For me, the hardest part about planning a trip is deciding where to go. I rarely return to the same place twice and have the longest list of places I’m dying to visit (like you, I’m an avid YOLO reader, so my list is never-ending). Thus, the bulk of my trip-planning is spent deciding what to tick off next. This usually boils down to a few factors.
First, I look for places I hope will strike the perfect balance between relaxed, easy-going, natural vibes and enough comforts for it to feel like a treat. I work really hard throughout the year (what entrepreneur doesn’t?) and when I’m off duty, the biggest luxury is to have everything fall into place in an unassuming, effortless way. (I realize as I type that this is exactly the experience I hope people have with my designs, so I guess it’s not surprising that I’m looking for the same thing for myself.)

Next, I talk to my partner and decide how adventurous we are feeling—does a road trip and constantly moving around sound exciting, or are we looking to chill? We love to do both; what feels right just depends on what’s been happening in our lives.
Finally, time of year plays a big role in our decision-making. Of course, there is the obvious weather factor. But also, I like uncrowded places. With so much of my work life occurring around so many dynamic, inspiring people—I realize how lucky I am to be able to say that—having time to completely switch off and just be quieter is so critical for my well-being and my creativity.
This year, I was planning a trip for late June. This was my short list:
1. A road trip from the Médoc to Île de Ré and up through Brittany. I love road trips through Europe, stopping in small villages and seeing the expansive landscape, and after hearing Yolanda’s tales of France’s West Coast, this trip has been at the top of my list for so long.
2. A trip to the Alps. I have always wanted to stay at Villa Flor in the Engadin (my friend Silka told me about it, and you never go wrong with a recommendation from her). Or Waldhaus Sils (my friend Akari told me she is visiting this summer and is another friend whose word you just trust blindly). I went to Gstaad one summer when my mom came to visit—we started in Zurich (loved our dinner at Kronenhalle and swimming in the lake the next morning after too much wine), and then drove into the mountains. I honestly think the Alps are one of the best-kept summer travel secrets—the air is so fresh, the sun so bright, the food so yum… the definition of gemütlichkeit.
3. As I was debating these two choices, I decided I was craving proper summery beach feels by the sea. Yes, the West Coast of France is on the ocean, but I wasn’t sure how warm it would be in mid-June, especially up near Brittany. I also have been travelling a lot for work lately, and was feeling more chill, less road trip. And that’s how I turned my attention to Greece.
I’d visited Patmos the previous summer (another YOLO rec) and fell in love with it. I made sure to go in July before the August craze, and it really was perfect. It’s not the easiest to get to, but I am sure that’s part of what protects its charm.
In Patmos, I’d stayed at Pagostas, and loved chatting with the owner, Gregoris, who invited us to dinner one night with his friend who had just been to Sifnos and was raving about it. She said if we liked Patmos, then Sifnos would be perfect for us. A few months later, I was trading travel tips with my friends Aziz and Serena, who said they also love Sifnos. We’d trusted their recommendation to check out Pantelleria the summer before, so knew we shared a vibe.
The first task when planning a trip to a Greek island is figuring out the best route. Often you need to fly to one island and hop a ferry to another, and the times rarely stack up. For Patmos, we had to fly to Kos and then get a private boat, which cost the same as the flight! Or else overnight on Kos before an early morning ferry, which would have cost just as much and we’d have lost a night… not ideal. At first, I thought we would be in the same boat (pun intended) with Sifnos—it looked like every flight from London to Athens would get us in after the departure time for all ferries… but luckily my stubborn side kicked in and I found a way via Santorini. There was a helicopter option from Athens to Sifnos that wasn’t too unreasonable (similar to a private boat), but the baggage allowance was limited, so we’d have to pack very light.
With our flights sorted, the next order of business was figuring out where to stay.
Practically every article I read about Sifnos recommended Verina Astra or its sister property, Verina Terra. Both were booked out for the entire summer by the time I looked, and my friend Aziz recommended we investigate an Airbnb. After scouring hundreds of properties, I found what looked like the most perfect place… but could it be too good to be true? The cynical side of me was very concerned but honestly, it just looked perfect… so I took the plunge.

I am pleased to report it was even more perfect than I imagined. Kavos is a cluster of little houses perched about Fassalou Beach, at the center of which is a communal pool and a bar run by the nicest people. It’s basically the best of both worlds—you get to have your own private home with a terrace and kitchen, but still have a place to grab a coffee or a snack or drink. I am an early riser while my partner sleeps late, so having our own terrace and space to be in the mornings is so nice for me. I do yoga, catch up on emails, read, have a coffee… It’s nice. The vibe at Kavos is so chill, and the views are breathtaking. It was in a great spot on the island, too. There isn’t one perfect spot to base yourself, since there are great things to see in the north, south, east and west, so be prepared to drive. I am a very happy passenger and luckily my boyfriend loves to drive, so it works for us. We loved listening to tunes and checking out the landscape as we discovered the island. On that point, make sure you reserve your car (and flag if it needs to be automatic) ahead of time—you will definitely need one. (We used Rent-a-Car Sifnos – info@rentacar-sifnos.gr.)
Lastly, I looked for recommendations for beaches and restaurants. Luckily my friend Chris did a pop-up last year on Sifnos for his London sushi spot, Urchin. I knew Chris would send me in the right direction. Here are a few places we loved:
Beaches

Spend a day driving to the remote beach in the north of the island called Vroulidia. You can drive all the way down, but I would park before the road becomes gravel-y and then walk down. Even to get to that point, take heed – the road is not for the faint of heart! But it’s worth it. We loved it so much we went twice. There are two beach tavernas and we tried both, but I think the better one is to the left when you get to the bottom of the hill.
For a more lo-fi beach day, Chrisopiggi Beach is really nice. You just bring your beach towel and lie in the sand. The taverna there is great for lunch, too. It’s low-key and relaxing.
Vathy Beach is also great. There is an organized beach club towards the end of the beach if you want a lounge chair. I was not a fan of the very poppy pop music, but I suppose you need a little dose of that when you’re on a southern European holiday! And you must eat at Manolis for lunch. Don’t go anywhere else. Trust me.

Paralia Seralia – This is a great little swimming spot my friend Christie told me to check out. It has a cute lunch place called Captain George, which opens at 1:30 and has just 5 tables, so if timing works to eat there, that’s the move. We always left the house too late (again, Max sleeps in), so we were more on the 4pm lunch train. but I wanted to share as Christie loved it, and I know that means it’s great.
We stayed just above Fassalou Beach, and I went there on my own one morning while Max was sleeping (haha Max is going to kill me when he reads this!). Lucky for him, he didn’t miss much. The beach was nice, of course, but I wouldn’t make a day trip for it if you aren’t staying at Kavos–—I also didn’t think the taverna was the best, but good to check out if you have a free morning due to a late sleeping partner (ok, ok Max, I’ll stop now).
Restaurants

Cantina – this is where to go for a special night out. It’s a set course-sharing menu and the restaurant is nestled in a valley and into the rocks. The food is delicious, and the team is wonderful. Try to get the table high up above everyone—it’s a great view and feels really private.
Pelicanos – This restaurant is also owned by Giorgas, who owns Cantina. We loved it here so much we went twice. The crab cacio e pepe is insane… it’s the sort of restaurant I wish there were more of. It’s food you really want to eat but can’t easily make for yourself at home.
The taverna at Vroulida (see above in beaches), when you make a left at the bottom of the hill, was so good. Max and I shared a Greek salad and I fell in love with amaranth greens.
Manolis at Vathy Beach is great. Try to get a table near the ocean.
To Limanaki – A taverna at Faros that was so yum. We went there on our first night—it’s just 5 minutes from Kavos and was the perfect authentic Greek meal to set the tone.
Bars

We stopped by the Kastro, a mountaintop village, on our way back from Vroulidia one evening and checked out Loggia, a really cute wine bar with incredible views and good music (I did a lot of Shazam-ing that night). We weren’t super hungry for dinner due to our late lunch habit, so just had some nibbles at Loggia before heading back to our house for an early-ish night under the stars.
Chris told me about a local scene to watch the sunset at a beach café called Paralia Beach Bar at the Kamares port – we didn’t make it, but wanted to pass along the tip.
And lastly, I didn’t make this either, but I would be completely remiss not to share a friend’s exuberance about Botzi Bar, which apparently is really fun. I am imagining it like something from the bar scene in Call Me By Your Name—I’m not sure why I have ‘80s Italian disco in my head, but as I didn’t end up going, someone else will have to go to tell me more!

And there you have my Sifnos tips. It was the perfect choice for a late June getaway –just what the doctor ordered. We were able to really go with the flow and chill.
A final bit of advice: I like to do all my research ahead of a trip so that when I get somewhere, I can completely detach. I don’t love having to make reservations or planning when I am on holiday; I really like to go with the flow. So if you are like me, and want to avoid reservations and too many crowds, it’s best to avoid August, like most of the Greek Islands or southern Europe, for that matter. Which is why exactly why—surprise, surprise—I am planning a little getaway to the Alps in August!
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