Sailing in the Greek Islands: Are Sailing Trips Right For You?
Sailboat Orientation
Day one of our sailing trip took place in Mykonos, learning how to live on a sailboat for the next 10 days. We discussed how to store items so they don’t get tossed around when the boat tilts on its side (the boat is going to tip on its side???), how to stay low on the front deck to avoid being taken out by the swinging boom (the WHAT?), how to move around a rocking boat safely, how and when to send a distress signal (😳), how to used the boat toilet, how to light the stove without starting a kitchen fire, how to avoid seasickness (🤮).
I’m not going to lie, I did wonder more than once if I had chosen the right trip. It sounds amazing, doesn’t it? I loved telling my friends “I’m going on a sailing trip on the Greek Islands.” But, was I really cut out for this sort of adventure? I won’t keep you in suspense - I loved it! And, I also had the realization that not everyone would love it. Keep reading to see where you fit in.
Is a Sailing Vacation Right for You?
Take this little quiz by answering true or false to the following statements.
You don’t mind the wind.
I don’t why it didn’t occur to me ahead of time, but we had a good deal of windy conditions. Sailing requires wind. During the first half of our trip, it was quite windy and our skipper was excited. We were able to travel by wind power alone for a few days. It was thrilling, and a little chilly. I wore pants, a wind jacket, and a low-profile down vest in the beginning. But, mid-trip the weather changed. The wind died down and the temperatures got warmer. We ditched the extra layers and were allowed to lounge on the deck as we motored from island to island. The thing is, it is hard to know what you will get for weather. Our trip was in mid-May and we feel like it was a nice balance of experiences transitioning from truly sailing to summertime cruising.
2. You are okay with staying in basic accommodations.
Our sailboat could accommodate 11 people (10 guests + the skipper) and we had a full boat. It was my family of 4, two couples (one from Seattle and one from just outside of London), two solo male travelers (one British expat living in Houston and one millennial nomad) and our wonderful skipper, Mack, from Poland. G Adventures trips do not have minimum guest requirements, so it is possible (and fairly likely) that a trip would not be completely full. We met up with another G Adventures tour and they had 9 total people on the same size boat.
Recently, I heard a river cruise boat described as a floating luxury boutique hotel. I would describe our sailboat as a nice floating camper. Once we docked in port, we would plug in to the power and water sources, just like at a campground. There were 3 double rooms, 2 rooms with bunk beds (all with ensuite bathrooms) and the skipper’s room (aka the captain’s coffin). Our rooms were not spacious, but we had our own space and some storage. Below deck, we shared the saloon area - kitchen and dining table. On deck there were plenty of seats in the cockpit, and on calm days we had the deck to sprawl on.
3. You like hands-on experiences.
The skipper trained us to be his crew right from the start. We learned how to hoist the sails, drop the anchor and even steer the boat. If you wanted to be involved, you could. We all walked away with some basic knowledge of how to sail. We were also responsible for shopping for food, preparing our own breakfasts (hello Greek yogurt!) and lunches, and tidying up after ourselves.
4. You don’t mind arriving in port looking a little windswept and disheveled.
It’s the life and look of a sailor! Remember, sailboat living is a bit more like camping. We did have a shower in our bathroom, but it was a handheld showerhead and not the easiest to use in the small space. Therefore, once the weather got warm, I relied on swimming in the ocean and rinsing off with the outdoor shower to keep me somewhat clean.
Some of the islands (I’m looking at you, Mykonos) attract folks who like to get dressed up. We’re talking beautiful dresses with heels, buttoned-up-tucked-in attire that definitely made me feel a bit underdressed at times. Their hair looked clean and styled, while mine was generally in a ponytail or under a hat. I tend not to mind too much about that sort of thing, but others might.
5. You like staying in the center of town.
We would arrive in a new port and tuck our beautiful boat into the main harbor within a short walk of many restaurants and shops. When we tied up in the port, we could come and go as we pleased too. It was a nice perk to have easy access to every new island.
We walked and walked all over those islands. Every island we stopped at had at least one church/monastery on top of the highest hill in the town and we walked to all of them (which was a nice complement to all the sitting we did while on the boat).
Syros Harbor
6. You enjoy tasting the local cuisine.
Our skipper, Mack, has discovered all the best places to eat on the islands. We ate really well! In fact, it was a definite highlight of the trip. Dinners were not included in the cost of the trip, and generally we paid around $20/person for an amazing farm-to-table meal.
We ate in Greek tavernas most evenings and the items on the menus were similar, so it was fun to try new dishes every night. From souvlaki to fresh seafood to lamb to moussaka to a daily Greek salad, we sampled it all. Possibly my most interesting and most delicious meal was octopus in honey! We also ate a lot of baklava and gelato because why not?
7. You can handle sharing a relatively small space with a group of people (potentially strangers) for 7–10 days.
We shared the sailboat with a wonderful group of people and now have new friends around the US and across the pond. There is plenty of time to get to know each other and bond, which we did rather well. We all opted to eat dinner together every night as well. It was a great experience.
If the thought of being “stuck” in close quarters with an unfamiliar group of people is not appealing to you, you might consider putting your own group together. G Adventures, at least, will create a private group situation with a minimum of 8 people. Navigating logistics for group travel is something I am happy to help with.
8. You are good at going with the flow.
We were presented with a basic itinerary but mother nature didn’t entirely cooperate. Some strong winds kept us longer on Naxos, which allowed us to do an amazing inland tour. An earthquake in Santorini closed the ports there for a day or two and forced us to reroute to another island (we chose Milos) and we were so happy we got to go there. There is some unpredictability with sailing trips, so it is a good idea to be able to adapt.
If you can honestly answer “true” to at least 7 out of 8 of these statements, then maybe you should give sailing a try. If you choose to go to the Greek islands, here are a few island specialties you can look forward to.
Greek Island Hopping Highlights
🌀 Mykonos
Charming alleys
Inundated by cruise ships
Many great restaurant options
The windmills
🏝️ Paros
Mykonos for locals (no cruise ships allowed)
Winery tour at Moraitis Estate
Great gyros stand in the maze-like pathways
🏛️ Naxos
History, hiking, inland towns
Rooftop dining with sunset views
Temple of Apollo
Apeiranthos – the marble village
🌊 Iraklia
Mellow bay (we anchored offshore)
Try Pera Panta Restaurant for octopus in honey
Pera Panta Restaurant with our boat in the background
🌅 Milos
Sunset view from Plaka
Sarakiniko Beach (drone photo credit: Mack Nickesh)
Young tourists taking advantage of all the Instagram-worthy spots
🌸 Sifnos
Low-key and peaceful
Beach cafes
Morning climb to a monastery
🏰 Syros
Capital of the Cyclades
Amazing architecture and marble town square
So. Many. Cats.
Two hilltop churches = two great hikes
🏺 Delos
Ancient uninhabited archaeological site
Birthplace of Apollo
Temple of Isis
Terrace of Lions
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If after reading this you think sailing is a good fit for you, you should reach out to me so I can help you find a great trip. You should also sign up for my email list and read my latest newsletter about things to consider when choosing a sailing trip.Thank you for reading! Feel free to reach out if you have more questions.
