An overseas trip for my family is a big deal. We do not have these opportunities often so planning out a detailed trip ensures that we make the most of a trip of a lifetime. We recently went on the trip of a lifetime to Greece. Here I will give you access to my Greece Itinerary along with what I would change about my trip.

3 Days and 3 Nights in Santorini

My family and I spent 3 nights and 3 days in Santorini which is a part of the Kiklahdes islands of Greece. We stayed in the Exo Gonia area, centrally located in Santorini. Over the course of 3 days we explored the southern and northern portions of the island. The island is only three miles wide and a total of 10 miles long. When deciding which locations of Greece to visit, I loved gleaning information from Amanda Monique Brown and her Instagram and blog posts.

The architecture of Santorini and food were amazing. Spending time exploring various villages such as Emperio and Megalochori were lovely to stroll around. Fira, Imergovoli, and Oia were beautiful as well; however, crowds in Oia were not enjoyable.

On our second night in Santorini, we ate at Metaxi Mas in Exo Gonia and it was an amazing dinner experience. The environment and vibe of the place was welcoming and relaxed. The restaurant is tucked away down a street that is behind a church. Without the sign at the main road you would not know it exists but it is a delightful experience. One aspect of Greek culture I loved was every evening meal was meant to be enjoyed late at night with no rush. Our dinner reservations were not until 9:30 p.m. The restaurant provided complementary aperitifs and appetizers as well as dessert to close out the meal. When discussing our trip, the whole family remembers this evening fondly.

3 Days and 2 Nights in Milos

Milos was amazing! I wish we would have stayed longer in Milos. It is such a wonderful island. While it is larger than Santorini, it very much has a small town feel with buses taking you to many locations for only 2 euros per person.

We entered the port town of Adamas in the evening after taking a ferry over from Santorini. The ferry ride was around three hours long. We were able to walk from the port to our accommodations, The White Suites of Milos. After settling in, we strolled down to the waterfront and ate at Gyros of Milos. It was such a wonderful outdoor eating experience.

For our only full day in Milos, we rented a semi-private sailboat excursion with Polco Sailing. Hands down, this experience was the highlight of our entire trip. We left port at 9:00 a.m. and did not return until after 7:00 p.m. While aboard, we were fed breakfast, lunch, dinner, and dessert. Our excursion stopped at four different locations allowing for us to swim, snorkle, paddle board, and explore – a pirates cove was included! Kleftiko beach and the Blue Lagoon were our favorite stops. While sailing we passed the colorful fishing village of Klima.

The evening after our sailing excursion, we ate at Mikros Apoplous. This was a fantastic restaurant that I wish we would have been more alert to enjoy. A day at sea drained us but the seaside setting of this restaurant was gorgeous. The service was amazing and the food delicious with complimentary lemon souffle`s at the end.

On our last day in Milos, we took a bus to Sarikiniko Beach which is known as the “moon beach” because of the white rock that covers the entire area. This beach was unlike any other beach I have ever visited. It was stunning! Buses run multiple times a day to Sarikiniko, just make certain you pay attention to the last bus leaving the beach.

1 Day and 2 Nights in Athens

My family flew in and out of Athens. Based on a friend’s recommendation, we checked out Athens at the end of our trip. While the history is amazing, my family and I greatly enjoyed the islands moreso than the city of Athens. Multiple outlets shared that Athens would not be worth more than a full day’s visit.

Athens is a large city and there are very pretty portions of the city. There are other areas that look pretty run down. My overall complaint was the heat. It was not enjoyable to walk around in 94 degree heat.

My son and I did check out the magnificent Acropolis and its lovely history and architecture. We arrived just before 9:00 a.m. and the crowds were already heavy. I would recommend booking a ticket time for 8:00 a.m. at its opening in order to hopefully have smaller crowds.

After touring the Acropolis, we met up with the rest of my family and ate lunch in the Plaka neighborhood then toured the National Archeological Museum of Athens. Plaka is a beautiful neighborhood and I would have liked to explore it a little more.

For our last evening in Greece, we were very chill. We ended up walking to a restaurant that was just a few blocks away from our hotel. We stayed at the Delice Hotel in Athens. Our last meal in Greece was an authentic, local fare filled with gyros and kebabs. The name of the restaurant was in Greek but translated it means, “Olive & Bread”. After dinner we strolled to a nearby grocery store to load up on new snacks to take on our journey home as well as stopped by a local bakery, International Classic Patisserie, to get some sweet treats.

What I Would Change…

Transportation – make sure you know everything there is to know about your mode of transportation between destinations. In hindsight, I would not have waited at the airport seven more hours for a quick flight to Santorini. I would have booked the six hour ferry and we would have been moving in the direction of our destination instead of waiting in an airport terminal (which was delayed by an hour due to plane technical difficulties).

The metro was the cheapest and easiest way to navigate Athens but it was extremely difficult to locate the actual entrance to the metro. I would make sure I knew beyond a shadow of a doubt where the Metro was located before heading out to catch a ride.

Lastly, I would have changed the order of days at our destinations. Instead of staying in Santorini for 3 days and 3 nights, I would have stayed there 2 nights and 2 days. This change would have allowed us to stay in Milos for 3 nights and 4 days. Milos was absolutely stunning and we didn’t even get to explore all of the island. Milos is much less crowded than Santorini and it had many more beach options to visit.

Creating an itinerary gives a little guidance as to what sites and excursions are available at a destination. Planning my own travel ititnerary is one of my favorite things to do. I share some of my tips for itinerary planning, here. I would love for you to check it out! Please take and use this blog post as a help to you when planning your own Greece trip!