A Women-Only Journey · October 1 – 11, 2027
Crete Luxury Escape for Women 2027
Finally, Luxury with Time to Enjoy It
Luxury Chania escape for women 45+: culture, connection, and Cretan serenity
We believe this is exactly what you’ve been waiting for.
A journey where luxury isn’t just the hotel we stay in or the places we dine. It’s waking to the Cretan Sea in your Grand Deluxe Room with your own heated private pool. It’s unpacking once and knowing that magnificent room is yours for ten nights. It’s private experiences created just for us, beautiful meals in extraordinary settings, and days with enough space to actually enjoy where we are.
It’s being spoiled without being scheduled to death.
That’s why Stacey Ray, our Founder & CEO, has created and is personally hosting this very special escape.
Together, we’ll sail the Cretan blue, meet remarkable women and artisans, create with our own hands, share incredible food and wine, and experience Chania not as somewhere we’re passing through, but as somewhere we belong for a little while. And we’ll end it all with a private Farewell White Night Gala at a 15th-century Venetian estate that we promise will be worth packing something fabulous and white for.
If this is the kind of luxury you want and need now — with beautiful places, extraordinary experiences, wonderful women, and enough time to savor all of it – we hope you’ll come experience it with The Sisterhood.
Where You're Going
Your journey, mapped
Picture Yourself Here
See where you're going
Trip Highlights
Moments you'll talk about for years
- Unpack Once in 5-Star LuxuryMake the Hilton Chania Old Town Resort & Spa your home for all 10 nights, staying in a Grand Deluxe Sea View Room with your own heated private pool, just minutes from Chania's enchanting Old Town and Venetian Harbour.
- Experience the Luxury of TimeLeisurely mornings, completely free days and meaningful downtime are intentionally woven throughout the journey, giving you the rare luxury of actually enjoying the resort, Chania and your time with your Sisters.
- Discover a More Personal Side of CretePrivate experiences connect us with the island through its people, traditions, food, wine and creativity, from local artisans and family-run businesses to experiences created exclusively for our small group.
- See Yourself Through a Different LensStep into the beautiful streets of Chania Old Town for your own private editorial-style portrait session with a professional female photographer. No studio backdrop and no ordinary vacation snapshot, just you and the timeless beauty of Chania creating something truly personal.
- Travel with Stacey & Your SistersPersonally hosted by Stacey Ray, this intimate journey is as much about the women you'll share it with as the places you'll experience. Expect laughter, long conversations, shared meals, spontaneous moments and the kind of new friendships that have always been at the heart of Sisterhood Travels.
- An Unforgettable White Night GalaDress in white for a magical private celebration at a 15th-century Venetian estate, where candlelight, music, dinner and a few carefully guarded surprises bring our time in Crete to an extraordinary close.
Our Itinerary
11 days, day by day
Tap any day to see what's planned — and where you'll rest your head each night.
⬇ Download the Itinerary (PDF)
1 Arrive. Exhale. You’re in Crete.2027-10-01
Welcome to Chania, where your Cretan luxury escape begins. Upon arrival at Chania International Airport, you’ll be met and transferred to our home for the next ten nights, the magnificent 5-star Hilton Chania Old Town Resort & Spa.
And from that moment on, the day is entirely yours. Unpack. Settle in. Step onto your balcony and take in the sea view. Slip into your own heated private pool. Wander down toward the harbor. Take a leisurely stroll into Old Town and find a café for lunch. Or close the curtains, climb into that beautiful bed, and take a nap.
After an overnight flight and a long journey to Crete, we think the greatest welcome we can give you is time. Time to arrive. Time to rest. Time to explore if you feel like it. And time to begin this journey entirely on your own terms. Your room is unpacked. Your private pool is waiting. And you won’t be touching that suitcase again for ten glorious nights.
2 Journey Across the Cretan Blue2027-10-02
Your first full day in Crete begins exactly as it should: slowly. Sleep in. Enjoy a leisurely breakfast. Take a morning swim in your private pool. Wander into Chania’s Old Town, browse the shops, linger over lunch, or simply spend the day enjoying our beautiful resort. There is nowhere you need to be until late afternoon.
Then, as the day begins to soften, we’ll come together for our first shared experience in Crete: a private sailing journey through the beautiful waters of Chania Gulf, with views toward Thodorou Island.
Our spacious private vessel has been selected with comfort in mind, with generous outdoor lounge areas, shaded spaces, dining facilities, and well-appointed restroom and shower facilities. Weather permitting, there will be time to slip into the crystal-clear Cretan Sea for a swim or simply stretch out on deck and enjoy being exactly where you are.
As afternoon turns to evening, watch the colors of the sky change over the water while Chania provides the backdrop to a very special beginning. And tonight, you’ll be spoiled. Our Welcome Dinner will be served on board, turning our first evening together into something far more memorable than dinner in a restaurant. We’ll dine on the water, toast the journey ahead, and watch the Cretan sky put on its evening show.
3 The Soul of Chania2027-10-03
Enjoy another relaxed morning before we set out to discover the Chania that exists beyond its beautiful postcard views.
With our private guide, we’ll wander through the atmospheric lanes of Chania’s Old Town and Venetian Harbour, where cobbled alleyways weave between Venetian mansions, historic churches, hidden courtyards, and beautifully preserved neighborhoods. Along the way, we’ll uncover the fascinating layers of civilizations and cultures that have left their mark on this remarkable city.
But today isn’t simply about Chania’s history. It’s about the people who keep its traditions alive. We’ll step inside the workshops and businesses of local artisans and family-run food producers, meeting some of the makers behind the products and flavors of Crete. There will be opportunities to taste, discover, ask questions, and experience a side of Chania that is much easier to appreciate when you’re not rushing through it.
We’ll pause along the way for lunch at a local restaurant, enjoying the flavors of Crete before continuing toward Chania’s magnificent Venetian Harbour. Historic waterfront buildings line the water as the Egyptian Lighthouse rises beyond them, creating one of the most recognizable and beautiful scenes in Crete. By early afternoon, we’ll make our way back to the hotel.
And the rest of the day? Completely yours. Return to your private pool. Find a shady table beside the harbor. Go back to that little shop you noticed earlier. Treat yourself to a spa appointment. Take a nap. Or simply enjoy the luxury of having absolutely nowhere else you need to be.
4 A Piece of Crete, Created by You2027-10-04
Today, we’ll trade sightseeing for something far more personal: creating our own piece of Crete. Overlooking Chania and the Cretan Sea, we’ll be welcomed into the creative world of a talented female mosaic artist for a private hands-on experience designed exclusively for our Sisters. We’ll divide into two intimate groups of approximately 12 women, giving everyone plenty of space, individual attention, and time to enjoy the creative process without feeling rushed.
Before we begin, our artist will introduce us to some of her remarkable larger mosaic works, including an ever-evolving project she has been creating over many years. Then it will be our turn. Using locally sourced Cretan stones, sand and gravel, along with colorful tiles, traditional tesserae, and a handcrafted ceramic element, each of us will design and create a completely personal mosaic. There is no need to be artistic and no masterpiece expected. This experience is about experimenting, creating, laughing, and seeing where a little inspiration takes you.
While one group spends approximately 3½ hours immersed in the workshop, the other will enjoy another beautiful side of Chania, including a visit to the Venizelos Graves and time for coffee and homemade Cretan sweets at a special location with sweeping panoramic views across Chania and the sea. Then we’ll switch, allowing every Sister to enjoy both experiences at an easy pace. At the end of the day, your finished mosaic will be carefully prepared for the journey home. Not something you bought in Crete. Something you created in Crete.
5 Through Her Lens: Your Private Portrait Experience2027-10-05
Today is yours to enjoy Chania almost entirely at your own pace, with one very special appointment reserved just for you.
At your designated time, an escort will meet you at our hotel and accompany you into the atmospheric surroundings of Chania Old Town, where a professional female photographer will be waiting for your private portrait session. For the next 15–20 minutes, you are the subject.
Using carefully chosen outdoor locations among Chania’s beautiful streets and historic architecture, she’ll create an elegant, editorial-style portrait that captures something far more meaningful than a vacation snapshot. And don’t worry about knowing what to do in front of the camera. You’ll be professionally guided throughout your session, from where to stand and where to look to those little adjustments that help you feel comfortable, confident, and completely yourself.
Following the trip, your photographer will carefully select and professionally edit your hero portrait, which you’ll receive both digitally and as a beautifully printed photograph.
Before and after your appointment, the day belongs entirely to you. Sleep late. Enjoy your private pool. Wander through Old Town. Have a leisurely lunch overlooking the harbor. Shop. Book a spa treatment. Find a café and watch Chania go by. Your portrait appointment is the only place you need to be. This evening, we’ll come back together for dinner at Almyvita Restaurant, sharing a beautiful meal after a day spent very much on our own terms.
Because sometimes the best souvenir from a journey isn’t a photograph of where you’ve been. It’s a photograph of who you were while you were there.
6 Chania, Entirely on Your Own2027-10-06
No alarm to set. No tour to meet. No place you need to be. Today, Chania is entirely yours.
Spend the morning beside your private pool or enjoying the resort. Wander back into Old Town and explore the streets you’ve come to know. Browse the boutiques, linger over lunch beside the Venetian Harbour, return to a favorite café, book a spa treatment, or do absolutely nothing without feeling as though you should be somewhere else.
After a full day to spend exactly as you please, we’ll come together this evening for a memorable Mediterranean dinner at Periplous Restaurant, set directly on the waterfront in Chania’s historic Tabakaria district. Once the heart of Chania’s leather-tanning industry, Tabakaria’s remarkable 19th-century stone buildings rise directly from the water. Tonight, one of those historic industrial spaces provides the setting for our dinner, beautifully reimagined as a contemporary restaurant where the architecture, sea, and cuisine all become part of this exclusive experience.
7 From History to Hands2027-10-07
Today takes us beyond Chania and into the Cretan countryside for a day filled with history, tradition, and the hands of the artisans who continue to preserve it. We’ll begin at the historic Sacred Monastery of Arkadi, one of Crete’s most important symbols of faith, freedom, and resilience. Surrounded by peaceful countryside, this centuries-old monastery holds a powerful place in the story of Crete and offers a fascinating glimpse into the island’s religious and cultural heritage.
From here, we’ll continue to the traditional village of Margarites, where pottery has been part of village life for generations. We’ll visit a local pottery workshop to discover how this ancient craft has evolved while remaining deeply connected to Cretan tradition. Surrounded by the work of local artisans, we’ll learn about the techniques, forms, and designs that have been passed from one generation to another.
And then we’ll get our hands in the clay. With guidance from the artisans, each Sister will have an opportunity to sit at the potter’s wheel and experience for herself the skill involved in transforming a simple piece of clay into a small vessel. There is no pressure to produce a masterpiece. Half the fun may be discovering that the potter makes it look considerably easier than it actually is. Before leaving Margarites, each Sister will receive a small handmade pottery piece to bring home, a beautiful reminder of the artisans and traditions we discovered today.
We’ll also slow down for one of the pleasures of being in Crete: lunch at a local taverna, where we’ll gather around the table and enjoy traditional Cretan food in the relaxed, unhurried way it was meant to be enjoyed.
8 Chania at Leisure2027-10-08
Today is completely yours.
There are no scheduled activities, no meeting times, and nowhere you need to be. Spend the day relaxing at the resort, wandering through Chania, or simply enjoying time with your Sisters however you choose. After all, sometimes the luxury is having absolutely nothing on the calendar.
9 A Private Evening at Manousakis Winery2027-10-09
There’s no need to hurry this morning. In fact, there’s nowhere you need to be until late afternoon. Later this afternoon, we’ll leave the coast behind and travel into the foothills of Crete’s Lefka Ori, or White Mountains, for a private evening at Manousakis Winery.
This family-run winery has a story rooted in Crete, family, and a dream of returning to the land. Our experience will be led by Alexandra Manousakis, bringing an especially meaningful connection to female leadership and the next generation of this Cretan family legacy. We’ll begin with a private introduction to the winery and its story before settling in to taste five Manousakis wines, accompanied by local Cretan delicacies, olive oil, and sea salt.
And we’ll stay for dinner. A beautifully presented Cretan dinner will showcase traditional dishes thoughtfully paired with the wines we’ve been discovering throughout the evening. For Sisters who don’t drink, an equally considered alcohol-free pairing will be offered so everyone can enjoy the complete experience. Good wine. Wonderful food. Family stories. A beautiful setting in the Cretan countryside. And absolutely no reason to rush home.
10 Private White Night Gala2027-10-10
Tonight is the night we’ve been waiting for.
After a leisurely day to enjoy Chania and our beautiful resort, we’ll dress in white and leave the coast behind for a very special evening created exclusively for our Sisterhood. Our destination is Metohi Istoria, a beautifully preserved 15th-century Venetian estate hidden in the peaceful Chania countryside, surrounded by olive trees, avocado groves, and Mediterranean gardens.
And for one night, it will belong entirely to us.
What awaits is our Farewell White Night, a private celebration of Crete, friendship, and the women who have shared this extraordinary journey. There will be cocktails beneath the Cretan sky. Candlelight and music. A beautiful dinner. A few surprises we’re keeping to ourselves.
And at the heart of the evening, our private portrait experience from earlier in the journey will come full circle in a way we hope you’ll never forget. As the evening unfolds, a private musical performance will provide the finale before the night gives way to dessert, music, laughter, and celebration.
As for what to wear? Something white. Flowing and fabulous if that’s your style. Simple and elegant if it isn’t. There are no fashion rules here. Wear whatever makes you feel comfortable, confident, and beautiful.
This isn’t simply our Farewell Dinner. It’s the finale this journey deserves.
11 Until We Meet Again2027-10-11
Enjoy one last breakfast overlooking the sea before it’s time to say goodbye to the place we’ve called home for the past ten nights. Private transfers will be arranged to Chania International Airport for your journey home. You’ll leave Crete with beautiful memories, new friendships, a few treasures you’ve created with your own hands, and perhaps a little more of Crete with you than you expected.
Where you'll stay
Sometimes the greatest luxury is finding somewhere extraordinary…and staying awhile.
Hotel Hilton Chania Old Town Resort & Spa
For our entire Crete escape, you’ll unpack just once at the new 5-star Hilton Chania Old Town Resort & Spa, a sophisticated waterfront retreat that gives us the best of both worlds: the amenities and indulgence of a luxury resort with the enchanting streets, restaurants, shops, and cafés of Chania’s historic Old Town just a five-minute walk away.
And we didn’t choose just any rooms.
Each Sister will retreat to a beautifully appointed Grand Deluxe Room with Sea View and Heated Private Pool, where contemporary Mediterranean design opens onto your own outdoor space overlooking the sea.* Step outside in the morning with your coffee, cool off in your heated private pool after a day of exploring, or simply sit quietly and watch the light change over the Cretan coastline. This isn’t simply where you’ll sleep. It’s part of the experience.
Beyond your room, the resort offers plenty of reasons to linger. Take in sweeping Aegean views from the heated rooftop infinity pool, indulge in a treatment at the L’Occitane en Provence Spa, relax in the indoor heated pool, wander through the rooftop botanical garden at sunset, or enjoy one of the hotel’s sophisticated restaurants, cafés, and lounges.
Best of all, you never have to choose between resort life and being in the heart of Chania. Step outside and the waterfront is at your doorstep, while the entrance to atmospheric Old Town is only minutes away. Wander its narrow lanes, discover a little restaurant for lunch, browse local boutiques, linger over coffee, or stroll the historic Venetian harbor whenever the mood strikes.
There are no suitcases to repack. No changing hotels every few nights. No constantly starting over somewhere new.
For ten glorious nights, this is home.
*Single occupancy rooms have direct sea views; Double occupancy rooms have side sea views.
Trip Inclusions
Everything that's already taken care of
- ✓10 nights/11 days luxury accommodations with balcony and private heated pool
- ✓17 meals (10 breakfasts, 2 Lunches, and 5 Dinners)
- ✓Roundtrip transfers between airport and hotels
- ✓Hotel porterage
- ✓Professional photography session on Chania streets including one professionally edited 12x16 professional portrait
- ✓Private White Night Gala
- ✓All sightseeing tours, exclusive experiences and excursions as listed within this itinerary
- ✓Deluxe, private transportation throughout the itinerary.
- ✓Private Tour Director
- ✓Sisterhood Travels Group Leader
- ✓Sisterhood Travels Swag
The Art of Staying Flexible
Pricing & Payments
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Deposits & Payment Schedule
Deposits and interim payments are non-refundable. Rates are guaranteed once your deposit is received and your reservation is confirmed.
Double Occupancy
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Book This TripKnow Before You Go
Activity Level: 3-Moderate
This luxury escape has been intentionally designed with a slower, more relaxed pace, including ten nights at one beautiful resort and several full or partial days at leisure. However, experiencing Chania and Crete still requires a moderate amount of walking. Travelers should be comfortable exploring pedestrianized historic areas on foot, navigating cobblestones and uneven surfaces, standing during guided visits, and walking between locations that cannot always be accessed directly by vehicle.
Walking & Standing
Chania's beautiful Old Town and Venetian Harbour are largely explored on foot. Expect extended periods of walking through narrow pedestrian lanes, cobbled streets, historic neighborhoods, artisan areas, and along the waterfront during our guided exploration of the city. Because much of Old Town is pedestrianized, vehicles cannot always provide door-to-door access. Additional walking should be expected when traveling between the hotel, restaurants, shops, photography locations, and other venues within the historic center. Your private portrait experience also takes place outdoors in Old Town, requiring a walk from the hotel area to the selected photography location and some standing and walking during the session.
Terrain & Transportation
Historic areas of Crete frequently feature cobblestones, stone paving, steps, curbs, uneven surfaces, and occasional inclines. Good balance and comfortable walking shoes are important. Our private sailing experience requires travelers to board and disembark the vessel. Those who choose to swim should be comfortable independently entering and exiting the water using the vessel's available access system. Swimming is entirely optional. Transportation outside Chania is provided by private vehicle or motor coach. Because vehicles cannot access many pedestrianized areas within Old Town, travelers should be prepared to walk reasonable distances between vehicle drop-off points and some attractions, restaurants, and experiences.
Pacing
Although this is an Activity Level 3 tour, the overall pace is intentionally relaxed. We stay at the same resort for all ten nights, eliminating hotel changes, repeated packing and unpacking, and long transfer days. Several mornings begin leisurely, multiple afternoons are free, and two days are almost entirely at leisure. The mosaic workshop, pottery experience, winery evening, private portrait session, and Farewell White Night are also designed to be enjoyed without rushing. This generous amount of downtime provides an important balance to the walking required during sightseeing days.
Overall Experience
There are no strenuous hikes, demanding physical activities, significant altitude concerns, or long touring days built into the itinerary. The single hotel stay and generous leisure time make the overall experience considerably more relaxed than many traditional European touring itineraries. However, travelers should not interpret the slower pace as a sedentary vacation. Chania is a wonderfully walkable city, and much of its charm lies within pedestrianized areas that simply cannot be experienced from a motor coach. To fully enjoy the included experiences and explore Old Town independently, travelers should be comfortable spending meaningful time on their feet.
Important Information
The details — please read carefully
⬇ Download Important Information (PDF)
Please Read This Information Carefully▾
There will be up to 24 Sisters on this tour, including your Sisterhood Travels Group Leader. Roommate matching is available.
Arrivals & Departures▾
- International airfare is not included in your pricing. You will fly roundtrip Chania (CHQ).
- You can arrive at any time on October 1, 2027, and you can depart at any time on October 11, 2027.
- Check-in time at our arrival hotel is at 3:00 pm.
- All international flight arrangements must be submitted to Sisterhood Travels on or before August 1, 2027. If you need help making flight arrangements, or to submit your independent flight arrangements, please click here for Airfare Information.
- Arrival transfers are provided only on October 1, 2027, from the Chania airport to our hotel. Departure transfers are only provided on October 11, 2027, from our hotel to the Chania airport. If you arrive or depart outside these days and times, or you’re needing transfers or hotels elsewhere, you are responsible for making your own arrangements at your own expense.
Entry Requirements▾
- Complete valid passport information is required on or before June 1, 2027. You are required to travel with a passport that is valid for a minimum of 6 months beyond the date of your return. If you fail to submit your complete and accurate information on time, we cannot guarantee your travel arrangements, and you will be responsible for any additional costs incurred.
- If you are traveling through the United Kingdom, an ETA will be required for entry, even as a transit passenger. Applications are accepted online, at the approximate cost of £10, subject to change based on governing authority. For more information please click here.
- You will be required to obtain an ETIAS tourist visa for travel within the European Union. This will become effective for all travel sometime in 2027. Applications are not yet available, but we will notify you when it is time to apply electronically. For more information please click here.
Gratuities, Travel Insurance & Optional Expenses▾
- Gratuities for your Tour Director, local guides, and drivers are not included in your pricing. We will provide you with tipping guidelines for your trip.
- Travel Insurance with Cancel for Any Reason coverage is strongly recommended and is not included in your pricing. We will send you a quote via email.
- Any optional expenses or expenses related to anything not specifically listed in this itinerary are not included.
- Please don’t schedule any optional excursions on your own for this trip as we cannot promise that you will arrive in time at any location to make your independent excursion. Sisterhood Travels won’t be liable for any expense you incur because of this.
- There are no refunds for unused portions of this tour.
General▾
- Dates and times of itinerary as well as hotels listed are subject to change without notice due to operational or logistical reasons.
- Rates are guaranteed once your deposit has been received and your reservation has been confirmed by Sisterhood Travels. Until trip departure, pricing may change, and any increases in government taxes or fees, mandatory fuel surcharges, or currency exchange rates may still apply.
- We cannot accommodate wheelchairs, assistive devices, scooters, walkers or rollators, or Zimmer-frames. You must be able to ambulate independently with no assistance from devices or others on the trip. It is imperative that you read the activity level description below.
- You will receive an invitation soon after you book your trip for our travel app, “Trip Plans”. You will need to download this app to your smart phone as this is where you will find the most up-to-date, accurate information regarding your itinerary in addition to all of the critical information you need to know.
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Reserve Your SpotCrete Luxury Escape for Women 2027
October 1 – 11, 2027
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