9 October 2015

September Set Sail

Athens, Greece
By Haleigh In Non classé

Some things about living on a boat aren’t easy. Resources are limited, like fresh water for one. With a mane like mine things can get a bit out of hand after a week without a proper wash and twice daily sea breeze blow dry. And then there’s space, or lack there of. Things are tight on board so you get to know people quickly. Does the idea of boarding a boat for a week with eight strangers excite or scare you? Personally, I think it’s thrilling…some combination of both. At first they’re your skipper, or the one with the tattoos, or the faux hawk, or the mustache, or the tall blonde. But by the next day and a few hours spent together at sea they’re people that come from places, with names, stories, ideas, and jokes. Personalities. And all these people, they just begin to fall into place. Josh at the wheel, both Emilys on the bow, Natalie and Sasha in the hammocks, Swirl and Evan at the stern, Monica and Miguel with their feet dangling starboard. And me, most likely a bit all over the place with one hand holding my camera and the other keeping me from going overboard. Each morning the engine turns on at 9am no matter how late the night before ended. You don’t want to miss a thing, so you always get up with it. Time moves slower than you’d think. What you don’t spend swimming you fill with talking, singing, reading…anything you like, but simple things. The day is punctuated — breakfast at the port, a stop for a swim, and then another Greek island. But it’s not the destination, it’s the journey. So goes life, and your vacation. Seven days of heaven. Because what started as a small boat, after a few days feels like a whole world. You’ve got everything you need right there to be happy. And those people that started out as strangers, they’re your friends. Come Friday, today isn’t like the last seven, and you feel like your heart is breaking as Athens appears on the horizon and you’re forced to go back to the world you came from. You jump into a cab to the airport before you can even say goodbye, because they always make you cry and it’s too sad to leave it all behind. From four knots gliding on the sea to four hundred miles per hour in the sky, headed towards the forty or so square meters in the city you felt quite at home in before. But now it’s hard to imagine who needs so much space all to them self. You stare at your faucet running fresh water into the tub. Finally, you can wash your hair. So you sink under the water, filling it with the salt you wore home and the saline tears you avoided crying before because you miss the sea,  you miss the boat, and you miss the people. And at midnight in a tiny tub of salty water you feel the most at home since you stepped off the boat that morning. Which is fine, because as far as you’re concerned you can sit there until next summer when you can go back to Greece and live that week all over again.


My journey to Greece began with a special invitation for me and Emily from Medsailors. Medsailors offers skippered sailing trips for 20-35 years olds in Greece, Croatia, and Turkey. How could we say no? Seven days and six nights sailing the Mediterranean, only a fool would refuse. While you can book a boat for an entire group of friends, our boat was a mix of couples and friends from all over the globe. Each week about 10 – 15 sailing yachts embark on the trip, so you’re always in the good company of other Medsailors, making new friends from different boats at each island or port. Each day brings a new destination, a new swim spot somewhere along the way. Breakfast and lunch are served on board, and afternoons and dinner spent exploring the islands. Below I’ve shared some snapshots and tips from my favorite places along the way…


Not to be confused with Paros, Poros has charms of it’s own. Emily and I loved walking up and down the quaint little streets that climb the hill, all the way to the top where you’ll find a beautiful church and a vantage point over the port and across the way to the mainland Pelopponese. There is also an outdoor cinema in the summer here playing movies many nights, seriously beautiful sunsets, great restaurants along the water, and a decent bar scene including a night out with with the whole Medsailors group that was hilarious and fun!


Spetses was my absolute most favorite island of all those that I have visited in Greece this trip and on other trips. If you are looking for a quaint and beautiful island that really has it all, this is the place. We rented a four wheeler and drove around the island, stopping at pretty beaches and getting lost along the way to find cute things like darling rows of residential neighborhoods you would dream of living in, boat yards being colonized by talkative geese, and little churches. There are also cute shops here selling leather sandals made locally, pistachio vendors around the port, funny old ladies swimming at the beach worth people watching, horse drawn carriages, amazing gelato and an adorable bakery with cookies galore. There is also a stunning five star hotel here called the Poseidonian Grand Hotel that is ultra class.


Agistri is just a one hour trip from Athens, and so it’s a great option for visiting considering its proximity. In addition, it has three beautiful towns ranging from quiet and mostly locals to happening and touristic. There are plenty of cute little funky hotels lining the beaches that they fill with loungers and palm umbrellas. There are cute cafes and coffee shops, and some pretty streets in the old town areas you can walk up to in the hills.


Steeped in fascinating history, the enchanting village of Ermioni is the second destination on the Medsailors Greece trip. Having been inhabited since 3,000BC, there’s plenty to explore. You can go snorkelling in jaw-droppingly beautiful Bisti, an underwater archaeological site, drink sunset cocktails on board boat yacht or at the Medsailors “punch party”, and then feast on Greek delicacies in the lively town.

Special Thanks

Emily — My little Hawaiian Coconut for being the ultimate travel companion on this trip. You can see A MILLION more photos by her of this trip over on her blog, (where you can also see a photo of our really cute skipper who will definitely make you blush) and you can follow her on Instagram too! And for keeping me safe while she drove our bright orange four wheeler on Spetses, for singing with me everyday (and putting up with my awful singing when she was not singing with me) and sharing our tiny cabin amongst all my camera gear and all her cosmetics.

Medsailors — Thank you so much for Medsailors for inviting us on this amazing experience, and making the dream of sailing the Med (and Adriatic) with friends accessible, affordable, and everything we ever imagined and more! We honestly loved, loved, loved this trip and cannot wait to take another one next summer. See you then for a million more photos and videos and another amazing week at see that we will never want to leave. We honestly cried when we had to go home this time! Below you can see the map of the Medsailors route…


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  2. Veronika 9 October 2015

    I am so happy you’re keep blogging. I totally love your posts. Your photos are bright and beautiful and I find them very inspirational. I also adore your personal style. It’s so unique. Always look forward to the new outfits of yours. Hope you will post some pictures from your apartment soon since I really like your home decor…
    Have a wonderful time. 🙂

  3. maria 9 October 2015

    Hi sunshine! I am glad you had a good time whilst in Greece! Maybe I don’t leave comments quite that often anymore (mostly because I dont like to repeat myself-I just love your work/art, you know that – however I always visit MM (now Lancome too!) to check for a new post of yours! Over the years you have always been my fave blogger!
    Hugs from Crete!

  4. Rebecca Maureen 9 October 2015

    Again really wonderful post Haleigh! Not only did I get to live vicariously through the trip but your photos are always an inspiration in and of themselves too. Really enjoyed it.

  5. h 9 October 2015

    Sounds like an amazing idea! When sailing around the Greek islands, did you have any experiences or encounter with refugees? Given the situation over the summer (and now), I’m curious if this changed or affected the trip in any way?

  6. Martha Jane 9 October 2015

    These photos are actually dreamlike! I don’t think I’ve ever seen such a magical summery post, just stunning x

    Martha Jane | http://www.marthajanemusic.com

  7. Such stunning photos, thanks for sharing! Ahh, almost as good as being there…well, not quite.

  8. Kristina | lettersfromk 10 October 2015

    Stunning photos! You have beautifully captured the spirit of the Greek islands. This post definitely has me wishing I was back in Greece

  9. Julia 10 October 2015

    So lovely! Thank you for taking me on that beautiful trip with you. Thanks for sending me over to Hawaiian Coconut for more pictures.

  10. Michelle 10 October 2015

    Such beautiful photos! I am soooo happy to read this new post! Thank you Haleigh for always making your post super extra special!

  11. Ylenia 11 October 2015

    Ugh this post makes my heart ache for summer!
    You’ve always had an amazing gift at story-telling not only with your words but also with your photographs… have I ever told you how much I love your photos? I wanna print them all and keep then in a cute album.
    Anyways, this post seriously is wonderful, like taking a peek at someone’s personal travel diary 🙂
    I barely finished reading and I’m already obsessing over the idea of doing a trip like this next summer!
    I’m so glad you got to spend an amazing week sailing, disconnected from the world and that you are now sharing it with us <3

  12. Lexie Day 12 October 2015

    What a lovely post! Thoroughly enjoyed reading this! I am definitely looking into doing this myself!

  13. Joyce 12 October 2015

    This summer I went to Athens, Santorini, and Mykonos and absolutely fell in love with Greece. I can’t wait to go back and visit some of the smaller islands, I think your boat adventure sounds amazing! Love your dreamy photos, as always. Looks like you had an amazing time!

    Characters & Carry-ons

  14. Emily 12 October 2015

    Totally crying.

  15. Natalia 15 October 2015

    Good morning from New York, and thank you for this beautiful post.

    Your photographs are stunning, of course, and I always appreciate how you curate such gorgeous items, moments and angles to bring a sense of beauty and calm to the moment for for your readers. Your story-telling language is spot on as well. As I pour in my heart into building up my own blog, your site was a source of calm and clarity. Thanks, love!
    She’s Very CHIC: Be Confident, Happy, Inspired and Connected. It’s truly very CHIC!

  16. Meg 17 October 2015

    Oh gosh this looks like the DREAMIEST thing EVER….. miss you ladybird

  17. Marla 19 October 2015

    You’re blog is absolute heaven and one of my biggest sources of photography inspiration. This entire site is just magic!

  18. Amelie 24 October 2015

    I thought it was weird writing about being on a boat in Greece with strangers, but having a vacation, when THOUSANDS of people right now make that journey as refugees and actually risks their lives. I feel quite bad for mentioning it but we can’t really NOT mention it.

    • Haleigh 5 November 2015

      There is absolutely no benefit to bringing up politics in my posts and it’s not something I want to be a part of this blog at all. These are my PERSONAL MEMORIES and the area of the Mediterranean that I was traveling in was not one directly receiving any refugees. It is an entirely different side of Greece. I leave all politics to political people to discuss online and my own personal views on the situation are not something I prepared to share nor to share. I very deliberately choose to not discuss political issues of any kind on this blog and very deliberately chose to not mention it it. If people want politics they can read another blog.

  19. Jessica 31 October 2015

    These images are bright and beautiful and your prose here particularly soulful.

  20. ANDY 4 December 2015
  21. Hannie Arden Blaise 22 February 2016

    Woah, the photography is stunning! I need to get to Greece soon.

    Hannie Arden from missingwanderer.org.

  22. Desirae 29 March 2016

    Beautiful pictures, Haleigh! Are the white overalls/romper that you are wearing towards the bottom vintage, or is there a chance I can purchase them somewhere? I’m in love with them!

    Thank you!


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