Sailing Greece: Exploring Greek Islands with A Dot in the Blue

If you're looking to for an amazing experience sailing Greece, look no further than A Dot in the Blue - the best company for sailing the greek islands! |

Disclosure: I was a complimentary guest of A Dot in the Blue. All opinions and recommendations are my own. This post also contains affiliate links.

The roar of an engine. The splash of waves. The rays of sun streaming through the window. I jolted awake, confused. Where was I? Then I remembered. I was on a boat. A sailboat, to be exact. It was our first day sailing, so I hurriedly grabbed my camera to capture the remains of the sunrise. Little did I know, I’d be treated to many enthralling sunrises that week.

While I’m no five-star hotel diva, I’m hardly the outdoorsy type either. So how did I end up spending a week in Greece, sailing my way through the Ionian Sea with eight others?


Last fall, by some amazing stroke of luck, my little sister, Nancy, won the first prize in Valerie’s blogiversary giveaway. Her winnings? One spot sailing in Greece with A Dot in the Blue.

The captain and organizer, Fernando, encouraged Nancy to bring a plus one, and a few months later, we were both confirmed to make our Sisterhood of the Traveling Pants dreams come true (although we didn’t visit Santorini this time).

I was, admittedly, a teeny bit nervous about spending a week on a sailboat. I like my modern amenities like unlimited running water, fancy toilets, and 24-hour electricity. Still though, I couldn’t pass up this once in a lifetime opportunity, which is how I found myself on a catamaran at the port of Lefkada, Greece on August 12th.

I had no idea what to expect from sailing so I wrote this handy guide for those considering spending a week sailing in Greece (specifically with A Dot in the Blue). This was my first sailing experience and I have no intention of it being my last. So without further ado, this is what it’s really like to spend a week sailing in Greece.

Pssst Interested in sailing the Greek Islands but a Dot in the Blue’s dates don’t work for you? Check out these awesome sailing trips by my favorite travel company instead!

Sailing the Greek Islands with A Dot in the Blue

Day 1 and 2: Lefkada

Nancy and I clearly hadn’t done enough research before our trip since we were under the impression that we’d be leaving from Athens, not Lefkada, the port town 5 hours away. Oops. Although Fernando usually hires a bus to transport everyone from Athens to Lefkada, only three of us were actually coming from Athens, so we were driven by Chrysa, our fellow boatmate.

We arrived in the late afternoon and were long overdue for lunch. We headed to Dalton’s for some massive gyros and were joined shortly after by the rest of our boatmates. About half of them were Greek.

After unpacking, we all made our way to the beach for some swimming and bonding time. I was incredibly impressed by the color of the water at Agios Nikitas Beach but Fernando informed me that there’d be even clearer water at some of the islands we’d be visiting. We were in for quite the week!

Although we were due to set sail the following morning, the windy weather had other plans for us. We took advantage of the day to tan on the boat, explore the town and do grocery shopping for the week. Nancy and I were still a bit jetlagged as we had arrived in Greece just a couple of days before, so we were happy to have the day to relax, eat an early dinner and catch up on sleep. The rest of the crew had a big night out on the town, but no FOMO will get in my way when I’m tired!

The next morning, I woke up to the sound of the engine roaring and the boat moving. Ahoy, matey! We were finally on our way!


Day 3: Ithaca

We swam and sailed for a few hours before anchoring at the small deserted beach not far from Frikes, Ithaca. With the exception of the few people camping, we had the beach to ourselves. It was a nice and secluded spot where we swam and tanned before cooking lunch on the boat. One of our boatmates, Bora, did an excellent job of navigating all the nooks and crannies of the kitchen.

If you're looking to for an amazing experience sailing Greece, look no further than A Dot in the Blue - the best company for sailing the greek islands! |

The part of the island where we were anchored was at the bottom of a small, rocky, cliff, so in order to get to the town, we had to take the dinghy. After swimming and napping all afternoon, we were starving. That evening, we climbed our way up the main road and ended up at this delicious restaurant in town called Rementzo where I had the most amazing goat with apricot (not pictured because I was worried about dropping my camera in the water). Everything we ate was spectacular, including the appetizers, dessert and other people’s meals that I sampled (sharing is caring!). If you ever find yourself in this part of Ithaca, Rementzo is the place to go!


Day 4: Ithaca

The following day was quite action-packed. We anchored at Vathi, the main port on Ithaca, just in time for lunch. One thing I love about Greeks is that they love to share food, so we always made a point to order a bunch of appetizers for everyone to share before our main meal. We ended up at Kohili with appetizers, meat, seafood – the works. Not only is eating in Greece delicious, but it’s inexpensive as well.

If you're looking to for an amazing experience sailing Greece, look no further than A Dot in the Blue - the best company for sailing the greek islands! |

At this point, the group split up and Nancy and I took this as an opportunity to explore the town. We walked all over, marveling at the colored houses, taking photos of the buildings, and stopping for ice cream. When we got back to the boat, a bunch of us decided to go to the beach. It was a bit of a trek from our boat, so we loaded up two dinghies to head in that direction.

Just before we arrived, one of the dinghies ran out of gas, leading to a bit of an afternoon adventure. Fernando went to find gas while the rest of us hiked to the beach. Meanwhile, the wind picked up a ton – meaning we couldn’t swim and Fernando couldn’t use the dinghy #1 to rescue dinghy #2. Let’s just say it ended up taking us a couple of hours to get back to the boat that day. Never a boring moment while sailing in Greece!

By evening, everyone was ready for a real night out on the town – one that didn’t involve us boating to shore. Our big night out started on the boat with music and dancing (until Fernando was finally able to usher us to dinner). Greeks typically eat around 10 pm, but that night we ended up eating around midnight…so we get our gyros fix before the bar instead of after. Greece is definitely a country that comes alive at night so despite the fact that we arrived at 1 am, we were the only ones there. I instructed the DJ that we were there for reggaeton, and once the music improved to my liking, we all danced the night away (some people, quite literally).


Day 5: Kefalonia

I woke up late that morning but was super excited to discover that we were still at the port so I could get my espresso freddo (iced coffee) fix. We had a late start and had a long day of sailing ahead, so we stopped a few times to swim and cool off along the way. By the time we arrived at Antisamos in Kefalonia, it was nearly 7 pm…and the restaurants all close at 8 (not very Greek of them!). It was hilarious to see how quickly everyone got moving and ready once we all realized that it was our only food option for the night. Everyone was pretty tired that evening, so we all hung out on the boat for a bit before heading to bed early.

Headed to Greece? Check out which gorgeous places you should visit (a couple are in Kefalonia!)

Day 6: Kefalonia

Luckily for me, most of the group was just as addicted to caffeine as I am, so most of our mornings included coffee runs. Some of the others rented jet skis for a bit, but I have a clumsy tendency to fall off moving vehicles and was happy with a few minutes as a passenger instead. That afternoon, we sailed to Assos, another part of Kefalonia. A few people opted to go to the beach, but the rest of us decided to explore the town and climb up to the Agios Georgios Castle instead. We didn’t realize just how long it would take and by the time we arrived at the castle, Nancy and I were *super* hangry (we hadn’t had lunch that day). The views from the castle were pretty (I couldn’t get a great photo since it was so dark) but we were both only thinking about dinner at that point. Luckily, we ran into the rest of the group once we got back to the main part of town, and had a really nice (last) group dinner together. We ended our night at the local ice cream shop before heading back to the boat.


Day 7: Lefkada

Unfortunately, this was our last full day with A Dot in the Blue and it was very bittersweet. We arrived back to Lefkada in the late afternoon, only to discover that three of our boatmates were returning home that evening rather than the next day. We spent the rest of the day hanging out, packing up, and cleaning up the boat. We enjoyed one final group dinner at Lighthouse Tavern, followed by drinks at Taratsa, an incredibly cool outdoor lounge. It was the truly the perfect end to the week, which suddenly felt far too short.

The next morning, we took our group photos, said our goodbyes, and made our way back to Athens.


Why go sailing with A Dot in the Blue?

Greece is paradise.

Just type in “Ionian Islands” into Google images, and you’ll get an eyeful of the crystal-clear water and soft, sandy beaches. Or check out A Dot in the Blue’s Instagram account. I’ll let the pictures do the talking.


Sailing is a blast (even for introverts)!

A few years ago, a friend of mine did a similar sailing trip in Croatia, and when she told me about it, my first thought was “that doesn’t sound very fun.” I’m an introvert and was nervous that I would feel obligated to hang out and party with people 24/7. To my delight (and surprise), the entire week felt very at my own pace. I read when I wanted to, ate when I wanted to, and went out (or not) when I wanted to. I never felt pressured to do what I didn’t want to do (which happens often on group trips), which made me love the experience and group that much more. That being said – Greece certainly knows how to show you a good time, and the trip was the best mix of good food (and coffee!), amazing beaches, and lively parties.


You’ll be supporting local travel.

When given the option of traveling with a US company and a local company, I always choose a local company for two main reasons. Firstly, the money I spend goes directly into the hands of locals and the local economy (yay sustainable tourism!). And secondly, locals know their own city way better than any foreign tour guide. In the case of A Dot in the Blue, Fernando (captain and owner) grew up in Greece and spent his summers sailing. August is the height of tourist season in Greece, but the islands we visited weren’t overcrowded because we went where the locals went. WIN.

Safety comes first.

On our first two days, we didn’t leave the port due to windy conditions. Fernando took our safety very seriously and although we could have still sailed anyway, the trip would have been uncomfortable and stressful. Instead, Fernando arranged for beach days and exploring in the town rather than risk our safety on the water, something we all appreciated. Additionally, all boats included both a captain and local skipper. I know skippers aren’t always mandatory depending on the company, but this was not the case with A Dot in the Blue.


Most expenses are included.

Your booking with A Dot in the Blue includes almost all of your costs: port fees, fuel, the skipper, final boat cleaning, etc. The only costs not included are food (and quality food is super affordable in Greece). We ate most dinners at port and the rest of the meals and snacks on the boat. Our crew went grocery shopping twice and split the cost at the end of the trip, which made everything easy.


You’ll make new friends.

Cue the cheesy “awwww” here, but I’m totally serious. Our group is already discussing plans to do this again next year.


Other things to note:

  • Leave your floaties at home – Fernando brought along several floaties and a paddleboard. Do bring snorkeling and diving gear, though.
  • Everyone pitches in to cook and clean up during the week.
  • There’s no WiFi on the boat, but you can purchase an inexpensive SIM card in Greece and get signal everywhere. But honestly, just disconnect and enjoy #boatlife.
  • Bring a back-up battery or two. There was one plug on that boat that worked all the time (the plugs in the room worked intermittently depending on the port we were docked in). With 9 people and 20-30 electronics, the thirst for charging was real.


What to visit other parts of Greece? Check out this guide to Milos, this one to Santorini or this one to Thessaloniki.


What to Pack for Sailing in Greece:

First of all, pack lightly! You’ll spend most of your day in your swimsuit anyway. Clothing wise, you really only need pajamas and some cute, lightweight outfits for dinner and going out. Also, storage is extremely minimal on the boat, so don’t bring anything larger than a soft, carry-on size bag. I recommend the Tortuga Outbreaker, hands down the BEST backpack I’ve ever traveled with. Plus, it’s waterproof!

  • Travel insurance: Because accidents can happen.
  • Goggles
  • Cute and sturdy waterproof sandals. Don’t even think about bringing high heels or non-waterproof shoes. On the boat, you’ll go barefoot but there will be times you’ll take the dinghy to shore, walk through the water to get to the beach, and traipse through towns. Bring sandals are comfortable and waterproof like these or these.
  • Multi-port charger: Your boatmates will thank you.
  • Dry bag: You might think you don’t need a dry bag, but the number of times we were transported to the island in a dinghy made me incredibly thankful to have one.
  • Lifeproof phone case: Because boats and phones don’t mix well.
  • GoPro + waterproof case
  • Waterproof selfie stick
  • Sunscreen: Honestly just buy a giant bottle once you get to Athens and use it all week on the boat. It’s much easier than bringing a bunch of travel sized ones.
  • Earplugs: My group wasn’t loud enough to warrant these but just in case.
  • Other things to bring: swimsuits, swimsuit cover ups, a quick-dry towel, a hat, sunglasses, outfits for the evening, pajamas, underwear, makeup, and toiletries.


Book it!

Sailing is the experience you never knew you wanted to do. You’ll disconnect from real life, experience gorgeous landscapes, swim in crystal clear waters, and marvel at epic sunrises and sunsets. If you’re looking for a fun-filled, relaxing weeklong trip in Greece, I highly recommend A Dot in the Blue. Now that I’ve gotten my first taste of sailing, it’s something I want do again and again.

You can find more information and book your trip here and learn how to get a cheap flight with my handy tips. If you have any questions about my experience and/or about sailing with A Dot in the Blue, feel free to ask me! And if you’re spending some time in Athens, check out this budget guide to the city and my food tour review.

More Greece Resources

Planning a trip to Greece soon? Check out ALL my posts on Greece below:


Tell me: Is Greece on your bucket list? Would you consider doing a sailing trip? Share in the comments below!


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13 thoughts on “Sailing Greece: Exploring Greek Islands with A Dot in the Blue

  1. Lori Simonetti Sorrentino says:

    Oh…wow… that water. This might just be my dream trip! And how great is it to be the +1 of the prize winner 🙂 The scenery, the culture, and the food (that octopus was perfectly cooked!) would be right up my alley and I can’t think of a better way to see it than on a sailboat. Best of all, I like how you noted the fact that going out with them was supporting a local company, something I always try to do. It sounds like you had an amazing time!

  2. Marta Cunha Grilo says:

    Those pictures… that water… it makes me want to forget about my future plans to go on a cruise in the Greek Islands. Absolutely stunning! I’ll definitely check that company for further trips to Greece 😉 seems a great way to spend a week relaxing and enjoying its beautiful islands

  3. Candy says:

    I’m an introvert myself and understand your response to your friend when she told you about it. I’m happy to hear that it was a lot of fun and how cool that your sister won this trip! I get sea sick immediately, so I’m not sure I would ever be able to go sailing. I love all the gorgeous photos you took!

    • Sally E says:

      Surprisingly, it was a great time to be introspective and chill by myself! I had lots of downtime. And I actually sometimes do as well – dramamine is your best friend. Although maybe it’s better to go for a day trip instead of a weeklong excursion to start. 🙂

  4. Sonal Kwatra says:

    Lovely post! Out of this Kefalonia looks the most interesting to me and I’d love to explore it one day. Just like you, I’m also a caffeine addict and would have not managed to wake up properly without my daily dose of espresso.

  5. Daphne Po says:

    What an amazing photos!! Day three looks fantastic, first swimming, napping, and having dinner at Rementzo… Will defenitely try the goat with apricot! Kefalonia looks great! Good to know the restaurants close at 20 pm.

  6. miieloise says:

    I would just LOVE this trip. I was so envious reading your article. I love sailing and doing it with a local to get tips and also explore less touristy spots is just perfect. I cannot believe your sister won that trip. Why wasn’t I in the competition? ahahah
    If I can travel to Greece, I’ll definitely consider a small sailing cruise like this. If you plan to visit Australia, we have great sailing destinations too 🙂

  7. Vibeke Johannessen says:

    Greece looks so amazing. Always wanted to do a sailing trip there. So good you include a packing list so important to bring a dry bag, go pro and a life proof phone case 😀 Good to know that you don’t need to bring floaties but snorkel set. I wish I had my own snorkel set when I was in the Galapagos islands.

  8. Catamaran Emelia says:

    You should definitely come back to the same experience but… in the Cyclades!! The number of heavenly beaches is just amazing and the islands are really welcoming

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