Every time someone at work asked me what I was doing for my upcoming vacay, I dreaded the very words that were about to spill from my lips because, bougie.

Oh, we’re heading to Greece with friends to do some island-hopping for just over a week…on a privately hired catamaran…”

Nope. No other way to not sound like a douche-bag when responding to that question.

So i’m back. It was an experience and yes I would do it again. And now that I have the experience of what a sailing vacation looks like; I’m going to share with you the bits I wish I knew in advance of this trip, which essentially were the parts no other blog cared to share with me. No one told me it would be glorified glamping!

Poros, Greece

Poros, Greece



Storage space

Pack, then unpack and then re-pack 30% of what you initially packed.
With all the corporate and personal travel that goes on in my life; I’d consider myself a bit of an expert packer; and that wasn’t always the case.
I am proud to say that I am now the one who bypasses baggage drop, glides through TSA pre-check or CLEAR (when it’s available at the terminal) and settles into my lounge of choice within what feels like 10 minutes of arriving at the airport. The closest I have gotten to teleportation. EVER. Quite frankly, I like it, a lot. Smells like ease, with a splash of indulgent comfort.

Back to packing, yeah, I promise you, you need to pack way less than you think. While onboard, you will want to be comfortable so for a one week sailing trip, I’m talking:

  • 2 - 3 pairs of shorts/hotpants (whatever makes you happy)

  • 5-7 tops/t-shirts

  • 1-2 light long sleeved tops (don’t let the night breeze catch you off-guard)

  • 1 light waterproof jacket

  • 1 pair of flip flops (do boat shoes if you’re precious)

  • 3 bikinis or one piece swimsuits with an dose of coverups to protect you from the elements

  • 1 pair of sandals

  • 1 pair of comfy shoes for hiking

  • 1 pair of aqua shoes for swimming in rocky waters

Keep your Emmy Award-worthy frocks for dinner and nights out on land.

Now, our home for the week was a 40ft cat complete with 4 bedrooms and 4 bathrooms - sounds pretty luxe right? It certainly was but storage was negligible! Don’t think for a minute that you can bring the usual hard-framed boxy suitcase you wield around on your regular trips and store in standard size hotel rooms. Being on a catamaran, with two in a room, there is no place for it. There is barely enough room to get into downward facing dog. Do as I did and bring a duffel bag. I opted for this rolling North Face kind (so as not to put unkind pressure on my suffering shoulder) which has a solid base but the soft sides made for easier maneuverability and storage capability. Glad it arrived the day before my trip!

Personal Space

As far as company is concerned, choose your crew carefully. Make sure you all get along because you can’t run away very far if you don’t. Luckily we did not have that issue. The diversity in our professions made for some inspiring, growth-promoting conversations. With all the downtime you will have sailing between islands, there’s everything right with fueling yourself mentally and spiritually through communing with your crew mates.

And for those self-reflection hours onboard, there was nothing like staring out into the deep waves or the black night sky to tune into myself.


Err, we had our list of islands ready, prepped and researched. MONTHS of research and voting went into this. MONTHS.
As we checked into our cat and got to know our captain, he asked us which islands we wanted to hit. I pull out our pre-aligned to list, clear my throat and begin…

Me: Kythnos

Captain: Ha…No

Me: Milos

Captain: Not possible

Me: Antiparos and Ios?

Captain: [scoffing at us now] No way

Me: [folds list away]

Basically, our hopes of going back to the Cyclades for a second consecutive year were out due to bad weather. If you only knew how badly I wanted to get back to Milos, especially Tsigrado beach…MAN.

The point here is, be open to a change of plans and trust your skipper. Through him, we discovered 7 of the Saronic Islands, just off the mainland in the Aegean gulf. Beauty we may not have ever seen otherwise.
But Milos though….damn. I’ll never get passed that.


Curb the hunger pangs you are inevitably going to incur in-between islands by making sure you stock up the fridge before you set sail. Plus, apparently, sailing etiquette says when you hire a captain, his meals are on your tab so, he will be looking for something to munch on in the fridge too. Some ideas to get the juices flowing:

  • Everything you need to make your fave basic sandwich

  • Some good cheese

  • Fruit: grapes, nectarines, blueberries and pineapple

  • Greek yoghurt (get the sheeps milk kind. Authentic) and honey. Perfect with a sprinkle of blueberries if you are a light breakfast eater like me.

  • Your fave beverage. Ours was Tsipouro (a traditional Greek distilled spirit).


These next three items for sure aren’t must-haves but came in handy for me. The reasons for the first 3 are pretty obvious, but the fourth; perhaps not so much.

  1. A stainless steel water bottle to keep your cold water satisfyingly chilled for 24 hrs. Here’s mine. So glad I brought this little thirst-saver with me. Great for the beaches and accidental 4-mile hikes up through mountains to a monastery that was closed when we go there (don’t ask. Long story).

  2. A hip flask. First time owning one. Saw it in a store, thought it was cute, so I picked it up. And it sure did come in handy. Tsipouro on-the-go anyone? Hurrah for foresight.

  3. Motion Sickness wristbands; great as a just-in-case. Better safe than sorry.

  4. Palo Santo

    This one needs some elaboration. You see, my friend Chrisa was due to leave the US to meet us in Poros, Greece the following day and kindly asked me if I wanted her to bring me anything to help me settle into our new waterborne digs for the next week.

    My answer:

Palo Santo please?!

I am not going to justify my bougie request because I need what I need and that’s just that. But for your own benefit, you need to know that there are certain not-so pleasant smells that tend to linger in the small quarters of a boat. Namely due to the lack of the sophisticated waste disposal systems we are used to on land.

Palo Santo is my latest obsession. It’s warm, woody fragrance has a significant de-stressing effect on me. Makes me feel at home and centered. It is easy to see why this South American holy wood is referred to as an energy and space cleanser. Perfect for being in a confined space (albeit luxe) like this one! So after dinner one night in Agistri, I bought myself a lighter and the following day, off I went Palo Santo smudging around the boat. Ciao odors!

So if you are planning a boat trip as a first-timer, I do hope something in the above was useful.
For those expert yachters out there, do share your tips in the comments below.