ESBT Greece 2026: Island Secrets in the Cyclades
My Greece group trip is back for the fourth year in a row!
Once again, I am partnering with George and Greece Less Travelled to offer a custom itinerary for ESBT followers for 2026. We’re offering another multi-island trip but like 2025, this is land-based not a sailing trip; we will be using the local ferries to transfer between islands and staying in (adorable) boutique hotels on each island.
This is a laid back and relaxed itinerary with a focus on local island life, beaches, and delicious Greek wine and food! The islands we are visiting aren’t typical tourist spots and we’ll be focusing on supporting local businesses throughout our stay.
If you think you’d like to join my next Greek adventure, then read on!
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 things like 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 typically 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. I do aim to make my trips as inclusive as possible and will do my best to ensure everyone’s needs can be safely met.
Dates
This itinerary is 7 night and 8 days and will run from June 6-13th, 2026
Start: Syros, Greece
End: Samos, Greece
Again, this is a land-based trip but we will be using ferries to travel between the three islands. June is still on the early side of the season but it can still be hot! Don’t worry all hotels have air conditioning and we have beach time factored in, but keep in mind Greece does get quite warm in the summer and even this early, it is possible that we may experience temperatures around 30C+.
Itinerary & Islands
Day 1-2: Syros, Greece
Welcome to Syros! This island is the capital of the Cyclades chain and also George’s home island- so you know he’s planned the best things for us! But don’t let the title of ‘capital’ fool you, Syros is a lot less crowded than many of the other islands in the Cyclades giving it a distinctly local feel.
We will be spending two nights here and our itinerary includes a welcome meeting at 5pm on June 6th followed by a cocktail class in Hermoupoilis, the capitol of Syros. The neoclassical arthitecture here is beautiful to photograph and after our cocktail making class, we will have a chance to explore the area and grab dinner in one of the many local tavernas.
Day two offers a relaxing beach morning after breakfast then, after lunch, we’ll head to an immersive farm-to-table experience for a dinner under the stars.
Insider tip: Syros is a charming island with lots to explore. If time allows, I suggest coming early to explore a bit before we get started. Ano Syros, the old town on the hill, is especially picturesque and there are some great beaches (and awesome restaurants) around the island as well.
Days 3-6: Ikaria
On day 3 we’ll depart Syros after breakfast and take the ferry across to Ikaria, our home for the next 3 nights. Ikaria is a little-known Greek Island in the Cyclades that is best known for being one of the world’s 5 ‘Blue Zones’. Ikaria is a slow island with amazing food and beautiful nature.
We’ll have lunch upon arrival and in the afternoon, we’ll visit a local women’s cooperative where we get to try various local delicacies. The evening is yours to enjoy so settle into the hotel, explore the village of Armenistis, wander along the coast, or settle in for a sunset drink.
Day 4 will be a relaxing beach day, Ikaria has many beautiful options on the island. Following our day in the sun and sea we’ll head to a local winery for a sunset wine tour and tasting.
Day 5, as of right now, is up in the air. This is because Ikaria has many festivals in June and, at the time of planning, we don’t yet know the schedule for 2026. As such, we have left a free day to (hopefully) work one in for an authentic and unique Greek experience! If timing does not work out, we’ll continue to explore the island- hidden beaches, hot springs, and boat trips are all possibilities for the day.
Day 6- We’ll check out of out hotel in Ikaria after breakfast and head to Agios Dimitirios, a small village known for delicious food. We’ll have some time to explore and grab lunch before catching an early afternoon ferry to Samos.
Day 6-8: Samos
Of final stop of this Greek Island adventure is Samos. Wine enthusiasts and mythology lovers especially will love this quiet island which is also full of adorable villages and beautiful nature spots.
After we arrive by ferry, we’ll explore the village of Pythagorio before enjoying dinner at a local restaurant.
Day 7 will take us to one of the island’s many beaches where we can relax and soak up the sun. We’ll be grabbing lunch at a renowned tavern and have some time to relax before our final night out where we’ll enjoy dinner, drinks, and live music in the town.
Our final day is departure day with check-out after breakfast. Samos has a domestic airport for those who need to make their way back to Athens to head home. Alternatively, if time allows, you can stay longer and continue to explore Samos or neighbouring islands as you wish.
Cost & Inclusions
The total cost for this trip is 2660 euros. Please note the cost in this trip is EUROS (not the typical Canadian dollar) as George’s business is based in Greece.
The cost for this 7-night 8-day trip includes:
- all local transportation as scheduled in the itinerary (ferries between the islands, transit on the islands to our activities and events)
- accommodation in locally-owned boutique hotels (3-4*). Pricing is based on shared accommodation but single supplement is available for 540 euro.
- 7 breakfasts and 3 lunch/dinner meals
- Welcome drink and cocktail class in Syros
- Farm dinner experience in Syros
- Women’s cooperative visit and tastings in Ikaria
- Winery visit and tasting in Ikaria
- Beach visits and walking tours as per itinerary
External flights, meals and activities not included in the itinerary, travel insurance (mandatory), and tips for our guides are NOT included.
*Tips are at your discretion but the suggested amount is 10 euro/day.
A non-refundable deposit of 800 euros is required to reserve your space, the final amount is due February 15th, 2026. All payments after this date are final and non-refundable.
If you would like a single supplement (540 euro per person) please notify me upon booking.
How to Book
Booking is now open!
If you would like to join this group trip please email me at hannahlogan21@gmail.com with the following:
- Email title: ESBT Greece 2026
- Your full name as per passport
- Your birthday (dd/mm/yy)
- Your nationality
- Your passport issue and expiration dates (dd/mm/yy)
- The best email to reach you at
For this pricing, we need a minimum of 10 people to run this trip. Once we hit that threshold I will pass on your info to George who will reach out with the links to pay the deposit.
Terms/Conditions
- Deposit is needed to confirm your space. Keep in mind the 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 February 15, 2026. Due to booking requirements, cancellations after this point are non-refundable. I highly suggest you get health insurance AND cancellation/interruption insurance to cover all of your bases.
- Payment transactions are in EURO.
I’d love for you to join me on this latest Greek adventure!
Questions? Please get in touch!