Why I Broke My Own Travel Rule — and Went Back to Crete

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Earlier this year, I did something I never thought I would: I went back to the same vacation spot twice. Revolutionary, I know. I’m a textbook Sagittarius that chases the allure of new experiences. But when my parent unexpectedly passed away earlier this year, I didn’t feel like chasing novelty — I wanted somewhere I remembered feeling wildly happy.

One night, over dinner in Chania, we met an older British couple who told us they’d been vacationing in Crete for twenty-five years in a row. Granted, that’s a little easier when you’re already across the pond — but maybe that conversation planted the seed. Because when life felt too heavy this year, I knew exactly where I needed to go back to. Buh-bye emails, hello souvlaki.

Why This Island Feels Different

I always tell people that Crete helps me understand how mythology once existed. As Greece’s largest and southernmost island (and the legendary birthplace of Zeus) it feels like it’s still connected to something bigger, deeper. Mountains are speckled with wild herbs and Minoan ruins, ancient fortresses that tumble into turquoise coves, and the whole place has a magic that doesn’t feel man-made.

My “plan,” if you can call it that, was to not really have one. In fact, I think Crete rewards that kind of energy. Eat, swim, nap, brain go quiet, repeat. By the time my flight touched down at Chania’s airport, I was ready to do exactly that. 

Starting Slow in Chania

My first stop was Chania, a compact harbor town on Crete’s northwest coast that’s lively, easy to navigate, and literally layered with history. Modern conveniences (yes, there’s a Sephora) coexist with the island’s past — like Venetian and Ottoman influences alongside Minoan ruins that date back nearly 5,000 years. It’s the perfect place to downshift from a go-go-go routine into the slower rhythm that defines Crete. You can sit, savor, and space out for a while — no one’s coming to rush you off so the next brunch crowd can sit down.

I checked into La Maison Ottomane, a small property in Kastelli, the oldest part of Chania. From the terrace, you can spot the site of a former Venetian cathedral destroyed during WWII, where Minoan ruins were later uncovered beneath the square. My room, the Roxelane Suite, was a welcome sight after a day of travel with its (ginormous) alcove bathtub and velvet-draped furniture. Mornings begin with a terrace-side breakfast spread of homemade jams, thick Greek yogurt, and a few coffee refills to blast through my jet lag. It’s also when you’ll likely meet Andreas Romanos, the charming owner always ready with a story or a tip.

When it comes to food in Chania, the best spots are tucked away — so save these on Google Maps. Start with coffee and a kalitsounia (a flaky cheese-filled Cretan pastry) at Οικοτεχνία Κρητικών καλιτσουνιών Γιανναράκη, a bakery by town hall with a few outdoor tables.

For something heartier, go to Apokoronou, a family-run joint locals actually eat at. (Do as they do and order the lamb chops and greens). Or opt for something quick from the souvlaki legend Oasis. Three-euro pork pitas, perfectly grilled and eaten standing on a street corner. Then end on a high note at Bougatsa Iordanis, home of the bougatsa that will ruin all other pastries. Sugar-dusted filo, warm myzithra cheese, sweet-salty perfection.

To eat as much as possible, walk it off between meals — and maybe do a little souvenir hunting while you’re at it. At Παντός Χαιρού, I found handmade prints and folk-style textiles and a few streets away, Douka Jewelry Workshop became my repeat stop for gifts. Between the food, history, and friendly shopkeepers, Chania makes it easy to slip into the rhythm you’ll need to explore more remote parts of the island.

Exploring Crete’s Southern Coast

A rental car in Crete isn’t optional — it’s essential. Public transit technically exists, but it’s infrequent, and most of the island’s best spots are far off the main routes. While obviously worth the effort, driving south toward Hora Sfakia does mean zig-zaggy mountain switchbacks and deep gorges in a tiny Fiat Panda. I based myself here for a week — long enough to explore the coastline by car to the east and by ferry to the west.

I stayed at the Authentic Village Boutique Hotel, a bright and modern stay with a surprisingly well-stocked mini fridge (restocked daily) and air conditioning that’s worth its weight in gold come August. The staff was endlessly kind, indulging my broken Greek every morning and pointing me toward the bakery around the corner. Hora Sfakia might be small for a long stay, but it’s strategic. From here, you can hike or ferry-hop to beaches and villages unreachable by car.

To the east, it’s easy to reach Frangokastello Castle, Plakias, and the postcard-perfect Kalypso Beach by car. Head west, and the roads stop — so you’ll need to take the ferries, like the Anendyk or Athitis lines, that connect the coastal villages. Pro tip: Snap a photo of the departure schedule at the port; the times vary and it’s easy to lose track. And if you miss the last boat, taxi captain Stavros can save your day with a flexible (and slightly rogue) water ride.

As far as stops go, don’t miss Loutro: a tiny, whitewashed village accessible only by water that feels frozen in time. Marmara Beach is a short boat ride away, where cliffs frame electric-blue water perfect for cliff-jumping or floating the afternoon away. From there, hike the rugged coastal trail to Lykos Beach, a half-hidden cove where Georgoshouse Taverna & Rooms waits at the finish line. I arrived overheated and promptly dove into the sea before ordering a cold drink and a dakos salad (another Cretan must-try) to refuel. Sitting there, salty and sun-dazed, waiting for the ferry back, I realized my “brain go quiet” plan had actually worked.

Resort-Style Rest in Rethymno 

I’d never stayed at a resort or done the all-inclusive thing before, and honestly, I wasn’t sure it would be my vibe. I thought I’d miss the thrill of finding tucked-away tavernas and little coffee spots. But LuxMe White Palace Crete turned out to be exactly what I needed to close out my time on the island — and, frankly, to recover from a year of trying to hold everything together.

While it was an adjustment for a restless traveler like me (I blame my Virgo moon and Capricorn rising), once I settled in it was pure bliss. The property has that classic Greek look — crisp white walls, blue details, and an endless sea right outside the glass doors. When we checked in, the staff surprised us with an upgrade to a junior suite with a huge balcony and pillow menu (yes, pillow menu). It was just the start of LuxMe putting everything I could need at my fingertips.

The team seemed to anticipate needs I didn’t even know I had. When I mentioned I didn’t drink, they secretly swapped the champagne in our room for a bottle of non-alcoholic wine before we even unpacked. Here, the overthinking brain can finally rest. In fact, the only real thinking you’ll have to do is deciding which of the seven on-site restaurants to eat at. Meals require advance reservations through the hotel app (and they can fill up fast), but the staff can usually help squeeze you in if you’re short on time like I was.

For two days straight it was just me, my Kindle, and a perfect loop of ocean dips, freddo cappuccinos, and naps in a beach cabana. But I can only lounge for so long and one afternoon we decided to look into LuxMe’s list of activities  —  booking parasailing and mini golf a little thrill of adventure. What I didn’t expect was cracking jokes with the parasail crew (being American, there’s plenty of material to work with) and chatting with the mini golf owner for an hour. Even in a resort bubble, that thread of connection somehow still weaves everyone together.

My only regret was that I couldn’t spend a few extra nights at LuxMe  —  I unfortunately had a plane to catch. It takes a minute to get into the resort rhythm, but once you do, it’s really hard to go back to real life.

What to Pack & What You Can Buy There

Learning this firsthand from my first trip: you don’t need to bring half the stuff you think you do. Crete is sun-drenched and full of pharmakeia — local pharmacies that double as beauty boutiques. They’re stocked with European sunscreens, skincare, and every travel-size product you forgot. Don’t waste precious suitcase space on SPF or shampoo; save that room for olive oil and honey on the way back.

What you should bring are the things that make you feel pulled together with zero effort. Here were a few of my carry-on winners:

Versatile T-shirt: Perfect White Tee’s Hendrix V-Neck

Even though I packed a few planned outfits, I ended up living in this tee and denim cutoffs. It’s a basic that’s been painstakingly perfected yet looks completely effortless. Slightly boxy fit, breezy soft cotton, somehow makes you feel put together in just a t-shirt and jeans. I will never not pack one in the future. 

All-Terrain Sandals: Chaco Mega Z/1 Wide-Strap Classic Sandal

If you plan to do any exploring (and you will), skip the flimsy sandals. Chacos handle rocky beaches, hikes, and steep cobblestones with ease so you don’t roll your ankle. They’re waterproof (keyword!), adjustable, and cute in that crunchy gorpcore way.

Throw-On Dress: Doen Nessie Dress

This was my MVP piece — lightweight, flattering, and compact enough to roll up without worrying about wrinkles. Ideal for hot days when you want as little fabric touching your body as possible or dressed up for evenings out. And for the petites (I’m 5’2”), Doen’s minis hit that just-right length.

All-Purpose Tote: Baggu Standard Bag

You probably already have one, but it bears repeating: bring a Baggu. An ultra-foldable tote almost always saves the day. They’re roomy enough for your “just one more thing” purchases and perfect for separating wet swimsuits or sandy shoes. My little hack is to slip the handles over both shoulders, so you can wear it like a backpack if you need to free-up more hands...for more things. 

What Stayed With Me After Crete

I left Crete a little lighter — metaphorically, not in luggage weight, thanks to the olive oil situation. Going back wasn’t about checking more places off a list; it was about getting a little perspective after a rough year. Somewhere between the (mildly terrifying) hairpin turns, endless iced coffees, and the freedom of having no plan, I remembered what it felt like to not be in constant fix-it mode. Which, in my opinion, is the ultimate indicator of a successful vacation.

So if you ever find yourself booking a ticket to Crete — whether it’s your first trip, your second, or your twenty-fifth like that one couple — I hope it gives you exactly what you need, too.