Romantic white washed villages, crystal blue waters, incredible food and culture that goes back several centuries—Greece offers something for every kind of traveler.  While there are a few obligatory must-sees where you’ll wade through crowds of people—think the Parthenon and Santorini sunsets—with over 200 inhabited islands, it’s quite easy to get off the beaten path and find yourself alone on a pebbled beach or wandering solo through the narrow walkways of an ancient village.

My husband Tim and I spent two weeks exploring Greece and worked with Liz (@elizabeth.b.walsh) at The Local Foreigner (@thelocalforeigner) to plan the trip. Liz was amazing and booked all of our private transfers, any excursions we were interested in and offered perfect restaurant recommendations. 

Many of the Cycladic island vendors aren’t “online” so she was a godsend in organizing the entire trip and keeping everything (and us!) organized in the Local Foreigner app.  

Just a quick note: we weren’t paid or sponsored for any leg of the trip so all recommendations are our own… I hope they might help you to create an amazing itinerary that is uniquely yours!

First Stop: Athens

Go for: the history, baby!

Athens is widely agreed upon as the oldest capital in Europe.  Plan to stay a night or two upon arrival and make an early morning trek up to the Acropolis to see the Parthenon.  

The views of the city are incredible from this vantage point. We hired guide @daphnestefanidou, a history teacher and anthropologist, to get a history lesson and see it from a local’s perspective. She was terrific—knowledgeable and passionate about Greek culture and Athenian history.

Where to Stay

The New Hotel (modern) or Hotel Grande Bretagne (luxury) are both great options!

Where to Eat

Most rooftops have a spectacular view of the Acropolis at night. The Art Lounge restaurant atop the New Hotel boasts a few patio tables with an incredible Acropolis view. Make a reservation, plan to have your first of many Greek salads (they taste so much better in Greece) and be sure to ask for a table with a view!

Next Stop: Milos 

Go for: the beaches and stunning sunsets!

A quick flight from Athens, Milos looks unlike any of the other islands, as it’s volcanic with little vegetation and resembles a moon-like appearance in many places. The sunrises rival the sunsets but in the mornings you won’t see anyone, as most people stay up late and sleep in.  Wake up early and head to Sarakiniko Beach—the white wind blown rock formations in the pink morning light felt other-worldly.

One of the best ways to see Milos is by boat. We booked a private full day sailing trip and it was one of our trip highlights! Our captain @algarau   was the right mix of mellow and fun and took us to so many special spots: our favorites were the bright blue waters of Polyaigos and the boat-only accessible Kleftiko with its caves and unique rock formations. Bring loads of sunscreen and a hat!

Lastly, Medusa was probably the most “influencer-hyped” place we visited on the entire trip. It’s a taverna in Mandrakia with iconic views of the boat garages and octopus drying on a line. We ended up grabbing a few photos but skipped the long wait of eating there and instead opted for dinner at a quaint taverna in Pollonia which felt more like our speed.

Where to Stay

We loved the Melian boutique hotel in Pollonia. The rooms were charming and cozy with to-die-for sunset views (dare I say better than Santorini), the staff was extremely attentive and our stay included breakfast (which was off-the-charts delicious!)

Where to Eat

Dinner in the tiny village of Plaka is a must!  Get lost in the narrow walkways and explore this charming town.  We ate at Avli, an outdoor 8-table restaurant with tasty, simple Greek food and a great spot for watching lovers stroll by.

Don’t miss Mrs. Rose cafe in Pollonia…go for an espresso & dessert and enjoy on the charming back patio.

Up Next: Sífnos

Go for: gastronomy & traditional pottery

Only an hour ferry ride from Milos awaits Sífnos! It’s incredible how different the landscape varies from island to island.  The first thing we noticed was how green Sífnos is compared to some of the other places we’d visited in the trip—the island also features beautifully constructed rock walls throughout. This island was our favorite part of the trip and I think a big part of that was our hotel (see below)! 

Sifnian pottery is famous throughout Greece, so we sought out two famous potters.  We met Giannis Apostolidis, who generously showed us his workshop and demonstrated how he creates his beautiful ceramics. 

Tim and I both got to take a turn on his pottery wheel to play with the clay and to create. We also sought out Atsonios Ceramics in Vathi… if you can find it, it is completely worth it (and an adventure)! I’ll give you a clue: go to the far end of the bay in Vathi and look for the stone steps in the mountainside…keep going!!

Where to Stay

Just bury me at Verina Astra… but like, for real. This was one of the most magical hotels we’ve ever stayed at. The 180 degree views of the Aegean Sea and steep cliffs dotted with blue domed churches were a literal dream. I audibly gasped when our car turned the corner and saw the incredible view for the first time. Each morning we watched the sun rise from our wind-swept veranda over the sea—I don’t think I’ll ever forget it. 

From the hotel, there are two beautiful hikes that we really enjoyed. One morning we hiked down to the little church that is just below the hotel and then continued to the sea. The water was rough so there wasn’t anywhere to walk or relax on the beach, but the views were spectacular.  

The following morning we set out for the medieval town of Kastro to visit the Chapel of the Seven Martyrs. Both hikes were a workout…think loads of cobblestone, steep hills and lots of direct sun. Go early and bring water but don’t let this deter you—both hikes were definite highlights of the trip for us.

Where to Eat

Try the restaurant at Verina Astra! Definitely sample their version of a Greek salad with Sifnian cheese, olive seeds and onion and garlic flowers. It doesn’t look like a traditional Greek salad but when you close your eyes and take a bite, it tastes exactly like the version we’re used to here in the States—however, this version is even prettier to look at.

One of our best meals on the entire trip was at Omega 3 for dinner. You’ll need to make a reservation a few weeks in advance, but it’s a must. There are tables in the sand and some in the taverna. All of the plates are meant to be shared. Don’t miss the ceviche or the scallops!

Next Stop: Amorgos

Go for: getting away from it all & high mountain views 

Because you can only get to Amorgos by boat, it seemed to be the least populated with tourists. I don’t think we met another American couple during the three days we were there. Like all of the islands, you’ll need a rental car and be sure to watch out for goats—they’re everywhere! Our highlights here were the beautiful high mountain views, snorkeling at Mouros & Agiana beaches and visiting the capital town of Chora. (We loved it so much, we went twice!)

Where to Stay

We stayed at the Aegialis Hotel & Spa, a 55-unit hotel on Aegiali Bay. I think if we were to go again, we would look for something a little smaller and more quaint. We drove by a cute little sand spit with a small hotel called Aqua Petra that looked simple, clean and might be worth a shot next trip!

  

Where to Eat

Do not miss Ston Pyrgo! It’s a hunt to find it in the tiny village of Arkesini, but we had our single best meal here. I have thought about the goat in olive oil with potatoes a thousand times since we were there—it was THAT good. Tim was similarly struck by the fava beans.  For most of the meal, we were the only patrons there and it was a full family affair, with the young daughter waiting tables, her mama cooking behind a little Dutch door, and it is an experience I don’t think we’ll forget!

 

If you go to Mouros Beach, plan to have lunch at the cafe above—the views are killer! 

Lastly, Chora was a magical town to visit for sunset…the village’s narrow paths were so fun to wind through and explore. We ducked through tunnels and wove our way up to Apospero, a one-of-a-kind spot to enjoy a leisurely dinner and people watch.

Final Stop: Santorini 

Go for: sunsets & whitewashed caldera views 

We weren’t sure whether we wanted to visit Santorini, as we had heard how crowded it has become, but I have to say we were pleasantly surprised by how much we enjoyed it. Yes, it is very crowded, but we were able to avoid the crowds for most of our stay. 

We stayed two nights at Canavas Oia and mostly lounged in our plunge pool while enjoying the beautiful views from there. This was the only island we didn’t rent a car and truly just relaxed at the hotel—it was the perfect way to end the trip.  

It gets crowded at sunset with most people heading to the western most end of Oia to get a photo of the sun setting on the sea. At sunset, we climbed up and headed east instead and wow! I loved the views of the Caldera with the sunset behind it… we only saw a handful of people and I would definitely recommend giving that a try if you’re looking to capture sunset photos and don’t want to wade through a massive crowd. The photos in Oia were some of the most beautiful from our entire trip; I completely get what the allure is now.

Where to Stay

Canavas Oia was a great location in Oia. Our room was built in the side of the Caldera like a cozy cave.  We loved having the plunge pool outside our room. Pro tip: if you go, ask for a room with a private plunge pool so there aren’t folks walking by you on the way to their room.  

Where to Eat

Snag a reservation at Lauda… this was our most elevated meal and the staff didn’t miss a beat. Michelin star rated chef Emmanuel Renaut’s skills were on full display with the six course tasting menu. Our waiter placed a multi course amuse bouche on our table and we just knew it was going to be an incredible dinner.

Take the 200 steps down to Amoudi Bay for sunset and dinner at Dimitris. Note: There is donkey poop (a lot of donkey poop) the entire way down, so if that feels a little too gnarly, you can take a cab down as well. Our table at Dimitris was on the edge of the dock with the waves gently splashing up against it and the sailboats bobbing back and forth in the bay—truly a great final meal for our trip! Pro tip: Get the lobster spaghetti for two!

Hot Tips

• Book early. Many of the best hotels book a year in advance and foodie spots like Omega 3 and Lauda will need advance dinner reservations too. We worked with Liz at The Local Foreigner who booked our hotel stays, restaurant reservations, personal excursions and all our transfers (car rentals, ferry tickets, flights, and a few car transfers). Her fee was minimal in comparison to the service we received and SO worth it…I will never travel without her again.
• Buy or rent snorkel gear! We brought snorkel masks and used them everywhere… the water was warm, teeming with fish and we were glad to have them.
• Don’t forget your paperwork: an international drivers license, Passenger Location Form (needed to board the flight to Greece), COVID vaccine card (or negative test) and a negative COVID test to return to the US. Liz helped us with all of this and the Local Foreigner app was a life saver! Our daily agenda and all pertinent information was in the app and we used it several times throughout the day.
• Bring seasickness medication if you are prone to seasickness! The waters can get pretty rough when the wind blows—quite a few people were sick on each ferry that we took. I get motion sick easily and was so happy that I had a prescription with me.

This is my favorite vacation that we’ve ever taken.  I left feeling like my cup was full & inspired with so many ideas and designs swirling in my mind (stay tuned)! It was the right amount of adventure and relaxation. 

I fell in love with the Greek people; they are so kind and proud of their culture. The food was gooood (like really good) everywhere we went—we didn’t have one bad meal. I just loved how easy it was to get off the unfrequented path and avoid tourist traps. We felt very safe everywhere we went. The locals are also very helpful and kind. Three days in each of the smaller islands was the perfect amount of time, although I would have stayed forever at Verina Astra in Sifnos if they let me.  It was really that special. 

Thanks for following along! 

xx

Jillian | Founder & Lead Designer