What you need to know to plan your Santorini vacation

Yes, Santorini, Greece really is as gorgeous as the pictures make it look. Even with all our dreamy filters, what you see with your eye will honestly really look like the pic your favorite blogger just posted. So, if you’re wondering IF you should go there, the answer is yes. Solved that part. Now, you just need to know HOW to plan the best Santorini vacation.

Here’s what you need to know to get a solid game plan in place.

Santorini blue dome chapel and buildings behind it in Santorini Greece

Get your timing right

The Greek islands really heat up in the summer. Both literally and figuratively. You want to strike a balance between visiting when it’s warm and sunny and everything is open, but not going when it will be the most crowded and excessively hot. Those little alleyways and walkways fill up with people fast and the sun is strong. I would recommend targeting early May – early June or early September – early October. If your trip is part of a larger island hopping strategy, then you may want to be closer to the “summer” edges as some of the other islands (such as Mykonos) have a shorter season more condensed to summer. I did 3 nights on this island and it was a good amount. You could do a little more (maybe up to 5) but if you want to see a few things beyond Santorini (recommended) then 2-3 nights will do it.

Landscape view of Oia in Santorini Greece

Book in Imerovigli

You started looking for a hotel and you’re confused, right? There are loads of amazing places to stay and one looks better than the next. Oia or Thira? High up or down low? How will you ever decide? Let me help you. I totally stand behind choosing Imerovigli as your base and here’s why. It’s situated between Oia and Thira but is a little quieter and doesn’t have the cruise ship invasion the other areas have during the day. Since you’re right in the middle, you can easily get to either side and you also have a gorgeous view of the sparkling lights of both sides at night. When you’ve done some exploring and it’s hot AF and you’re ready for pool time, you’ll be in a quieter area and will be able to truly just relax and watch the *amazing* sunset.

Sunset and boats over Aegean Sea in Santorini Greece

It’s Santorini – go for the resort

AirBNB vs.resort. It’s always a tough call. While I am fully an AirBNB girl in certain situations, for Santorini I say go for the hotel resort. Santorini is a place you want to be pampered and the resorts offer infinity pools fully staffed with bartenders for all your sips as well as delicious Greek breakfasts with views for days. My favorite boutique resort is Astra Suites  which I would recommend all day and night for the breathtaking views, the service and the value you get for a luxury experience! For more info on the resort, check out my Luxury Resort Spotlight feature article.

Plan your arrival

You have a couple of options for getting to Santorini. The least expensive option is you can fly into Athens and take a ferry across the Aegean which is about 8 hours on the big Blue Star (traditional ferry) or the large high-speed catamarans (Hellenic Seaways) which will be closer to 6 hours. If sea-sickness is a thing for you, you may want to go with the slower Blue Star. You’ll also see the SeaJet option for high-speed service (about 5 hours) but this is a rougher ride for that long of a trip. Something to note though is that the ferries don’t always operate right on schedule. It can sometimes take off late so don’t plan anything for right after you’re supposed to arrive just in case. Book your tickets in advance directly with the ferry companies if you’re going to go this route. I tried both the Blue Star and Hellenic and while they are nice, they do take a while. Blue Star has an outdoor area while Hellenic is more like an airplane and you will be inside.

What I recommend doing instead of the ferry is taking one of the multiple flights that service Athens to Santorini. It will be about 45 minute flight and may be about $40-$100 more than the ferry, but I really think it’s worth it. You will not lose so much of your day to traveling and you can maximize your time on the island. You can look up flights in Google Flights or check out Aegean Air and RyanAir.

Either way you go, ask your resort about arranging transportation for you either from the ferry port or from the airport. They should have no problem taking care of this for you.

Boat on Aegean Sea in Santorini Greece

Pack like a pro

You’re going to need a mix of things for Santorini. Being in a stunning landscape, you’ll also want some pretty outfits to complete your shots. BUT, it’s important to remember that heels are basically not a real option there. You will be walking up and down a ton of stairs and you’ll be walking a LOT. Furthermore, even when it says it’s going to be sunny and 75, it will feel like 100 degrees certain parts of the day with the sun beating on you with very little mercy. Here’s my short list of what to pack:

  • Hat (even if you’re not a hat person – be one for this trip)
  • Swimsuit(s)
  • Sunglasses
  • Breezy outfits (linen, etc that will keep you cool)
  • Low-heel sandals
  • Scarf/wrap for at night
  • Book or Kindle
  • Sunblock
  • Camera
  • Tripod (to capture sunsets)

So, here’s my recap:

  1. Go in spring or late summer
  2. Plan to stay about 3 nights
  3. Stay in Imerovigli
  4. Choose a resort over an AirBNB
  5. Take the short flight vs the ferry
  6. Pack for heat, sun and chillin

There you have it. Get planning for the ultimate Santorini vacation! For other destination inspiration, keep the party going to fuel your wanderlust!

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Marissa is a travel consultant and digital marketing professional from Chicago, USA. Her business, Sips & Sojourn, specializes in helping busy people with full-time jobs travel more and travel better. Travel is Marissa's absolute passion but she believes you can hold down a successful career AND travel the globe. Marissa enjoys unique destinations, design hotels, sampling a culture's food and drink and meeting local guides focused on small, immersive experiences.

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