A few years back, before we discovered the beauty of cruising, we visited Santorini in a land based holiday for 3 nights.

We were back in Santorini recently, this time stepping off a tender from the Xcel, and it got me thinking about the last time we did this island — no cruise line doing the thinking for us, no shore excursion desk, just me and a couple of friends, and a very detailed spreadsheets of flights and travel plans. That was 2017. We flew in, figured it out as we went, and left with a system that still holds up almost a decade later, even if half the prices have crept up since.

If you’re the type who’d rather work it out yourself than hand €150 to a tour operator, here’s how we did it then, and what I’d actually tell you to do now — whether you’re staying a few nights or just have a handful of hours off a ship.

Getting there: the flight rabbit hole is worth it, sometimes

Back in 2017 we spent an embarrassing number of evenings on flight comparison sites trying to shave the cost of getting to Santorini down as far as it would go. What we landed on was a connecting flight with a red-eye leg thrown in — not glamorous, but it was noticeably cheaper than flying direct. If you’ve got the time and you’re not precious about arriving a bit crumpled, this is still a solid way to do it. If you’re short on days or just can’t face a 4am layover, pay the bit extra and fly direct — you’ll get more actual holiday out of the trip.

Obviously none of this applies if you’re arriving the way we did this time, by ship. But it’s worth knowing, because plenty of people do a land stay before or after their cruise, and the flight-in leg is where most of the money gets wasted if you don’t plan it.

Shoulder season taught us more than the guidebooks did

We booked October, mostly because we wanted to celebrate a friend’s birthday in Santorini — it was also fit around leave/PTO — and it turned out to be a good shoulder season. Fewer crowds, air with a bit of an edge to it in the evenings (bring a cardigan, you’ll still be in shorts by lunchtime), and food that cost noticeably less than what we’d seen quoted for July and August. The catch: some restaurants start closing for the season, so if there’s a specific place you’ve read about, check it’s actually open before you build a day around it.

This one’s really for the land-based trip rather than a cruise stop — you don’t get to choose which day your ship calls. But if you’re tacking extra nights onto either end of a cruise, October (or May, for that matter) is where I’d point you.

Where to stay, if Fira and Oia aren’t it

Everyone tells you Oia for the sunset and Fira because it’s central, and both are fair enough. But if you’re staying over rather than just passing through, look at Imerovigli. It sits higher on the caldera rim than either of them — around 300 metres up, at what a lot of locals just call the “Balcony of Santorini” — and it’s quieter without giving up any of the view. Same caldera, same volcano out the window, considerably fewer people elbowing you for the photo.

Even as a day visitor it’s worth the mention: if you’ve done Fira and Oia before and want somewhere calmer to sit with a coffee and just look at the water, Imerovigli is a short bus ride and a different pace entirely.

Getting around without a hire car

This is the part that actually saves you money, and it’s the part most people skip because they assume it’s too complicated. It isn’t.

The local bus (KTEL) runs out of a central station in Fira to pretty much every village and beach on the island. Fares depend on distance — Fira to Oia is about €2.20, Fira to Imerovigli is the same, and it climbs a little for the longer runs like Perissa or Vlychada. Buses to Oia run roughly every 30 minutes through the day in high season, less often outside it, and they do get standing-room-only around sunset, so don’t leave your return trip to the last possible service unless you fancy a long taxi wait instead. This was basically how we got around the whole island in 2017, and the network hasn’t really changed — just the prices, a bit.

If you’re coming off a ship, you’ll almost certainly land at the Old Port by tender, since Santorini doesn’t have a dock ships can pull up to. From there you’ve got three ways up the cliff to Fira: the cable car, the 588 steps, or a donkey. Take the cable car. It’s about a three-minute ride and current one-way pricing sits somewhere in the €6–10 range depending on when you check (it’s gone up more than once in the last couple of years, so treat that as a ballpark and check the board at the station), plus a small extra charge per bag if you’re carrying luggage. The steps are free but steep, exposed, and shared with the donkeys — meaning also sharing what the donkeys leave behind. Skip it unless you’re genuinely up for the workout. And on days when more than one ship is in, budget real queue time for the cable car itself; thirty to sixty minutes isn’t unusual, so get off the tender early if you can.

Once you’re up in Fira, the bus station is a short walk from the cable car’s top exit, which makes it easy to hop straight onto a bus to Oia or the beaches if that’s how you want to spend your hours ashore.

Lunch doesn’t need to be a sit-down affair

Some of our best meals in Santorini in 2017 cost less than a bottle of the local wine did. Gyros and souvlaki stands are everywhere in Fira and Oia, and they’re the easy answer when you want to eat well without giving up an hour and a full restaurant bill to do it. Grab one, find a step with a view, and you’ve got lunch sorted for a few euros rather than twenty. It’s also just a nicer way to eat on a day where you’re trying to fit in a bus ride, a viewpoint, and a cable car queue — you don’t want to be waiting on a table when your return tender’s on a schedule.

The bit that hasn’t changed

Coming back this time on a ship, with a few hours instead of a few days, made me appreciate how much of what we figured out in 2017 still works at any pace. The buses still run the same routes. The steps are still there if you want to prove a point to yourself. And the gyros are still better value than anything with a tablecloth. Whether you’ve got four days or four hours, Santorini has something to see and offer, you have your choices.