8 Days of Sailing through the Greek Islands with Yacht Getaways

The only thing dreamier than a summer holiday island-hopping through Greece is a summer holiday sailing through the Greek islands! A few weeks ago we had the opportunity to team up with Yacht Getaways to set sail on the Mediterranean Sea and explore the Greek Cyclades for 8 nights, and we’re still frothing a bit from the magic of it!

Our journey started on the Island of Paros, and ended on the mainland close to Athens. Each day after breakfast we would sail a few hours before anchoring on a new island to swim, relax and eat lunch before sailing a few more hours to our evening destination. We had our own skipper and host who sailed the boat and cooked us breakfast and lunch every day (they even take care of any/all dietary needs), and we had the evenings free to spend on land at a different island each night to explore, shop, and have dinner. Then we would head back to the ship to sleep in our cabin before setting off again in the morning!

So our daily itinerary basically looked like this:

  • 7am: wake up in time to watch the sunrise

  • 7:30-8:30am: shoot around the island early in the morning before any crowds

  • 8:30am: breakfast on the catamaran

  • 9:30am: set sail (aka time for tanning, napping, and reading on the boat)

  • 12:30pm: anchor at a new destination for lunch, swim/snorkel/SUP, and a chance to explore something new! (one day we saw a sunken WWII fighter plane, another day we explored through caves via kayak, we walked through an abandoned prison, and another day we walked through the ancient ruins of Delos)

  • 3pm: more sailing + relaxing

  • 5pm: arrive at a new island! (watch sunset, explore, and have dinner)

  • 12am: sleep on catamaran

AND REPEAT. Literally the dream vacation!

There are a few different boat options and classes to choose from with Yacht Getaways as well as the option to charter your own boat! The routes vary from year to year and depending on which part of Greece you’ve chosen, but our route was called The Greek Cyclades Explorer and looked like this:

  1. Paros

  2. Antiparos

  3. Koufonisia

  4. Naxos

  5. Mykonos

  6. Siros

  7. Kea

  8. Athens

(note: the map shows Ios as a stop but we ended up going to Koufonisia instead)


We loved each and every island that we anchored at each night, but here are some highlights from our favorite 3 islands:

Antiparos— This tiny island was so adorable and exceeded all of our expectations! Like most Greek islands, it completely livens up at nighttime and has such good vibes! There is one main street that we explored the most full of boutiques and restaurants, and a never ending supply of bougainvillea... need I say more?! We fell in love with Antiparos and hope to visit again to see even more of it!

Mykonos— If you’ve ever pictured what it would be like to visit Greece, you’ve probably had an image of Mykonos or Santorini in your mind! Mykonos was as busy and touristy as they come, but still an absolute must for any trip to Greece! From its iconic windmills, stunning beaches, and cute windy streets with a picture perfect church on every corner— there’s just so much to love about this famous island!

Siros (or Syros)— Siros was a complete surprise because before this trip, we had never even heard of it! It honestly felt like we were in the South of France or somewhere along the coast of Italy because the buildings are not your typical white and blue Greek architecture— Siros is full of so much color and unique charm! We felt like we only scratched the surface of what this island has to offer, and (again) we really want to come back asap to see more! Our two favorite things about it were the endless supply of amazing coffee shops and the seasides views. They were among some of the most beautiful views we’ve ever seen and the island as a whole felt a lot less touristy than others!

The catamaran we sailed on fit 8 guests as well as the captain and host, making a total of 10 people. It was such a cool way to meet new friends and really get to know each other throughout the week. We were so excited to sail with Ryan and Sam from Our Travel Passport and be able to share this experience with our good friends! While this was our first experience with Yacht Getaways, Ryan and Sam have done a number of their destinations and highly recommended them all. Yacht Getaways also offers trips in Croatia, Turkey, Italy and the Caribbean- so our only question now is which one to try next! We’ve been imagining how much fun it would be to book a trip with our family and now we are adding this idea to our list of never-ending goals to make happen asap. ;)

We weren’t sure at first if we would get tired of being on a boat for so long or get sea sick at all, but the trip was divided up so well with time on and off the boat, that it was the perfect balance. Neither Zach nor myself ever felt sea sick, and it was the longest either of us had ever been on a boat before! I can honestly say that this was one of our favorite experiences we’ve ever shared, and felt like a trip of a lifetime! If you’re looking for a fun and easy way to see so much of Greece in a short amount of time, I cannot recommend booking a trip with Yacht Getaways more highly!!

As always, if you guys have any specific questions about this trip, don’t hesitate to ask! And if you’re interested in booking your own sailing experience, feel free to click the button below! :)

Until next time!

Xo- Tara