20 September — 2 October 2026 · Athens & Sifnos
Your Greek
Odyssey
12 nights. 8 guests. One island you'll never want to leave.
I am so excited to invite you to join me on this intimate experience to slow down, eat and drink extraordinarily well, and to discover the slow, beautiful rhythm of Greece most people don't ever experience. We’ll explore at a gentle and leisurely pace. We’ll sleep like the Gods. Eat like the Locals. Drink wine like Onassis. And slow down, breathe deeply, and relax into the Greek way of life. This is a highly curated trip featuring my pick of the best hotels, restaurants and experiences - giving you access to the inaccessible.
Everything is (mostly) included so you only need to get yourself to Athens and home again.
YOUR JOURNEY
Athens is for people who walk instead of rushing. Who care more about energy than luxury clichés. Who want a city not a checklist. This is where we'll start our journey. Arrive and relax at the hotel before we meet for drinks and dinner.
The next day we will stroll to lunch at one of my favourite haunts. That night we will start to immerse ourselves in Greek timings — dinner here is late, which gives us plenty of time for an after lunch siesta to build up an appetite for dinner.
HOTEL TBC
We'll start our journey today taking the ferry to Sifnos. Arriving at Kamares we'll be whisked to our barefoot luxury retreat by the sea. We'll either take a late lunch or early dinner with our feet in the sand overlooking the longest beach in the Cyclades, Platys Gialos. Maybe you feel like a swim before or after, or simply to sit and take in the island. Its rhythm is slow and tranquil.
Over the next 4 days we will explore, taste, drink, swim, rest and get into the rhythm of the island. One day we take to the water completely, heading to neighbouring islands on our own private motor yacht. We'll moor up for lunch, stopping for swims along the way. Dinners we will most often be near the sea, to the sounds of the lapping waves and a canopy of stars above us.
Today we move to Poulati, in the island's northeast, and check in to Verina Astra. Perched on a steep hillside with nothing between you and the Aegean, the views are breathtaking — all that deep, endless blue stretching to the horizon. Jasmine-scented gardens hum with bumblebees. The infinity pool glitters. In my opinion Verina has the best view on the island and a certain stillness that I find completely calming.
Mornings unfold at your own pace here — breakfast on your private terrace, coffee in hand, the sea doing its thing below. From here, we'll explore Vathi, Kastro and Cheronissos, with some very special access to the people who make this island what it is. Restaurateurs. Local legends. Experiences you won't find on any itinerary but this one.
Afternoons are yours. A massage at the Verina Spa. A siesta in the shade. A slow lap of the pool. And evenings? Dinner and sunsets. Late drinks at Botzi (it doesn't get going until midnight)… or an early night to wake with the sun. No pressure. Whatever and however you choose.
We leave Sifnos for Athens. One last night together. Our last Greek dinner. Morning breakfast, then you're whisked to the airport. Body rested. Soul full.
HOTEL TBC
Who is this trip for?
My private adventures are built around a shared set of values rooted in kindness. I believe in prioritising connection (whether with locals or fellow travellers), keeping an open mind through all experiences, and being adaptable with all that travel may bring. This trip is open to people of all ages, that do not require mobility assistance as some activities require moderate exertion, walking across coastlines, cobbled streets, and steps.
INCLUSIONS
All accommodation as itinerary
Full day private motor yacht charter
VIP return ferry tickets
Breakfast daily · 9 lunches · 12 dinners
Hand-selected Greek wines (curated by our Sommelier) & soft drinks at every group meal
All luxury ground transfers
60-minute personalised massage at Verina Astra Spa
All gratuities
All taxes incl. Climate Crisis Resilience Tax
EXCLUSIONS
Airfares
Visa or entry requirements
Travel Insurance (strongly recommended)
Transfers outside of arranged activities
Personal hotel expenses such as room service, bar tabs and laundry services
Meals and beverages not specified in our itinerary
Terms and Conditions
Please note any deposits paid are strictly
NON REFUNDABLE
Please note, for this trip to proceed, a minimum number of people must reserve a place. We will provide confirmation once this number has been reached, so you may proceed with booking your airfares.
If you choose to book your airfare in advance of final confirmation, please book refundable fares or obtain travel insurance to protect yourself against additional charges should final dates change or cancellation occur.
Travel with Tess strongly recommends that each traveller purchase full comprehensive travel insurance, that includes cancellation, full medical and loss.
Please note, all efforts are made to provide the itinerary as presented, Travel with Tess reserves the right to make any changes to the final itinerary deemed necessary or due to reasons beyond our control (change in flights, cancellations, political disturbances, natural disasters/phenomena, etc).
Photographs or video recordings of guests may be used for promotional purposes by Travel with Tess or a host group/organisation.
For any questions, please contact me directly: hello@travelwithtess.co or I’d be delighted to have a chat +61 408 234 838