropped off at the airport, where we took a bus back to the city center. We had a quick meal before heading back to our hotel to pack for our trip back to Athens the next morning.
Day 15
Chania - Athens
There are two options to get back to Athens from Crete, flying or ferrying. It is a long distance between the two, so the ferry ride is long and overnight. Ferrying is the more affordable option, saves money on another night at a hotel, and prevents you from having to wake up early the next day to catch a flight. Because we already had the hotel booked for the night, we ended up flying. We were able to catch an early bus to the airport, arriving with plenty of time before our flight. You do not need to arrive to this airport very early, it is small and was pretty vacant this early in the morning. Our flight went smoothly and we arrived at the Athens airport, just in time to get our luggage and check in for our flight home.