Greece Itinerary: 10 Days, 3 Islands, Countless Memories

This was a trip I’ve been wanting to go on since watching Sisterhood of the Traveling Pants in 2005 (IYKYK) and it did not disappoint. We went to 3 Greek islands in 10 days; Santorini, Milos, and Mykonos. It was such a special trip because each island had such unique experiences to offer and they are pretty close in proximity. We traveled between them by ferry and flew into Santorini and out of Mykonos to maximize time at each! I recommend doing at least two islands if you have the time because you can pack in such a dynamic vacation. I think it was the best mix we’ve had of adventure, relaxation and true cultural experience that we’ve had together.


FLIGHTS: We flew from Seattle to Athens, and then Athens to Santorini (30 minute flight). You can take a Ferry from Athens to Mykonos but it’s 5 hours so I definitely recommend the quick flight over that.Couple in santorini greece

4 days, 3 nights – I felt like this was the right amount of time for us to experience Santorini, we could have done one more day if we had the time but we really maximized our time and saw plenty. Santorini is smaller than I expected so we were able to see beautiful Oia, take a cooking class, go to the black sound beach, and get in plenty of lounging and great meals.

HOTEL: Acroterra Rosa Luxury Suites & Spa – we loved this hotel. They have the inclusive fresh Greek breakfast of your dreams (seriously they did not stop bringing us fresh juices, cheese plates, and Greek pastries) and a gorgeous pool. The staff here was extremely hospitable and rooms have a great view. The one thing to note is the hotel is a little off the path of touristy spots and taxis aren’t cheap in Santorini, however it is close to a beautiful spot to watch the sunset and feels more secluded then the hotels in Oia where you have less privacy. Overall though it was a great value. Another hotel I have heard recommended is Santo Maris which is a luxury hotel a short walk from Oia.

TRANSPORTATION: Transportation in Santorini adds up quickly, I would recommend finding a taxi/uber driver you like and getting their WhatsApp number and arranging rides with them directly. You can rent a car but the streets are narrow and windy so we didn’t feel comfortable renting there. I saw plenty of people of ATVs and scooters but our drivers told us there is an insane amount of tourist accidents, so proceed at your own risk. Like any place where there are a lot of tourists who don’t know the roads, it makes things a little extra sketchy.

Cooking class
Black Sand Beach (Perissa Beach)
Sunrise photo shoot in Oia
Shopping in Oia: This is where the picturesque white houses are, this is what you think of when you think Santorini and you can spend a day walking around admiring the architecture, shopping in boutiques, and eating/drinking here.

Good Heart Restaurant: Amazing sunset views on the South Side of the island (near where we stayed)
Jojo: $20 for a chair and have food and drinks on the black sand beach!
Pitogyro: Go for Gyros!
Dimitri’s in Ammoudi Bay
Nocturna: Great place for sunset
Fanari restaurant: In Oia, amazing views!


Ferry: We used FerryHopper to book an express ferry from Santorini and it was 2.5 hours. It was insanely choppy the first 30 minutes of the trip but after that it was a piece of cake. We left Santorini at 3pm and got to Milos in time to check-in to our Airbnb and have dinner!

Hotel/Airbnb: Because Milos is a small Greek island and has less tourists we chose to stay in an Airbnb to get a more authentic feel! I’m so happy we did this, it ended up being one of the highlights of my trip to wake up every morning to a fresh home cooked Greek breakfast. It was the second home of a family that owns a shop right in the village and the location was AMAZING. They live right next door so she drops off breakfast in the morning and is easily accessible if you need anything. She had amazing local recommendations. Honestly though, the standout of this place wasn’t really the accommodation as much as it was the location. You are right in the middle of the most popular village in Milos, Plaka. So when you walk out your door it feels like you are transported in time, and you have boutiques, cafe’s, bars, and restaurants available to you. Despite the location being in the “thick of it” it wasn’t loud at all and we slept fine, and it is superrr affordable. Linked here.

TRANSPORTATION: We rented a car while we are here and I 100% think that was the best decision. Because Milos isn’t as popular as Santorini it doesn’t feel overcrowded to drive. You’ll also want a car to get to Sarakiniko Beach early before the crowds!

ACTIVITIES: The activities here were the highlight of our trip to Greece, the beaches are just absolutely.. unreal.
Boating Day Trip:  We booked through TripAdvisor and did a day cruise/snorkeling excursion to Kleftiko (pictured right) and a couple other hidden gem beaches that you have to get to by boat.

Sarakiniko Beach: this is a MUST. This beach is so unique, it looks like moon rock and you can jump off the rocks into the sea. Even if you don’t jump it’s fun to watch everyone do it!

FOOD/BARS: There are 3 main areas to eat in Milos. At the port, in Plaka, or Apollonia. You can’t go wrong with walking around these areas and popping in to see which menu speaks to you! The fresh seafood is amazing all over Milos since it was caught that day.

  • Utopia Cafe (best place to get drinks and watch the sunset over the sea)
  • Mikros Apoplous: fresh seafood at the port
  • Akrotiri
  • Medusa
  • Deck (breakfast)
  • Astakas in Klima


FERRY: We used FerryHopper again to book an express ferry ticket from Milos to Mykonos. It took 2 hours and 45 minutes and was an easy ride- it picked us up from Milos early so we got to Mykonos by 10am to check-in and explore the rest of the day.

We were here 4 days and 3 nights which felt like the perfect amount of time – if I was here with a bigger group I probably would add an extra day.

HOTEL: We stayed at Damianos Mykonos Hotel and loved it. It’s a boutique hotel run by a local family and all the staff were so friendly and accommodating. They picked us up from the port where the ferry dropped us off carried our bags in and gave us an overview of all the things to do nearby. They serve a huge breakfast spread every morning; greek yogurt, pasties, eggs, meats, fresh juice/coffee etc. The location was super walkable – it was up the hill from downtown Mykonos where the shops and windmills are. We definitely got our exercise walking back up the hill but it wasn’t too bad. They also have a shuttle that takes you to the airport free of charge!

TRANSPORTATION: We didn’t end up renting a car here because our hotel was so central, but of all the islands it seemed like the easiest place to drive a car. Mykonos also has a good bus system, if you want you can get to most of the beaches around the island using the bus. We used Uber here twice and had a great experience both times.

ACTIVITIES: We lived our best lives in Mykonos. I went in thinking everything was going to be a rager like Lindsay Lohan Beach Club but you can really find whatever your vibe is in Mykonos, and our vibe is very relaxed, kind of bougie. We did a beach day club at Super Paradise one of the days and spent the day on plush beach chairs overlooking the sea and ordering wine and bites, swimming in the sea, and taking in the music/views. Things definitely get a little crazier at night so if you are looking for something relaxing I would recommend getting there early, we got there at 11am and we basically had the beach to ourselves the first couple hours. Pro tip: get there around this time if you want your selection of front row chairs/cabanas. There were boat and jet ski rentals from this beach too, they looked so fun – if we go back we’ll definitely take advantage. We both agreed that spending the day here was one of the highlights of our whole trip.

At night we went to Scorpios for the sunset party and it was a total vibe. They have live music, killer sunset views, and this place is GORGEOUS. If you are looking for the spot to get dressed up and take pictures, this is your spot. Note: this place is a little spendy.

Mykonos downtown is very walkable and has endless shops and restaurants to pop into. It’s located on the water so it’s really lovely to spend hours down there. The famous windmills are not far from the main downtown areas so you can walk over to those and then reward yourself with a drink on the water after. You may even run into Peter the Pelican like we did!


  • 180 degree sunset bar (pictured right): I would rank this a must for dinner in Mykonos, the view of the city, sea, and obviously the sunset are killer! The food was amazing too. It’s really popular so make a reservation in advance, you can pick your seating – they all have different costs to reserve but it goes towards your food and drink minimum. The main terrace is what we picked and we loved it.
  • Scorpios: another place to make sure you reserve well in advance but you can spend the whole day here getting food and drinks and have a fabulous time. Like I mentioned above there is a DJ for the sunset party so check ahead to see if it’s someone you know. They have great artists!
  • Nusr-et Mykonos (owned by “Salt Bae”): Definitely overpriced burgers but they were delicious and it’s in a convenient spot right downtown next to the shopping. I would recommend for lunch. You can get nice steaks and have dinner here too but I don’t think it was a cool enough atmosphere to want to spend a long dinner there.



Write A Comment

Pin It