Greek Islands Itinerary
In September of 2023, I was eligible for my 1 month sabbatical from HubSpot. My best friend Andrew and I decided that we would take a 10 day trip to the Greek Islands. Below is our itinerary, and our highlights to share with family and friends.
Planning notes:
Hotels and ferries: Book in advance (hotels we booked 2-3 mo in advance, ferries a few weeks in advance.) This was important, as most of the hotels were full by the time we arrived. If you want to do a sailing trip, I recommend planning that in advance as well! Once we arrived, a lot of the excursions we had our eyes on had booked up.
Scuba, snorkling, rental cars, etc can just be planned as you go!
If you offer to pay with cash (euro), there is often room for price negotiation. “Is there a cash price?”
Olive oil: but it in the little markets, rather than the dedicated shops and farms. You’ll find the same local brands for 1/2 the price.
Fly to Athens
Our original plan was to stay at a downtown hotel, meet up with a local friend for dinner, and explore Athens before hopping on our ferry the next morning. However, to our surprise, there was a ferry strike scheduled the following day. Apparently, strikes happen all the time in Greece. Thank goodness I had a friend DM me on Instagram and provide us a heads up (thank you Aliki!)
SO, we decided to skip our night in Athens (forgo our paid hotel reservation) and catch the soonest ferry to Milos. This required some last minute scrambling to get a new ferry, cancel an existing ferry reservation, book a hotel room that night in Milos, schedule a car transfer, etc.
However, we did check into our hotel (Green Suites Boutique) and enjoyed the roof deck pool restaurant and bar while we figured out our plans / scrambled and then ubered to the port to catch the ferry out of Athens.
So after 36 hours of travel (3 flights to Athens and a 4 hour ferry to Milos), we arrived at our Milos hotel and fell asleep. Whew.
2 days in Milos
We absolutely adored our boutique hotel En Milo in Pollonia. The pool was beautiful, quiet and serene. The hotel was right on the ocean and walking distance to the local restaurants and cafes. The hotel staff served us a custom breakfast each morning. There was a little rental car spot steps away. Everything was so seamless.
Milos adventures included:
We were quite jet lagged so we really enjoyed our time at our hotel pool the first day, and just walking around the quaint town of Pollonia. Second day was when we rented a car and explored the island.
Tsigrado Beach: you can only access by climbing down 2 sets of very sketchy ladders. The beach is stunning and private.
Visting the small fisherman village of Klima and taking photos in front of all the colorful homes (I heard you can rent these on Airbnb and I think that would be such a unique experience)
Cliff jumping Sarakiniko Beach with the masses. Super fun experience.
Visit Kymbe Ceramics - handmade ceramics shop. They are closed in the afternoon so I recommend visiting this town for dinner and stopping into the shop in the evening. Be sure not to take a photo in there…the owner scolded me.
Dinner recommendation: Yialos (when we asked anyone where to eat in Pollonia, this was the recommendation. We did lunch here and it was delicious. One of our fancier meals of the trip.)
2 days in Paros
A word of caution about the ferry: We hopped onto the ferry and arrived in Paros. Andrew and I both agreed that the Greece ferry experience is a complete liability. There are hundreds of people rushing to get on and off, and the ferry staff are rushing you. The reason why there was a ferry strike on our first day, was due to a passenger death, so you can imagine how insane this scene can be. I told my sister that I wouldn’t want my mom or dad taking the ferry in Greece due to the insanity. She agreed, having visited a few Greek islands 2 years ago.
Anyway, we arrived in Paros and enjoyed taking a water taxi to local beaches (Monastiri and Kolimpithres), meeting other travelers, swimming, shopping in Naousa. We purchased masks and snorkles. I think if we were to plan this trip again, we would want to stay in Naousa! There were lots of cute little streets, shopping, restaurants to explore.
Avocado toast / smoothie / lunch or dinner spot: Sousouro Cafe - love.
We did not rent a car here, but opted to take the local bus.
2 days in Naxos
The ferry from Paros to Naxos was quick, 40 minutes. Arriving, the wind has picked up. Naxos is known to be windy and wow, the reputation is right! However, its a beautiful island and seems to be a major favorite amongst the locals.
Our boutique Hotel Grotta was wonderful, and run by 7 incredibly hard working women! The hotel was overlooking the cliffs and walking distance to old town which made it the perfect location. Breakfast was soooo delicious, with so many different options of freshly made dishes, juices, coffees, breads, etc. Staff and service was just amazing.
We decided to rent a car for 24 hours (40 euro) and explore the island. We also made friends with a lovely couple who were honeymooning and spent a lot of time with them. Vacation friends!
Highlights include:
Visiting the Olive Oil Museum - a quick 30 min visit to get the tour and also sample different olive oils and spreads. (Its free)
Scuba diving (we did the beginner Discovery Dive, as I am not certified) - it was a great experience. Our instructor was named Nacho and he is a dive pro from Chile.
Lunch at an incredible local joint off the beaten path that Andrew discovered. This was probably my favorite meal of all. Taverna Axiotissa.
Hawaii Beach
Enjoying the private “spa” at the hotel (pool, sauna and hot tub) at our hotel
Walking around old town and getting apps / drinks while watching the sunset
2 days in Santorini
Santorini is inundated with tourism and people. I was overwhelmed by the thousands of people getting off at the port. I know everyone is looking to stay in Oia or Fira, and get those classic photos you see in marketing ads, however Andrew and I both were looking to get away from the crowds and decided to book our hotel in the southern part of the island, down towards Caldera Beach and Akrotiri.
This was our fanciest hotel of our trip, Marillia Village. It was a beautiful hotel and designed really well. Every turn was a photo op of something pretty. Location was nice (the beach was a 2 minute walk) and it gave us the opportunity to really experience Santorini in a more quiet way.
Sunset: We drove to watch the sunset from Akrotiri Lighthouse which was beautiful and overlooked the volcano
Dinner: Kali Kardia Family Tavern (another favorite little spot of mine) Really chill, older restaurant, local vibes.
Beach time: My favorite moments in Santorini were relaxing on Caldera Beach, away from all the people. Its a beautiful quiet little black sand beach, with easy access to a nice little restaurant. There are a few reefs you can swim out to and snorkle.
Of course, we had to drive 40 min accross the island to Oia to see what the fuss was about. It really is so fancy, stunning, and just jaw droppingly beautiful. The crowds can be intense, but I think visiting in mid September perhaps allowed us to experience it without it being overwhelming. Even though it was a drive to get there, and I was convinced I was going to hit at least 200 people en route, we both agreed it was worth seeing. (Don’t buy anything in Oia…you can get everything you see there for half the price in Athens. My sister gave me this little heads up before the trip and she was 100% right.)
Dinner in Oia: Karma (be sure to make a reservation) Really delicious dinner and the prices were really fine for Oia.
Athens and home
Even though you can take the ferry, we decided to fly back to Athens from Santorini. Its a lot quicker! Looking back, ferry would have been fine as well. Just depends on what you prefer and where you are staying in Athens etc. Our final night we walked up towards the Parthenon, got dinner, did some last minute shopping and just enjoyed our last night in beautiful Greece! We were happy to see a little bit of Athens, finally :)