The Sunday Series

The Sunday Series

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The Sunday Series
The Sunday Series
A love letter from me, to islands everywhere.
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A love letter from me, to islands everywhere.

plus, islands at the top of my wishlist—penned from Zakynthos, Greece

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Kayla Douglas
Aug 17, 2025
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The Sunday Series
The Sunday Series
A love letter from me, to islands everywhere.
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Happy Sunday from the gorgeous Greek island of Zakynthos!

First thing’s first!!!! Coming here was a bit of a hairbrained, last-minute endeavor fueled by a remote work week. While I’m typically in the office Tuesday, Wednesday, and Thursday, a scheduling change just ahead of a work trip on the books created a window of opportunity for me to be nimble. Naturally, I ran with it. That said, this stretch of days means maximizing morning sun before being on my computer to stay on task with various projects and meetings once New York wakes up. Fortunately, I’ve honed the discipline I need over the years to make stretching the time zones look easy…even if no one is seeing the 1 am sessions on my laptop in a hotel bed (including the one that got me over the finish line to send this very newsletter—my fourth session sitting down to work on it…cue perfectionist Virgo *sigh*).

I mention this all because I think the perception of what frequent travel entails and the reality are quite different—any of my travel industry colleagues reading this who are constantly fieled with accusations of, “but you’re always on vacation!” can relate. I used to get annoyed by these comments. Now, I realize they are actually compliments. It’s a gift to have a bit of flexibility, and as a maximizer by nature—I’m someone who always wants to make the juice worth the squeeze, if you will—I’ll always try have work and personal travel intersect in a way that reaps optimal impact. So, as I find myself on an Ionian island that I had zero plans to visit about a week ago, I thought today’s letter could be an exploration of my island obsession.

I’d begun to feel a huge pull to Greece earlier this summer (oh, the power of social media!), and considering I haven’t been back since college, when a friend and I spent a couple of weeks bopping between Crete, Santorini, and Mykonos, a seed was planted. Islands like Paros, Antiparos, Milos, Kos, and Sífnos have been earning IG bookmarks from me left and right…not just for their freddo espressos and towering mounds of fresh feta, but for the lesser-trafficked beaches and boutique hotels that may not have the name-brand appeal, but a whole lot of soul. Suddently, I felt woefully overdue to return. Watching

Julia & Thomas Berolzheimer
and
Lucy Williams
’ (I’m linking up Lucy’s epic island breakdown below) recent Greece trips were the ultimate catalysts in swaying my need to come back for myself!

Remotely by Lucy Williams
Everywhere we stayed in Greece this Summer
It wasn’t a conscious decision but we ended up staying entirely at hotels for this 3 week trip to Greece. A total luxury for sure but I do find it a lot easier when you’re moving around a bit - no last minute rush to buy breakfast supplies, confusion over lockbox codes or crap wifi and hotels can store your bags for you after check out which is really helpful for afternoon ferries. I love a great Airbnb but sometimes finding them for two people with outside space where you want to be is quite hard I find (my husband is 6ft 3 so those cute iron-framed antique beds are a deal-breaker too sadly). So we based ourselves at hotels for this trip and didn’t have a single dud stay the whole trip which felt like a big win. Let’s go through everywhere we stay on this mini tour through some of my favourite islands plus one newbie…
Read more
20 days ago · 140 likes · 8 comments · Lucy Williams

There was a lot to learn coming to Zakynthos because while I’ve had this island on my radar for a couple of years, I actually didn’t know much about this particular brand of Greek paradise until arriving yesterday. The destination really came about as a viable idea based on its connectivity to Athens (where I flew from New York a few days ago), and it offers a direct flight to Amsterdam, where I need to be in a few more days. So, voilà! Logistics I thought worth mentioning in case you too are looking for a cheeky Greece extension one of these days and want to circumnavigate the somewhat unpredictable Greek ferries…

Despite my 6:30a alarm this morning to get more time in with The Sunday Series, today wasn’t an official workday. This meant we got out on the island to explore with a seven-hour, seventy-mile boat journey around Zakynthos jam-packed with highlights that included seeing a sea turtle in the clearest blue water to reading my latest book happily teethered on a tube to our boat for just long enough not to get burned before stopping at the famous Shipwreck Beach.

But, I’m getting ahead of myself! Since I’ve practically just arrived and don’t tend to do guides for places unless I’ve visited multiple times and feel I really, really understand the destination on a granular level (enter A No-Gatekeeping Guide to Mallorca, A Mini Formentera Guide, Your Ultimate Paris Guide, Your Guide to Bozeman, Your Guide to Nantucket) today’s edition of The Sunday Series isn’t about Zakynthos or our time precededing it on the Athenian Riviera, but instead, a more broad love letter to islands, and an attempt at an expoloration into why I/we can’t seem to get enough of them—incuding, the ones I’ve loved most and those on the top of my list to get to next.

  • An island-inspired packing edit

  • The Vault (Paid Subscriber Exclusive): A love letter to islands. Why I adore them, which ones I’d go back to, and the top islands on my hitlist.

  • The Vault (Paid Subscriber Exclusive): A curation of things I’ve consumed and loved this week: stories that have caught my eye

If you’d like to access the complete version of today’s and future posts, please consider upgrading your subscription! Paid subscribers of The Sunday Series unlock an exclusive section of paywalled content in each send, access to the full archives (including Your Local’s Guide to West Village, A No-Gatekeeping Guide to Mallorca, A Mini Formentera Guide, Your Ultimate Paris Guide, Your Guide to Bozeman, Your Guide to Nantucket, 100 Hotels I’m Dying to Check Into, My Holy Grail Rules for an Overnight Flight, 31 Ideas for Your Next Birthday Trip, A Playbook for How to Make Friends As An Adult, and 16 Prompts for a Personal Quarterly Review), the commenting feature on each post, exclusive giveaways, and more. Plus, your support directly helps ensure this newsletter can continue to grow! Subscriptions are $8/month or less than $7/month if paid annually—also known as less than one fancy Starb*cks order. But don’t let me be the one to tell you why you should upgrade! I’ll leave that to a fellow reader…

“I've been following your newsletter for the past few months and it's such a delight! It always makes me smile and I feel like your content is thoughtful and unique every week. I'm glad to finally be able to support you with a subscription.”
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But, before we get into the island adoration of it all, can we talk about the fact that packing for a beach trip is half the fun? I’ve managed to do these two or so weeks away in three different countries and climates in a carry-on, much in part to the fact that packing for a beach trip is a breeze! In this mini packing edit, I’m sharing some faves to keep on your radar. But first, I’m linking up a post from April where I dive into the nitty-gritty, including my favorite suitcases, packing cubes, beach-friendly makeup, and travel tech.

Shop My Beach Trip Curation

what's in my bag: carry-on to the Caribbean

Kayla Douglas
·
Apr 6
what's in my bag: carry-on to the Caribbean

happy Sunday, lovers…

Read full story
  • Athleta Retreat Linen Top and Retreat Linen High Rise Wide Leg Pant | Funny enough, I’d already drafted this section when I got the below texts from my bestie, Lianna. She was looking for my link to buy a second set! So here you are with the links to buy my fave travel set—literally wore it yesterday on the plane from Athens.

  • With Nothing Underneath The Boxer: Seersucker (Rain Blue Stripe) | If you follow me on Instagram (@curatedbykayla), you know I rideeee for With Nothing Underneath. Their linens and seersucker sets are a dream for any beach trip.

  • Lavanda Orquidea Pareo | This wonderfully versatile piece features tie fastening at the waist and can be mixed and matched with bikini sets and one-piece swimsuits alike.

  • Dôen Pamelina Ruffled and Lace Yellow Midi Dress | This is one I eyed in the Bleecker Street boutique, then saw on someone and was like oh WOW that’s fun!

💸 Aaaaaand as a disclaimer, this shopping section—as always—includes affiliate links. These little babes help me continually reinvest in making The Sunday Series better. I make a small commission when readers click and shop through my links at no additional cost to you—so if you found something through a link I sourced, please do consider purchasing through that link so I’m credited! Speaking of, I’ve been using the ShopMy platform for several months and love it. Want to start making commission on the links YOU share? Sign up with my referral link for a 10% bonus on your fist six months of linking.

ShopMy closet

Today’s edition is dedicated to my undeniable pull to islands. That visceral, inexplicable desire to be surrounded by turquoise water and a salty breeze. The healing warmth of vitamin D. The evergreen allure of boat day. The impossible-to-replicate pleasure of eating grilled seabass caught that morning mere hours later, served barefoot at a beach club. The freedom of diving into the sea, knowing your phone is on airplane mode—or, better yet, being on a body of water that doesn’t get a signal to begin with. The beautiful mess of a paperback getting wet—its pages waving and wrinkling—knowing you’re going to leave the book behind at the resort for the next person to discover. The restorative power of poolside giggles with my girlfriends. The sweet spot when the third cocktail sets in, beach lounger situated in the sun, a fire playlist in your ears. The giddy delight of winding through olive-tree-lined backroads.

When I reflect back on some of the islands I’ve been lucky enough to visit—Mallorca, Menorca, Formentera, Ibiza, Zanzibar, Pemba, Ile de Ré, Ibiza, Sicily, Saint Martin, Anguilla, Turks and Caicos, South Caicos, St Lucia, Aruba, Jamaica, Grenada, Puerto Rico, Nantucket, and more—it’s not just the places themselves, but the impression they’ve imprinted on me, each different in their own right.

And because I know many of you share this same magnetic pull toward islands, I’ve put together something special on the other side of the paywall: a guide to the island experiences I think are most worth prioritizing. Think of it as the short list—the places where the boat days hit on an even deeper level, the beach bar/chiringuito/taverna/bar de plage is worth flying across the world for, and the UV index is hopefully hovering at a solid nine.

Islands that live rent-free in my head

  • Anguilla: I went on a girls’ trip to this magical Caribbean island a few years back and it remains a top trip in my memory bank. We did a split stay between Cap Juluca, a Belmond Hotel and Malliouhana and fell in love with each of them for different reasons. The spa at Cap Juluca was just redone, so I’d say that’s reason enough to go back!

  • Île de Ré, France: When it comes to nostalgia, my memories tied back to this tiny island off the West Coast of France date back over a decade, from when I studied in La Rochelle. I had the chance to go back a couple of years ago with a stay at Hotel de Toiras, which is super historic and charming, but next time, I’d like to check out Villa Clarisse.

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