Looking for outfit ideas to wear on your dream trip to Greece this fall? If so, you’ve certainly come to the right place! I just wrapped up a seven-day trip to Greece and it was nothing short of incredible.
However, this wasn’t just any trip… I sailed on a private yacht for a week, island hopping to six different spots. These were all smaller, less populated islands than everyone’s favorites Santorini and Mykonos, so we were able to get the full authentic feel. It was magical!
Because we were traveling by boat we spent lots of time swimming— I’d say about 2/3 on the water, 1/3 on land. October is the perfect time to visit Greece because you skip the crowds and unbearable heat and are instead met with the most perfect weather. High seventies and sunshine + water temperatures warm enough to swim every single day. It really is the dream destination.
Today I’m sharing all thirteen outfits I wore during my trip complete with links to shop so you can build the perfect vacation wardrobe. Enjoy!
I had been saving this sexy black one-piece from one of my favorite swimwear brands Kotomi for months. I knew it would get the grand reveal it deserved on this yacht trip to Greece and boy was I right. I couldn’t dream up a more flattering swimsuit if I tired.
Everything from the plunging neckline to the placing of the mid-drift stitch to the cheeky bottom were perfectly executed. And to my surprise, this was an incredibly durable bathing suit as well—I jumped off the boat at least 30 times and didn’t have to adjust this once. 10/10 for quality, fit and design.
photo location ✈ Monomevasia, Greece
What’s more perfect than a linen set that’s white and blue with all kinds of Greek symbols on it?! This matching set was made for an end-of-season trip to Greece. I wore this buttoned-up with sandals for an afternoon exploring Poros and on the boat layered over a bikini.
Such a versatile set and so comfy. My adorable raffia bag is from a small boutique I found in Agenia, Greece. It was handmade and on sale for $28… I had to have it. Perfect size tote for souvenir shopping and a “just in case” bikini. 😉 You never know when the opportunity to swim may present itself here—always better safe than sorry.
photo location ✈ Poros, Greece
I’m a sucker for a good linen dress, especially a maxi! If you’re traveling to Greece this fall, you should definitely consider packing a few. October has the most beautiful weather so you’ll be comfortable wearing just about anything. You can never go wrong with an easy breezy cotton dress!
This one was so perfect for Greece — the blue, the print, the puff sleeves. I threw this on with gold sandals from Steve Madden and a simple clutch to complete the look. So effortless!
photo location ✈ Ageina, Greece
I try to bring one solid white bathing suit on every trip I take and this one from Sema always seems to be my first choice. This small business has the softest, sustainably sourced fabrics. Their swimsuits are buttery soft, feeling almost like a second skin.
I love a good underwire top. This one has adjustable straps and a silver clasp along the back. The bottoms are super simple with your classic hipster cut and a ruched-cheeky butt! I ended up wearing this several days— a sturdier suit that has no ties ended up being just what I needed for long days jumping on and off the boat.
photo location ✈ Kiparissi, Greece
How precious is this pink maxi dress?! I grabbed this dress and several other pieces I wore on this trip from a small Australian online boutique called Fortunate One. They have an amazing selection of vacation wear and you can use my code MCKENZIE10 to save an additional 10% off your purchase.
Anywho, this linen number was perfect for a wine night on the boat and an evening exploring the island. I ended up styling with simple gold sandals!
photo location ✈ Monemvasia, Greece
The last time I went to Greece I packed all kinds of skimpy going-out clothes and mini dresses. This time I knew better and packed tons of oversized linen to throw over swimsuits. They were definitely necessary as we spent the majority of our time lounging on the boat rather than on land exploring.
I got two of these pink linen sets so Sam and I could match and I’m obsessed. The perfect button-up to toss over a bikini top and these shorts have a real drawstring waist.
photo location ✈ middle of the sea
set || bikini top || bikini bottom
Wearing another linen dress for shopping, dinner, and drinks in the town center. This was another Fortunate One find and I’m obsessed with the grommet lace details along the front. It cuts a little lower so it gives your boobs a little extra perk + the lace-up details along the back are just too cute.
Accessorizing with my favorite raffia accessories as always!
photo location ✈ Spetses, Greece
Nothing screams Greece quite like a royal blue and white bikini. I found this one on SheIn for less than $10 and knew it would be perfect for this trip! Just a typical triangle top and a pair of tiny bottoms. These have minimal coverage as you can tell and the fabric is not stitched into place so these move around quite a bit.
Definitely more of a “tanning on the boat” rather than “playing mermaids in the water” type of suit, haha. I love those tassel details so much!
photo location ✈ middle of the sea
bikini || sunglasses
Thank God I packed these two pieces because I literally wore them every single day. Definitely suggest bringing an oversized button-up to throw over your bathing suit as a coverup. My favorite style is the “Go Big” from American Eagle. Super oversized and boxy in all the right ways.
These striped linen pants were a $10 Boohoo find that I can’t stop wearing. With a drawstring waist, pockets, and a lightweight fabric these were the best pj-like pants to throw on in the evenings when the temperature dipped or as we were sailing from one island to the next.
Great comfy basics should be a non-negotiable when packing your Greece suitcase; trust me!
photo location ✈ Dokos, Greece
Nothing I love more than a good smocked bikini. This was another $10 SheIn find. The mix of white and blue flowers is perfect for a Greek vacation. This one self tied along the top and bottoms— make sure to tie in a knot and then a bow so you don’t lose any fabric jumping in, hehe.
photo location ✈ middle of the sea
bikini || sunglasses
If you’re off to Mykonos and plan on hitting the nightclubs, this Whitefox set is perfect. They have the best two pieces on the market, all made of a super strechy spandex fabric. I’m warning you, their mini skirts are mini and tend to sit a little lower on the hips, hugging all your curves.
Love the light blue and flower details.
photo location ✈ Poros, Greece
top || skirt || sandals || clutch
I can’t think of a dress better suited for Greece than this blue maxi from Buddy Love. I love a good maxi dress, especially one with this full skirt. The perfect piece if you’re planning on twirling the night away. At 5’2 this style ran a little long on me—I’m giving it a little lift with my baby Dolce Vita block heels.
These have a super short heel, only about one inch so they are perfectly comfortable and manageable for walking around the cobblestone streets! Sam’s dress is from Red Dress and coordinated perfectly.
photo location ✈ Spetses, Greece
That pink dress that everyone loved? I have it in the blue too! When I like something I can’t resist getting it in every colorway and I knew this blue would be perfect in Greece. This dress has such a unique detail along the bodice. The open back and plunging neckline are so flattering. This runs a little tiny so I suggest sizing up for a little extra wiggle room.
photo location ✈ Athens, Greece
Well, that’s a wrap for everything I wore during my trip to Greece. To be honest, I ended up dressing far more casually than I expected to but I’m not complaining! I had the best week ever and cannot wait to share more details in my travel guide coming soon.
If you’re looking for more Greece outfit ideas, check out this blog post from my visit to Mykonos last year. it’s packed full of good outfit inspiration and pretty scenery. I know for a fact this won’t be my last time here… stay tuned to see when I make it back next!
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