Greece is easily one of the top travel destinations in the world, and we definitely saw why during our 16 day journey through the mainland and two islands. Planning for Greece can be very overwhelming as there are so many islands to choose from. Do you go with the most famous islands like Santorini and Mykonos, or do you go for something a little more relaxing?
For us, we decided to balance the islands with a few days exploring the beautiful mainland. Our trip took us from the birthplace of democracy to monasteries in the sky, from the edge of an ancient volcano to the longest gorge in Europe. It was simply magical!
The trip we took was not necessarily the trip we planned, which is why we ended up spending so much time in Santorini. We loved it, but if we had more time to plan we would have seen another island or two. But what can you do when plans change due to closed borders!
Regardless, we hope this itinerary will help give you ideas for what to do in this magical country!
Table of Contents
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Day 1 – Athens
On our first day in Greece we landed in Athens around 10:30am. Getting through security was very smooth and easy, and before long we were looking for our rental car company – Lotus. We had booked a rental car through them because it was cheap and seemed like it was a great deal.
It was a very strange rental experience and we don’t recommend going through this company. Immediately we understood why it was so cheap. Lotus was not located at the airport and we needed to contact someone to shuttle us over which was surprisingly difficult. The cars they had available were old, sketchy, and were certainly not what we had reserved online. The gas tank was nearly empty as well. All in all it was just a very weird experience and we would recommend going with a different company.
From the airport we drove into downtown Athens to our hotel, the B4B Athens Signature Hotel. We would highly recommend this hotel. It was in a great location, walkable to the Acropolis and downtown while still being very clean. The views of the Parthenon from the rooftop restaurant really set it apart. The breakfast and hotel staff were also fantastic!
One thing to note about Athens – petty theft is a significant problem. If you rent a car (like we did) do not leave anything valuable in the car, even if you lock it. We had read that in advance, but our hotel front desk reminded us when we checked in as well.
After checking in to the hotel we made our way to the world famous Acropolis. We booked a skip the line pass which is 100% worth it. We visited in 2021 before tourism really recovered, and even then the skip the line ticket made a big difference. This particular one also included access to other archeological sites across Athens which made it an even better deal!
The structures on the Acropolis are perhaps the most famous ancient ruins in the world. Built mostly in the 5th Century BC as tributes to the ancient Greek gods, these buildings are a living testament to this incredible culture. The most famous ruin, the Parthenon, was absolutely incredible. How it has survived nearly 2500 years is amazing in itself.
We spent a couple of hours exploring the Acropolis including the aforementioned Parthenon, the Propylaea (monumental gateway), and the Temple of Athena. This was our first time seeing ancient ruins and they surpassed our expectations. The single best thing to do in Athens is exploring the Acropolis, so be sure to give yourself enough time up there!
After we left the Acropolis we made our way to some of the other sites included in the skip the line pass, including the Roman Agora, Ancient Agora, and Aristotle’s Museum. While these were also really cool to see, we didn’t really enjoy walking around the streets of Athens. It felt, not necessarily unsafe, but not super welcoming. We were glad we only had a day in Athens before heading out to enjoy the rest of the country.
By this point the jet lag had really caught up with us and we were ready for dinner and an early night at the hotel. We ate at our hotel’s restaurant which featured good food and had an incredible unobstructed view of the Acropolis!
Day 2 – Meteora
We began the morning with breakfast at our hotel before beginning our drive to Meteora, 3.5 hours north of Athens. Meteora is a spectacular region of Greece featuring beautiful monasteries precariously perched on the tops of cliffs.
Once we arrived in Meteora we checked into the Hotel Doupiani House, an incredible property with gorgeous views of the Meteora mountains. We really enjoyed the garden with great views and would recommend it for anyone wanting to visit the area.
After checking in we hiked to The Great Meteoran and the Varlaam Monasteries. Both of these monasteries have fantastic elevated views of the valley below. The hike isn’t overly strenuous, but if you prefer you can also drive to the top. The hike is, unfortunately, along the road for much of the hike which did take away from the experience a bit. To actually visit each monastery you must pay generally 5 euros (costs seem to have gone up since we visited in 2021) and it is cash only. There is also a strict clothing policy so be sure to have your knees and shoulders covered or they won’t let you in.
After our hike we ventured into town for dinner. We stumbled upon Restaurant Meteora where we had delicious lamb skewers and veal meatballs. The portions were very large and the food was great! We walked through town and ordered some local pastries before quickly making our way to Sunset Point to watch, as the name suggests, the sun set over this beautiful landscape.
Day 3 – Meteora and Delphi
We woke up and had breakfast at our hotel (with a lovely view) before driving to visit two of the remaining monasteries we hadn’t seen yet – Roussanou and Holy Trinity. We loved the Holy Trinity Monastery and would highly recommend it. However, we didn’t think Roussanou was worth it. It is very small and, at least in our experience, it was run the the nuns who are not the friendliest. We think you might as well save your money on this one and either visit one of the others are enjoy the surroundings of Meteora.
After exploring these last two monasteries we began our drive to Delphi. The drive took about 2.5 hour and, while not overly difficult, it was not a super smooth drive. The wind rages through the mountains and the road meanders around hills. We recommend having a very good rental car – which we did not unfortunately!
We explored the Ancient Ruins of Delphi, which was the spiritual and cultural center of Greece more than 2500 years ago. Most famous for the Oracle of Delphi – where ancient priestesses would predict prophecy for kings and commoners – there are many other ruins as well including the Temple of Apollo, a theater, a stadium, and more. We spent a few hours exploring and would definitely recommend it, but just know it is out of the way so determining if it’s worth a visit depends on how much time you have in Greece!
For dinner we grabbed a bite at one of the local restaurants that had a nice view over the valley. After dinner we had to drive back to Athens for our early morning flight to Santorini. We did not feel like we had enough time in Delphi due to all the driving we did this day, so we’d recommend planning that out better so you won’t feel as rushed.
Day 4 – Santorini
We began the day with an early morning flight from Athens to Santorini, one of the iconic Greek islands. It’s just a short 45 minute from the mainland to this paradise in the Aegean.
Upon landing we picked up our rental car from Hertz – it was a very smooth and easy process. We were able to pick it up right outside the airport and we were given a nice, new Kia Stonic which we really enjoyed. The price also wasn’t too bad!
After going to Santorini, however, we don’t know if a car is necessarily worth it We enjoyed the freedom of having it but if you want to save the money you definitely do not have to rent a car. Parking is very limited on the island, even when we were there in 2021 before tourism returned. You can also rent an ATV instead of a car which might be a bit easier to park and they’ll even drop it off at your hotel!
If you choose not to rent a car you will definitely want to stay in either Fira or Oia as those towns contain most of the amazing views, restaurants, and shops are! These two main towns are about 15 minutes apart and there is a cheap bus that runs between them regularly. Unfortunately, the incredible wineries are on the other side of the island but you can sign up for a winery tour (like we did)!
We highly, highly recommend making dinner reservations as far out as possible. We’ll note the restaurants we ate at (each of which we loved), but making reservations is super important during the busy times (and Santorini is always busy!). Also, we learned that the best seats are given to guests who booked the furthest out. If you want that perfect sunset view in Amoudi Bay make sure to book several months in advance!
After picking up our car we made our way to Athermis Suites in Megalochari, a wonderful, luxurious hotel with an amazing view. Breakfast was included each day and was simply incredible. We were able to choose several different dishes to eat and enjoyed a great view of the caldera. The hotel is very private and quiet!
We really enjoyed how nice this hotel was and it had tons of great amenities, however we’d actually recommend staying in either Fira or Oia due to the central location of both of those towns. We did have a room with a private pool, but we would say not to spend the money on it because the pool water was very cold! We ended up not using the pool very much and most hotels have their own anyway, so we didn’t find it necessary.
After getting settled in at our hotel we drove to Oia for lunch. We settled on Apsithia which was a fantastic choice! The food here was delicious and the views were incredible (though that’s probably true for nearly every restaurant in Santorini!).
After exploring Oia for a bit we made our way back to our hotel for our wine tasting tour around Santorini! We did a bunch of research before deciding on this tour as we really wanted to end up at Santo Winery for sunset. Plus, this tour had some of the highest ratings we’ve seen. We absolutely loved this tour and would highly recommend it!
This tour picked us up directly at our hotel which made it very easy to visit the wonderful wineries of Santorini. It began at 3:30 and took us to 3 different wineries – Anhydrous, Hatzidakis Wine Cave, and finally to Santo Winery for an incredible finish at sunset. We were treated to 12 different wines, some cheese, snacks, and local tapas. This was a truly wonderful wine tour and we highly recommend it to anyone visiting Santorini!
Each of the islands and regions of Greece specializes in different wines. Santorini specializes in the Assyrtiko varietal, a delicious and crisp white wine that was perfect to sip on with the views of the caldera. Santorini also has some of the oldest vines in Europe thanks to them withstanding the blight of the 19th Century which wiped out most of Europe’s vineyards. The wine was so good and we ended up buying multiple bottles to take home with us.
Day 5 – Hike from Fira to Oia; Athenian House
After starting with a wonderful breakfast at our hotel we drove to Fira to explore some of the shops before starting our hike to Oia. This is a very popular 6 mile one way hike that connects the two major towns of Santorini. The path begins in Fira before descending to the cliffside for several miles. The entire hike features incredible views and is not overly challenging, though the ~4 mile mark is fairly steep and uphill before descending down into Oia. Definitely make sure to wear sunscreen and a hat as there is no shade on the path!
On the hike we also added a quick detour to Skaros Rock, a unique rock formation just outside of Fira. We really enjoyed the hike and would recommend it as a thing to do while in Santorini. Walking around the shops of Fira and Oia were great bookends to the hike. After completing the hike and exploring Oia we took the bus back to Fira for our car before heading back to our hotel.
In the afternoon we swam in our private pool – just a reminder it was super, super cold! We aren’t sure if that’s the norm in Santorini, but in late summer we were very surprised that it was that cold.
For dinner we went to Athenian House in Imerovigli. This is a wonderful fine dining experience featuring stunning views of the caldera. It is pricey, but there are a few different set menus to choose from that are each delicious. Make sure to book your reservation as far in advance as possible in order to secure the best seats! We loved our dinner experience here and would definitely recommend it for a wonderful dinner in Santorini.
Day 6 – Catamaran Cruise
Our next day in Santorini began with another wonderful breakfast at our hotel before being picked up for our catamaran sail around the caldera! We were picked up from our hotel at 9:30 and were on the boat at 10. Despite being in the late summer it was still pretty chilly in the morning on the boat.
We stopped to swim a couple of different times and the water was wonderful! It is so clear and refreshing, especially as the day warms up. The scenery on the cruise is wonderful and drinks (wine and beer) are complimentary! We also were served an incredible lunch that we ate right on the catamaran. After about 5 hours of sailing we returned to the port and headed back to the hotel to relax for a bit before dinner.
For dinner we actually went to Pacman, a fantastic Asian Fusion restaurant that was actually recommended to us just two days prior on the wine tour. We absolutely loved it! It had amazing sushi and cocktails with a stunning view of sunset as well. The restaurant is pricey, but we highly recommend it and really enjoyed the cool vibe. Pacman is part of Adronis Hotel, a luxury upscale hotel that you should definitely check out!
Day 7 – Wineries and Amoudi
This was our original last day (more on that below) on Santorini and we intentionally left it free so that we could explore the island on our own. Because we had our car we were easily able to drive around to different wineries, but if you don’t rent one then we highly recommend renting a four-wheeler for the day – most companies will even drop it off at your hotel in the morning!
We visited three wineries, and while we had luck dropping in on the first one the others we made reservations for the day before. Santorini was not super busy when we were there because travel hadn’t recovered from Covid yet, but reservations for the popular wineries are recommended.
We first visited Gavalas Winery, a nice family run winery located in the village of Megalochori. You can visit this winery easily even without a car as it is just a 10 minute walk from the closest bus stop. After enjoying the wine here we made our way to Anyhdrous, a relatively new winery that opened just before we visited. It specializes in Assyrtiko, as do many of the other wineries of Santorini!
We ended our personal wine tour at Venetsanos, one of the two most popular wineries on the island (along with Santo). It was very beautiful and we really enjoyed it, but it was extremely windy! The view is fantastic. Many wine tours go here instead of Santo, but we personally preferred Santo a bit more. Either way this is a great winery to visit and we recommend making reservations!
For dinner we went to Ammoudi Fish Tavern at 7 (with reservations). It is located in Ammoudi Bay at the bottom of several hundred steps from Oia. There is also a back road that you can take if the steps seem like too much, but you’ll likely need to taxi as parking is extremely limited.
Ammoudi Fish Tavern had amazing seafood and was located right along the water. As with most other restaurants in Santorini, the best seats are reserved for those who book reservations far in advance or who are extremely nice to the host. The food was very good and it was a truly lovely experience. We ended up eating again in Ammoudi Bay later in our trip and we encourage everyone to have at least one meal in this beautiful area.
Day 8 – Crete
This morning we checked out of our hotel in Santorini before heading to Crete. We originally had planned to go to Crete and then head to North Macedonia for a few days, however Covid wrecked those plans during our trip! Unfortunately borders closed while we were in Greece and we had to change our plans. Instead, we last minute decided to return to Santorini because we loved it so much, but there are so many other islands to choose from that we know are great as well!
Our ferry wasn’t until the late afternoon, so we returned to Fira for lunch at Lucky’s, one of the highest recommended gyro shops on Santorini. It didn’t disappoint! Afterwards we explored Fira, taking in all the shops and getting an idea of things we might want to buy when we returned in a few days.
With a few more hours to spare before our ferry to Crete we went back to Santo Winery for a tasting because we loved it so much. It was just as good the second time and is worth a visit on your own as well!
Then we made our way down to the port for our ferry to Crete at 4pm. The ferry took a bit less than 2 hours and was a very easy and smooth experience. We took our car with us and easily drove onto the ferry as soon as it arrived, then got out and took our seats. Once we arrived in Heraklion we were able to drive right off and be on our way – overall very simple!
After arriving in Heraklion we immediately drove 2 hours to the lovely city of Chania, famous for its immaculate Venetian Harbor. In Chania we stayed at Nival Luxury Suites, a hotel we highly recommend with a perfect location in Old Town. Check in was a bit challenging as there is no front desk and parking is extremely limited, but we loved the hotel overall thanks to the walking distance to the Venetian Harbor.
It was fairly late by the time we arrived, so we walked around a bit before finding Faka for dinner. This was a very good restaurant located slightly outside the main tourist area. The food was delicious, it was quiet, and we would highly recommend it to anyone visiting. One quick note on food in Chania – no matter where you go, you must get mizithra cheese. It was probably the best cheese we’ve ever had and something Crete is known for!
Day 9 – Wine and Olive Oil Tour
Our first full day in Crete we set out on a tour of the countryside around Chania, specifically exploring the wonderful wine and olive oil culture of the island. The first farm we stopped at included the purported oldest olive tree in the world – the Olive Tree of Vouves – yes, it even has its own name! It’s impossible to tell exactly how old the tree is, but everyone agrees it is at least 2000 years old, with some estimates placing it at more than 4000 years old! The most amazing part is that it still produces olives to this day!
Our next stop was at Anoskeli Winery for a wine and olive oil tasting. The wine was so good but the star here was definitely the olive oil. The guides taught us how to properly taste it to enjoy all the distinct flavors and it was amazing. We loved it so much we bought some olive oil to bring home, and later we learned that they sell it in the US!
For lunch we stopped at Eleas Thea, one of our favorite restaurants on the trip. We recommend trying to go on your own, but it’s only open Saturday and Sunday from 1-6:30pm. The food is incredible and the view over the olive tree groves was spectacular. It was full of locals so we knew it was going to be good, and it definitely didn’t disappoint!
Our tour guide took us through some of the surrounding hills for a view into the interior of Crete before we returned to Chania. That night we walked around the Venetian Harbor and popped into a couple of shops before heading back to the hotel for the night. We ended up skipping dinner because we were still so full from our delicious lunch!
Day 10 – Samaria Gorge
Our next day in Crete was dedicated to hiking the Samaria Gorge, the longest gorge in Europe at 10 miles. The best way to do it (because the hike is 1 way) is to book a tour, so we did exactly that with Get Your Guide. The tour picked us up at 6am for the start of our very long day!
The experience of hiking through the gorge was really cool, but the travel times in both directions were extremely long. A tour is pretty much required because there is no road to take you back to the beginning of the hike. The hike down was very easy and is easily doable for all levels, as it’s little more than a 10 mile walk downhill to the beach.
We finished the hike around 1:30 and explored the town a bit before getting lunch at one of the local shops. After we ate we changed into our bathing suites and enjoyed some time on the beach until our ferry left at 5pm. The ferry and bus back to Chania took about 3.5 hours, so we didn’t return until about 8:30. It was a fun, really unique day but definitely tiring and we were ready to be back by the end of it!
After we returned to Chania we were very tired and wanted a nice, quick dinner before heading to bed. We had seen Veros on our previous explorations of the Harbor so decided to go there for dinner and it was very good!
Day 11 – Chania, Marathi Beach, and a Cretan Cooking Class
For breakfast on our last full day in Chania we went to Salis, which was very nice, before walking around the Harbor.
After exploring a bit around the Harbor we drove 30 minutes to Marathi Beach. Unfortunately we didn’t have time to go to either Balos or Elafanoisi Beach as those were each over an hour away. We hadn’t planned to go that far as we had to be back for our cooking class later in the evening, but Marathi was still an excellent option very close to the city. One day when we go back to Crete we will definitely visit the famous beaches!
In the afternoon we were picked up for our real Cretan cooking experience at 3:30. This was easily one of the best parts of the entire trip! The tour takes you about 30 minutes outside the city to a local house with an incredible view over Chania and the sea. The tour begins with a wine and cheese tasting led by one of the best local guides we’ve ever had.
We then were given a great tour of the house and property where they regaled us with a bunch of fantastic Cretan and Greek history. Our tour guide was Giannis who was super friendly, energetic, and so knowledgeable about anything you can imagine! We were able to feed the goats and grind our own wheat using an old millstone. We then moved on to making delicious stuffed peppers, tomatoes, zucchini, zucchini flowers, and grape vine leaves, a cheese pastry, tzatziki, Greek salad, and a Cretan rusk. This was one of the best cooking classes we’ve done and we can’t recommend it enough!
After the outstanding cooking class we went to Nama for a night cap. The cocktails were super fancy and delicious, and the vibe was really fun. However, unfortunately a lot of people smoke in Greece so it was somewhat hard to escape it while trying to enjoy our drinks.
Day 12 – Wineries and Heraklion
This morning we went to Pallas for breakfast. This was incredible and was easily the best breakfast we had on Crete. The food is absolutely delicious and we highly recommend going here at least once during your time in Chania!
After breakfast we walked around the Venetian Harbor one last time before heading out of Chania. We first drove to Manousakis Winery, a beautiful and very good winery less than 30 minutes outside the city. You normally need to have a reservation, however we were able to grab a glass and stand on their patio to enjoy it. If you are staying in Chania you can even book a tour to the winery!
After enjoying our wine at Manousakis we continued another 30 minutes to Karavitakis, another great winery where we were able to do a tasting and enjoy our time. It is a wonderful winery that’s worth visiting in the Chania region.
Our final stop along the way to Heraklion was Dourakis winery which was about an hour away and much closer to Heraklion. This was a truly beautiful setting that featured excellent wine.
After enjoying our last wine tasting we drove the remaining 1.5 hours to Heraklion. We didn’t plan to spend much time in the city as we didn’t see very good reviews. We stayed very close to the port so that we would be near the ferry early the next morning. The highlight of our short time in Heraklion was definitely Mia, a nice shop where we ordered loukoumades (Greek doughnuts) that were well worth the hype.
Day 13 – Back to Santorini
In the morning we took the ferry back to Santorini with our car. We unfortunately weren’t able to go to North Macedonia due to Covid travel restrictions imposed mid-trip, so we decided to go back to Santorini because we liked it so much. The best part about the Greek islands is how easy intra-island travel is by ferry. You actually can’t usually travel by plane directly from one island to another (except in rare circumstances) and most flights route through Athens, so ferrying is definitely the way to go!
When we arrived we went to Fira for a fantastic brunch at Volkan on the Rocks. This restaurant featured a beautiful view of the caldera and had incredible food! The pancakes with Greek yogurt and fruit is an absolute must. Definitely get the orange juice as well because it is freshly squeezed right at the restaurant!
After brunch we drove to one of the black sand beaches of Santorini. It was cool, but it was not nearly as nice as Crete’s beaches. The wind whips on these beaches and the sand can be picked up and driven into you while you sit on the beach. If you are going to another island we would recommend enjoying the beaches on those islands while spending time taking advantage of the other amazing things Santorini has to offer!
We then checked into our second hotel in Oia, You and Me Suites Oia. It is in a great location with a fantastic view, and staying in Oia was a great change of pace from our first hotel. This allowed us to experience more of the city ambiance which we really enjoyed!
For dinner we went to Dimitri Amoudi, another wonderful restaurant in Amoudi Bay. The seafood was great and the seats were directly on the water for one of the best sunsets one can imagine! While we really enjoyed it, we actually would probably pick Amoudi Fish Tavern if we only had a single dinner to choose from.
Day 14 – Hike Santorini (again)
Our hotel in Santorini this time did not come with breakfast, which we were fine with because it allowed us to try other breakfast places. We began the morning by going to Thalami for breakfast where the star of the show was the pancakes with Greek yogurt, fruit, and honey – it’s one of the most delicious foods we’ve ever had! Whether you get it at Thalami, or somewhere else, you must try these pancakes!
This was a fairly simple day which featured a hike from Fira to Oia for the second time. Much like the first one this was a wonderful way to spend a few hours being active on this beautiful island. To start the hike we needed to bus to Fira, which was very simple as well.
When we arrived in Oia we took some time to shop around and enjoy this truly beautiful town perched on the top of the cliffs.
For dinner we went back to Pacman for the second time. It was so, so good and easily warranted a second trip. We love the vibe, the food, and the drinks! We highly recommend visiting at least once during your trip!
Day 15 – Santorini Wineries
For breakfast we went back to Volkan on the Rocks, one of the best restaurants on the island. It was fantastic yet again and we would have gone back again and again if we could.
For our last full day in Santorini we wanted to do another winery day, so we started the day with a trip to Domaine Sigalas. It was a winery fairly close to Oia and the wine and view were very nice!
Next we went to Estate Argyros, a beautiful winery closer to Fira. We were actually able to do a tour here which was so cool and we learned so much about the unique wine making on the island! It was definitely the most informative vineyard we went to on our trip and we really liked it!
After this winery stop we went back to Fira to shop and get a few final souvenirs and gifts for our family.
Then we went back to Santo Winery for an amazing sunset dinner over the caldera. For dinner we highly recommend making reservations in advance to secure the best seat (or any seat really). The views are magical, the sunset was perfect, the food was delicious, and it was the perfect way to end our trip! We even were treated to a firework show from a wedding taking place just next door.
The next day we had an early morning flight from Santorini to Athens before our direct flight home to Washington DC. All in all this was a fantastic trip that we loved, even if we had to change our plans in the middle of it! We hope this will help you plan your next adventure!