I recently returned from a sailing trip in the Aegean Sea off the coast of Greece. This was my second sailing holiday in Greece; my first was September 2015 touring around the Saronic Islands. Both trips were lovely, relatively inexpensive, and a lot of fun, with amazing food and gorgeous scenery.

Note that I use affiliate links in this post, which means that if you click on anything I’ve linked here, I might earn a little money, which I will gratefully use to keep this blog running!

The harbor at Kythnos, Greece - a typical small port town

The harbor at Kythnos, Greece - a typical small port town


Of course, taking this type of trip isn’t always smooth sailing (sorry, couldn't help myself). Being on a 42-foot sailboat is a completely different world from taking a weeklong cruise around the Caribbean (my only previous offshore vacation experience). After taking two sailing trips, here are a few things I learned about how to have a happy and comfortable vacation. While the tips are based on my experiences in Greece, I think they'll apply to other sailing destinations as well. If you have little to no sailing experience and are interested in taking your first trip, read on.

First things first: choose your sailing mates carefully.

During both trips, I was lucky that we had a friend along who could skipper (e.g. steer/captain) the boat—not an easy job considering some of the tricky navigating needed to dock in the tiny Greek harbors! I also went with a few people who had taken sailing courses and were totally comfortable raising sails, lowering the anchor, etc. That meant that we saved money (at least 1100 Euros) by not having to pay someone to sail the boat for us.

Whether you hire a skipper or not, who you bring along is almost as important as who steers the boat. Remember that you’ll be with these people for about 6-8 hours a day while traveling from island to island, and nights too if you’re all sleeping on the boat each night. Quarters are close, and if personalities clash, there’s not a lot of room to escape!

Consider expectations: are people hoping to hang out in a group or scatter once they're on shore? Does one person want to scuba dive all the time, while the others want to dock in a bay and swim? If that's the case, the logistics could be tricky. Similarly, thinking about how much money people want to spend is important; our trips went smoothly because the whole group enjoyed going to out to sample the delicious Greek food at a restaurant every night (which is inexpensive compared to going out in Denmark), but those on a tighter budget might rather cook on the boat or stick with gyros. Talk about your expectations ahead of time and try to choose people with similar energy levels, or people you know well. A group of laid-back, helpful, positive friends will make the trip extra lovely.

Homemade gin and tonics on the boat after docking with the crew - mmm!

Homemade gin and tonics on the boat after docking with the crew - mmm!


Don’t expect luxury

Sailing is not the same as a cruising, unless of course you're spending enough to hire a super-yacht with a cook and maid. In fact, being on a sailboat can feel a little bit like camping... ok, maybe like glamping. This is especially true if things don't work as they're supposed to (for example, on our second sailing trip the water pump stopped working well so our showers were pretty dribbly—not great for trying to wash hair or shave legs). The boats I’ve been on were cute and well-maintained, but simple.

It’s also important for everyone to pitch in to keep the boat clean and tidy, as things can get grungy and cluttered pretty quickly with 8 people in close quarters. If, like me, you aren't going to help with raising the sails and lowering the anchor, washing dishes, making lunch, and offering cups of tea to the skipper will be highly appreciated. 

Lunch on the boat, which we ate while at sea almost every day. We would all pitch in with buying groceries on shore, making lunch, and cleaning up.

Lunch on the boat, which we ate while at sea almost every day. We would all pitch in with buying groceries on shore, making lunch, and cleaning up.


A word about the toilet situation: it will be less than ideal. You might have to pump out the waste (some boats have flush toilets, but not the ones I’ve been on). You’ll have to collect the used toilet tissue in a trash bucket, which can get smelly. Out of consideration for the rest of the passengers and in the spirit of keeping the harbors clean, we tried to time our longer toilet visitations (ahem) until we were parked in a harbor and could use an on-shore bathroom in a coffee shop. This can become a bit stressful for the, er, less regular.

Raid the pharmacy before you go

If you’re like me, you’ll definitely need some hard-core mosquito spray with DEET. You'll want to keep the windows open while sleeping, and the mosquitoes were quite active in Greece both in May and September.

I also recommend bringing sea sickness pills even if you've never had an issue, as a small boat will move around much more than you might be used to. I didn’t take sea-sickness pills the first time I went, but I ended up needing some the very first day during a choppy trip out of the Athens harbor. Plan ahead and take them at the first sign of rough waters as they take about 30-60 minutes to kick in.

Pack light

The cabins are super tiny and storage space is limited. I brought a carry-on size soft bag both times, which worked quite well. You’ll need less clothes than you think—the nice thing about being on a boat is that you can wear the same thing every day and no one cares. Don't bother with hair dryers or straighteners; in my opinion, it's not worth the weight, and your hair will dry quickly. Some things you will want to bring: 

  • I did a lot of research and ended up buying a soft rolling carry-on size bag from Eagle Creek. The one I bought many years ago is no longer available but it’s been replaced by the Eagle Creek Load Warrior 22 inch which looks very similar. It is soft like a backpack but has wheels for people like me who don’t like to carry a lot on their shoulders, and it opens from the front, zipping open all the way so you don’t have to dig around from the top which is a huge help when you’re in a tight space.

  • I also love Eagle Creek packing cubes to help keep things tidy; I have bought many different shapes and sizes including the Tube Cube, which is just perfect for underwear and bras, compression cubes, which help fit way more clothes (yay!), and this clever 2-sided cube for keeping dirty laundry separate from clean laundry. As you can tell, I’m a little obsessed (I even gifted my boyfriend this amazing garment folder to keep his shirts unwrinkled on business trips which he also loves!). These packing cubes are not cheap, but I’ve now been using them for 4+ years and they are still going strong after many trips and machine washes.

  • Layers, like leggings, pants, and a jacket, as it can be quite windy on the boat even if it’s hot on land

  • A sleeping mask (I’m obsessed with the Bucky eye mask because it feels so light against my face and doesn’t catch my hair; I use them daily until they wear out and then buy another!)

  • Earplugs which are helpful for the light sleepers; I love Quies wax ear plugs which you can shape to fit your ear.

  • Baby wipes, hand sanitizer, and dry shampoo—basically, anything that you can use with little to no water is a good idea

  • Swimming goggles and water shoes are nice to have. I bought a pair of Teva Tirra sandals which are super comfortable for hiking and double as water shoes for stony beaches.

  • A hat and sunscreen

  • A couple swimsuits

  • Clothes and shoes you don't mind getting wet and dirty

  • A little backpack for on shore excursions (if you will do a lot of swimming to shore, a wet bag is nice, but not absolutely necessary)

  • A Gopro or waterproof camera could be a great investment—the water is super clear in Greece so you'll get some amazing shots!

  • A couple outfits to change into for dinners on shore (but leave the high heels at home; they're not worth the space and are hard to get on/off the boat with)

If you forget something, don’t stress. There are shops and pharmacies in most harbors, and it’s easy to pick up things like sunglasses, towels, and sunscreen on shore.

Our small but cozy double-bunk cabin

Our small but cozy double-bunk cabin


Be patient and flexible

Using the dinghy to go ashore

Using the dinghy to go ashore

This is a hard one for me. When we were pulling into the lovely harbor of Hydra, I couldn’t wait to jump off the boat and explore the beautiful port city. But it was a tiny harbor and took us a while to find a spot to moor (in fact, we had to tie off someone’s boat and climb across three or four other boats to reach the shore!). Sometimes we could spend up to an hour figuring out where to dock, or waiting for a space to open up. Other times, we had to anchor in the bay and take a small boat to the shore and back.

Weather conditions vary, and bad weather might mean you have to skip a stop. Ultimately, the skipper gets to decide where you go and when, so try not to have your heart set on particular stops, and definitely forget about having a set schedule. This is your time to try to be zen-like and go with the flow.

A few times we had to anchor the boat (ours is in the middle) since there was no space in the harbor. Anchoring can also be lovely and quiet at night.

A few times we had to anchor the boat (ours is in the middle) since there was no space in the harbor. Anchoring can also be lovely and quiet at night.


Bring old-school entertainment

In Greece, you will have wifi in every cafe on shore, but not on the boat, and you might not have network coverage either. Being on a boat for a week is a great excuse to do a digital detox. I personally enjoyed giving myself a week off from Facebook on both trips. I got through a couple paperback books—when else will you get the chance to spend hours on the deck of a boat reading?

For other entertainment, games might be a good choice for some (but avoid anything the wind can blow away). We also made sure to load up on offline music so that we could plug our phones into the boat’s speakers and listen to music during our sails.

Don’t be afraid to get off the boat

If you need a night (or two) away, you can check into a B&B. On our first trip in September, I was having trouble sleeping on the boat as it was quite hot at night in the cabins. Because of this, my cabin-mate and I checked into a B&B for a couple nights of A/C. You can get a hotel room for as little as 40 Euros on many of the smaller Greek islands, and it's usually not a problem to walk in and reserve a room on the spot.

If you’d rather book ahead of time or read reviews, you can find many options for places at all budgets in the Aegean islands through Booking.com. We visited the islands of Seriphos, Sifnos, Milos, and Aegina during our trips in the Aegean sea. Sometimes you just need a nice shower and some privacy!

I’d also recommend looking for a place on Airbnb if you’re looking for a more cultural and local experience or just want a room in a house. If you’re new to Airbnb, you can earn money back after your first qualifying stay by using my personal link.

Boats are docked close to each other; for the most part, fellow sailors are respectful and friendly neighbors

Boats are docked close to each other; for the most part, fellow sailors are respectful and friendly neighbors


All of these tips might make it sound like I don’t like sailing—that’s far from the case! I had an incredible time on both sailing trips in Greece. The crystal-clear waters, gorgeous sunshine, lovely little whitewashed cities, and amazing food all make it a perfect place for a vacation. When on a boat, you get to see places you wouldn’t otherwise. Some of my nicest memories from Greece include jumping off the boat and swimming to shore when we docked in a secluded bay, and having gin and tonics on the deck after pulling into a harbor.

As long as you have good company, halfway decent weather, and bring along a good attitude and the right expectations, you can’t help but have an amazing sailing trip.

We anchored in this relatively secluded bay, dove in, and swam to shore—incredible!

We anchored in this relatively secluded bay, dove in, and swam to shore—incredible!


If you go…

  • If you’re interested in taking a sailing trip of your own, you can rent a boat and even hire a skipper and crew. We rented our boat from Sunsail, which has many destinations worldwide (I’ve even heard that they’ve upgraded to flush toilets in the Athens boats since we went last September). You'll be expected to bring an experienced skipper (with a license) or hire someone to sail the boat. There are also websites where you can sign up to sail along with someone who owns their own boat, but you'll need to be quite flexible with dates and locations if you want to do that.

  • Another pro-tip: I’m able to afford to travel to more places and do things like renting sailboats in Greece partly because I am a host on Airbnb and always rent out my apartment when I travel. I love being able to share my space with others! Since I’m not using it, why not let someone else enjoy the space for less than they would spend on a hotel? I only rent to guests with good reviews and I know that I’m covered by Airbnb’s insurance policy so it feels easy and safe. If you have never hosted and want to try, you can earn money back when you sign up using my personal host link (note that I’ll also receive money toward an Airbnb stay if you sign up with this referral link). It’s a great way to be able to finance your travels around the world!

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