Planning for Greece 2014

street in Chania

This is a great two-week itinerary for a first visit to Greece, built around bucket list items in Athens and the islands.

Planning for Greece 2026

Stelios Place with pink flowers

We planned this to be a pretty relaxed trip, organized around spending time at the beach and doing some walking.

Santorini Sunset Sail

Santorini sunset

We splurged a bit on a sunset sail while on Santorini. There are some views you can really only get from the water.

Hike to Ancient Thera

view from trail

Even if — like us — you don’t make it all the way to ancient Thera, it’s still a hike with beautiful views.

Santorini

palapas and the sea

Santorini is a unique place worth visiting. I don’t care how touristy it is. The caldera is beautiful from the water and Perissa is our favorite beach town. This time we spent seven nights.

Hike to Angali Beach

torch flowers

This was far from an easy hike but it was scenic. It can be challenging to find the trail once you get down near the beaches.

Folegandros

bougainvillea

The Chora of Folegandros is charming and leafy, in contrast to the ruggedness of the island. The walking trails were better sign-posted than we expected. We didn’t get to experience the beaches since it was cooler (low 70s) and very windy but we enjoyed our four nights there anyway. It was quiet and serene.

Milos Sailing Trip

Kleftico

Our sailing trip to Kleftico along the south coast of Milos was as beautiful as we hoped for. Try for a day that’s not windy.

Milos Beaches

aqua water wave

Milos has LOTS of beaches. We sampled a few, including Firopotamos, Agia Kyriaki, Plathiena.