The Sunday Series

The Sunday Series

Travel Guides

Where I'd go for Euro Summer if I were you...

18 ideas for an epic holiday—none of which involve competing with fellow New Yorkers for a table in Capri.

Kayla Douglas's avatar
Kayla Douglas
Apr 19, 2026
∙ Paid

This week was charged with the hum of New York waking back up from winter. We were graced with several 80° days, and in turn, the evening streets were buzzing with the soundtrack of clinking glasses, the smack of flip-flops freshly out of storage, clattering silverware, and laughter practically echoing off the pavement.

I felt feral for it all. Relieved to be outside without a jacket, I was struck by the condition that often afflicts me in these conditions: I forgot how to cook for myself. In fact, this past week, I ate out more times than I can even count, savoring new and old favorite bites that deserve their own moment in the sun. The fried chicken sandwich at Empire Diner. The burger and exceptionally creamy vanilla custard at Wild Cherry. The oven-roasted chicken that tastes like Paris at Raoul’s. A scoop of pistachio and cannoli ice cream from Salt & Straw. The shaved brussels sprout salad from Left Bank. The mint chocolate chip smoothie from Sunlife Organics. My favorite lunch for when I’m just a ~littleeee~ hungover: the chicken caesar wrap from Edith’s. The fried artichokes at Hudson Clearwater…actually, come to think of it, I had fried artichokes three times this week, including at Bottino, a beloved spot that returned our request for the check with a receipt showing no amount due, just “THANK YOU!” scrawled in Sharpie.

God, I love New York.

There was real work, workouts, therapy, 10,000+ steps a day, and lots of laundry, too. But for the sake of the letter, let’s talk about what this warm weather did to my psyche…naturally, it had me fixated on summer plans. Or rather, my lack thereof. I became particularly obsessed with how and where I’ll spend Labor Day, a holiday that just so happens to fall the day before my birthday this year.

If you’re new around here, perhaps you don’t know about my birthday trip tradition. Let me catch you up about just how insufferable I am!!!!! Since turning 21 in Barcelona, I’ve made a point to be away on my actual birthday (Virgo much?) every single year. From Sri Lanka to Vietnam to Mallorca to Mexico, I’ve held strong on this shtick for a decade and counting. So, with years and years of recon under my belt, I’ve got lots of ideas about where to celebrate your birthday solo, with a partner, or with a gaggle of friends.

31 ideas for your next birthday trip on my 31st birthday

31 ideas for your next birthday trip on my 31st birthday

Kayla Douglas
·
September 9, 2024
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If I’m being honest, for many years, my birthday trip plans have fallen together rather last-minute. But not this year. No, this year, I have a clear vision of the twelve-room hotel in Northern Africa where I dream of waking up the morning I’ll turn 33. So instead of hemming and hawing and trying to line something up via work, I did something unusual for me. I went straight to the hotel’s website, booked and paid in full for our stay, five full months in advance.

Committing to a trip of this caliber when there are soooooooo many other destinations I could choose instead has historically been hard for me. I like to change my mind!!! I like to see what might pop up!! But having something to look forward to—and actually relishing the anticipation of that—feels like progress in a different way.

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And it’s exactly this indecisiveness, this constant urge to keep options open, that gave me the idea for this Substack. I’ll never be able to take all the summer trips I dream up (at least not in one season), so I figured I’d feed you a few of them—some from places I’ve visited and loved, others from the ever-growing list currently on my radar.

My credentials for compiling such a list? I’ve worked in the travel industry for more than a decade—and if there’s one thing I know how to do, it’s Euro summer. Naturally, travel is ever-present in what I share here, and paid subscribers to The Sunday Series have access to my travel guides, in addition to my top hotel stays of all time which includes the check-ins around the world that are at the top of my list.

155 Hotels So Special, They're the Destination.

155 Hotels So Special, They're the Destination.

Kayla Douglas
·
December 21, 2025
Read full story

And on that note, the majority of this letter will be reserved for paid subscribers, as I want to make sure those who support my work here are genuinely feeling that value. These recommendations are the result of more than fifteen years of investing in my own travels—and I really appreciate the support that allows me to keep doing so!

While places like the Amalfi Coast, Capri, Lake Como, and St. Tropez surely have their appeal, I’m not personally in a season of life where I’m gravitating towards these hotspots in high season. To me, going somewhere super trendy during peak June, July, or August dates is just asking to be amongst a heavily American jetset crowd, and that doesn’t do it for me. I mean, if I wanted to wind up at a restaurant cozied up next to a table of my NY neighbors in summer, I’d just go to the Hamptons! No need to trek to Italy for that. So, my Euro summer suggestions are going to be a bit more off the beaten path.

Turkish Riviera Meets Greece—Combine Bodrum and Kos: I turned 30 at Maçakizi Hotel, and my mind wanders to this Bodrum paradise often. I desperately want to go back, and this time, I’d combine it with Kos, a Greek island that you can reach by ferry in about half an hour from Bodrum. I’ve personally got my eyes on Ikos Aria in Kos, which feels easygoing and unfussy. The island is known to be flat and bikeable, unlike many Greek islands, making it ideal for cycling from beaches to town.

My friend Jenna captured this perfect moment of Chelsea and me at Maçakizi…TAKE US BACK ALREADY!

Charter a Turkish Gulet with Friends: I looked into booking a gulet boat for the same birthday and know it’s an idea I’ll come back to one day. What makes it so appealing is just how attainable it is, price point-wise—especially when split among a group—without sacrificing any of the magic. Think slow days hopping between hidden coves, long lunches on deck, and the kind of sun-soaked, slightly unstructured rhythm that makes for the best kind of group trip.

A Greek Island Hopping Trio with Athens, Milos, and Sifnos: I fell in love with Athens last summer. We combined a few nights at the Four Seasons Astir Palace Hotel Athens with Zakynthos (loved Lesante Cape and our boat day, but the towns on the island weren’t the most charming IMO), which reminded me how much Greece has to offer. For my next island-hopping adventure, I’d combine the mainland with Milos, where Skinopi Lodge looks like actual paradise, before taking a ferry to Sifnos, where Stamna Sifnos has my eye.

Blues for days from Four Seasons Astir Palace Athens

The Car-Free Greek Island Calling My Name: I once read a book set on Hydra (Beautiful Animals by Lawrence Osborne), and the island has been humming in my subconscious ever since. Perhaps what appeals to me most is that cars are banned here, and if you didn’t know this already, I actually don’t have a driver’s license, so this is my literal dream! I’m crushing on Bellevalia Hydra, which sits between the mountains and the sea with just eight rooms.

Marseille over St Tropez: Some of the chicest girls I know are forgoing St Tropez for Marseille and its surrounds. A grittier, more multicultural version of the Riviera, Jacquemus is just one of many creatives hailing from the region—a place that acts as a hub for chefs, artists, and entrepreneurs. Specifically, Tuba Club, located forty minutes from town in a small fishing village, stands out as the cool-kid hotel with its rocky swimming cove and yellow beach chairs that seem to have my name all over them.

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