Santorini and Milos

My first post is about mine and Kevin’s trip to Greece. We started our “adult” jobs in the summer of 2014 and took our first international trip together (not counting all-inclusive resorts in Mexico) to Santorini and Milos the following May.

Day 1:   Travel to Santorini and Kamari

We arrived in Athens and boarded a flight to Santorini without leaving the airport. Upon landing in Santorini, we took a taxi from the airport to our hotel (Chez Sophie) in Kamari Beach. Santorini is shaped like a backwards letter “C” and hotels near Oia (the north end of the “C”) or ones on the caldera side are significantly more expensive that ones at sea level, on the other side. My intention was to save some money and stay a few nights in Kamari (south end of the “C” on the non-caldera side). Ultimately, this was a huge mistake and I wish we had invested the money in a hotel with caldera views for our entire time in Santorini. The hotel itself was fine – close to the beach/boardwalk/restaurants, had a nice enough pool (which we never used), with slightly outdated furniture.

Our first afternoon was spent eating lunch on the boardwalk at Family Tavern, buying beer and chips at the local convenience store, visiting Kamari beach (Santorini’s black beach), and eating dinner at Hook. We found the restaurant on Google Maps and it was pricey and underwhelming. Rather than googling restaurants, I suggest asking your hotel for recommendations – they can help avoid tourist traps on top of suggesting places with good food. Before dinner, we found a small local travel/excursion agency along the boardwalk and purchased a full-day boat cruise for the next day.

Day 2: Full-day boat cruise

If I can recommend one thing to do in Santorini, although it’d be hard to choose just one, it’d be this boat cruise. And Santo Wines. I lied, I can’t choose. It gave us a PHENOMENAL overview of the island in one day and we did it all by boat! We got on a tour bus in Kamari beach and took a short ride to the ship dock. Here is the cruise itinerary:


We boarded the ship and sailed to the first stop, a volcano. Here we got an opportunity to hike to the top of the volcano with an hour or so of free time. The hike itself is not strenuous but you are hiking a volcano with black lava all over the place so it get’s HOT!

Hot Springs

Once everyone is back on the ship, it sails to the hot springs. By sail to the hot springs I mean the boat docks relatively close to them and you have to jump off and swim (with no life jacket) about 2 lap pool lengths. The jump is high, the water is cold, and the swim long, but worth it in our opinion. You get about 15 mins to awkwardly sit in a large, natural bath tub with strangers but hey when in Greece.


Swimming back to the boat is even more exhausting but extra physical activity equals more gyros! Upon docking in Thirassia, we had two choices for the way to the top – by foot or by donkey. Kevin refused to get on a donkey so I was forced to sprint to the top of the island in an effort to avoid getting stuck behind a tribe of pooping donkeys. We then explored the island, ate lunch at a cute little restaurant (which proudly displayed a “we have wifi” sign on a piece of cardboard) overlooking the sea, got some coffee, and boarded the ship.


The last and final stop of the excursion was Oia (pronounced EE-A). At the bottom of the island we were once again faced with a choice of foot vs. donkey. You guessed it, we sprinted to the top and I still regret not riding a donkey. We stopped by a liquor store to buy some wine and found a prime location for sunset viewing. I HIGHLY recommend getting a spot early on or making a dinner reservation for a restaurant with caldera views. We got there 1.5 hours in advance and the place was already half-full, rightfully so as sunsets in Oia are not over-hyped. After the sun had set, we boarded our tour bus, arrived back in Kamari, and grabbed a quick bite on the boardwalk near our hotel.


Day 3: Exploring Santorini

It’s hard to pick a favorite day in Santorini but this was definitely one of them.  We ate breakfast at Varkes (it was NOT good, even by cheap Greek food standards), I got a fish pedicure (VERY weird experience that I can’t say I regret but definitely did not enjoy), and walked to an ATV rental shop in Kamari. We used Motor Inn and rented a large twoseater, which was perfect for exploring the island.

Kamari sunrise
IMG_2219Ancient Thera Entrance and Parking

Our first stop was driving up to the Ancient Thera, which required extreme ATV maneuvering skills (thanks Kevin!). We did not go into the ruins but the view and getting to and from the top was really fun.

Santorini Brewing Company

Stop two was a small craft brewery in Santorini, which offers free tours, tastings, and souvenirs.

Santo Wines Winery

If you have a limited amount of time in Santorini, PLEASE go here. The views, the wine, the cheese boards, I can’t even. We did not do the tour but nevertheless spent about 3 hours enjoying the scenery and tasting 18 of their wines.


After taking a mini nap on the grass outside of Santo Wines, we drove our ATV to Gavalas George, a small local winery. It was difficult to find and the tasting room seemed small so we did not taste any of their wines and moved on to Boutari, another local winery. This winery, while not as impressive as Santo Wines, is definitely worth a visit for their rustic tasting room.

Red Beach

Next, we headed to the Red Beach to enjoy the sunshine and relax on the warm red sand.

Akrotiri Lighthouse

After spending an hour at the Red Beach, we drove the scenic route to Akrotiri Lighthouse, which is located at the south west tip of Santorini. The sunset was not as impressive as the Oia one, but seeing the caldera and Greek countryside from a different perspective remains one of my favorite Santorini moments.

After a jam packed day, we drove back to Kamari, showered/got ready, and enjoyed dinner at Zafora in Fira. This place had some of the best lamb I have ever had (Kevin can confirm) and incredible nighttime caldera views from the restaurant’s rooftop. Since we were already in Fira, which contains the majority of the island’s nightlife, we danced till 2 AM at The Highlander, Murphy’s Bar, and Saloon Bar.

Day 4: Imerovigli

After eating breakfast at our hotel, we packed our belongings and relocated to Remezzo Villas in Imerovigli. I cannot recommend this hotel enough and wish we had stayed there the entire time. We spent the day lounging at our pool, exploring Fira, and dining what would be my favorite restaurant in Santorini – Argo (ask your hotel to make reservations). Post dinner we had drinks at Two Brothers Bar (gorgeous panoramic views and a chill atmosphere), and stayed out way too late dancing at The Highlander (the music was just too good).

Day 5: Skaros Rock and Fira

Because our hotel pool was awe inspiring, we once again spent the morning lounging around and ordering room service. In the afternoon we walked the route from Imerovigli to Fira and back. Along the route, we climbed all the way to the top of Skaros Rock, which I am not sure is entirely legal and should definitely NOT be performed in flip flops (oops). While in Fira, we found our favorite souvlaki place – Lucky’s Souvlakis. It was so good, we got it three times in two days! For dinner our hotel recommended Anogi and it did not disappoint (I can still smell that delicious fried pork belly).




Day 6: Fira and Ferry

Since we were catching a 6 PM ferry, we spent our last few hours in Santorini exploring the shops and boutiques in Fira, where I discovered that frozen GREEK yogurt is better than ice cream. In the evening, we boarded the ferry and headed to Milos, a small island north west of Santorini. I picked this island as our second Greek destination because I liked that it was remote and secluded. However, I wish we had gone to the more popular Mykonos or Naxos instead – there is a reason tourists swarm to those destinations. While Milos was unique and beautiful, it REALLY paled in comparison to Santorini and we were left underwhelmed. We arrived late and had dinner at Mikros Apoplous. This restaurant is close to the ferry dock and serves fresh caught calamari, still the best I’ve ever had.

Day 7: Milos Boat Trip

We woke up early and walked to the Adamas port to meet our Oneiro Milos tour group for an all-day boat tour. The weather was on and off rain so perhaps we didn’t get to truly appreciate the full beauty of the island but we did visit some gorgeous sights:

Cape Vani – beautiful volcanic rock formations.

Sykia and Pirate’s Cove– caves and snorkeling.

Kleftiko – beach with turquoise water and white cliffs. We docked here and the captain (Elias) cooked an out of this world fresh seafood pasta lunch while we snorkeled.

Fisherman’s Village – colorful houses right on the beautiful water.

The tour itself was worth every penny and we felt like we got a really good overview of the island by boat. My favorite part was visiting some secluded caves and seeing mountain goats. For dinner we had O Chamos but would not recommend it. Maybe it was our entrees (goat) but the meal ended up being expensive and underwhelming. Because Milos has virtually zero night life (another reason why we should have gone to a bigger island) we stayed in and watched Netflix on our computer.

Lunch on Kleftiko
Fisherman’s Village

Day 8: Sarakiniko and Athens

Before heading to the airport we spent a few hours at Sarakiniko beach – a unique rock beach, which feels like another planet with turquoise water surrounding white rock formations.


On the way to the airport we stopped at a small seaside tavern for lunch and boarded a plane to Athens. We arrived in Athens at 8 PM so we only had time to drop off our bags, see a side view of the Acropolis, and eat dinner in the city center before heading to the airport for a 6 AM flight back to Chicago. From the little that we saw, the city seemed VERY dirty and even sketchy in some parts so I have no regrets about not exploring Athens. Some would tell you to spend at least a day there to explore the history but we’re all about that island life.


Here is a short list of tips based on our experience:

  1. Stay in Imerovigli, Oia, or Fira – caldera views and access to the isalnd’s best bars and restaurants is worth every dollar
  2. If you decide to go to islands other than Santorini (because Sanotrini is a MUST), pick a more well-known island – there will be more activities and it will be easier to get around (and get to and from)
  3. Ask your hotel for restaurant recommendations and reservations
  4. Eat as much souvlaki and Greek salad (including the giant block of feta) as you can possibly fit into your body
  5. Book trip excursions locally once you know with more certainty what the weather will be like – there are plenty of local travel agencies and tours usually do not fill up more than a few days in advance
  6. Rent ATVs or scooters, nothing else will give you such an ability to explore the whole island in one day

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