Grab Your Spot in Greece

Spring Retreat Dates - May 17th - 25th, 2026

Welcome to the magical island of Syros — where sisterhood meets the soul of Greece!

Nestled in the heart of the Aegean Sea near the famous islands of Mykonos, Paros, and Naxos, Syros offers a more authentic and soulful Greek experience. This vibrant Cycladic gem is where neoclassical charm meets island bliss, with boutique shops, elegant cafés, seaside tavernas, and sun-soaked beaches around every corner.

Join us this Spring for a journey that blends culture, connection, and community. Whether you’re here to unwind, explore, or rediscover yourself, Syros is the perfect place to slow down, connect deeply, and create memories that will last a lifetime.reflection, and connection.

Where You’ll Stay

Your home on the island is a stunning boutique escape overlooking the Aegean Sea. Each suite blends modern Cycladic style with luxurious comfort, creating a serene haven for rest and relaxation. Guests in the premium single occupancy package will enjoy elevated privacy, high-end amenities, and the peaceful elegance of a property crafted for slow living, sea breezes, and unforgettable sunsets.

If you decide to opt for the standard single occupancy package your stay on Syros features charming Cycladic rooms offering a cozy blend of rustic design and modern comfort. Guests in the standard single occupancy package will enjoy a simple yet comfortable accommodations,

What’s in store for you?

🏛️ Arrive in Style – Sail into Syros by ferry and step into the charm of Ermoupoli, where you’ll be whisked away to your boutique accommodations in the heart of the city.
🍷 Welcome Dinner & Drinks – Get to know your fellow travelers over a delicious Greek meal as you toast to the start of an incredible adventure.
🏝️ Beachside Bliss – Spend a sun-soaked day at a stylish beach club, complete with brunch and crystal-clear waters.
⛵ Sail to Delos – Step back in time on an exclusive boat charter to the mythical island of Delos, one of Greece’s most legendary archaeological sites.
🍽️ Greek Cooking – Learn the secrets of traditional Greek cuisine and bring the recipes back home with you!
🍷 Private Winery Tasting – Sip and savor the rich flavors of Greek wine at a private vineyard experience.
🌿 Retreat & Recharge – Midway through the trip, escape to a tranquil Syros retreat, where you’ll stay in chic bungalows with pool access, unwind with on-site massages & yoga.

This isn’t just a trip—it’s an experience of a lifetime, designed to inspire, connect, and rejuvenate your soul. 💫

City Escape + Countryside Retreat

During this retreat, you’ll spend five unforgettable nights in the heart of Ermoupoli — the vibrant capital of Syros — where you can soak in the island’s charm through boutique shops, authentic restaurants, and stunning sea views. From there, you’ll escape to the peaceful countryside for a rejuvenating stay in a quaint seaside village, surrounded by minimalist-chic bungalows designed for rest, reflection, and connection.

Get the Details:

  • ✨ Double Occupancy — $2,500 per person
    ✨ Single Standard Occupancy — $2,800 per person
    ✨ Single Premium Occupancy — $3,100 per person

    • 8 nights of accommodations

    • Arrival Transfers & Departure Transfers in Syros

    • Welcome Dinner Upon Arrival 

    • Select Meals*

    • Guided Walking Tour 

    • Private Cooking Class with Wine & Cheese Pairing 

    • Private Half Day Boat Charter

    • Private Guided Tour of Delos 

    • Entry fee to Delos

    • Private Yoga Session

    • Private Wine Tasting

    • Farewell Dinner 

    • Transfers to and from all scheduled activities 

    • Airfare

    • Travel insurance

    • Any optional excursions or activities not specified in the itinerary will be at your own expense

    • Any entrance fees to sites not explicitly mentioned in the itinerary

    • Meals and drinks not listed as included in the itinerary

    • Personal expenses such as souvenirs, laundry, or minibar charges

    • Tipping and gratuities for drivers, guides, hotel staff, and restaurant servers, which are at your discretion

  • Liability Waiver & Code of Conduct

    All attendees will be required to sign a Liability Waiver and Code of Conduct to ensure a safe, respectful, and inclusive experience for everyone throughout the retreat.

    Allergies & Dietary Restrictions

    You will have an opportunity to share any allergies or dietary needs in your participant intake form so our team and partners can best accommodate you.

    Room Assignments

    Double Occupancy rooms are reserved exclusively for guests traveling together—such as friends or family members. All other guests will enjoy their own private room and bathroom for the entire retreat. Please note that during our countryside stay, accommodations are bungalow-style and every room will have two twin beds (which can be made into one bed for single occupancy)

    Travel Health Insurance

    Travel Health Insurance is required for this retreat and must be purchased separately from standard travel insurance. This coverage protects you in the event of medical emergencies while abroad. Once registered, you will receive a welcome packet with recommended providers.

    Mobility Notice

    This retreat is open to participants ages 25 and up and involves light to moderate activity. Syros is known for its stairs, so guests should feel comfortable walking on inclined terrain.

    Trip Planning Assistance

    If you’d like help arranging additional activities, transfers, or extending your stay to explore more of Greece, our team is happy to assist. Please note that we are unable to book airfare.

    Questions

    For any additional questions, feel free to contact us at info@caracelestewest.com.

The Itinerary

  • Sunday, May 17th, 2025 - Arrival Day

    • Arrival to Syros (Ferry or Plane)

    • Taxi Transfer to Accommodations (included)*

    • Check In

    • Welcome Dinner & Drinks (included)

  • Monday, May 18th, 2025 - Getting to Know Syros

    • Brunch

    • Walking Tour & Swim (included)

    • Community Lunch (included)

    • Optional Pottery Class

  • Tuesday, May 19th, 2025 - Enjoy the Flavors of Greece

    • Half - Day Cooking Class & Lunch with Wine & Cheese Pairing (included)

    • Sunset Dinner at Kini Beach (transfers included)

  • Wednesday, May 20th, 2025 -

    • Brunch & Shopping in Ano Syros

    • Community Dinner

  • Thursday, May 21st, 2025 -

    • Half day Boat Charter to Delos & Rheina with private tour guide (included)

    • Ladies Night Out

  • Friday, May 22nd, 2025 - A Cycladic Experience

    • Transfer to Anassa Cycladic Village (included)

    • Hiking & Beach Time

    • A Cycladic Experience (included)

  • Saturday, May 23rd, 2025 - Yoga & Spa Day

    • Breakfast on site (included)

    • Morning Yoga Session (included)

    • Lunch (included)

    • Pool Time & Relaxation

    • Massages (optional)

    • Dinner (included)

  • Sunday, May 24th, 2025 - A Final Farewell

    • Breakfast on site (included)

    • Lunch on site (included)

    • Wine Tasting & Tour

    • Farewell Dinner (included)

  • Monday, May 25th, 2025 - Departure Day

    • Breakfast on site (included)

    • Departure Transfer (included)

🚀 Ready to make it happen? Secure your spot with 20% deposit & get a 10% discount when you book your spot by November 20th, 2025 using CODE (SYROS).

Double Occupancy

Stay in the heart of the city in a beautifully designed two-story suite featuring your own kitchen and plenty of space to relax and unwind (please note this option is for those traveling with a friend or family member).
Package Cost: $2500 per person — SOLD OUT!

Book It

Single Standard Occupancy

Stay in a cozy hotel within a quick walk to the city center with breakfast served daily with all the amenities you need for a comfortable stay in Ermoupoli.
Package Cost: $2800 per person — only 4 spots left! ✨

Book it

Premium Standard Occupancy

Enjoy spacious accommodations near the town center, just a short walk from Syros’ charming shops, cafés, and seaside views. Experience the perfect blend of comfort and convenience in the heart of the island.
Package Cost: $3,100 per person — 1 spots left! ✨

Book it

Executive Single Occupancy

Enjoy premium accommodations in the heart of the city along with your own private pool and sea views.

Package Cost: $3,300 per person — 2 spots left! ✨

Book it

Cancellation Policy: You may cancel your stay with 100 % refund by February 1st, 2026. After this date your payments are non-refundable.

Terms & Conditions:

Your selected accommodation package covers the first five nights of your stay in the city of Syros. Following this, the group will transfer to the countryside retreat, where all attendees will enjoy the same charming bungalow accommodations for the final three nights of the trip.

Syros is a stunning island known for its hillside views and charming cobblestone streets — but that also means there are plenty of stairs! Some accommodations may require stair access to reach your room. I recommend keeping your mobility and comfort in mind when considering this destination.

Please note the itinerary is subject to change based on weather conditions and vendor availability.

Questions About the Trip: You can reach out via email at info@caracelestewest.com and my team can help to answer any questions you have about the trip before you commit.

Digital Nomad Babes & Beyond Alumni Reviews:

On the fence about joining us this fall? See what other Digital Nomad Babes & Beyond Alumni have to say about previous trips:

“Everything about this retreat was very well planned, thoughtful, fun, and clear with expectations. Cara did a phenomenal job with timely arrangements and accommodations prior and during the trip. Had an amazing time. Can’t wait for 2026.” - Natalie

“This was more than a trip, so much more than another passport stamp....it was deeply spiritual. The hostess Cara and her assistant Chenyeri set a beautiful tone. She is relatable and accommodating. I think all of the ladies in attendance will agree that a bond was formed....we connected, we empowered each other, we were pampered, we were awakened....such a magical experience!” - Joan

“Cara planned an outstanding trip for our group! She paid attention to detail, was organized and thoughtful, and she was extremely attentive to our needs during the duration of our stay. She added activities we requested and handled everything so that we could simple enjoy being in the moment with each other! The videos and the poem were thoughtful additions to our incredible experience with Cara!” - Misty

Your Retreat Host:

Cara Celeste West

With over a decade of professional experience in the travel and hospitality industry working with VIP clients—including roles at HomeAway and TurnKey Vacation Rentals—I bring expert planning, seamless organization, and a deep understanding of what makes a trip truly unforgettable. These retreats are designed so you don’t have to lift a finger: every detail is thoughtfully arranged for you from start to finish, including boutique accommodations, airport transfers, curated activities, and unique local experiences. All you have to do is arrive, exhale, and enjoy.