Deciding Between Mykonos and Santorini

Ah, the Greek Islands – sun-drenched landscapes, turquoise waters, and ancient charm. But when it comes to Mykonos and Santorini, two of the most famous islands, choosing the perfect one can be daunting. Which one is right for your travel style? Below we consider the vibe (atmosphere), pros, cons and key questions to consider when deciding between these two incredible islands.


What can you expect from a stay on Mykonos? Think endless stretches of golden sand, vibrant beach clubs pulsing with music, and cosmopolitan charm. Mykonos caters to the social butterfly: those seeking lively nightlife, trendy boutiques, and the chance to rub shoulders with celebrities.

waves and windmills in Mykonos Greece

Imagine yourself indulging in champagne showers at Paradise Beach, dancing into the sunrise at Super Paradise, or exploring the narrow, whitewashed alleys of Mykonos Town. Mykonos offers charming Mykonos Town, windmills, and scenic coastal walks. This island perfectly caters to diverse interests, whether you want to relax on golden beaches, indulge in luxurious spas, explore Delos Island’s ancient ruins, or hit the vibrant nightlife scene.


  • Perfect for short trips 3-4 days
  • Flatter landscape – better for those with mobility concerns
  • Lots of variety available
  • Soft-sand golden beaches


  • Not as dramatic scenery as Santorini
  • Fewer activities are available in the off-season – most of the island is closed.
  • Not very many wineries to enjoy

Questions to Ask When Considering a Mykonos Vacation

Who am I traveling With? – Mykonos is perfect for families, large friend groups with diverse interests, and multi-generational trips or folks with mobility concerns.

How do I feel about Crowds? – In the quieter “shoulder” season you can actually escape the crowds on Mykonos. The slightly wider streets and larger island also offer some crowd relief, so if crowds aren’t your thing Mykonos is the best option.

Do I want an Active Adventure or More Relaxation Time? – Mykonos offers more relaxing on soft sand beaches, go with the flow vibes. There is a greater focus on wandering, relaxing and indulging.

[Photo Credits: Courtney via Shared Adventures Travel]


What can you expect from an adventure to Santorini? Picture dramatic cliffsides crowned by whitewashed villages, breathtaking volcanic landscapes, and panoramic views that melt your heart. Santorini entices the romantic soul: those yearning for candlelit dinners with caldera views, intimate sunset strolls through Oia’s charming streets, and exploring ancient ruins steeped in myth.

A happy couple with the white washed walls and blue domes of Santorini Greece behind them

Witness the fiery magic of the sunset, sail around the volcanic caldera, or indulge in a wine tasting amidst the vineyards. Santorini offers volcanic hikes, wine tastings, boat tours, and cultural immersion. It’s the perfect destination for outdoor adventures.


  • Unbelievably stunning dramatic views and vistas
  • Perfect for hiking and outdoorsy activities
  • Romantic atmosphere which caters to honeymooners and couples
  • Over 20 wineries to enjoy
  • Plenty to do and see – could easily spend a week on the island


  • Lots of hills and stairs – challenging for those with mobility concerns
  • Longer tourist season – expect to find crowds from early April – November
  • Volcanic pebble, rocky, or course sand beaches

Questions to Ask When Considering a Santorini Vacation

How much Time do I have? – There’s enough to do to spend a whole week here and you can take your time to enjoy Santorini. It’s worth spending more than a few days, if budget permits.

sunset over the ocean santorini greece

Do I want an Active Adventure or More Relaxation Time? – You can, of course, spend time relaxing on Santorini but with its dramatic cliffs and volcanic landscape it’s great for active travelers who enjoy hills, stairs, hiking and water adventures like kayak and boating.

How do I feel about Crowds? – Santorini is well known and its narrow streets don’t offer a lot of breathing room. While the shoulder season is less crowded there will almost always be crowds. But, as Santorini makes an effort to become a year-round destination, more hotels and activities are available in the cooler months. (The only thing you won’t find open in winter is beach clubs/ pools)

[ Photo Credits: Alicia & Jay via Shared Adventures Travel – read about their family adventure to Greece here! / Christina via Shared Adventures Travel]

No matter which famous island destination you choose – you’re sure to have an incredible time soaking up the sunshine and beautiful Greek culture! If you’re ready to start planning your Greek Island Adventure – or want to find out about some hidden-gem island options — let us know!

A Family Adventure in Greece

Long-time clients Alicia & Jay came to us for some help with a bucket-list trip to Greece with her mom, dad, sister, and brother-in-law. The whole family wanted a mix of sightseeing, relaxation, luxury hotel amenities, gorgeous beaches, and incredible food! We were thrilled to put it all together for them. Here’s their feedback:

We can’t thank you enough for planning such a perfect family trip to Greece! We had an amazing time! We had beautiful, warm, and sunny weather for most of the trip.


As you already know, when we arrived in Athens on Saturday morning, there was a mixup with our transportation and we ended up just taking taxis to the hotel. However, after this, the trip was mostly seamless! The Athens Gate Hotel was wonderful and very helpful in confirming our transportation for the following day. When we arrived on Saturday, we had lunch and explored Hadrian’s Arch and Monastiraki Square. We had drinks and dinner at the Athens Gate rooftop, which had beautiful views of the Acropolis.

On Sunday, we had our tour of the Acropolis. When we got to the meeting point, there was no one there to meet us for the tour. We contacted the tour company and they arranged for someone to meet us back at our hotel so we could leave from there. The tour of the Acropolis was amazing and our tour guide was incredible. It was definitely good to do it early in the day because it was 90+ degrees, and it wasn’t too crowded as we were climbing up, but on our way down we noticed that the crowds had increased significantly.

After the tour, we grabbed lunch and headed to the airport.


We absolutely loved the Minoa Palace Resort in Crete! What a beautiful resort, which certainly earns its 5-star status.

We spent the next four days mostly between the beach and pools and walking to nearby restaurants for dinner. The hotel staff couldn’t have been nicer, arranging taxis and even salon appointments for us. We loved our rooms with the private pools!

The Cretan Cooking Class was an incredible experience and one of the best meals we had the entire trip. It was amazing to see the family’s villa high up in the mountains with incredible views.

We also explored Chania Old Town on Wednesday, which was beautiful. We stopped for lunch along the water at the perfect time because the skies opened up and gave us quite a storm. I think that was the only time it rained the entire trip in Greece!


I think Santorini was collectively our favorite place! The Petit Palace Hotel blew us away with its incredible views. Talk about a grand entrance – the hotel’s entrance is literally two doors on the side of a cliff and all you see is the water below when you walk through. Our rooms were again spacious and impressive – from the unique bathrooms to the balconies. We saw the best sunset of our entire trip from our hotel room balconies. The hotel had a shuttle that runs back and forth to Fira, and the staff was very helpful with arranging taxis for us elsewhere.

We spent time exploring both Fira and Oia, which was my favorite place, as well as the black sand beaches – we spent a day at one of the beach clubs called Wet Stories. Marissa, Joe, and Bob did a hike from Fira to Imerovigli, which they said was amazing! We also did a tour and wine tasting at Santo Wines, which was great!

The highlight in Santorini for all of us was the Sunset Boat Tour. The tour ended up being all adults and relatively small (we lucked out with a fun group). The crew was spectacular and the food they prepared was delicious. We all swam in the Aegean Sea and enjoyed drinks, good music, and beautiful views.


We all agreed that it was so nice to have one extra night in Athens at the end of the trip. We loved the Sofitel – the convenience of the two-minute walk from baggage claim was ideal. We had dinner at their rooftop restaurant and it was great to be able to freshen up and get a good night’s sleep before the long flight back to Boston.

Overall, you knocked it out of the park again! This was the most memorable family trip. Thank you from all of us for planning the best escape to Greece!


Afternoon Tea and Gyros

I am VERY late in posting this wonderful trip report from Andrea and Eric’s June “escape” to London and Greece. But in some ways the timing is just right, as the snow falls outside and we all start dreaming about summer vacation. So enjoy this little daydream of Europe. And then give me a call to start planning your trip for 2020 🙂

Hi Ann — We got back yesterday evening and both agreed that was a trip of a lifetime. It was fantastic! We’ve adjusted back to east coast time pretty quickly, but getting on Europe’s time required some effort. 

Greece had so much to offer. Our stop in London was brief but we squeezed in quite a bit. St. James Court hotel was just a few blocks from Buckingham Palace, so any time we wandered out we got to pass by and appreciate the view. We booked an afternoon tea time at One Aldwych Hotel. The tea party theme was Charlie and the Chocolate Factory and was so well done. We then did an afternoon ride on a hop-on-and-off bus tour. Unfortunately, Big Ben was covered in scaffolding and the tour guide said it’ll be under construction for the next few years. 

In Athens we had our skip the line walking tour you booked us for the Acropolis and the museum. It was really interesting and helped us appreciate the history much more than I was expecting. Our hotel was centrally located in Athens and fairly basic but nice. Everything was walkable and we had a great view of the Acropolis from our hotel.  

A perfect trip combo- Greece & London! Oh the sites you can see and the things you can do! Here's a potential itinerary

Mykonos was our next stop and was our favorite! The Myconian Utopia Resort was so well kept and so impressive. Words can’t describe this place. The views, the infinity pool, the service, and private beach were all fantastic. We’d love to visit there again someday. Our days here were spent either on the resort or the private beach (we even jet skied), not much else was easy to travel to with our limited number of days there. But that was perfectly okay by us.


infinity pool in Santorini Greece

We then got to Santorini by ferry and we were unsure on that process, but it was pretty easy. Our transfers to and from the ferry didn’t work out. The pickup car in Santorini didn’t show, so we ended up having to take a shuttle to the hotel. The hotel views of the caldera were so amazing it’s hard to describe. Our hotel, Chromata, was literally on the cliff! The town of Imerovigli, where our hotel was, was great since there’s so much there. There are little markets, rental car shops, and plenty of places to eat so we felt less bound by the hotel than we did in Mykonos. Our room itself was pretty basic, but the view was fantastic. They were completely booked so they didn’t have any available upgrades.

The hotel service was amazing. We took a semi-private sunset luxury boat tour through Volcano Yachting. We booked it very last minute – the night before. It’s the best thing we could have done in Santorini. It traveled through the caldera and stopped at the red beach for swimming, stopped at the volcanic island for us to swim in the hot springs, and included free drinks and dinner. The sunset was unbelievable. They even picked us up and dropped us off at the hotel. The next day we rented a tiny smart car and drove to the black beach. It’s actually black and pretty cool. But since the sand is black is extremely hot to walk on. I wish I brought my water shoes. Flip flops weren’t enough!

View of Santorini Greece on the cliff
a beautiful balcony overlooking the sea

Our trip came to an end and we had a very long day traveling back (Santorini to Athens, Athens to London, then London to Dulles). We were extremely lucky that we made it to London a few minutes early, we knew there was a United flight from London to DC at 12:15pm and thought just maybe we could get lucky and get on that flight instead of our 4:40pm flight. We stopped at the United desk, they called the gate, and they let us onto the 12:15pm even though they already finished boarding everyone. This was the moment having no checked bags really paid off! Ha. So glad because we got home 5 hours earlier than expected.

By the way, we ate a lot of gyros – all were great! Oh, and I attached a few pictures from our trip! We have hundreds on our phones need to sort through still 🙂


the view from the stair of Santorini

Thank you again for being so available and helpful with this entire process. Booking this trip on our own just seems so daunting and I’m glad we avoided the black hole of reading hotel, tour, and other reviews online. Made our lives much easier. Thanks again!

 Andrea & Eric

An Epic “Escape”

Christina and Chris were celebrating their second wedding anniversary, and contemplating the reality of starting a family at some point in the future, and wanted to go cram in as much of Europe as possible before “settling down”.  Because Chris is a teacher, their summers are flexible, so Christina blocked a few weeks out of work and they sat down with me to plan an epic adventure. In the span of three weeks, they did a pretty good job of exploring Belgium, Italy and Greece. While you might not want to replicate their breakneck pace, you could take their tips and suggestions (below) and make any one of these three countries into a very nice vacation on its own:

Our European Escape

Although our trip was just over a three-week span according to the calendar, it feels like my husband and I were away for months!  Now looking back at the photos and reminiscing about the adventures from the beginning of our trip, the moments already feel like a lifetime ago.  I am so grateful for this feeling and for your expert planning for our travels abroad!!


Mons, Belgium was the first destination on our whirlwind tour.  My dad has been living there for just over a year now, and we joined my step-mom, brother, and Loofa (my dad and step-mom’s bichon frise) for five fun-filled days.  We sampled beers in every town and city, reveled in the chocolate, and devoured the waffles.  We began our time together in the city center of Mons, and then branched out to Tournai, Waterloo, Brussels, Ostend, Bruges, and Ghent in the following days.  Each place reflected its roots – French speaking Wallonia or the Dutch speaking Flemish countryside.  A Flemish city always seemed to be organized and clean!

two people and a puppy in front of the canal in Ghent BelgiumSome highlights include Notre-Dame de Tournai, the cathedral in the center of the city, and Tournai’s large open city square with rows of fountains, the museum and Lion’s Mound overlooking the countryside at Waterloo, the Grand Place in Brussels, the expansive beach at Ostend, the architecture and beauty of Bruges, and Michelangelo’s Madonna and Child.  This sculpture is remarkable for a number of reasons, one of which is that it was the only sculpture to leave Italy during Michelangelo’s lifetime.  (I can’t believe how fortunate we are to have seen both Michelangelo’s Madonna and Child in Bruges and the Pietà in Rome on the same European trip!).  We took a hilarious and wonderful horse-drawn carriage tour of Bruges while in the city, as well!

CD - BrugesI was least familiar with the places to see in this country, relying mostly on my dad for our itinerary.  I did, however, consult your Destination Guide email that introduced us to Belgium via the web.  This was a great resource!  Because of this email, my family specifically decided to take our last full day together to travel to Ghent, Belgium.  The city was described as a “less-touristy” Bruges, and we were excited to explore it as a family.  It did not disappoint!  The city offered a castle, boat tours along the city’s canals, and a beautiful skyline of medieval architecture.  There is a wealth of history in Ghent, and we only just tasted a sample!

a happy group in front of the unique architecture of Tournai

Belgium is beautiful.  I may have underestimated it because of its size, but it has so much to offer!  I am very grateful for the time we were able to spend together exploring this lovely country with my family.


After a farewell breakfast with my family, Chris and I were off to our first stop in Italy – Venice!  Ann, your instructions and maps for transportation from the airport to our hotel were clear and incredibly helpful – thank you!  We spent the evening wandering the streets, eating dinner, and people watching in Piazza San Marco.  The next day we traveled by water taxi around the canals and took one to the island of Murano.  In addition to watching some very skilled glass blowing demonstrations, we ate our best gelato here!  We grabbed a late afternoon snack of wine, cheese, and charcuterie at this local well-rated hole-in-the-wall type place that was amazing (Hostaria Vecio Biavarol)!  After this we wondered the streets some more, ate a delicious dinner, and took our long-anticipated gondola ride.  A perfect introduction to Italy and the days to come!

Our second stop was Cinque Terre.  We stayed in La Spezia, which was a great choice – especially with our luggage (thank you Ann!).  We took the train to Manarola for dinner on the first night (the local trains are very easy to navigate here!).  We ate a delicious meal and then explored the town, hiking to see the views at sunset.  We took the ferry the following morning to get from town to town. We didn’t hike as much as we would have liked, but we hit the beaches at Monterosso al Mare, Vernazza, and Riomaggiore instead!  We spent our final evening hours walking the streets of La Spezia, which is a very lively town in the evening!

a man with arms wide and the cliff side town in Cinque Terre Italy behind him

We took a train to Florence the next day.  Our hotel was very close to the train station and perfectly located for exploring the city.  Again, you gave us a wonderful recommendation to try the Central Market in Florence.  This was our first stop – and it was huge!  We grabbed a quick, delicious lunch from the upstairs floor that was filled with a number of great Italian restaurants.  We met our Accademia tour guide in the afternoon, Brenda from ArtViva.  Having now seen the David twice, I can attest to the value in touring the Accademia with a guide.  Brenda gave many more insights about the sculpture than I knew on my own, and hearing her talk about the details with the David in front of us was incredible.  After the tour, we ended up buying tickets to an opera for that night, held in a small church.  We were skeptical of our purchase when we first saw the venue (it was so small!), but the talent was impressive!

The next day we actually decided to book a day tour in Tuscany with Walkabout Florence – we couldn’t resist!  Even though we were disappointed to cut our time in Florence, we ended up being very happy with the tour purchase.  The tour took us to Siena (Florence’s “rival” city from years past), an organic farm and vineyard in the Chianti region for a Tuscan lunch and wine tasting, San Gimignano, and a final stop in Pisa!  The whole experience was wonderful, from learning about the horse races in Siena to the delicious meal at the vineyard to the spiraling, sea-legs-like climb of the Leaning Tower.

The following morning we took a high-speed train from Florence to Naples where Fabrizio picked us up for a stress-free transfer to Sorrento.  Along the way, we had scheduled a tour of Pompeii.  Our tour guide Barbara introduced us to the ancient city.    It is terrible to think of the fate of these people, but I am very thankful we were able to see this historical site in person.  Fabrizio was kind enough to wait for us at a coffee shop (and keep our luggage safe!) while we toured with Barbara.  He finished our transfer with the drop off at our hotel in Sorrento.  Chris and I were excited about this hotel because of its rooftop pool!

the cliff side town of Positano lit up at night Since we only had a little over a day to see the Amalfi coast, we split our time between a bus ride to  Positano on our first evening and a boat tour around the island of Capri the next day.  Positano was gorgeous!  We hiked up and down the town, dug our toes into the black sand, and grabbed a Spritz from a cliffside restaurant before taking the bus back to our hotel.  Capri was also stunning – offering grottos of orange, green, and blue that you can tour with a group or by renting your own private boat.  We decided to go with the group tour for the cost savings, and toured the entire island of Capri, including a stop in the famous Blue Grotto.  After our island tour, we took the ferry back to Sorrento with enough time to hit our hotel’s rooftop pool and explore the town famous for its limoncello.

The next day we took a morning transfer and train to arrive in Rome by noon.  After checking into our beautiful hotel, we explored our surroundings – including a stop at the Spanish steps!  Our first night in Rome was our two-year anniversary, so we ate dinner at a restaurant picked out by my husband.  He did a great job researching!  We had wonderful service and a mouthwatering meal at Matermatuta (we highly recommend this spot!).

We woke up bright and early the following morning for our CityWonders’ Vatican skip-the-line tour.  Having visited the Vatican before (but without a guide!), I was looking forward to the insights we would learn as part of the tour group.  We were not disappointed!  Not only were we able to “skip-the-line” and listen to our knowledgeable tour guide, we were able to enter the museum before it even opened!  The early start time of the tour was totally worth it – and it included a skip-the-line tour of St. Peter’s Basilica, too.  Chris and I even climbed the dome afterward!  After this we actually went back to our hotel to nap – which helped us enjoy the evening of sightseeing around the city.

Our final day in Rome we did a tour of the Colosseum, Palatine Hill, and the Roman Forum with CityWonders. This tour was very informative and also let’s you skip-the-line! After the tour we tried to hop on a tour bus of the city, but I wouldn’t recommend this bus to others.  The line for the hop-on, hop-off bus tours was long and the ride itself was not as informative or enjoyable as we would have liked.  After we “hopped off,” we wandered the streets of Rome to sightsee and grabbed a later lunch before heading back to our hotel for our transfer to the airport.  We were off to catch our evening flight to Greece!


Our private driver was waiting for us (even with our delayed flight!) and drove us to our city center Athens accommodations.  Everything went smoothly, allowing us to get a good night’s rest before our 8:30am walking tour of Athens the next morning.

The tour group was the two of us and four Australian friends.  We were happy to have them along since our tour guide was not the chattiest!  It was relaxing to walk to the major sites in Athens, including the Parliament building with its symbolically dressed guards, the first modern day Olympic stadium, the Temple of Zeus, and the Acropolis.  Once at the Acropolis, we were on our own to explore.  We spent time on the mount itself – a massive example of Grecian achievement – and followed the tour with a visit to the New Acropolis Museum.  This museum was incredibly well done!  If you visit Athens, this museum is a must-see!  For the remainder of the day, Chris and I grabbed a late lunch and then toured the city streets that night.

a couple in front of the blue and white houses of Santorini GreeceEarly the next day we flew to Santorini!  Thank you so much for booking us a gorgeous, newly renovated resort in Fira!  The location was a small hike to the main streets of Fira town, but completely worth it for the peacefulness of the accommodations.  We loved it!  We enjoyed the pool and amenities at the resort first, and then walked into the town of Fira to explore and have dinner.  After a day of on-and-off rain (so rare for the island!) the sky surprised us with a gorgeous sunset while we ate dinner on the cliffside of Fira.  A relaxing, beautiful first day in Santorini!

a man on a donkey climbing up the steeps steps in SantoriniOn our second day, we woke early to catch a cable car down to the pier.  I would highly recommend taking a cable car in the early morning!  We had no line and barely had to wait before our car zipped us down the cliffside to the pier.  We strolled along until we found what we were looking for – donkeys!  We heard about taking donkeys up the cliffs of Fira, and we couldn’t resist!   The weathered Greek men practically tossed us onto our donkeys (or rather, mules, we realized), and off they trotted!  No instructions or warnings of how to ride them, we barreled up the donkey path – almost running into pedestrians and other donkey/mule riders along the way.  The experience was hilarious and definitely one of our favorites from the trip!

After we dismounted at the top of the cliff, Chris and I took a public bus to Akrotiri to see the famous Red Beach.  It was beautiful to see the contrasting red rocks with the deep blue water.  That evening, we took a public bus again, but this time to the other side of the island – to Oia.  Not only did the town offer gorgeous views, it hosts the majority of the iconic Greek Isle “postcard” landmarks.  Only eating our dinner paused my picture taking!  It truly is one of the most beautiful places on earth.

a stunning sunset of the bay with a restaurant balcony to the side in Oia Greece

The following morning we packed up for our final transfer before heading home!  We took the SeaJet ferry from Santorini to Mykonos.  Everything went smoothly with our transportation, and we were in awe when we arrived at the Myconian Imperial Hotel!  The service treated us like royalty, toured us around the amazing facilities, and left us to enjoy complimentary refreshments in our beautiful hotel room.

All of our meals at the resort were delicious – from the free buffet-style breakfast, to the lunches at the poolside restaurant, to the main dinner restaurant with the gorgeous views, to the amazing sushi restaurant that took reservations until midnight.  Definitely worth every penny!  We made use of the free shuttle to the main town one evening, caught the sunset with the famous Myconian windmills, and ate a traditional Greek meal at the quaintest restaurant, To Maereio.  We highly recommend this small, hidden eatery!  It was interesting finding the place though because the streets of Mykonos were designed to confuse pirates – and it definitely is easy to get lost!

On our final day, we had reserved a horseback riding excursion through the hotel.  Our guide, Angelika, was wonderful and so patient with us as we learned the ropes (literally!) of horseback riding.  We had a wonderful experience – the only downer was that the pictures made it seem like we would be riding along the beach the whole time (and even in the ocean!).  We actually rode on a trail to and from the beach, with a small amount of time on the beach itself.  Granted, I guess the horses really like to roll around in the sand when it’s hot!! So Chris got some action when he had to quickly jump off his horse to not be a part of the backscratching party, hahaha! Thankfully he was fine – and it now makes for one of our most hilarious stories from the trip!

Before heading home, we basked in as much Grecian sun and Aegean ocean water as we could!  We spent a total of three days at our resort on Mykonos, and it was the perfect way to relax, refresh, and reflect on our trip before returning home.  We’re so happy we booked this trip with you, Ann!  We would’ve never booked such a beautiful place for ourselves at the end of our trip, but it was the perfect way to top off our amazing adventures in Europe.

All in all, this trip was EXACTLY what we were hoping for and looking forward to – it was the trip of a lifetime!  Thank you so much for making it possible!

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)