ESBT Greek Sailing: May/June 2024

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****SOLD OUT*** I am currently taking names for the waitlist

My ESBT Greek Sailing 2023 trip was such a success that I’m doing it again in 2024!

Here’s what you need to know if you want to be a part of this pirate/mermaid adventure.


This trip will take place from May 28th to June 6th, 2024. We start and end in Santorini. You will need to ensure that you are in Santorini on the morning of May 28th to depart. If you are leaving right after the tour ends on the 6th, please book your flight later than 3pm to ensure you have enough time to get back to the island and to the airport.

Our Trip and Itinerary

This is a 10-day sailing tour in partnership with Intrepid Travel. The trip starts and ends in Santorini and will take place in late May/Early June. The seas aren’t as rough during this time making it easier for those new to sailing and ideal for calmer waters for swim stops. Plus, it’s not too busy yet with other tourists!

The goal is to visit 9 islands over the course of the trip (including Santorini) but the itinerary will depend on the weather and sailing conditions. Our skipper will be in charge of these decisions based on his professional opinions and availability in the ports. Some of the islands that we may visit include:

  • Ios
  • Amorgos
  • Koufonisia
  • Iraklia
  • Naxos
  • Syros
  • Mykonos
  • Folegandros
  • Sifnos

You can find the suggested full itinerary here.

Cost and Inclusions

The cost of this year’s trip is $2850 CAD (cheaper than what is listed on the Intrepid website!) In order to confirm your space, a non-refundable deposit of $700 CAD will be required. Final payment will be due 4 months from departure.

This includes the cost of the boat only. So, transportation between the islands and accommodation. Flights, meals, additional activities, and tips for our skipper are extra.

On our first day, each guest will also be asked to contribute 100 euros towards the ‘kitty’. We use this money to buy groceries for the group to do breakfasts and lunches on board. Dinners are usually at a restaurant on whatever island we choose to visit for the evening.

In the past we’ve also had enough money in the kitty to also cover rental cars in a couple islands and to contribute towards final tip for our skipper. Of course, this varies by group.

Additional spending money depends on your travel and spending style. To give you an idea, most of our group spent about an extra 500 euros during the trip.

What to Expect 

This is an adventure sailing tour in a traditional sailboat. It is not a luxury yacht. Accommodation is shared with two people per room. You need to be prepared to sleep in a bunk bed and, possibly, share a double bed given the room configurations. Due to this, this trip is marketed to women OR couples who can share a room. Since it is tight quarters you are expected to be respectful of fellow travellers and clean up and keep things tidy at all times. You can see more about the sailboat here.

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.

Our days are spent half on the boat and half on the islands. We usually depart from the port around 9am, sail for a few hours. Have a swim/lunch stop somewhere beautiful and unique, then sail for a couple more hours to get to the island for mid-afternoon where we have free time to explore. We generally do dinner as a group, but you are welcome to make your own plans. Nights are spent on the boat. There is no curfew but please be respectful of your fellow travellers.

The Greek islands can be uneven and rough terrain and many towns are built onto hills which may include steps/steep inclines. Taxis and buses are not always available so please bring appropriate footwear and ensure you are comfortable walking.

Finally, we do have an AMAZING skipper but he needs some help sometimes too! You may be asked to do some basic tasks around the boat. It’s a great way to get some sailing experience in!

This trip is very social since it’s on a boat but in my experience it’s been such a fun way to meet like minded travellers. Expect lots of laughs, fun photo ops (I love playing photographer!), delicious food, beautiful sunsets, plenty of swimming in crystal clear waters, and maybe even some cheeky skinny dipping! 

How to Book






The trip is officially open for sale now. It is first come first serve so please email me at:

Title the email: ESBT Greece 2024


-Your full name as per your passport

-Your date of birth

-the best email to communicate

I will then be in touch with some more information and Intrepid Team will send you the link to pay the $700 non-refundable deposit to secure your place. So please keep an eye on your inbox as the links do expire. Failure to pay the deposit within a couple of days may result in you losing your space. 

Important Notes

You are required to purchase travel insurance for this trip. I love and use SafetyWing. 

You are responsible for familiarizing yourself with any visa or exit/entry requirements for Greece.

Feel free to reach out if you have any questions! 

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