In preparing to go to Santorini, I scoured blog sites looking for any guidance on what to wear during shoulder season. There are so many posts about what to pack during peak season (summer), but almost nothing for what to wear outside of those few months. Below you’ll find my packing guide that takes into account the transitional weather as well as being prepared for the more popular activities that people do in Santorini. For reference, we were in Greece from late October into early November.
Midi dresses
Light, midi dresses are super cute and, you don’t have to worry about the hem dragging on the ground. I packed quite a few maxi dresses, and only one midi dress, but I wish I had packed more. This may be TMI, but, because there is a large stray cat and dog population as well as donkeys that trot through town on occasion, you do NOT want your hem to drag on the ground. I got this one a while back at the Kate Spade outlet when they were having a 70% off sale. The light material is cool enough but also provides good coverage so you don’t have to worry about your skirt flying up with a passing breeze.
Tassel earrings
These are light, easy to pack, and add a pop of color to any outfit. I got these at Target for under $15. They have similar ones here from their collab with Sugar Fix.
Outfits with red or pink colors
Santorini is full to the brim with bougainvillea so any red or pink hued dresses, skirts, or shirts really pop here. My skirt was $9 at Uniqlo from a few seasons ago.
Turkish Towel
If you plan to do any cliff jumping at Ammoudi Bay or swimming at Red Beach, a light, packable Turkish towel may be a great addition to your packing list. I also used mine as a shawl to wrap around me when watching the sunset at the castle ruins. I found mine on Amazon prime for about $12.
Tennis shoes
I found tennis shoes to be indispensable, especially for the hike we took from Imerovigli to Oia. It’s rocky, steep terrain in some parts, so you want much more than sandals. I also found it helpful to have more study shoes than my sandals as the town and stairs are paved in cobblestones that can be rough on the feet if you’re doing extended walking. I love my Nike Free Runs as they go with anything and still look athletic but not aggressively so.
Packable down
Believe it or not, Santorini gets a little chilly when the sun goes down, especially during shoulder season when we were there. I was thankful to have a light, yet effective layer to wear out to dinner or walking around town at night. I love Uniqlo ultralight down as well as Scandinavian Explorer.
Leggings
Super comfy especially for the flight in and out as well as for dinners when the wind picks up and it get a little chillier. I am in love with these durable, good quality, yet affordable ones from Nordstrom Rack.
Sun hat
Even during shoulder season (late october) the sun is intense in Santorini. You will be super happy you packed a hat with a wide brim.
Swimsuit
Of course, this one’s a no brainer.
Comfy Sandals
I constantly struggle with finding sandals that can keep up with the crazy amounts of walking I do when I travel. Either they’re comfy, but look like geriatric sandals, or flimsy but super cute. My Steve Maddens held up relatively well, but for as comfy as they are, they were sometimes not padded enough for the rocky cobblestone in Oia. I also found this pair, that I haven’t gotten to try out, but they look pretty comfy and not too geriatric.
jennifernishngo 
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