Santorini: The Ultimate Guide

First off, thank you for the amazing kind words of joy about Steven and my marriage! We so appreciate you sharing in the joy with us!


Before we had even chosen a wedding venue, we knew that we wanted to go to Santorini on our honeymoon.

The picturesque villages with whitewashed marble buildings built into the side of the cliff; blue domed churches; breathtaking sunsets; crystal clear, blue water and outrageously fresh seafood — we envisioned ourselves sipping crisp white wine on a catamaran as newlyweds, and boy did it not disappoint.

Many people, when they go to Greece, they “island hop,” and check out multiple Greek islands, but we wanted to have a relaxing trip where you only unpack once, and really get to know the flavor of the one island. And Santorini being known for honeymooners, we knew that this is where we wanted to be.

So fasten your seatbelts, sit back, relax and get ready to travel 9.5 hours across the world to truly the most beautiful place on earth: Santorini, Greece.

Greece is seven hours ahead of EST, and it boasts over 300 days of sunshine per year!

Santorini is one of the most famous of Greece’s 6000+ islands! It’s part of the Cyclades islands in the Aegean Sea, and it was formed by a volcano (which is what you’re looking out at: aka – the caldera). As a result, not only does it have red, black and white sand beaches, but its soil is full of minerals which makes their 40 varieties of grapes so flavorful and unique! (And why there are over 20 wineries on the island).


This is a “hot take,” but I would suggest staying in Fira over Oia.

Let me back up: The two main villages of Santorini are Fira and Oia. Fira is in the middle of the island, and where the cruise ships come to port. It has nightlife, lots of shopping and restaurants, is where the bus hub is, and is truly the central point of the entire island.

Oia is on the tip of the island, and is where everyone flocks for the sunset every night, since it is the western-most point of the island. But here’s a little secret: anywhere along the western coast has a gorgeous view of the sunset! Oia was beautiful to spend a day in, but it was just way, way too crowded, and Steven and I much preferred the pace in Fira.

We stayed at Enigma Suites (not sponsored), and this was the most beautiful place I have ever been, and truly a luxury experience. We got the honeymoon suite, complete with a private patio overlooking the caldera with its own private jacuzzi– and protip: YOU MUST BOOK EARLY! Since it is such a honeymoon meca, the cliff-side suites with the private hot tubs book up wayyy far in advance. We booked ours in November for a June trip, and at that point, there were only a few honeymoon suites left on the entire island. So don’t wait!

On that note, I would definitely splurge for a suite with a caldera-view balcony — and hot tub if possible. We watched the sunset every single night from our private balcony. We opened a bottle of wine and luxuriated while watching the sky turn all types of pinks, oranges and purples, and then would go for a late dinner at 9:00pm. Otherwise, you have to fight people for a 7:30 “sunset dinner” reservation, as all the restaurants are outdoor and on the cliffside, where you can watch the sunset if you don’t have a private balcony.

Or your final option is to line up along the side walls with the masses…which is beautiful, but a little hectic.

Long story short: go for the private balcony.

But back to Enigma Suites, it is truly a phenomenal experience: they greet you with a cold bottle of local white wine, the concierge is so helpful booking excursions, taxis, dinner reservations — they have “ins” with many of their neighboring restaurants, so they can always get you a table.

And they serve you a gourmet breakfast (for free) every morning on your balcony. The night before, you fill out what you want on their menu, indicate what time you want it delivered, and then bam, the next morning you wake up to a white table cloth breakfast fit for a king waiting for you on your balcony overlooking the caldera.

The rooms were so chic and beautiful and clean! They cleaned our room twice a day and turned down the bed every night, and left a little “goodie” — whether that was a face mask, pillow mist, cookie, etc.

Do NOT Stay: Elea Resort in Oia.

I am usually not a negative person, but I’ve just got to say: do not stay at Elea Resort in Oia. We actually booked this place by accident — (We thought we were booking Elea Suites, but we actually booked Elea Resort…The Suites is on the caldera side, and the Resort is not…and they are not affiliated with each other. It’s location is really tough with a steep driveway hill that takes about 10 minutes to walk up, just to get to the streets of Oia. And then the room was kind of…falling apart a little bit and we didn’t feel that it was clean. Plus, the hot tub, when we arrived was ice cold…and tiny. Steven and I could barely fit comfortably.



This is one of those ultimate Santorini experiences. Every evening at sunset, you’ll look out on the water and see hundreds of catamarans on the water watching the sunset — and that’s because there’s nothing like experiencing it from the water.

The sunset cruises have unlimited beer and local wines, and they cook you a traditional Greek dinner. For four hours, you cruise around, you stop and swim/snorkel at red and white sand beaches, you visit a hot spring, and see the beauty of the island from the water. We made some great friends, and it was such a highlight of the trip!


Though Santorini is not known for its powdery, soft sand beaches, it does have “volcano beaches” where the sand is either black or red. We went to Seaside Beach Club and spent the day in an umbrella cabana! Just be warned: the beaches are pebbly/stony. However they’re still beautiful and worth the trip. Just be sure to wear TEVAs or some sort of sporty sandal that you can wear in the water. I wore these, and they were awesome because they were cute enough to wear with a dress day or night, waterproof, AND comfortable enough to wear hiking

Which leads me to my next “must do” activity:


Listen: I love an active vacation. And so when I heard “a cliff-side hike through the little villages and seaside of Santorini,” I was all for it. And thankfully, so was my husband.

Were we a little unsure if we were making the correct decision, as it was hot and full sun that day, but oh my gosh the views were just spectacular. It took us about 2.5 hours, and we stopped for lots of photo opportunities along the way. Definitely wear a hat, and either sneakers or active sandals.

We added another 30 minutes onto the end of the hike, and finished our trip at Ammoudi Bay and had lunch at the Ammoudi Bay Fish Tavern, which was such a good decision! Be warned: there are 314 steps down a steep slope to get to the bay – but it is worth pushing through, even though you’re tired. It’s fish that’s caught literally inches from your table in the water that morning. Best meal I have ever eaten, hands down.


This is a “no brainer,” but it is really fun to take a day (for each town) and just explore the winding cobblestone, pedestrian-only streets! By not having an agenda, you can pop into little art galleries, jewelry shops, etc. You can stop for gelato, have a leisurely lunch, take lots of photos, etc! We ate at two very different lunch spots on the days we explored Oia and Fira on foot. In Fira, we ate at this beautiful cliff-side cafe where Steven had the most amazing leg of lamb. And in Oia, we found the most adorable crepe cafe that was built into the side of the cliff like a cave, that was also overlooking the water. Nothing quite beats a crisp glass of white wine at lunch time…that’s how you really know you’re on vacation.

Speaking of wine…


You can sign up for semi private wine tours that will take you to three or four vineyards around the island. And it was so special. We were with only one other couple (who randomly were from my hometown, and our parents know each other) and another woman who was traveling alone. We had the best tour guide, and it was really fun. You end up, not only learning a lot, but you get to see a lot of the island too! (And drink fabulous wine!) We’re going to actually order a case of our favorite wine from the tour!


Sometimes, you just want to have a taste of a luxurious life. Well, in Santorini, there are lots of opportunities to sample “the good life.” This girl we met who went to UCLA and worked at her father’s jewelry shop recommended Cavotagoo to us. It’s connected to the hotel of the same name, and it’s got this gorgeous infinity pool with floating beds and cabanas that people rent out for the day or for sunset. And so we hopped on the bus in Fira to go to this swanky hot spot. We were the only ones there, and again: you’re greeted with a free bottle of wine and a fresh fruit plate, and you have the afternoon to just look out over the most beautiful view you’ve ever seen.


One of our favorite memories was going to Mass in Santorini on Sunday. St. John the Baptist church has one multi-lingual mass on Sundays at 10 am. The priest is so jovial and says Mass in Greek, then Spanish and then his english translator. And at the beginning he invites everyone to respond in their own language, creating a “word salad” – it was truly so beautiful to be there with all our fellow Catholics from literally all over the world. Arrive early because it was standing room only!


NAOUSSA Local Restaurant:

This restaurant is the personification of your “Greek fun-uncle.” Which, I’m not exactly sure that’s really a troupe, but for the sake of this article, it is. Think: My Big Fat Greek Wedding personality: there’s family-style Greek music pumping through the speakers, the jovial owner throwing plates on the ground to choruses of “Opa!” and clapping, big portions of delicious Greek food. But the best part is when the owner hands YOU a couple plates to smash on the ground! It’s dinner with entertainment to say the least. And all, cliff-side overlooking the sunset.


This is totally Steven’s domain. He loves street food. And the Greek Gyro — or as it’s called in Greece: Souvlaki. A warm, chewy pita stuffed with rotisserie-roasted meat, french fries, and some veggies. It’s cheap, fast and apparently utterly delicious. Steven’s favorites were from: Nick the Grill and Lucky’s Souvlakis — both are practically next door to each other in Fira.

Ammoudi Bay Fish Tavern/ Sunset Ammoudi

Whatever you do, get some fresh fish in Santorini. They’re known for their Sea Bream, which is a flakey, mild white fish. And it just melts in your mouth. These two restaurants were absolutely divine — book a reservation for sunset at Sunset Ammoudi (splurge on the terrace level seating), and have lunch at Ammoudi Bay Fish Tavern. Both exquisite.


This was the best value dinner spot we found in Fira, and we absolutely loved it! It’s not on the cliff-side, so you don’t get the sunset, but it is phenomenal food! Red checkered, plastic table cloths and pitchers – not bottles – of wine, plus friendly service — it was a great place to feel like you’re scoring a deal!


I will say, Steven and I are kind of music “snobs” (Latin reggaeton for the win!) so when we discovered that these bars all play the same 2019ish/oldies pop play list, we were a little underwhelmed.

That being said, 2 Brothers, Town Club and Tropical Bar were pretty fun. We stayed for a drink at each place, but that’s about as much as we could take of the vibe. (Jeez, am I getting old???)

We really liked Tango night club. They do charge a cover. But they had the best vibe — think cocktails and champagne with chic elevator music.

But our favorite was Kira Thira Jazz Bar — hit them up on a night when they have live music playing.

What You Need to Know:

1) First things first: we’re going to get this right out of the way — the bathroom situation in Greece is dismal. Not the actual toilets, but the pipes. The entire country has literally ancient sewage pipes, and therefore, you cannot flush toilet paper down the loo. Instead, you have to put it in a bin beside the loo.

I was, not surprisingly mortified when my newly married self learned of this nightmare situation, so understandably, this was not a welcome surprise.

But — by bringing a couple bathroom savior products with me, everything was fine, and I still left my husband with an air mystery.


Let’s talk money. Most everywhere takes credit cards — but no where takes American Express. Even if you reserve your hotel online with your American Express, they will not charge it, and when you get there they will ask for another form of payment.

That being said, though everywhere takes card, they prefer cash — to the tune that many places will actually discount the price if you pay in cash over a credit card. This is true for excursions, tourist shops, jewelry, cab fares, etc. So it’s always best to use cash.

And THAT being said, the ATMs in Greece absolutely gouge you. Some charged a 17% fee, just to use it, on top of the exchange rate. Our hotel’s concierge gave us a tip though: to only use the Greek National Bank ATMs…they do not charge a usage fee, only the exchange rate. So for example, to withdraw $500, I would only be charged $540 instead of $620 dollars, which is what some of the other ATMs wanted to charge.

3) The sun is HOT, so use lots of sunscreen and a hat.

4) Be prepared to do a lot of walking, and specifically, a lot of stair climbing and descending. Proper footwear is essential, and if you have bad knees…pace yourself.

5) Utilize the buses! They’re cheap and reliable — and private taxis are about $40 USD between villages one way.


On your way home, stock up on Greek olive oil and wine! It is truly such a delicacy, and Santorini wine is some of the most unique in the world. Also – and this is random, get some pistachios when you arrive to snack on throughout the trip! They’re known for exceptional pistachios, and make a really great and healthy snack!

So there you have it, sports fans!

Santorini was the absolute best vacation of my entire life. I can totally see why it is consistently rated one of the top vacation destinations in the world. In fact, my sister-in-law and my parents are both going plan trips there after hearing how magical of a time it was!

Some other things to make the trip easier:

When you arrive in Fira or Oia, because they both have pedestrian-only streets, the taxis from the airport can only drop you off as far as car traffic roads go. So for example, in Fira, you have to walk up a steep hill with your suitcases. In full disclosure, Enigma Suites had a bellman meet our taxi, and he carried our luggage up the hill, but having good luggage was essential.

We got *this* new luggage in our registry, and it was phenomenal. (And it’s 30% off right now).

Also – Steven is Mr. Security, and so he had the brilliant idea of putting Apple Air Tags in all of our checked bags. That way, we could not only know for certain that the bags made it on the plane, but that, God-forbid something got stolen, we’d be able to track them down.

We used an anti-theft money/passport belt — we didn’t necessarily need it in Santorini, but in Athens we were thankful to have it, especially at the Acropolis. (I’ll do an Athens post next!)

Lastly, you’re going to want to capture these gorgeous sunsets, and Steven and I really had a lot of fun using his Canon camera. You can find it here.


Truthfully, part of the reason Greece was on our bucket list was that it has such allergy-friendly fare! Anywhere you can get a Greek salad (no cheese), and fresh fish with olive oil and lemon. And contrary to how it is here in America, that’s just how they cook it: simply and with high quality, clean ingredients. So from that stand point, meals were a no brainer.

Also – there are so many juice or smoothie bars around that you can pop into for a quick snack. Also, fruit stand polka dot the street.

I would still recommend carrying with you some travel-friendly snacks though. I brought two dozen Larabars with me for our 10 day trip and I ate every single one. (Carrot Cake is the best flavor!)

Also, these RX bars: the vanilla almond one is far and away their best flavor.

I also brought pumpkin seeds, almond butter packets, and almonds with me on my trip.

(And by the way, with today being Amazon Prime Day, all these items are on sale!)

So there you have it! I’m currently helping my parents plan their own trip to Santorini, it was that good!

Thank you for making it through this behemoth of a post! I’ll talk to you guys tomorrow, friends!

25 responses to “Santorini: The Ultimate Guide”

  1. Wow, Caralyn, you guys have so many beautiful, fabulous photos! I knew that Santoreni was beautiful, thanks for the wonderful tour. I am so happy for you guys! 🥰😊🙏🏻

  2. Wonderful to experience Greece on such a great occasion. We live on Crete, and totally agree with your observations. Moved here 2 years ago due to beauty, pace and food.

  3. Congratulations, and thank you for sharing such a beautiful journey. You guys were smiling all the time…was there something in all that sunshine…or food? 🤣❤️🙏

  4. Wonderful review of your trip. My husband and I will be going to Greece and Turkey in October, so I will be able to use some of your travel suggestions personally. What a beautiful beginning to your marriage journey.

  5. So good to hear about your honeymoon and the wonderful time you had. It sounds like you will have several family members and who knows, friends following in your footsteps. May you continue to enjoy wonderful surprises in your marriage!

  6. WOW, this is amazing. Awesome is an understatement. We are so ecstatic with your trip. Y’all portray such happiness, joy, and excitement. Hugs and Love 🤗 ❤️

  7. Oh, sweet Caralyn, It’s been too long! First, congratulations to you both!! What a stunning bride! Your honeymoon pictures and details are nothing short of breathtaking! The scenery, food, history, and of course, you two adorable humans! God bless you on your new marriage and thank you for taking us with you on your trip! I’d love to go to Greece!!! Much love and blessings, sweet lady! 💛

  8. Anita and I only had three days in Santorini when she was teaching at the University of Athens. Though I don’t remember the name of our hotel, it was a less expensive one without a caldera view, but very clean and wonderful service. It was someplace toward the south near the Heart of Santorini. However, we rented a tiny car and explored the entire island from Akrotiri Lighthouse to Oia and Ormos! We took a boat ride out to the central island for the hot springs of Palea Kameni.
    The history of the island fascinated me. Can you imagine being there when the volcano erupted, creating the caldera!!?
    ❤️&🙏, c.a.

  9. What a wonderful summary of your trip, and great recommendations! So happy y’all had a fantastic time on your honeymoon. I was wondering what brand of sunscreen/sunblock you were using–the sunshine was so bright, especially on the water, yet you and your hubby never looked sunburned?

  10. Amazing! I hope one day to visit that beautiful place. So glad you had a great honeymoon. God bless your marriage with much joy, peace and prosperity! 🥰

  11. This is by far my favorite of your posts. We visited Santorini last year on an NCL cruise 🚢 and it was magical, but we only got to stay a few hours. Just long enough to take iconic photos of the blue-roofed churches ⛪️ and posterize ourselves with the epic backdrops on the island. So glad you had a great trip and posted tips and details for us to enjoy with you. Such fond memories. Congratulations again on your wedding and honeymoon. Blessings on you and Steven.


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