ESBT Greek Island Sailing 2025 (June)

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About Eat Sleep Breathe Travel Group Trips: I started running ESBT Group Trips with the intent of offering fun, adventurous trips to various destinations around the world to friends and followers. The goal is to take the stress out of travel and to connect with like-minded people while exploring and learning.

As such, ESBT group trips tend to be busy itineraries that aim to provide the best value for your money. This might mean longer drive days, lots of walking, or back-to-back activities with limited free time. We also may go ‘off-grid’ at times and have little, or no, internet access. These are travel adventures, not laid-back vacations. Please always read through the itinerary to understand the plans, schedule, and level of activity involved. I also strongly recommend that you to do your own destination research to check things like climate and weather to ensure it is something you are comfortable with.

In addition, ESBT group trips are meant to be inclusive, safe spaces where everyone is welcome. In joining these tours, you are agreeing to continue to promote this theme and to treat all other travellers with kindness and respect. Along these lines, it is up to you to ensure that you are healthy enough to join. Rooms and spaces are often shared so I ask you to be considerate of your fellow travellers and seek medical attention ahead of time if you are unwell.

If you have any concerns or questions about the itinerary or destination based on your personal needs, please reach out to me.

ESBT Greek Sailing 2025

Mama Mia! Here we go again!

I’m headed back to Greece again in 2025 but this year I am offering two trips. One of which is the ever-popular Greece Sailing adventure. This year I’m changing it up a little bit so even if you have been on a previous Greece Sailing trip with me please make sure to read through all the details.


Greek Island sailing will take place from June 7th to June 14th, 2025. This time of year isn’t too hot or crowded yet and the seas tend to be a little calmer making it ideal for swim stops.

You will need to be ready to go at our starting point in Paros at 1pm on June 7th. If you are planning on leaving on the 14th, please note we are off the boat by 9am but it is recommended no ferries before 11am and no flights until 12:30pm. I do advise you to come at least one day early as flights and ferries can be cancelled. Paros is also one of my favourite Greek Islands so I do suggest staying longer and exploring.

About this trip 

For this trip, I am partnering with Greece Less Travelled (GLT) a local, family-run company that promises immersive and off-the-tourist-trail experiences. Our host, a good friend of mine, has been working in the travel industry for many years as a skipper and has helped me put together this itinerary with a focus on the smaller, lesser-touristic islands in the Cyclades.

This is a sailing tour which means we travel by, and sleep on, a sailboat. Working with a new company also means that we have a new boat this year. Our boat for this trip is cushier and does include air conditioning. That being said, it is still a sailboat which means smaller space and sharing (more on this to come).

A typical day on this trip means departing the island early in the morning, sailing to a swim stop where we spend about 1.5-3 hours, and then another couple of hours sailing to our island stop for the night.

Note that the proposed itinerary below could change depending on the weather. Our skipper will have the final say and proceed as he thinks best and safest for the group.

Proposed Itinerary

This year we will be starting and ending in Paros. It’s one of my favourite Greek islands and is easily accessible by flight and ferry. I highly suggest spending an extra couple of days here and will share more details upon booking about the island and how to best arrive.

From Paros, we plan to visit the following islands:

Irakleia: This tiny Greek island is one of my favourites to just chill. The port here is small, meaning it won’t be busy with other boats and tourists. There’s a nearby sandy beach perfect for swimming and a small, charming Chora all within walking distance. It’s a great place to escape the tourist crowds commonly found on other islands in the Cyclades.

Koufonisi: Considered to be one of the most beautiful islands in the Cyclades, Koufonisi is famous for its turquoise waters and unique rock formations. There are some great beaches here along with local tavernas and a very cute windmill bar, perfect for after-dinner drinks! All are within walking distance from where we dock.

Amorgos: We will be spending two days on Amorgos Island. There’s plenty to see and do here including the UNESCO Heritage Monastery of Hozoviotissa and some incredible beaches (‘The Big Blue’ about freedivers was filmed at the famous Agia Anna beach). Side note: this island also has the best moussaka I’ve ever tasted. I’ve been dreaming about it since I first had it in 2019.

Dondousa: Dondousa only has 130 inhabitants spread across 3 tiny villages. We’ll be anchoring in Kalotaritissa Bay for the night with plans for a beach BBQ and a night under the stars.

Ios: This island has a reputation for being an affordable party island, but don’t worry. We’re more into the amazing sunset views, cute little chora with fun shops to explore, and the delicious food and cocktails. For cheese lovers, 10/10 recommend the feta fondue, nicknamed among our pirate crew as the Greek Orgy.

Paros: We’ll spend our final night back in Paros in the small port of Piso Livadi. Again, this is a beautiful island so if you can come early or stay late I highly recommend it. I have lots of Paros tips and suggestions and can help you make plans.

What to Expect 

Ready to join my pirate mermaid crew? I’d love to have you on board, but before you say ‘AYE’ there are a few important things to be aware of for this type of adventure.

As mentioned above, we usually spend part of the day on the water and part of the day exploring islands. As such, we tend to eat breakfast and lunch on board. Each member will be asked to contribute 100 euros on the first day to our ‘kitty’. We will use the money in the kitty for purchasing food for breakfast, lunch, and snacks as well as drinking water and other beverages. While there is a (small) kitchen on board, breakfasts and lunches tend to be simple things like sandwiches, veggies and various dips etc. rather than cooked, hot meals. Dinner is usually done as a group at a taverna on the island.

Now to the fun stuff.

This is an adventure sailing tour in a traditional sailboat. It is not a luxury yacht or cruise.

Accommodation is shared with two people per room. Due to room configurations on this boat, beds are double beds- not singles. This means you MUST be comfortable sharing a bed if you would like to join this trip. Because of this, this particular trip is marketed to women (my main audience) OR couples/male friends who are ok to share a bed. Those who know each other will be put together, otherwise, I do my best to partner like people together (ie early risers vs night owls). I know that it is not ideal, but because of the design of most boats, it is common in these types of sailing tours. This is part of boat life and part of the adventure. If you are really determined to come but adamant you don’t want to share, you can still join but will have the pay for 2 spots. On this same note, there is VERY LIMITED luggage space. Backpack/small duffel bags only. There is nowhere to store big suitcases so if you have one, you will have to arrange to find luggage storage before departure. 

There are 5 cabins on board, so two people per cabin. There are three bathrooms on board that are also shared. This is our home for a week and shared quarters so you are expected to keep things tidy at all times. There is no curfew but please be respectful of your fellow travellers. Ear plugs are strongly encouraged over headphones and white noise machines as we may not always have access to electricity.

We do spend a lot of time on the boat and in the water so you should be comfortable in these conditions. There can be big waves and swell, which can cause some people to be nauseous at times. If you are prone to seasickness (or unsure if you get seasick) then please make sure to bring medication.

On land, there are not always buses or taxis available (especially on these smaller islands) which means we will be walking. The Greek landscape can be hilly and involve stairs or steep slopes in some areas. Please ensure you are comfortable on this type of terrain.

While many activities, including island exploring and dinners, are typically done as a group, you are always welcome to do your own thing. I encourage you to bring a book to read on board, take a walk by yourself in the morning before we leave or when we arrive; whatever works best for you. Again, there is no expectation or pressure to always be with the group, but it is up to you to create the opportunity to recharge your batteries as needed.

Cost & Inclusions 

The cost for 2025’s Greek Island Sailing adventure is $3200 CAD per person.

This includes:

  • Accommodation and transportation by sailboat for the duration of the trip
  • The best skipper ever (George, obviously) and a pretty fun co-skipper (me)
  • Bed sheets and towels for the bathroom (bring your own beach towel)
  • All port fees, cleaning fees, and fuel
  • Night at anchor & beach BBQ
  • Many, many, many photographs of our adventures together

Not included:

  • Flights and transportation to/from our meeting and ending point
  • Travel insurance (essential)
  • Kitty contribution (100 euros each- whatever is left will be divided equally at the end)
  • Tips for our skipper (at your discretion, but the suggestion is 10 euros/day per person)
  • Meals
  • Anything else not included in the itinerary

There is a non-refundable deposit of: $1200 CAD per person required to secure the sailboat and your space on it. The deposit is higher than normal due to the fact that we have to put a large deposit down to secure the boat. I have 9 spaces available and there will be a waitlist if required. 

How to Book

If all of this sounds good to you then I would LOVE to have you join my mermaid/pirate crew! 

Here’s what I need from you:

An email titled ESBT Greece Sailing 2025

-Name as per passport

-Passport issue and expiry date

-Date of Birth


-Best email address to reach you

Send the above information to:

I will then send you an invoice via PayPal for the deposit which you must send to me within 3 days of booking on. If I do not receive the deposit in time, you risk losing your spot to someone else on the list. Again, the deposit is non-refundable. (Canadians, if you prefer, we can do an e-transfer instead of PayPal). 

*Since this is a boat rental and requires a large non-refundable deposit immediately to secure the boat, this trip does need to sell within one week in order to run. 


  • Deposit is non-refundable.
  • All group members must have travel insurance to join this trip. Details will be requested at the time of final payment. (I use and trust SafetyWing).
  • Final payment is due 3 months before the departure date (March 7, 2025). Given the nature of this trip (sailboat rental) this payment is also non-refundable. I highly suggest you get not only health insurance, but also travel cancellation/interruption insurance to cover all of your bases.
  • Payment transactions are in CAD. You will be asked to send the money via PayPal and will be invoiced accordingly. If you are Canadian and would prefer interac e-transfers, that can also be arranged.

Boat Photos


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