Travel Log | Destination SantoriniPart I: Planning a Trip to Santorini

I recently had the opportunity to visit Greece and, wow, did it live up to everything I hoped for! We stayed in Santorini for the majority of our trip and Syntagma Athens before we headed home. This trip was a brand new experience for me and I’ll be sharing my adventure along with tips over this three part series on the blog. This is all based on my personal experience, your’s may vary, but either way, I’m sure you’ll enjoy Greece!

(This is Part I of a four part series)

Fira Santorini Photo | Delighted Images | SF • Seattle • LA |


The high season in Santorini starts in May and lasts through the summer. After receiving a tip from my cousin that roundtrip airfare from the Bay Area to Greece was $600 in May, I had to check it out. Using the Hopper app, we found an even better rate for two weeks earlier than our original dates. We also found that the hotel rates were way better at that time. Naturally, it made me skeptical about the weather or why it might be low season. It turns out the weather was perfect, mid 70s to mid 80s, and April is just not high season for travel! We booked on February 19 for a trip to Greece April 26-May 5th, with a stay in Santorini from April 28-May 2.



Santorini is known for it’s gorgeous and dense cliffside caves on the western, Caldera, side of the island. In my opinion, Oía in the north is one of the most popular locations right now, at least from what I’ve seen on Instagram. Oía has the icon blue domed churches and windmills nestled into the cliffside with the hotels and cave. As the largest town in the north, Oía has plenty of shops and restaurants, with the best view of the Caldera. The sunset was also touted as the best in the island, but I beg to differ, granted the time of year will change where the best vantage point is for the sunset.


+ Bustling town with shops, food, and iconic scenery.
+ Great views of the Caldera and sunsets.
+ Large town.
+ Most paths and walking grounds are smooth and easy to walk on.
+ Great for larger group vacations with a variety of needs.


– Crowded in the center, you definitely don’t have the feeling of being immersed in a different culture. There are some quiet paths on the north edge that led to homes that feel much more authentic.
– Many paths that wind around the resorts are restricted (pro for patrons, con for visitors).
– Hotels are expensive.
– Many tourists, including families and tour groups.

Oia Santorini Photo | Delighted Images | SF • Seattle • LA | Oia Santorini Photo | Delighted Images | SF • Seattle • LA | Oia Santorini Photo | Delighted Images | SF • Seattle • LA |


About a two hour hike south down the coast is my favorite, Imerovigli. Contrary to what I read online during my planning, Imerovigli is actually the quietest part of the major coastal towns. With no shops, only restaurants and hotels, the foot traffic moves quickly and the noise is minimal. Imerovigli is has the aesthetic that I was looking for with whitewashed structures in sloping and clean lines. With a mix of resorts and private homes, Imerovigli is a great place to feel like you’re experiencing Santorini life. Because of it’s close proximity to the next two towns, Imerovigli is perfect for a quite, relaxing, and scenic stay on the Island.


+ Incredibly romantic and peaceful.
+ You feel immersed on the quintessential Santorini lifestyle of eating amazing food, hiking, and viewing the incredibly scenery.
+ Close to the next town, so you benefit from the activities without all the noise.
+ Whitewashed caves.
+ Footpaths are mostly open to everyone so you can explore freely.
+ Best for couples on honeymoon, or looking for a romantic trip.


– Steep stairs and hills.
– A mix of smooth and cobblestone paths.

Imerovigli Santorini Photo | Delighted Images | SF • Seattle • LA | Imerovigli Santorini Photo | Delighted Images | SF • Seattle • LA | Imerovigli Santorini Photo | Delighted Images | SF • Seattle • LA |


About a 15 minute walk from Imerovigli down an extremely scenic path is Firostefani. With small shops and restaurants along a narrow path, Firostefani is a small bustling town buffering Imerovigli and Fira, a large, lively town. I loved walking through Firostefani because it really felt like a nice transition.


+ Small town.
+ Plenty of casual dining options.
+ A mix of budget friendly and splurge worthy hotels.


– Narrow paths, which I was told become over crowded in the coming weeks.

Firostefani Santorini Photo | Delighted Images | SF • Seattle • LA | Firostefani Santorini Photo | Delighted Images | SF • Seattle • LA | Firostefani Santorini Photo | Delighted Images | SF • Seattle • LA | Firostefani Santorini Photo | Delighted Images | SF • Seattle • LA |


Connected to Firostefani is the larger town of Fira, known for a vibrant nightlife, narrow and bazaar like shopping, and a wide variety of dining options. Centrally located on the island, Fira’s bus terminal in a transfer point with buses that travels to all the corners of the island. Fira is crowded in a lively way.


+ Plenty of dining options.
+ Lively vibe.
+ Central located and easy to venture out with the bus terminal.
+ Great for younger vacationers who also want a nightlife.


– Not romantic.
– Cobblestone paths.

Fira Santorini Photo | Delighted Images | SF • Seattle • LA | Fira Santorini Photo | Delighted Images | SF • Seattle • LA | Fira Santorini Photo | Delighted Images | SF • Seattle • LA |

Anywhere you stay, the resorts are small, with only a few units. One of the most important aspects of what makes Santorini so transformative is the lack of large commercial chains. No McDonald’s, Target, or Forever 21 in sight. The only exception, to my delight, was Sephora in Fira.  

Getting there

By Plane

From Athens, the flight to Santorini is a brisk 45 min hop. But with normal air travel prices for even short distances, and standard fees/taxes, the cost start around 100 Euro. Not to mention standard airport security procedures.

Santorini Photo | Delighted Images | SF • Seattle • LA |

By Ferry

Standard Blue Star

The ferries in Greece are huge cruise liners with several indoor decks, garage, and eateries. A standard ferry trip from Athens to Santorini costs about 35 Euro per person and takes 7 hours, due to speed and making about 4 stops at other islands before reaching Santorini. We opted for this route to see some of the other islands and to see Santorini from a different vantage point. While I’m glad we did it this time, I’ll definitely be flying next time.

Tip: if you buy a regular ticket, you should plan to arrive at the ferry no less than an hour before to snag a good seat. The ferry is all open seating with a few exceptions for upgraded tickets. With the business class ticket being the first upgrade option at about 56 Euro per person, I didn’t think it was worth it because the seats are like rows of lazy boys with no tables, so you could be seated in the middle of strangers if you are traveling with a small group. I recommend arriving early to board early and take your chances. The open seating options are really nice. And if you’re unlucky, as the ferry makes stops, you can grab a seat before the next passengers come on board.

Santorini Photo | Delighted Images | SF • Seattle • LA |

High Speed Ferry

High speed ferries are also available and take about half the time. At about double the price of a standard ferry, it’s not a bad option at all. Based on my reading, the Standard was the more scenic option and the purpose of traveling by sea for me was scenery.

In Santorini


The buses were great, albeit the driving was a little scary. The buses are a mismatched collection of comfortable charter buses with storage below for large items. At 2 euro or less on average per person per ride, it was a pretty reliable way to get around.


We are totally ATV people and we planned to rent one, but after a bit of research my husband found that it’s actually illegal to drive one without an international driver’s license and your insurance won’t cover you in the likely event of an accident. The ATV rentals will rent to you with no questions asked and I was willing to check it out still, but when we arrived and saw how crazy the driving was, we easily decided against it. On one of our bus trips, the driver tailgated an ATV for several miles around a very windy cliff. So ATV at your own risk!

Things to know


Tipping is not customary in Greece, but has come to be expected in tourist spots, like Santorini. The normal practice is to round your bill up a couple euro, 10% is for excellent service.

Complimentary treats to end your meal

At “sit down” restaurants, it’s common for the restaurant to end your meal with a complimentary shot of ouzo or really nice sipping liquor, and sometimes with a small slice of pastry. As a dessert person, I have to say this was my favorite custom! It’s just such a nice touch. At our favorite restaurant, Anogi, on our last night in Santorini, they sent us off with two lovely desserts, one of the usual cakes they offer, and a second decedent marbled cookie/cake drizzled in chocolate representing the “sweet memories they hope we’ll have”. I LOVE that!

Santorini Photo | Delighted Images | SF • Seattle • LA |

Buy water

It’s not recommended that you drink the tap water on the island. To our surprise, a litter of bottled water was only .50 euro. That’s probably the least I’ve every paid for water, especially compared to what we’re used to with Hawaii. However, at restaurants, you also buy a bottle of water from them at a relative high mark up of 1.50 – 2 Euro. It’s not polite to pull out your own bottle of drinking water, and with the prices being lower than what we’re used to to eat at these lovely mid to upscale restaurants, the water was no big deal, but something to remember when deciding between water and wine.

Santorini Photo | Delighted Images | SF • Seattle • LA |

Must ask for check

On our first night, we arrived in Santorini exhausted from our ferry journey. At the recommendation of our fabulous hotel concierge, we went to great restaurant literally 20 steps from our front door. The food was fantastic and the Caldera sunset view was hard to beat anywhere on the island. Our servers were so friendly and polite, so when we finished the meal and were left to wait for as long as the entire dining experience, I was surprised. We watched other tables be brought their check and small glasses of liquor trying to see if there’s a code. I finally asked for our check, trying not to be rude, and I think they were relieved. They brought the check and the shot glasses of this incredible honey cinnamon liquor that I wish I wrote down, and we were on our way. My husband looked it up afterwards and found that in Greece, it’s impolite to rush people out with the check so they wait for you to ask. From that point on, the meaning of the European lifestyle of slowing down and enjoying the moment took with me.


Public restrooms cost about .50 euro to use, but are free in establishments you’re patronizing. In Santorini, more than the modern parts of Athens, you should refrain from flushing anything down the toilet. As a result, there are no seat covers. Practice your squats, ladies!

Lines suck

The most frustrating thing I found about Greece is the lack of order or queues. Less so in Santorini, but just about everywhere off the island, including the ferry and the airport, people just bunch up and squeeze in anywhere. On serval occasions I was waiting in what I thought was a line, but people would squeeze in in front of me like, it wasn’t rude and I’m waiting for nothing. I recommend that you treat any service counter like a bar and you’re trying to get the bartender to service you by squeezing in close to him.

Bank Holidays

If you’re planning to visit a site that requires admission or has operating hours, double check for bank holidays. Just about everything is closed on bank holidays with the exception of restaurants in tourist areas.

Treat yourself to a cave

There in no place like Santorini. A junior suite at a villa gets you a massive cave, private patio, and jetted tub with the most amazing views, and breakfast delivered to your patio every morning. Most other places, an upgrade for a junior suite gets you a couch in the room and maybe a kitchenette. For the same price as a standard room at the Waikiki Hilton, we got an incredible villa just before the high season. The same room, one month later, was going for 6 times the rate we paid. My point is, if there ever was a place to splurge on a hotel room, Santorini is that place because the experience is unmatched anywhere else. In my opinion, the cave experience was a large part of the allure of visiting Santorini and I could not be more satisfied.

Cave Villa Santorini Photo | Delighted Images | SF • Seattle • LA | Cave Villa Santorini Photo | Delighted Images | SF • Seattle • LA | Cave Villa Santorini Photo | Delighted Images | SF • Seattle • LA |

For Photographers:

No drones in Oía: I did see some drones in Imerovigli, but there were a lot of no drones signs in Oía.

Film: Don’t bring film rated higher than 800. Getting my film hand checked going into Greece was fine, but they kept refusing to do it on our way out. My exposed film went through three scanners (Santorini to Athens, Athens to Montreal, Montreal to San Francisco). Because my film speed was a max of 800, it was ok, but if I were to do it again, I would have paid the international shipping to ship my film directly to my lab. Definitely don’t pack film in your checked bag, the x-rays for checked bags is far more powerful.

Other places in Greece

We stared the trip in Santorini and spent the last two days in Athens. Originally, I thought we would get board of Santorini because we prefer to do a lot of activities when we travel, but Santorini was fantastic! If I were to book this trip again, I’d end in Santorini and leave on the sweetest note!

Duty Free wine

If you buy Greek wine from the duty free, be sure to have the clerk pack it in a sealed bag otherwise customs will make you toss it out…

I hope this post was helpful for anyone planning a visit. My next blogs will be more about my personal experiences, so come back for more!

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