3 Days in Santorini: Dream Itinerary for First-time Visitors (2021)


Santorini, Greece has to be one of the most romantic places in the world. Smooth, sparkling white houses baked
into the side of cliffs, overlooking a crescent-shaped bay. Plus world-famous sunsets, ideally observed from
your private jacuzzi with a glass of wine in hand.

On my first trip to Santorini, I was neighbors with a guy from Germany who’d been making an annual pilgrimage
Santorni for over 40 years. At one point, he just decided to stick around and make the move permanent.

Honestly, I get it.

Santorini exceeded my expectations in every way – which is saying something as a seasoned traveler. This Santorini itinerary
is the absolute best of this legendary island, packed into three days that balance adventure with leisure.

But the real questions you’re asking yourself at this very moment are probably:

  • Can I even visit Santorini now, in 2021?
  • When’s the best time to visit Santorini during the year?
  • Where should I stay in Santorni? Do I need to rent a car?
  • How can I make sure I’m in the best spot for sunset?
  • And most importantly, how do I do all this without going broke?

So let’s start with logistics before getting to the Santorini itinerary. If you’ve already researched
how you’ll be getting here, where to stay, and how to rent a car, click here to jump to the itinerary[1].

Can you visit Greece now? (In 2021)

As of April 19th, United States citizens are allowed to enter Greece (source[2]), as well as residents of the EU, Schengen states, and some other countries.

All travelers over the age of 5 must present a negative PCR test for entry, but if you have proof of a COVID-19 vaccination at least 14-days before arriving in Greece, you are NOT required to present a negative test.

An extremely important note about preparing to visit Greece in 2021: If you plan to visit Greece, regardless of your vaccination status, you must fill out a Passanger Locator Form (PLF) BY MIDNIGHT the day before you fly. If you do not do this, they will not allow you to board the plane.

Bear in mind, much of Greece is currently still in lockdown and masks are still required. However in some places, the lockdown has been relaxed[3]. According to this source, Greece is hoping to kickstart its tourism season from mid-May onwards.

santorini windmills
santorini windmills
Oia, Santorni

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The best time to visit Santorini

The best time to visit Santorini is from April to May or September to October. The weather is still hot and the skies are clear,
but there are far fewer crowds. We visited at the end of October and I still managed to get a really bad sunburn!

Don’t underestimate how hot Santorini can be. It’s even further south than mainland Greece, and the arid climate and lack of trees means
you’re often exposed to full sun.

Winters in Santorini are grey and rainy, and most restaurants and
accommodation close down.
When we arrived at the end of October, a number
of businesses had already shut their doors for the year. They typically close by the
end of October, so finishing your trip to Santorni before then is ideal.

That said, for us, October was perfect. We had sun almost every day, barely existant crowds,
plenty of privacy in our perfectly-situated cave house[4]. I’d go
again at this time for my next trip!

three domes of santorini
three domes of santorini
Three Domes of Santorni

Where to stay in Santorini: Cave hotels and houses

The first question you need to answer for yourself is where to stay in Santorini.
There are a couple of main options, depending on what you’re looking for:

Option 1: Oia — The most famous town, located at the northern tip of
the island. With fame comes crowds, so you’ll need to look for accommodation that
affords privacy (meaning, your front door is only accessable by private access).

It will be more expensive, but in my opinion, it’s the best place to stay your first time in Santorni.
Honestly I’d probably stay here a second time, too.

Click here to see my recommended cave house in Oia here[5]

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