Greece 8 Day Itinerary

October 2017


Day 1

This past fall we finally made it to one of our bucket list destinations - Greece. We had debated going here for our honeymoon and a few years ago when we opted for Italy instead, but after coming home on a honeymoon high a few months earlier, we couldn't help ourselves but just book it. Since neither of us had been to Greece, we wanted to visit more of the mainstream Greek Islands for this trip so we chose to do Mykonos first, then Santorini, and finally an afternoon (layover) in Athens.

We arrived in Mykonos around 9pm and knew in order to stay awake after our overnight flight from New York to Athens and then Athens to Mykonos that we would need to force ourselves out.  After a quick change and shower at our hotel, the Andronikos Mykonos, we walked the 20 minutes or so into town. The normal dinner hours in Greece, and especially the islands, don't really begin until 8 at the earliest, so we fit in perfectly at 10pm. We wanted a more traditional restaurant for our first night and were able to snag the single tiny table outside of To Maereio so we could also people watch.  By the time we finished dinner a little before midnight, the town was bursting with people and music even though it was the last weekend in September. We missed the real party season but got a glimpse of what Mykonos town is like in the weekend during the summer months.

Day 2

For our first full day in Mykonos, we knew we wanted to explore the blue and white streets in town as well as Little Venice and the famous windmills. We didn't have much more of a plan other than walk around and really get a feel for the town. We woke up late and enjoyed a tasty breakfast at our hotel before heading out around 11. We were hoping to get some time in at the pool but it was a little too breezy on our first morning.


Instead we started off toward the windmills which are a little detour from the main streets in town. This is also where you can see Little Venice. The waves really do crash up on the buildings here and it's such a pretty photo to get from where the windmills are. Vice versa, it's fun to sit in one of the bars in Little Venice to capture the lighthouses from that angle (especially at sunset). From there, we started exploring the narrow, winding streets in town with no direction. There are so many shops to stop into and restaurants to get a quick bite that you feel like you are never done exploring. Depending on the time of year you go though, be cautioned that the streets are tiny and it can get very busy. Even in the last weekend of September it was crowded so on a weekend in August with a cruise ship in port I would think the experience may be a little hectic. We stopped at Lotus Mykonos for a glass of wine and snack and had a late lunch at Pepper. While we liked the food, it definitely didn't live up to the hype of it's reviews. 


We were enticed by all of the 4 wheelers and quads around the island so we decided to rent one late afternoon to take a spin and also get back to the hotel instead of walking. It was so much fun and highly recommended! They are so cheap to rent and perfect for two people. It's such a fun way to see a bit more of the island outside of town and there are tons of places to rent them from. We drove through Ornos to Paradise Beach and Platos Gialos - I can see how this is a scene in the summertime!

For dinner that night we had made a reservation at Kastro's (reservations are recommended and most likely necessary depending on the time of year you're visiting). It has a great view of the windmills since it's situated toward the end of Little Venice, so you can plan around sunset if you want. We decided to watch the sunset at a bar a few doors down at Rhapsody and then went to dinner after.


Day 3

We really embraced the time change and slept later than usual again on our second full day but had to make it out of the hotel by 10am for a cooking class that we signed up for. We like to try to do as many "local" things as possible when we travel whether it's cooking, wine tasting, or just walking around and feeling like a local. We booked an afternoon class with Mykonian Spiti. I would recommend it for the spanakopita recipe alone but it wasn't my favorite class or tour we've done. That aside, the food we made really was delicious (the spanakopita was the clear winner but the tzatziki was really tasty too.)


After our class, we stopped back at the hotel to get ready to head back to town. We stopped at a tiny coffee shop, Sic Coffee Bar (which also doubles as a real bar) and sat outside for a quick cappuccino to perk us up after too much spanakopita. We were hoping to catch the sunset since the night before was overcast and then head to drinks and a late dinner. We wound up staying in the area at the Veranda which is toward the beginning of Little Venice. It's a big place with so many great places to watch the sunset but it does get really crowded around this time of day so be prepared to go early. We enjoyed the drinks but the sunset wasn't the best - the sun peaked out from the clouds from time to time but overall it was a bit disappointing.

We didn't have a plan for dinner since we weren't sure if we would even be hungry but since it was our last night in Mykonos we didn't want to miss the opportunity for more Mykonian food so we ended up at Caesars. It's located in the center of town and has a nice outdoor seating area as well as inside. We loved the fried feta appetizer there! Still getting over jet lag we headed back to the hotel after dinner but for anyone looking for a night life experience, this is definitely the place to go. There are tons of places from bars to night clubs to choose from as long as you are here during the popular tourist season.

Day 4

We spent the first part of the morning at the pool in our hotel - the wind finally calmed down enough for us to enjoy some warmth before heading to the new port and our ferry. In usual Greek style, the ferry was running over an hour late but luckily by this point we were able to bask in the sun at the port. The high speed ferries are a great way to get around the islands. They are easy to book, offer different options for companies (we used Hellenic Seaways) and they run pretty frequently and are reasonably quick. We were met by a driver from our hotel, the Andronikos Hotel Santorini and we highly recommend booking a car ahead of time. The port where the ferries come into is very small and secluded so to have a car waiting makes things much easier. By the time we got to our hotel, it was nearly time for our first real sunset since arriving in Greece. The sky was clear and our room had an incredible view of the caldera from the inside and from our balcony. I loved everything about this hotel and we really felt like we were in a dream staying here.


Day 5

Finally adjusting to the time change, we wanted to get an early start for our first day in Santorini. We chose to stay in Imerovigli (more on where to stay in Santorini here) and planned to spend the full day in Oia. We decided to do this on the first day in case we felt like there was more to see on one of the next few days. We debated whether to do the few hour cliff walk from Imerovigli or take a cab but our hotel recommended renting an ATV as a good way to get around the island on our own schedule so we decided to do this. It turned out to be a great way to get around and it was nice to see more of the non-touristy areas in getting from Imerovigli to Oia. Oia is a small town so you don't need too much of a plan to get around. Once you are there you can't really get lost even if you meander down every side street there is. They all seem to wind up back at the main road. 

One of the first places to stop off the main road is for a view of the three blue domes. It will probably be crowded so best to go early in the morning. To get there, first make your way to the main square in town, where you'll see Ekklisia Panagia Platsani, a Greek Orthodox Church. With the church to your right, continue walking straight down the main street until you see a small black hanging sign for Bulgari Alexandros. Right before the Bulgari store, make a left down the small path and keep going straight until you reach a brown door and fork in the path. From here you can't go wrong in choosing left or right. The left side will give a more zoomed out view, whereas the right side will get you closer to the domes. We tried both sides to get a few different views.


I loved pretty much every view in this area. Literally every way you turn is a beautiful mix of pastel colors buildings and those blue domes! It's worth it to allow for at least 15 minutes here to get all of the views and a photo or two of yourself!

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From here we continued down the main pedestrian path which gets very crowded - so plan to potentially take a detour if you are here during the summer. We picked up beers for the walk (perfectly acceptable here) and stopped in shops along the way. One place I knew I wanted to stop in was Atlantis books. I'm a big book fan and I had read that this was such a cool book store I knew I wanted to visit it. I spent awhile here looking at all the books and ended up finding a Greek mythology book to take home.


We were starting to get hungry from here and knew that we had a hike ahead of us down to Amoudi Bay so we decided to head down the 300 steps to sea level. If you aren't up for the trek down or up, you can hire a donkey for what I expect would be a fun experience. They looked a lot more sturdy than I was feeling. We had planned on lunch at the Amoudi Bay Tavern based on reviews we read before hand and would definitely recommend it. We shared a ceviche dish, seafood pasta and a bottle of rose and finally got some sun and no wind while we ate at the waterfront.

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After all we ate, I was actually looking forward to the hike up which was actually easier than down. Our next spot was to Oia Castle which is a must if you are visiting Santorini. The spot of the old Oia Castle has beautiful views of the town and it's known to be the best spot for sunsets. When we were there it was already so crowded though, and since we loved the view of the sunset from our hotel room we scratched our plan to stay in Oia and decided we would just grab a bottle of wine and do the sunset on our balcony. Standing at the Oia Castle balcony was one of my favorite views from Greece. Seeing the town and how it is built into the rocks with all of the beautifully colored buildings was incredible. 


We spent some more time walking around some off the beaten path streets in town before heading back to Imerovigli on our ATV and popping into all the shops along the way. There are so many things to see and do here; I can see how people spend days walking around.


Day 6

We couldn't go to Greece and not spend a day on a boat! We had read that sailing was a great way to see the island from the water and booked an afternoon tour with Sunset Oia. This was definitely one of the highlights from our trip and we really lucked out with weather. The days seemed to be getting progressively warmer even as we got further into October and we were loving it. The boat was beautiful and there were only about 12 of us on board. We had splurged for a bit more expensive package with a less crowded boat and for the minimal price differential this was worth it. The boat we chose was the Amorgos Lagoon 520. One of the highlights was the lunch cooked onboard which was one of our favorite meals of the entire trip. We stopped for a few different swim spots and spent time lounging on the deck. It was a perfect way to spend an afternoon. For dinner that night we stopped for take out souvlaki near our hotel at Let's Eat which was quick, cheap and tasty.

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Day 7

Our last full day in Santorini was spent doing one of our favorite things in the morning - wine tasting. What was almost as fun was surprisingly our afternoon activity hiking from our hotel in Imerovigli to Fira town. We hadn't seen this part of the island and didn't know how the hike would be but it was such a fun way to get from here to there and the walk was incredible. We left early in the morning for our tour with Santorini Wine Adventure Tours. Our guide was so knowledgeable and is actually oenology professor at a University in Athens during the school year and wine tour guide during the summer months. The Santorini style wines weren't my favorite but we ended up loving Vinsanto, a white sweet dessert wine.

A little foggy from our morning spent in wine tasting rooms, we forced ourselves right back out the door in the afternoon to make it to Fira. We had dinner reservations at night in Fira town at Argo so we planned to stay until then. From the moment we left the hotel the walk was so scenic I couldn't put my camera down. Planning this trip, I heard so little about the other towns in Santorini outside of Oia so it was a nice surprise to find that we liked Imerovigli, Firostefani and Fira just as much.

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Day 8

Sadly, all good things must come to an end and we spent our last day en route from Santorini to Athens for a quick layover and trip to the Acropolis before heading home to New York. But, like many places we've visited, we are already thinking about our next trip back to Greece..