I Take Multiple Trips to Greece Every Year, and These Are the 15 Things I Always Pack — From $18

Greece usually dictates when my summers start and end. My first trip of the season is typically Santorini, before the crowds swarm the cave hotel-strewn cliffs of sunset hotspot Oia. I’ll sprinkle in a small-ship cruise through the Cyclades or along the coasts of the Peloponnese or spend a week hiking and wine tasting in Crete, Greece’s largest island. When I’m ready for a girls’ getaway, I’ll splurge on a quick jaunt to Mykonos (gotta love those cheap flights from Paris, where I’m based!) and don all of my Stevie Nicks-style beachwear for toes-in-the-sand dancing at Scorpios that goes from sunset late into the moonlit evenings. 

As a travel writer who has covered stories in Greece for nearly a decade, I’ve become a fan of the country’s homegrown designers and fashion — and I’ve also figured out how to capture this effortless, boho chic look without blowing through my summer birthday funds (as a Cancer, I believe the whole summer is worth celebrating). 

On a recent villa escape for a friend’s birthday in Crete, for instance, I lived in flowy linen pants, one-piece bone-colored bathing suits, and strappy leather sandals that could take me from a day poolside to an evening dining in a table on the sand on a tucked-away cove. The beauty of summer is that you can pack everything you need in a carry-on and have plenty of looks to last you a week or two — that is, if you know how to style them right. 

As I’m preparing for another trip to Mykonos later this month, followed by my annual August escape to perhaps my favorite island of the 6,000 in the Greek seas, Paros, I’ve scoured through deals at Amazon, Everlane, Madewell, and more to narrow down 15 of the must-have wardrobe essentials that’ll have you ready for everything from a swanky beach soirée in Hydra to coastal hikes in Crete and sundowners at chic cliffside bars in Santorini.

Steve Madden Donddi Sandal

Greece may be the land of leather sandals, but a pair that is a near dupe of some of the pricier designer styles you’ll find there is this look from Steve Madden. The subtle heel and buckle at the ankle are both functional and fashionable. You won’t be worrying about blisters after your first hour strolling through Oia’s uphill cobbled streets (or slip on them, for that matter). “These Steve Maddens are truly great quality, real leather, and they go with everything,” says one shopper. “I can walk around in them all day without complaint. They are a very simple design, yet have an elegant look to them.” 

If you’re only planning on packing one pair of shoes, these can go from the plane to the beach and still look put together for a nice dinner or evening dancing at a restaurant like all-night party hotspot Buddha-Bar Beach at Santa Marina, a Luxury Collection Resort in Mykonos. During my stay at the iconic resort at the end of last summer, I wore a similar pair while tanning on one of the sunbeds on the beach and dining at the stylish, see-and-be-seen open-air restaurant, Elais, and felt perfectly in place among the designer footwear around.

Cupshe Braided Strap Reversible Bikini

Swimwear is my weakness in summer, and I use the excuse that bathing suits hardly take up any space to pack too many of them. Even for two-week trips to Greece, I’ve found that I only need a bikini and one-piece and can rotate them out. This top seller at Amazon is the perfect solution to any packing woes, since the bottom is reversible. For just $33, this fashionable set is a two-for-one deal that seems too good to be true — just look at the gorgeous braided straps! 

And with more than 10,700 reviews, this set has proved to be a hit. “I didn’t think I would like this bathing suit, but it’s so flattering!” says one shopper. Another agrees: “There is something flattering about the cut of this. I don’t feel like I look good in a lot of two-pieces, but this made me feel different and the material feels good and comfy.”

Halife Sleeveless Halter Maxi Beach Dress

A flowy maxi dress is my one summer essential, whether I’m at home in Paris or at a beach club in Greece. Lightweight and easy to pack in a carry-on (why waste time waiting on checked luggage?), this is one of the most versatile wardrobe staples you could buy. On breezy evenings later in the season, throw on a denim jacket and pair of edgy motorcycle boots. For hikes to hidden coves, wear it over a bathing suit, tie it up on the side, and sport a pair of sturdy sneakers so you’ll have some grip getting down the boulder-strewn trails.

With a tie-dye print like this, all you need is a wraparound vintage-style gold belt and wedges or metallic sandals and you’re ready for a night out at beach bars and restaurants. Shoppers say it’s “perfect for a cruise” and “great for a beach cover-up or as a casual longer dress.” It also doubles as chic loungewear around your cave hotel in Santorini or seaside villa in jetsetter favorite Antiparos. 

Free People Tulum Tassel Sandals

Summer is raffia season, and I’ve already indulged in a pair of wedges and strappy sandals I’ve worn practically to death on multiple beach vacations (and unexpected hiking situations). After my recent trip to Crete, I wanted to find a pair of slides that capture the same vibe but are on the more durable side.

When these Free People Tulum tassel sandals by Seychelles popped up on my Instagram feed, I was instantly sold. Handcrafted in small batches by artisans worldwide, they embody Greece’s hippie spirit with their macrame strap and playful cream tassels, but unlike most slides, these ones are actually comfortable thanks to the square open toe (better for wide feet like mine!) and cushioned insoles. I’m looking forward to wearing them with a mix of printed linen shorts and breezy beach dresses on my trips this summer.

Aphoraeny Straw Beach Tote

The beauty of somewhere laidback like Greece (and this even goes for the celeb-filled islands) is that you can leave flashy designer purses at home and don something simple (and more practical) — like this straw beach bucket tote. If you only have space for one bag, this versatile choice, with its double, over-the-shoulder leather handles and structured oval bottom, make it great for travel (there’s even a zippered interior pocket for your wallet or phone). 

The lightweight straw design is about a half-pound, so it won’t get too heavy when you throw in a water bottle and Turkish towel for a day at the beach or sightseeing around ancient ruins in Athens or Crete. “This is the perfect summer bag — grab one for yourself!” raves one shopper. “You will love it! So cute and perfect with your summer clothes!”

Sunday Afternoons The Sunset Hat

Summer days can be scorching in Greece (last year, temps hit the 100s in Athens), so you’ll want to bring a hat that offers sun protection like this UPF 50+ cowgirl-style look. Roll the shapeable brim up or down, adjust the chinstrap so it won’t fly off while cruising the coastline or riding around the islands by ATV, and fold it flat to fit in your beach bag or pack in your carry-on. “I have not completely squished this hat while traveling — that’s been the death of other brands I’ve purchased,” says one shopper. “I can bend down one side of the brim slightly depending on where the sun is trying to get into my eyes. The more wacky the brim looks, the more compliments I get on it. My favorite!”

Farm Rio Garden Tiles High-waist Cargo Shorts

When I’m in Greece, I leave my denim at home and opt for something light yet structured. These high-waist cargo shorts from Farm Rio — the Brazilian brand that embodies endless summer vibes — are the perfect pick for day-to-night wear that embrace the throwback cargo trend in a more feminine way. The blue tile-inspired print feels right at home in the islands with their whitewashed buildings and azure domes that celebrate the colors of the Greek flag.

Pair with a tucked-in linen button-down, one-piece bathing suit, or a playful, off-the-shoulder crop top with a chunky gold chain choker for dinner at one of Santorini’s stylish restaurants like Mia’s, which shows off one of the best views of the caldera from Oia. (Pro tip: Arrive for cocktails before sunset and pose for photos on the terrace or rooftop.) 

Lnx High-waisted Wide-leg Linen Trousers

Once you get on board the linen train, you won’t want to wear anything else in summer. On a recent trip to Chania, on the northwestern coast of Crete, I wore my wide-leg cream linen trousers on the plane with a white denim jacket and T-shirt; with a crochet bikini top on hikes to sparkling turquoise coves; and with a one-piece swimsuit (I think of it as a summer version of a bodysuit) adorned with a gold buckle to mountainside tavernas for lunch.

This similar style at Amazon is an easy sell — at just $30, you can justify the splurge. Even better, since these tapered trousers fall mid-calf, they’re flattering for all heights and can be worn with sneakers, sandals, or more dressed up chunky heels or wedges. Nearly 6,000 shoppers are also fans. “Flattering, cool, and comfortable — perfect for summer,” raves one reviewer. “I am short (5’2”) and curvy — it’s hard finding pants that fit well. I liked these so much I bought a second pair (navy pinstripes)!”

Beneker Slip-on Canvas Low-top Sneakers

Whether you’re heading to a city or spending time along the coast, you’ll thank me for this recommendation. I’ve tried to go the espadrille route and friends have sported Birkenstocks, but for old cobbled roads and super steep cliffside treks, you’ll want more supportive footwear. Ditto if you’re touring hillside villages or uneven ancient sites (especially spots like the sacred island of Delos). 

Scoring more than 12,000 ratings, these low-top canvas slip-on sneakers have proven to be a winner. The soft in-sole ensures all-day comfort while sightseeing or exploring the islands, and the anti-slip outsole adds extra protection on sleek old stone streets or hikes. “I wasn’t sure since I have high arches and a sore big toe on my right foot, but I slipped these shoes on and fell in love,” says one shopper. “They fit perfectly, plenty of room in the toe box and they feel broken-in from the moment you put them on.” 

Madewell Embroidered Tank Linen Mini Dress

During the day, when I’m strolling around shopping in Naoussa in Paros or lunching down in Ammoudi Bay in Santorini, I want a simple dress that’s structured yet floaty — and doesn’t require much in terms of accessories for it to feel dressed up. This heavyweight linen mini dress from Madewell is my pick for the summer.

The embroidered square neckline is flattering on most figures, and you can skip a necklace, pull your hair into a topknot with a scarf tied around the bun, and sport simple raffia strappy sandals and voilà — you’ll look as if you summer every year here. “Will be wearing it all summer long with a pair of cowboy boots or my bright yellow espadrilles!” says one shopper. Another adds: “It’s a gorgeous classic summer linen dress.” The stark white also provides a beautiful contrast against rust-colored cliffs and the turquoise sea on islands like Milos.

Holipick One-shoulder White One-piece Swimsuit

While bikinis are great for tanning, on my past few trips to Greece, I’ve preferred one-piece swimsuits that provide more coverage (you’ll notice many Europeans do, too). One style that is still sexy while offering tummy control through its flattering, ruched design is this affordable find at Amazon.

I’m a huge fan of the one shoulder double strap, which you can slip down to avoid tan lines, as well as the low back, which makes it look almost like a tank top when worn with shorts, linen trousers, or a flowy pleated skirt. As someone with curves, the modest bottom is a huge plus — there’s nothing worse than having to keep adjusting a bathing suit bottom that won’t stop riding up. Reviewers agree: “Helps give a slimming look in the waist, flattens tummy, and very supportive for bigger chests that want to wear a one-shoulder swimsuit!” says one shopper. “Good quality and comfortable!” 

Kissmoda Lace Eyelet Shorts

Last year, I found a pair of high-waisted Zimmermann lace white shorts on sale and they became my go-tos while hopping between sister islands Paros and Antiparos. I wore them with a linen strapless top to a beach club, with a balloon-sleeved crop top and wedges to lunch, and with a bikini to the beach.

A style that’s similar and can be worn for just as many occasions, these elastic-waist pocketed shorts are structured but still loose enough that they can be worn over a bathing suit as a cover-up or with a light knit tucked inside. Comfortable to wear on shorter flights or high-speed catamaran rides between the Greek islands, these are sure to become your favorite travel shorts this summer. As one of the 6,000-plus reviewers raves: “The fit is perfect, the fabric is beautiful, the style is super!”

Anrabess Crochet Knit Cover-up

Embrace the free-spirited vibe of summer in Greece with a 1970s, boho-style crochet cover-up that you can throw on over a bathing suit before sitting down for lunch or heading to the market. “I love everything about this cover-up! I was so impressed by the quality and comfort that I bought two other colors!” says one reviewer. Another adds: “The length is just right, not too short, making it perfect for beach outings or poolside lounging. I even paired it with jean shorts and a little front tuck.” All you need is a floppy sun hat, straw tote, and pair of sandals and you’re ready for a day lounging on one of Santorini’s jet-black sandy beaches. 

Everlane Off-duty Sweatshirt

On my first trip to Greece, I was writing about an organic farmstay called Eumelia in the Peloponnese on the southern tip of the mainland, and the one piece I wish I had packed was a sweatshirt. For cool evenings and mornings — which is the case here in spring and pretty much year-round on the islands — a lightweight cotton jersey like this relaxed fit crew neckline version is an easy piece to throw over a dress or pair with linen slacks. Bone white makes an outfit appear elevated, even if the item is something as simple as a sweatshirt, and it can even double as a cover-up over a bikini with shorts on breezy beach days.

Farm Rio Festival Floral Linen Midi Skirt

White is the shade of choice in the Greek islands, but a pop of color with a bold print or pattern like this gives a linen skirt a distinctly summer feel. Midi skirts are great for day-to-night ensembles, since your legs will be covered if you’re dining seaside on cooler evenings. The side-seam pockets and playful hem are subtle design details that instantly elevate this piece and make it look as expensive as something you might see on the runways. I’d wear it with a white button-up vest or linen crop top with a stack of gold bangles and cognac-colored thick strappy leather sandals. I love matching sets, so if you are in the mood for a splurge, go for it and add the stunning matching crop top to your cart.

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