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Where to Stay, Dine, and What to Do on a 2 Week Island Hopping Dream Vacation in Greece

by | Jul 21, 2021 | Travel | 0 comments

Greece FAR exceeded my expectations. The food, people, hospitality, beaches, and sunsets absolutely blew me away. There are SO many things to do no matter where you are, you’ll never get bored! And you can never have too much feta! 

In this post, I’m outlining the top highlights from my 2 week, 4 location trip in Greece with a very *loose* suggested itinerary if you ever find yourself booking a Greek island getaway! 

Rather than doing a “day 1, day 2, do this this and this on this exact day” version (which feels restrictive to me – when I was looking up Greece blog posts prior to my trip at least!) i’m organizing it into STAY, DINE, and DO for each spot. 

And also, not an #ad but definitely putting in a HUGE plug for working with travel agent Brie Shelly at @theexperiencewithbrie for all your travel planning needs! I’ve never worked with an agent before but knew this Greece trip would be a bit more complicated than other trips i’ve taken considering we did 4 locations in 2 weeks, with 3 of them being islands. Brie was EXTREMELY helpful with every single detail to make sure my trip was the trip of a lifetime. 

She even helped me renew my passport in record time (also recommend It’s Easy for passport renewal! You can do it all through an app right on your phone!) and thought through every part of our trip to make sure it’s exactly what I wanted.


Besides the Acropolis tour, here’s what else I’d suggest in Athens. Besides the Acropolis tour, I’m not sure if there’s a ton to do and there are some shady spots from what I heard, so not the best for relaxing on vacation! I felt SUPER safe the whole time, but from what some locals and some of my Greek friends had to say, you just don’t want to go too far off the beaten path here.

Stay (Athens)

At the New Hotel which is about 40 minutes from Athens International Airport. The hospitality was amazing, especially after coming off a red eye where I didn’t sleep one wink and was so delirious and in such need of a long shower and cozy bed!

Dine (Athens)

Grab a quick lunch at The Greco’s Project which is also closeby lots of shops and convenience stores if you forgot anything at home or need an American → European charger adapter like I did! (Public store has everything you need if this is you!) They have amazing Gyros (pronounced “yee-ro”) which is a traditional Greek sandwich made with beef, pork, lamb, chicken or any mixture of meats seasoned and cooked with delicious spices and then piled into fluffy pita bread with grilled veggies and tzatziki sauce. Tzatziki is a creamy Greek yogurt sauce with cucumbers and fresh garlic that I wanted to douse over EVERYthing!

We had dinner at Kuzina which was amazing. The views and vibe were awesome!

gyro at the grecos project greece

Do (Athens)

Acropolis tour: the views of the city are unreal and the history is just super cool. You can read more about the history of the Acropolis here

Also check out the beautiful National Garden in Athens. According to discovergreece.com,The garden is home to 7,000 trees, 40,000 bushes and other plants, making up 519 species and varieties. More than 100 of them are Greek, with Judas trees, oleanders and carob trees the undoubted stars, while others come from countries all over the world, such as Australian pines or Chinese trees-of-heaven.” It’s beautiful, peaceful, and serene and just what we needed after being on planes and in airports for the previous 16+ hours!

national garden athens greece
beautiful national garden athens
national garden greece

Ahhh, next is magical Milos!

I am OBSESSED, like, beyond obsessed with little Milos! If/when I go back to Greece I would spend one entire week on Milos. I did NOT want to leave! This magical little island is still relatively new to tourism and it shows with their eagerness to please and have tourists! I’m absolutely positive this place is going to get SUPER popular, so go now while you can relish in the beauty with a bit more privacy! 

Milos is home to super unique “moon” like beaches (Sarakiniko beach), right on the water restaurants, some of the best hospitality i’ve ever experienced, and lots of cute stray kitties.

First things first, rent a buggy or ATV! It’s the easiest way to get around the island and sneak into small parking spots at any of the more crowded locations. Plus when i’m on vacation if I can choose a fun ride I don’t get to use back in the states, then sign me up! Who wants to be covered up in a car when you’re in beach mode? Not me! We rented through Pollonia Motors and they did drop off and pickup right at our hotel. 

Stay (Milos)

I cannot say enough great things about Milos Breeze boutique hotel. It was a quick 40 minute flight from Athens, followed by a 15 minute ride to Milos Breeze from the airport, and were greeted with the BEST hospitality. It was around 9am, breakfast time when we got there so they offered us whatever we wanted! Omelettes, special Greek pastries, Greek yogurt with fresh fruit, granola & the best honey i’ve ever had, and even crepes, waffles, pancakes, you name it they had it! Our room wasn’t ready that early so we enjoyed breakfast, chatted with some new chill down to earth friends we met (turns out they are Canadian YouTubers, check out their channel!) and hungout by the pool until our room was ready. 

We splurged (which I actually think is way underpriced for what you get/the location!) for a Deluxe Room Sea View. We could have breakfast right on our porch every morning or down by the pool. Breakfast is included with your stay and is DELICIOUS! The coffee is amazing too. A quick coffee note! In Greece, if you want “iced coffee” you’ll order “Freddo cappuccino” – they don’t really do iced coffee (coffee poured over ice) like we do here. We got quite addicted to freddo caps, they’re amazing! You won’t miss your American coffee, I promise! They do have regular American coffee hot as well. 

The beds are comfy, the views amazing, the vibe is so chill, pool (x2!) is to die for, hospitality amazing, stay here. You will NOT regret it! 

milos breeze boutique hotel sea view
the view from our room in milos!

Dine (Milos)

A quick 20 minute drive will put you in Plaka which is an adorable little town with cute little shops, great restaurants, and gorgeous sunset views. We loved this restaurant called Archontoula in Plaka so much that we ate there two nights in a row! It’s nestled into this adorable picturesque cobblestone walkway that’s perfect for people watching. The food is everything you came to Greece for and more. I got the same Greek salad both times we went because when I say it’s the best one I had our entire 2 weeks in Greece, I’m not kidding! 

greek salad at archontoula milos
eric's chicken dish at archontoula milos

After dinner at Archontoula, try to grab a table for coffee or treats to watch the sunset at Utopia Cafe. Both nights we tried they were completely full (but we also showed up quite late, oops) so we didn’t actually get to catch the sunset here but it was a super cool spot I’d highly recommend! 

For dessert while in Plaka, head across the street from Archontoula to Paleos Pastry which has some of the BEST gelato i’ve ever had. 

While you’re in Plaka, stroll the streets where you’ll find gorgeous bright colored flowers, fun doors and artwork all over the place. 

utopia cafe milos greece
gelato at paleos pastry milos
lexy in greece! milos is the best

Closer to our hotel in Pollonia was our second favorite restaurant out of all the ones we tried in Greece with was Gialos. We came back after an 11 hour (no, not a typo) boat cruise (more on that below – it’s a MUST do!) and ended up stumbling into this gem of a restaurant by pure luck. Waterfront dining doesn’t get more waterfront than this place! Check out the pic below – there’s literally a boat right at our feet! The food was amazing and the service was just the best.

yialos restaurant pollonia greece

We didn’t eat here (below), but this is an example of the vibe for restaurants in Pollonia:

pollonia restaurants milos greece

Do (Milos)

Kleftiko Cave & More Boat Cruise

Our travel agent signed us up for an 11 hour boat cruise and to be totally honest initially we were both like, “that’s a LONG time” haha! But after the cruise, we wished it had been even longer! I’m still confused why this is only $180 euro (so about $212 US dollars) because the value and experience we received was UNREAL. Our guide Giovanni Farinola from Excellent Yachting and his sidekick RJ truly went above and beyond to make our experience unforgettable. This boat cruise was truly one of the top highlights of our entire trip. 

As soon as we boarded the boat, Giovanni goes, “have I told you all today how much I love you?” swoon!!!!!

The boat tour brings you through a bunch of key spots where you can jump off the boat to swim, snorkel, and explore. 

We got to see all the key spots you could only see by boat, including the Kleftiko caves where we got to get in a little boat and literally go inside the caves to see the bioilluminesence! 

Do yourself a huge favor and book this cruise with these amazing people! I promise it’ll be the time of your life.  

milos cave boat tour
milos cave boat tour lexy
milos cave boat tour in the cave

Beach hopping via ATV or buggy (Milos)

This was probably one of my favorite days during our whole trip, in addition to the boat cruise I mentioned above. When we go on vacation we like to have a few key things planned but MANY days where we’re able to just go with the flow and this day is a perfect example of why! We got to hop in the buggy and just explore with nothing but a map and our bathingsuits! 

Milos is PERFECT for beach hopping because it has SO many cool beaches to explore, and we did 7 beaches within only 4-5 hours! They’re about 10-15 minutes from each other (some even closer!) and all have such different offerings. The pics below speak for themselves!

Our beach hopping day included:

Click each picture below in the gallery to view it larger!

Spend a day at Paleochori Beach

After the beach hopping and boat cruise days we wanted a full day to just chill at ONE beach. We stumbled upon Paralia Paleochori and parked our butts on some cozy beach loungers with macrame umbrellas and beach-side food/beverage service at Aqua Loca Beach Bar. The food and drinks were awesome (I think we got virgin pina coladas, coffees, and Greek salad.)

The water was the most beautiful blue, perfect temperature, and the mountainous beach backdrop was just SO cool. 

And if you need a beach hat or beach read suggestion, I highly recommend Hemlock Hat Co. for this adorable succulent patterned hat and also Beach Read (very meta, huh?) a rom-com by Emily Henry.

paleochori beach umbrellas and loungers
hemlock hat succulent

Overall: Milos had some of the BEST food, people, things to do, shopping, and sunsets of our entire two week trip in Greece. Truly cannot say enough great things about it! Super easy to get around, reallyyyy reasonably priced, and some of the best and coolest beaches i’ve ever seen (and I’ve been to Mexico, Jamaica, Hawaii, Cayman Islands, and grew up on Cape Cod!)

Now onto Sexy Santorini!

Santorini is literally built into the remnants of a volcanic erruption from thousands of years ago. Whitewashed buildings contrast amongst blue domes and lush purple flowers all overlooking the most sea my eyes have ever seen at one time to create a truly breathtaking experience. Pictures can’t really do it justice – its something you just have to experience!

It’s really a honeymooners dream and is VERY romantic. It felt like everyone in Santorini was in love! We saw maybe two families? It seemed to be mostly couples and for good reason. We can’t explain it, but it’s almost like there’s something in the air? Or maybe being SO high up nestled into the cliffs overlooking the Aegean sea feeling like such a tiny little speck in our beautiful world makes you feel dizzy with romance? IDK! 

Although we had a BLAST here, we would not return. It’s a place that was really cool to experience once, but overall wasn’t totally our vibe. There are some potential pros/cons of Santorini i’ll sum up here before diving into where to stay, dine, and what to do. If you know me, you know i’m brutally honest and don’t sugarcoat well so here’s my completely authentic opinion (and Eric agrees!) And since you’ll find no shortage of Santorini fan posts online, I’m just offering a few points I wish we had known prior to spending the longest leg of our trip there. 1-2 nights would have been plenty!


  • Absolutely breathtakingly gorgeous (see pics below!) 
  • LOTS to do. We went horseback riding, on a sunset boat cruise, explored a black volcano sand beach TWICE. You can do cooking classes, helicopter tours, and lots of historical sites, as well as an epic hike from Fira to Oia (which we skipped because honestly the steps of Santorini were enough for us, we were pooped!) 
  • Some of the most gorgeous sunsets I’ve ever seen

Cons: (not to be a party pooper, Santorini is wicked cool but there are just a few cons to keep in mind – that may not be cons for you, but they were for us)

  • Not a ton of beach options – which is FINE if that’s not a must for you. There is one we found and loved that i’ll describe below called Perissa beach. 
  • LOTS and lots and LOTS of steps. Like, a lot. Eric walks 15,000+ steps a day for work and HE was wiped out. We even got lost a few times going from the reception of our hotel to the restaurant to our room and such. 
  • It felt very much like people go here to get good pics for social media – which, if you know me is clearly not a priority for me haha! Santorini is very “instagrammable” which is cool if that’s what you’re into but it just felt very opposite of people living in the present moment. 
  • It’s expensive – your money goes MUCH further in spots like Milos or Paros (the other islands we visited.)

Stay (Santorini)

We stayed at On the Rocks in Imerovigli which was pretty reasonably priced for the great location. Each room (I believe!) has it’s own patio to take in the gorgeous ocean and sunset views from which is a HUGE plus. The hotel pool is SUPER tiny we didn’t even go in it because we felt so uncomfortable if anyone else even thought of going in at the same time! If I could, I would’ve stayed somewhere with a bigger pool especially since there aren’t a ton of beaches to explore here. Staying in Oia is also an option but SUPER expensive and a bit “busier” which we didn’t want. 


The place we REALLY enjoyed eating in Santorini was the Athenian House. It’s definitely pricey but very very VERY worth it! You choose from one of 3 menus and get, like, a BUNCH of different tastings. A few appetizers, a main course, and dessert. The owner would walk around and talk to all the guests making sure they were pleased with their meals and making small talk. The sunset views from here were breathtaking and it was such a great experience to be able to enjoy such delicious food while watching the sky get immersed in gorgeous sunset colors all around you. 

view from athenian house at sunset santorini greece
athenian house meal

Do (Santorini)

Horseback riding on the beach

This was super cool! We got to take pictures on our horses down by the beach and it was a 2 hour ride total through the backroads of Greece to the beach and back. The only thing is we thought we’d be riding on the beach for a lot longer. It was about 10 minutes riding along the beach or so? Still, very cool! Check out the company we used here. 

Perissa Black Volcano Sand Beach

We were told to skip the beaches in Santorini because they’re not as great as the other ones we’d see in Milos or Paros and not really what Santorini is known for but our beach bum selves couldn’t help it! We found a black volcano sand beach called Perissa. You can rent chairs & an umbrella for $20 for the whole day and trust me, it’s worth it! The beach was crafted from volcanic explosions and the “sand” under the water is more like (idk if this is true) but hardened lava? We like to pretend that’s what it is but don’t quote me on it!

We ate at a great spot right on the beach called Mezedaki where we got⁣ greek salad⁣, fries , tzatziki (which we dipped the fries in.) Highly recommend this Santorini black volcanic sand beach with a lunch at Mezedaki if you ever find yourself in Santorini!⁣

And finally, Picturesque Paros! 

Paros was our second fave spot after Milos. When I think of what I envisioned Greece to be like before I went there (since I’d been dreaming of going to Greece for YEARS!) Paros is exactly what I imagined. Delicious food, great shopping, beautiful whitewashed villages covered in pink flowers, and SO many gorgeous and unique beaches with vivid turquoise seas. 

There are two main areas of Paros. Naoussa is a quintessential Greek village known for it’s superb shopping, waterfront dining (even directly on a boat!) and a small castle. It’s also more “up and coming” for nightlife, but our bedtime is basically 10pm these days so we didn’t experience that! Parikia is the capital of Paros where the ferries drop you off. We loved wandering over to Parikia for a more lowkey experience away from the hustle and bustle of Naoussa. This is the best place to wander cobblestone streets in search of authentic Greek goods for a lower price tag than in Naoussa. 

naoussa village paros greece
parikia paros greece
eat on a boat in paros greece!

Stay (Paros)

We went from hustling bustling Santorini to cool, calm & cute Paros where we stayed at Mr. and Mrs. White. It was exactly what we needed after feeling kinda clustered in Santorini. They have two amazing pool areas (like, full size pools!) with cozy, relaxing lounge chairs and even huge beanbag chairs to lounge on! The service is amazing and similarly to Milos, you feel like family/at home. Our $$ went MUCH further here and upgrading to a Suite with a Sea View was SO worth it (our view is the picture on far left below.)

The hotel was a 5 minute ATV ride to Naoussa which we were grateful to be so closeby to once we realized how cool it was and that it was home to our new favorite Italian restaurant (keep reading!)

the view from our hotel room at mr and mrs white
lexy at mr and mrs white hotel by the pool
mr and mrs white pool

Dine (Paros)

I know you’re probably going to Greece for the Greek food – which you will definitely get PLENTY of but I encourage you to also check out this amazing Italian restaurant in Paros called Giacomo in Naoussa. We actually ate there two nights in a row! I guess that’s a pattern for us haha! I’ve never had anything more waterfront dining than this, and the food is AMAZING. Go for the Risotto with parmigiano reggiano and fresh truffles, Bucatini cacio e pepe with freshly ground black pepper and pecorino romano, Spaghetti carbonara with smoked pancetta, parmigiano reggiano and poached egg, and/or the Caprese pizza. 

caprese pizza at giacomo paros greece
giacomo restaurant paros greece
cacio e pepe giacomo paros greece

Barbarossa was our other favorite restaurant in Paros – right on the “dock” in Naoussa. From their website, “Barbarossa has a history in Paros. Its kitchen has served celebrities, members of royal families, people who have written history. But the ingredients remain simple. They are the building blocks of Greek island gastronomy. The foods that Paros produces. Bararossa’s kitchen is Paros, on a plate.” They also had some of the best service i’ve experienced in a restaurant. You can check them out here

Do (Paros)

We were total beach bums in Paros since this was our last spot before heading back to Boston. All we wanted to do after so many boat excursions, horseback riding, and exploring was just CHILL. We started out one day doing a beach crawl like in Milos but fell so in love with one beach that we ended up renting beach chairs/umbrella (only $16 for the whole day) for our only two full days in Paros at Faragas Beach on the south side of the island. 

Faragas beach has some of the most beautiful water i’ve ever swam in combined with the softest most beautiful sand to the point where you almost feel like it’s pool-like? There’s an area with rock formations and little cave-like entrances – it’s SO cool. One day our “umbrella” was a beautiful tree!

On land you get beach-side service for delicious food, refreshing smoothies and drinks if you so desire. They play music all day and the vibe is just generally so fun, upbeat and a good mix of families, singles, couples, and young and old people! We loved it. 

We also bopped around briefly to these beaches which we also recommend:

  • Chrissi Akti (Golden Beach)
  • Parasporos Beach
  • Kolymbithres Beach (unusual rock formations)
  • Santa Maria Beach
papafragas beach shade from a tree

Other Greece FAQ!

Getting Between Islands

I’m honestly not the person to ask because our agent booked this all for us! I know there are plane and boat options – but i’m not sure how it all works. We took a plane from Athens → Milos, boat from Milos → Santorini, boat from Santorini → Paros and a plane from Paros → Athens and then obvi a plane to Boston from Athens lol. I know there slow and fast boat options – we opted for the fast to limit travel time. Although one of our fast boats (1 hr ish supposed travel time) ended up being 3.5 hours – still no clue how but we made the best of it with like 100 games of rummy and lots of snacks!

Food for Special Dietary Requests?

I’m gluten free (celiac, ugh) and lacto-ovo vegetarian (no meat or fish but yes to eggs and dairy) and I found PLENTY of options while in Greece. My favorite go-to was Greek salad + fries dipped in tzatziki but I also ate stuffed peppers & tomatoes (a classic Greek dish), grilled veggie dishes, risotto, gluten free pasta dishes, delicious fava bean dip, and much more. We even got tacos one night to break things up, so there’s plenty of options in addition to Greek food of course!

Why not Mykonos?

Lots of people have asked if we went to Mykonos because it’s one of the most popular Greek islands and although we were somewhat planning on doing a day trip there from Paros, we decided against it because we heard it’s a BIG party spot (we’re both sober – and even though we like to party, we’re a bit more chill these days!) and very very VERY expensive. So, just not our vibe. But if you’re into that party scene, go for it!


In case you didn’t notice, I didn’t mention any breakfast restaurants! That’s because every one of our hotels had breakfast included. You’d either complete a breakfast form the night before and they’d deliver it during whatever time you specified (On the Rocks in Santorini), or you’d go down to breakfast during your chosen time and order whatever you wanted (Milos Breeze and Mr. and Mrs. White.)


We felt SUPER safe in Greece because of their restrictions for entry. (Writing this on July 22, 2021 so it could definitely change by the time you read this!) You had to either 

– provide proof of vaccination

– provide negative covid test taken within 72 hours of departure

And Greece prioritized vaccinating the tourism industry so all the servers, hotel staff, cab drivers etc. that we spoke with were vaccinated. There was sanitizer on every table and servers wore masks. 

I hope you enjoyed this post as much as I did living it, writing it, and re-living it! Please comment below any questions, your own Greece suggestions, thoughts, or just if you liked this post let me know! Be sure to follow me on Instagram @lexypenney for more food, body image, and occasional travel stuff!




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Blog Lexy Penney Nutritionist Boston Intuitive Eating

Hi, I’m Lexy!

I’m a Registered Dietitian, yoga teacher, & body image coach.

I help women make peace with food and built trust with their bodies so they can live the lives they desire and deserve.

Hop on my email list for your weekly dose of food freedom, body liberation and self-care!

Lexy Penney Nutritionist Boston Intuitive Eating

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