Sicily, Italy
Beyond the Postcard
September 15-24, 2027
About Our Sicily, Italy Tour
This Sicily journey is for women who want to go deeper, beyond famous sights and into the rhythms of daily life that make this island so unforgettable. Sicily is layered, expressive, and deeply human, shaped by centuries of conquest, creativity, resilience, and ritual. Here, history is not locked behind glass; it lives in kitchens, workshops, village squares, and conversations shared over food.
Over ten beautifully paced days, we move from Palermo’s raw energy to quiet mountain villages, from ancient temples and Norman cathedrals to working farms, family kitchens, and artisan studios. We meet people who carry traditions forward with pride - basket makers, bakers, potters, winemakers, farmers, and storytellers - and we’re welcomed not as spectators, but as guests.
Traveling in a small, women-only group allows this experience to feel relaxed and personal. There is time to linger, to ask questions, to laugh, to absorb details, and to enjoy Sicily without feeling rushed or overwhelmed. This is not about checking boxes - it’s about savoring place, culture, and connection.
If you love trips that feel rich, textured, and deeply memorable, where beauty comes from authenticity rather than polish, this Sicily journey offers something truly special.
Daily Itinerary
Welcome to Sicily! Upon arrival, you’ll be met at the airport and transferred to our hotel near Palermo’s city center. After settling in and resting from your journey, we gather in the evening for a relaxed tour orientation followed by our first shared dinner.
Over classic Sicilian dishes, we begin getting to know one another - setting the tone for a journey shaped by curiosity, warmth, and shared discovery.
We begin the day with a gentle walking tour through Palermo’s historic heart, starting at the Cathedral, a striking blend of Norman, Gothic, and Baroque elements that tells the story of how many cultures have shaped this city. From there, we move to Quattro Canti, the elegant crossroads that anchors Palermo’s old town, alive with movement and conversation.
We then step into one of Palermo’s oldest markets, where the city’s energy is unmistakable. Fishmongers call out, produce stalls overflow, and street-food vendors fry and assemble beloved local specialties. Here, we sample traditional bites such as arancini and pani ca meusa, learning why these foods are woven into everyday Sicilian identity.
In the afternoon, we drive to the countryside near Segesta, arriving at a family-run baglio. Welcomed into the kitchen, we take part in a hands-on cooking class, learning regional recipes and techniques directly from our hosts. The day ends gathered around the table, enjoying the meal we’ve prepared together before returning to Palermo.
This morning we head up to Monreale, where we visit its magnificent 12th-century cathedral. Inside, golden Byzantine mosaics glow softly, covering the walls with vivid biblical scenes that invite you to slow down and take them in.
From here, we continue along the coast to Cefalù, a town that feels effortlessly lived-in. Walking through its historic center, we pass fishermen’s houses, laundry-lined balconies, and small shops selling ceramics and sweets. We visit Cefalù Cathedral, then enjoy free time for lunch and wandering through its medieval streets and open piazzas.
In the afternoon, we turn inland toward the Madonie Mountains and on to Castelbuono, a centuries-old town of stone lanes and low traditional houses. We'll soon arrive at our local farm stay, where we'll first learn about manna. This naturally sweet sap is harvested from ash trees and we'll walk through the orchards to see how it’s collected and used in Sicilian cuisine, all before enjoying a tasting.
We then settle in for the night at our comfortable farm stay, while surrounded by mountain quiet.
This day brings us into Sicily’s agricultural and historical layers. We visit a working olive farm where active archaeological excavations sit beside living groves. Walking the site, we see the remains of an ancient olive mill before learning how oil is produced today.
A guided tasting introduces the nuances of Sicilian olive oil, followed by lunch prepared with ingredients grown right on the estate - simple, seasonal, and deeply connected to place.
In the afternoon, we explore two mountain villages, Petralia Sottana and Petralia Soprana. Wandering their narrow streets and main squares offers a quiet glimpse into daily life far from the tourist trail. We return to our farm stay for dinner and another peaceful evening in the countryside.
This morning we head to Isnello for a hands-on basket-making experience. Local artisans welcome us into their workshop to demonstrate how panari baskets are crafted using techniques passed down through generations. With their guidance, we try the process ourselves and learn why these baskets still matter in everyday village life.
Afterward, our hosts prepare an abundant aperitif-style lunch featuring breads, cheeses, cured meats, olives, and seasonal specialties.
In the afternoon, we'll take a guided walk through town, including a stop at a well-known pastry shop to taste a local sweet before finishing the day at a nearby wine producer for a tasting of Sicilian varieties and regional products. We then return to the farm stay for the night.
Leaving the Madonie behind, we drive toward Taormina, stopping first in Forza d’Agrò — a small village that feels like an open-air museum. Stone lanes, historic churches, and sweeping coastal views offer a vivid sense of Sicily’s past, and film lovers may recognize locations used in Il Padrino.
After a relaxed fish lunch at a local trattoria, we continue to Taormina. A guided walk introduces us to its historic center, lively streets, and panoramic viewpoints overlooking Mount Etna and the Ionian Sea. There’s time to wander, shop, or enjoy a coffee before we continue on to Catania, stopping briefly in the hilltop village of Castelmola for views and atmosphere.
We arrive in Catania in the evening, check in, and take an initial walk through the city with our tour leader.
Today we explore one of Sicily’s most dramatic landscapes: Mount Etna. Traveling by 4×4 with an expert guide, we move off-road through lava fields while learning how centuries of eruptions have shaped the land.
We take a short, easy walk to explore side craters and have the option to step inside a lava cave - a fascinating look at the volcano’s inner workings. On Etna’s lower slopes, we visit a top winery, learning how volcanic soil and elevation influence grape varieties and wine styles. A guided tasting paired with lunch rounds out the experience before we return to Catania for a free afternoon.
Today is rich with food traditions. In Palazzolo Acreide, we meet a family of bakers who show us how they prepare breads, pizzoli, focaccia, and cookies using methods passed down through generations - with plenty of tasting along the way.
We then visit a butcher shop to learn about the town’s traditional sausage, a Slow Food product still made using historic techniques. Lunch is a relaxed tasting of local specialties, including charcuterie and cheese.
In the afternoon, we drive to Syracuse and check in at our hotel before enjoying a walk through Ortigia - the city’s historic island - with its sea views, baroque squares, and narrow lanes. The evening is free for dinner at one of the many nearby restaurants.
This morning we take part in a hands-on Sicilian puppet workshop focused on the Opera dei Pupi, a traditional puppet theater recognized by UNESCO. Guided by a master artisan, we paint wooden figures and engrave metal armor, creating our own handcrafted puppets while learning about the stories and symbolism behind them.
The afternoon is free to enjoy Syracuse as you wish, visiting the archaeological park, exploring Ortigia’s markets and streets, or spending time by the sea. In the evening, we gather for our farewell dinner, sharing one last meal together and reflecting on our journey across this most memorable Italian island.
We have one group transfer to Catania Airport today, suitable for flights scheduled for noon or later. For those extending their stay, a transfer to the city center can be arranged.
What's Included
- Small group tour (maximum 12 women)
- Professional tour leader
- Local, English-speaking tour guides throughout the trip
- Accommodations (9 nights in 3*/4* hotels and a farmstay)
- Breakfast every day, 6 lunches, 6 dinners
- Transportation within Sicily (private air-conditioned vans/mini-bus)
- All mentioned activities and entrance fees
- Private arrival airport transfers
- One group departure transfer to Catania Airport
What's Not Included
- Flights to/from Italy
- Passport/visa fees (US, Canadian and European citizens do not need a visa)
- Travel Insurance (required)
- Meals and activities not mentioned in the itinerary
- Gratuities
Accommodations
We will stay in 3 and 4 hotels during this trip, as well as a wonderful family-run farmstay. You may book a single room or a spot in a shared room with two separate beds, which will be shared with another woman in the group. All rooms have a private bathroom.
Physical Demand
This tour requires a certain level of physical activity. Please note that the trip can involve the following: long days, walking tours of up to 2 hours at a time in uneven terrain, being outside in potentially diverse temperatures, a few long drives, early morning wake-ups and other similar scenarios.
Travel Information
Arrival Airport
Palermo Airport (PMO)
Departure Airport
Vincenzo Bellini Catania Airport (CTA)
Payment Terms
Deposit: Refundable for 10 days (minus 3% transaction fee)
Balance: Due 90 days prior to tour start date / Payment options include credit card (+3% fee), Zelle and check
Cancellations/Refunds: Cancellations made 90-60 days prior to start date receive a 50% refund of the balance only (minus 3% transaction fee) / No refunds for cancellations made within 60 days of the tour start date
This Sicily, Italy tour is operated by Women's Travel Circle, a trusted partner of Women Travel Tribe since 2023.
Tour Details
Pricing (USD)
Frequently Asked Questions
Explore the answers guests ask most often about Women Travel Tribe and this.
About Our Community
What is Women Travel Tribe?
Women Travel Tribe offers small-group tours designed exclusively for women 50+. With thoughtful itineraries and trusted partners, we bring you unforgettable travel experiences in remarkable places — and an incredible group of women to share them with!
We are also a global community for curious women aged 50+ who love exploring the world with kindred spirits. Since 2019 we have nurtured an active Facebook group and newsletter where members trade tips, share stories, and cheer one another on.
Is Women Travel Tribe a tour operator?
We work in partnership with a handful of carefully chosen, professional, small-group tour operators.
We created this Sicily, Italy trip alongside Women's Travel Circle, partners we have trusted since 2023. They operate the tour day-to-day; we focus on our community care and making sure every detail feels right for you.
All of the tour operators we work with must uphold the same high standards of service and integrity that we hold dear. Cultivating these relationships, developing a level of trust, and planning extraordinary, culturally immersive itineraries allows us to offer our members a kind of tour that you cannot find anywhere else!
Do I have to be exactly 50 (or well over)?
We welcome all women aged 50 and over. Whether this is your first small-group adventure or your tenth, you will find encouragement, camaraderie, and plenty of shared laughs.
Tour Basics
How many women are in each group?
We keep this journey intimate with 8–12 travelers, the sweet spot for connection and shared experiences.
Are flights included?
International airfare is not included in the tour price. Many travelers prefer to choose their own flights using points or preferred airlines.
Plan to arrive into Palermo Airport (PMO) and depart from Vincenzo Bellini Catania Airport (CTA). After booking we will send recommended flight windows and transfer details.
Do you accommodate dietary restrictions or allergies?
Yes. Once you reserve, the operator will ask about food preferences, allergies, and medical considerations so meals can be planned with you in mind.
Some destinations have limited options for specific diets, yet we will always advocate for you and offer suggestions before you depart.
Do I need to be physically fit? What activity level should I expect?
This itinerary is rated Moderate-High and spans 10 days.
This tour requires a certain level of physical activity. Please note that the trip can involve the following: long days, walking tours of up to 2 hours at a time in uneven terrain, being outside in potentially diverse temperatures, a few long drives, early morning wake-ups and other similar scenarios.
I usually travel solo. Will I fit in?
Absolutely. Many guests join our tours solo and quickly feel at home thanks to the supportive, women-centered group dynamic.
Booking & Payments
How do I reserve my spot? Is there a deposit?
Secure your place with a $1,000 deposit using the booking button on this page.
You can complete your reservation in just a few minutes through our secure checkout.
The Payment Terms section above covers cancellation windows and other important payment details for this departure.
Do all trips have guaranteed departures?
Each tour requires a minimum of 8 travelers before we confirm the trip. Once the minimum is reached, you will receive an email letting you know that you can now purchase flights. If the minimum is not met, deposits are refunded in full. We stay in close contact so you always know where things stand.
Safety & Health
Do I need travel insurance?
Yes. Comprehensive travel insurance that covers both trip costs and health needs is required for every Women Travel Tribe departure.
After you book we will recommend trusted providers and outline when coverage should begin.
What happens if I get sick during a trip?
Your tour leader and local partners are on call around the clock. They will coordinate care, help with logistics, and keep the group informed while you focus on feeling better.
How do you handle mobility concerns or medical equipment?
Review the Physical Demand section above for specifics on walking distances, terrain, and accessibility considerations.
If you travel with mobility aids or medical equipment, let us know after booking. We will collaborate with the operator to confirm how they can be accommodated on this itinerary.
Preparing for the Trip
How do I prepare for a trip?
Once your reservation is confirmed, you will receive a comprehensive pre-departure packet covering visas, packing tips, currency, adapters, and cultural insights tailored to this tour.
We stay in touch through reminders and checklists so you feel ready from the moment you book.
During the Trip
Who will be my tour leader?
We provide a seasoned tour leader who travels with the group throughout the itinerary, keeping everything running smoothly and joyfully.
Is there free time on Women Travel Tribe tours?
Yes. Every itinerary includes unstructured windows so you can relax, shop, journal, or explore at your own pace. Optional activities are offered, but never required.
Changes & Cancellations
What is your cancellation policy?
The Payment Terms section above outlines deadlines and cancellation timelines for this departure. Please review them carefully before booking.
Can I transfer my booking to another woman or a later date?
Transfers depend on timing, availability, and the operator's policies. Reach out to us or the operator as soon as possible and we will explore every option with you.
Still have questions?
Our team is happy to help. Choose the option below that's right for you and we'll get back to you shortly.
Ask about this tour
Have a specific question about this tour's itinerary, pricing, or details? Send us a message and we'll get back to you quickly.
You can also text or call us at (646) 481-6284
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