Imagine waking up to the sensation of breeze straight off the Aegean Sea flowing in through your window. You step outside onto your balcony and take in the deep blue of the ocean at the base of the cliffs below, dotted by neighboring islands in the distance and bordered by bright azure sky above. You head down to the veranda of our private villa for breakfast, where the aroma of freshly baked pastries greets you. You seek to determine the ethereal aromas: citrus, maybe orange or lemon, along with herbs and spices… clove, anise, maybe saffron. After a leisurely breakfast, you roll out your yoga mat on the deck overlooking the ocean, and enjoy a curated practice of yoga and meditation with your fellow travelers. Next, you pack your beach bag and stroll down the hillside to the beach, where you take a refreshing swim. You’ve heard some locals recommend a taverna a short stroll down the beach, and decide to meet your new friends there for a tasting menu of citrusy crudo, spicy croquettes, and pillowy soft local ricotta drizzled with lavender honey, polished off with a toast of ouzo. After making your way back to the villa, you decide to take a poolside nap before an easeful afternoon practice of yoga and journaling. As you roll up your mat, you hear the cheerful voices of the private chef team preparing traditional Sifnos dishes for dinner: an herbaceous stew cooked for hours in a woodburning oven; tender lamb braised with dill and red wine; and pumpkin cake laced with raisins, honey, orange, and sesame seeds. Dinner with your fellow retreat participants is boisterous and joyful, as we savor our meal and reflect on another sweet, blissfully simple day in paradise.

the experience

Greek Island Paradise

May 23-30, 2026 | Starting at $4,395

This boutique travel experience includes:

* 8 days + 7 nights in a unique and elegant private villa on the island of Sifnos, overlooking the deep blue of the Aegean sea. Each room is double occupancy with private bathroom. From our villa, we can lounge on the veranda to take in the view of the surrounding hillsides, access public transport, and walk to one of the island’s many beautiful beaches

* Private pool onsite, just for our group

* Most meals. Delicious breakfast + either lunch or dinner each day, prepared by our private chefs in traditional Sifnos style, incorporating fresh and local ingredients with recipes that have been passed down for generations

* Daylong private boat tour. We will sail, swim, and discover neighboring islands and secluded beaches only accessible by boat

* Farm tour + cooking class, where we will learn the history of Greek cuisine and how it evolved over the centuries while preparing traditional dishes together as a group

* Private guided hiking tour to discover some of the island’s ancient paths and secret corners tucked away in the hillsides, while surrounded by panoramic views of the surrounding bright blue sky above and vivid sea below

* Private transport to and from the port where you’ll arrive by ferry on arrival and departure days

* Curated yoga, meditation, and personal development practices led each day by Carrie + Kelly

* Gratuities for all the folks who take excellent care of us: private chefs, drivers, excursion providers, housekeeping staff

* Thorough pre-trip planning support, packing lists, and recommendations (including a curated guide to support you in making the most of your time in Sifnos (including the island’s most sought after restaurants!)

* Private What’s App group for community building and in the moment support before, during, and after retreat

About our location:

We will be spending our week on the idyllic Greek island of Sifnos, known for it’s graceful beauty and deeply serene atmosphere. Picture tranquil cliffside beaches, villages dotted with locally owned cafes and tavernas, and trails that meander the hillsides with jaw dropping views of the ocean below. This island is known as a foodie paradise! In fact, Conde Naste Traveler calls Sifnos “the most delicious Greek island.” Sifnos also has a network of well-established hiking trails meandering between olive groves, villages, and panoramic hilltops… some trails up to 3000 years old! We’ll be staying in a private villa on the island, with sweeping views of the sky and sea. From our villa, it's possible to hike downhill to the ocean. In one direction, your hike will take you to a village where you can enjoy an amazing meal at a number of local restaurants, and then walk directly from the patio into the ocean to cool off. In the other direction, your hike will take you to an iconic church built into the cliffs in the 1600's. From there, you can swim, float, and explore in the crystalline Aegean sea.

That’s a lot of goodness! What’s NOT included?

Airfare to and from Athens, Greece
Ferry tickets between Athens and Sifnos on arrival and departure days (a 2.5 hour ride)
Additional transport on the two “choose your own adventure” days if you opt to explore the island, and transport that falls outside of designated pick up and drop off times on arrival and departure days. Taxis, bus service, and walking are all possible ways of getting yourself around the island. Plus, public ferries are available to visit other neighboring islands!
A few meals. Breakfast and either lunch or dinner each day are provided, courtesy of our private chef team. For your other meals, we strongly encourage you to delight your palate through visiting the island’s many renowned restaurants and chef’s tasting menus. Sifnos is a renowned foodie paradise, and we have lots of suggestions!
Alcohol. Greek wine is absolutely delightful, and fortunately is abundantly available, and affordable!
Any additional activities you choose beyond those noted above in the retreat description.
Travel insurance, which we highly recommended for unforeseen needs while traveling internationally, and to protect your investment.

Frequently Asked Questions

How do I get to the retreat?

Upon booking, we will provide detailed recommendations regarding arrival and departure times. In the meanwhile, here are the basics: 1) Fly to Athens, Greece. 2) Take the daily ferry service to the Island of Sifnos. 2) Step off the ferry and hop into the van. We will be waiting for you with with hugs, ready to whisk you and the rest of our group off to our hillside villa!

I'm not actually that into yoga. Can i still come?

Absolutely! We are after all, "not your average yoga retreat!" All activities, including yoga and meditation, are optional. And, we offer practices to delight a range of levels, even including folks who have never stepped foot on a yoga mat. While we begin most days with a yoga and meditation practice, we certainly don't spend all day on the mat. There's so much of this beautiful island to explore! You’ll be provided with a detailed itinerary, so you can decide what you’d like to participate in, and what you’d like to skip.

I’m a solo traveler and don’t know any of the other participants. Can I still come?

Yes! Absolutely! Many of our retreat participants are solo travelers. Since all rooms are double occupancy, you’ll have the opportunity to share a beautiful ocean-view room with a new friend. Rooms can be arranged either with one queen bed for a couple, or with two twins for solo travelers. While you may begin the retreat on your own, you’ll leave with a community that very much feels like family (and probably will be, forever).

how many people will be on retreat?

This retreat will offer the opportunity for community among an intimate group of up to 12 participants.

What happens after I reserve my spot?

We do a happy dance and welcome you to the Explore & Expand family! And then, we send you a robust welcome packet, itinerary, packing list, and other vetted recommendations!

I have another question! What should I do?

Email us! We’re happy to help.

What is the physical activity level of this retreat?

This retreat offers a range of experiences to allow you to choose your own adventure. You may elect to lounge by the pool and take in the panoramic view between scheduled activities for a true “R & R” experience. You may also choose to take advantage of the island’s reputation as a hiker’s paradise, via its many established hiking trails and routes. Daily yoga practices will be tailored to the group, and are always “choose your own adventure” depending on what you personally need that day.

what do I do on "choose your own adventure" days?

The short answer: whatever you want! We will provide vetted recommendations for activities and restaurants. You may also find you'd like to simply nap by the pool, and savor our breathtaking view!

You Don't just have to take our word for it

Traveling solo was a big step out of my comfort zone, but I'm so glad that I did it! I felt so much of the trip was an invitation to deeper self-discovery and expansion, from meeting strangers ( who many felt like family by the time I left) to tasting new food/cuisine, also hiking and sharing during the workshop times. I felt like I have a deeper sense of integrity and also adventure / courage after going on this trip. Something about it gave me a greater sense of confidence to travel more in the future and invest in things that are generative for my creativity and good for my soul. It was a rejuvenating/inspiring experience from the hospitality on the island, to the incredible food and meals that we shared, to the gorgeous island views. It was a mix of soulful self/group reflection mixed in with playful adventure and exploration. It exceeded any expectation I had!