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Monto

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Two couples are hoping to go to Santorini for our anniversaries. I know the crowds are gone by then but will there be anything open? Restaurant’s etc? Will it be too cold to go swimming? Any information is appreciated. Thank you.
 
The temperature outside is bearable, but I think the water might be a bit too cold. Keep in mind that it can get pretty windy in Santorini
 

Tips for Santorini in a Bigger Group?

Hi all! I’m planning a trip to Santorini later this year with a bigger group—about 8 of us, all adults—and I’d love some tips from anyone who’s done it before.

We’re trying to figure out the best area to stay that’s scenic but also practical for a group (maybe with a villa or multiple rooms close together). Are Oia or Fira still good choices, or should we look elsewhere for better space and value?

Also, any advice on getting around with a group? Should we rent a van, book a driver, or rely on taxis? I have never traveled in a group this large before.

Favorite shops to buy jewelry in Santorini?

I’m thinking about going back to Santorini next year — I’ve been a few times before and absolutely love the island. This time, though, I want to do something a little different and focus more on shopping, especially for jewelry. I’m looking for cute, unique pieces — either handmade, local designs or anything with a Greek flair that doesn’t feel too mass-produced.

Any favorite shops or designers you’ve come across in Fira, Oia, or even the smaller villages? I’d love to hear where you found your favorite pieces? I want unique things. Like, a friend brought me back a bracelet that was made from beads cut from the Santorini lava stone, but funny enough, she bumped into this piece on Crete. So I thought, I should go to Santorini to get cool stuff like this! Do you have any favorite places to buy jewelry?

Great Walking Paths on Santorini?

I’ve been thinking about Santorini specifically as a place for walking, and I realized it’s something I don’t hear Greeks talk about as much as food, wine, or sunsets. I’m curious how people who know the island well think about walking it, not just as visitors passing through but as a lived landscape.

So I wanted to ask: what are some great walking paths on Santorini? Beyond Fira–Oia, are there routes you’d actually recommend for the views, the quiet, or the feeling of the island itself? I’m especially interested in paths through villages, near vineyards, or stretches that feel more local and less performative. Are there walks that feel better early in the morning, in the wind, or outside peak season?

I’d love to hear which paths you return to or remember most, and what made them stand out for you.

Guy's Night Out in Santorini?

A few of us are planning a guys’ trip to Greece next summer (still tentative, but Santorini is definitely on the list), and we’re trying to figure out what a proper guys’ night out would look like there. One of the guys will be celebrating a birthday, so we’d like to make it special without going too over the top.

We’re not looking for the super touristy spots packed with honeymooners—more interested in something authentic, fun, and memorable. Maybe a taverna with great food and live music, or a bar where locals actually hang out? A good view wouldn’t hurt either.

Has anyone here done a birthday or a group night out in Santorini with a bunch of guys? Is Fira better for nightlife than Oia? Any recommendations for tavernas, bars, or even local experiences we could include in the evening would be really appreciated.

How many days in enough is Santorini?

I’ve been to Santorini before and absolutely loved it—but this time, I’m going back with friends who have never been. We’re planning a bit of an island-hopping trip, and I’m trying to figure out how many days we should dedicate to Santorini without feeling rushed, but also leaving time for other islands.

I remember there’s a lot to enjoy even just soaking in the views, but I also don’t want them to miss out on the key experiences—Oia sunsets, the hike from Fira to Oia, maybe a winery, and some beach time. We’re not big into overly scheduled days, more go-with-the-flow types.

What would you recommend for first-timers? Is 2 full days enough to get the full experience, or is 3–4 ideal? Would love to hear how long others stayed and whether you felt it was just right or too short!
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