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Here are our favorite Santorini must-do experiences to help you squeeze every last drop out of your visit—without needing a vacation from your vacation.
Must-Do #1
Sailing the Caldera
If there’s a boat involved, count us in. There’s just something about being out on the water that makes exploring a new place feel extra magical. In Santorini, sailing around the Caldera is basically like getting up close and personal with a volcano—minus the risk of singed eyebrows. You’ll float past jaw-dropping cliffs, stop for a swim or a snorkel, and enjoy a meal and drinks with a crew that actually seems happy to have you aboard. You can choose a morning or afternoon trip, and if you pick the afternoon, you’ll get front-row seats to that famous Santorini sunset. Not a bad way to spend a day.
Tour Notes:
A quick heads-up: the sailboats aren’t wheelchair accessible, and there are a few stairs and narrow paths to navigate. It’s a bit awkward, but doable if you’re reasonably mobile. On our trip, we had everyone from twenty-somethings to folks well into their sixties, and everyone managed just fine. Since sailing depends on the weather (Mother Nature likes to keep us on our toes), book this for your first day so you have wiggle room if you need to reschedule. Honestly, this was our top Santorini experience—we wouldn’t dream of skipping it.
Must-Do #2
Wine Tasting Tour
Santorini wines have a flavor all their own, thanks to the volcanic ash in the soil. We joined a private wine tour with Santorini Wine Tours, stopping at two wineries for tastings, snacks, and a leisurely lunch. It was the perfect mix of learning and lounging—no wine snobbery, just good company and even better wine. If you’re looking for a relaxing afternoon that doesn’t involve a beach chair, this is it.
Tour Notes:
You’ll ride in a comfy, air-conditioned van (not wheelchair accessible, unfortunately), but the wineries themselves were easy to get around—just a ramp here or a step there. If you need to skip a spot or two, you’ll still have a great time and won’t miss out on the important stuff (read: wine).
Must-Do #3
Traditional Villages & Akrotiri Museum
Santorini’s story is literally written in layers of volcanic ash. Head out to the outer villages, and you’ll get a real taste of local life—far from the crowds and selfie sticks. The Akrotiri museum is a fascinating peek into ancient Greece, where you can almost feel the drama of the eruption that froze a city in time. It’s a little haunting, a lot interesting, and a nice break from the beach.
Tour Notes:
This private tour comes with a comfy, air-conditioned van and bathrooms at every stop (always a plus). It’s not wheelchair-accessible, since you’ll need to climb in and out of the van, and there are some uneven paths and steps in the villages and at the museum. Wear your good walking shoes and bring your sense of adventure.
Must-Do #4
Food Tour in Fira
If you want to see Fira like a local (and eat like one, too), join a food tour with a local guide. You’ll wander off the beaten path, duck into hidden spots, and taste your way through Santorini’s history—one delicious bite at a time. With only 8 people per group, it’s small enough for real conversation and big enough to make a few new friends.
Tour Notes:
No hotel pickup here, but the meeting spot in Fira is easy to find and close to the bus stop. It’s a walking tour with some uneven, narrow paths—so not wheelchair accessible and maybe a bit of a workout. Luckily, there are plenty of stops to rest, snack, and chat. We highly recommend it if you like your history served with a side of Greek food.
Must-Do #5
Cooking Class with a Local
This is your chance to hang out with a local family and cook up some of their favorite dishes in a traditional cave home. You’ll learn the recipes, sip local wine, and swap stories while you cook. The best part? You get to take the recipes home and relive your Santorini adventure every time you fire up the stove.
Tour Notes:
No hotel pickup, but the meeting point in Fira is easy to find and near the bus stop. It’s not wheelchair accessible, but the only real activity is standing while you cook (and maybe lifting a glass or two).
You Can’t Miss This.
Oia Sunset
I’m sure you’ve seen the Instagram posts of Santorini sunsets, and this is probably what put this on your radar. There are plenty of bars perched on the side of the caldera – all with prime viewing of the sunset. Spend an afternoon wandering Oia, grab a spot, and enjoy a drink while you watch the sun gloriously descend. It’s the Santorini experience not to miss.
Discover Wandering Tip:
Every guidebook will tell you to hike from Oia to Fira. We tried it, and let’s just say it was a workout—narrow paths, rocky terrain, and more hills than we bargained for. Sure, the views were nice, but honestly, we would have been just as happy lounging by the pool. Unless you’re a die-hard hiker, we say skip the trek and treat yourself to the hotel or one of our must-dos instead.
Want even more ideas? Check out our Santorini Viator Shop for handpicked tours and experiences to help you make the most of your trip & read our other posts on Santorini:
