Beach Getaway City Guide Food & Drink Fun & Adventure History & culture Itinerary Nature Village Life

Our 2-Week Whirlwind Tour of Athens & the Cyclades Islands

This trip was a long time in the making.

Greece had been on our travel bucket list for years. Finally in 2020, we decided it was time to cross it off the list. I dove head-first into research and planning mode. I booked all of the flights, ferries, hotels, cars, restaurants… and then, you guess it… Covid came along and ruined everything.

Luckily, all of the places we booked were happy to give us credit to use at a later date, and two years later, that date finally came.

By the time we finally rebooked everything for October of 2022, I was 6-months pregnant. Little did I know back in 2020 that the trip I planned as a romantic getaway would actually turn into a two-week “babymoon”… but hey, there’s a lot we didn’t know back then, and there are certainly worse places to visit as a pregnant lady!

This trip had it all: good food, great weather, museums, hikes, villages, and beaches.


Overview of our trip

There are literally thousands of Greek islands, around 200 of which are inhabited.

To simplify the planning and logistics, I decided to narrow in on the Cyclades region. From there, I chose islands that all had different things to offer. I ultimately settled on Naxos (known for quaint villages and some of the best cuisine on the islands), Milos (nice beaches and really interesting formations), and Santorini (famous for its stunning sunsets and cliffside towns). And to round things out and give some nice balance to the trip, we added Athens on to the list.

The first part of the trip was more geared toward history and culture in Athens with the second part all about good food and relaxation on the islands. Some people manage to visit a different island a day, but we decided to take it a bit slower to avoid mid-trip burnout and take our time getting to know each of the islands we visited.


Itinerary

Below is an overview of the itinerary with highlights from each leg of the trip.


PART 1 | Athens

Days 1-3

Sunset and city views from Lycabettus Hill, food tour through Athen’s Plaka neighborhood, and the Agora, Acropolis, and Acropolis Museum


PART 2 | Naxos

Days 4-6

Driving tour of the island’s charming villages, Mount Zas hike (the highest point in the Cyclades), and the island’s best sunset at the Portara


PART 3 | Milos

Days 7-10

Catamaran tour of the island, the lunar cliffs of Sarakiniko Beach, and the colorful fishing village of Klima


PART 4 | Santorini

Days 11-14

Caldera Hike from Fira to Oia, day of relaxation by the pool, and sunset catamaran tour of the island


Related Posts

Looking for more travel inspiration? Check out these other posts from similar trips:

You Might Also Like