Elements of Sicily October 2027 | Women's Small Group Trip to Eastern Sicily

The Experience

This Is Your Sign to Book

If you have been considering joining us for Elements of Sicily October 2027, this is your sign to book your place.

This is not a rushed coach tour or a wellness retreat full of forced activities. It is a thoughtfully hosted journey through eastern Sicily. It is designed for women who want beautiful days, memorable experiences and the ease of travelling with a small like-minded group.

Come solo or bring a friend, either way, you will leave with a new circle of women who love to explore, eat well, and savour the moment.

Sicily coastal view with turquoise waters

What Awaits

Trip Highlights

Nine days of curated experiences across Sicily's most captivating eastern destinations.

Ortigia & Syracuse

My home for 7 years and a place I know intimately. Think boat trips to hidden sea caves, long Italian lunches, evening aperitivos as the sun melts into the sea, fresh food markets, winding alleyways, cobbled streets, boutiques, baroque cathedrals and slow evenings by the water.

Mount Etna

Experience Europe's highest active volcano up close. We will explore the lunar-like landscapes, walk ancient lava flows, and enjoy a lunch on the volcano's slopes with local wines and Sicilian flavours.

Taormina

The pearl of the Mediterranean. Stroll the elegant Corso Umberto, visit the ancient Greek Theatre with its breathtaking views of Etna and the sea, and soak up the glamorous atmosphere of this hilltop town.

Noto & the Baroque

Wander through the golden stone streets of Noto, one of Sicily's most beautiful baroque towns. Admire the ornate facades, enjoy a gelato in the piazza, and experience the warm, welcoming energy of the Val di Noto.

The Destinations

Where We Are Going

Eastern Sicily's most enchanting locations, each offering its own unique magic.

Ortigia, Syracuse

Fresh food markets and local artisans
Boat trips to hidden sea caves
Baroque cathedrals and historic piazzas
Sunset aperitivos by the water
Winding alleyways and boutique shopping

Adventure

Mount Etna

Europe's highest active volcano is a landscape like no other. We will explore the otherworldly terrain of ancient lava flows, craters, and volcanic rock formations. The views from the slopes are nothing short of spectacular.

Guided exploration of volcanic landscapes
Panoramic views across eastern Sicily
Learn about the volcano's geology and history
Photo opportunities at every turn

Culture

Taormina

The pearl of the Ionian Sea, Taormina is Sicily's most elegant town. Perched on a cliff with views of Mount Etna and the sea, it offers a perfect blend of ancient history, charming streets, and beautiful beaches.

Ancient Greek Theatre with Etna views
Stroll along elegant Corso Umberto
Relax at Isola Bella nature reserve
Charming piazzas and gardens
Stunning coastal vistas

Heritage

Noto & Val di Noto

The golden city of Noto is the crown jewel of Sicilian Baroque. Rebuilt after an earthquake in the 18th century, its honey-coloured limestone buildings glow in the afternoon sun, creating one of Italy's most beautiful streetscapes.

UNESCO World Heritage Baroque architecture
Charming piazzas and ornate churches
Famous Noto cannoli and gelato
Scenic drives through the Val di Noto
Golden hour photography walks

The Journey

The journey

Element: Fire

Fire — Mount Etna & Taormina (3 nights)

We begin beneath Europe's most active volcano, one of Sicily's defining forces.

Our first stop is Taormina, a place many will recognise from the TV show White Lotus. We'll have time to explore its elegant streets, ancient theatre and sweeping coastal views.

A guided hike on Mount Etna brings you face to face with Sicily's raw power: Europe's most active volcano, a unique landscape, lava tunnels, volcanic soil and lunch in the forest.

Evenings are unhurried — long dinners, good wine, and that first deep exhale of being somewhere new.

Element: Sea & Sun

Sea & sun — Ortigia & Siracusa (3 nights)

A UNESCO World Heritage Site and a place close to my heart, Ortigia was my home for seven years. What still fascinates me is how it exists in the shadow of its own history, surrounded by the sea, welcoming travellers while local life carries on largely unchanged.

It's a place of contrasts: beautiful and messy, old and new, bohemian and traditional — all existing comfortably side by side. I love this tiny island, and I'm confident you will too.

Highlights include:

✦A tuk-tuk tour
✦Neapolis Archaeological Park, Greek Theatre, Roman Amphitheatre, Ear of Dionysius
✦Catacombs of San Giovanni
✦Boat trip around the island and out to the sea caves
✦Sunset aperitivo overlooking the sea
✦Time to explore markets, cathedrals, piazzas and the marina

This part of the journey blends history, daily life and the sea — the Ortigia I know and a glimpse into local Sicilian life.

Element: Earth

Earth — Noto countryside & olives (2 nights)

The final days take us inland, to the quieter south-eastern countryside. Travelling in October allows us to experience the olive harvest, a short, once-a-year period that is an integral part of the calendar.

Here, the focus shifts to the land: agriculture, the zero-kilometre food movement, and the olives that produce some of the world's finest olive oil.

Highlights include:

✦Time among olive groves near Noto
✦A guided olive oil tasting — learn what makes Sicilian oil distinctive
✦Long lunches built around local ingredients and seasonal cooking
✦Time to slow the pace before departure, without switching off completely

This is Sicily at its most grounded — agricultural, tradition-led, and deeply tied to the land.

What's Included

Everything you need for a genuine Sicilian tour

Nothing you don't.

Women enjoying a walking tour in Ortigia Sicily

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8 nights in boutique hotels Comfortable private accommodation throughout

☕

Daily breakfast Start every morning fuelled and ready

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1 aperitivo Sunset drinks and connection

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Traditional lunch after Etna hike Hearty Sicilian meal after the volcano

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Guided olive oil tasting Taste local liquid gold with an expert

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Archaeological Park of Neapolis Explore ancient Syracuse treasures

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Visit Noto Discover the Baroque gem of the south

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Experienced local driver Relax while we handle the roads

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Small group — max 12 women Intimate, supportive atmosphere

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Private room — no single supplement Your own space, no extra charge

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Welcome & farewell dinners Celebrate the start and end together

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Guided Mount Etna hike Walk Europe's most active volcano

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Private boat trip from Ortigia Crystal waters and coastal views

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Greek theatre entrances Step into ancient history

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Visit Ortigia Island Charming historic heart of Syracuse

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Private transport throughout Seamless transfers and day trips

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Hosted throughout by Chloe Guidance, care and local insight

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Pre-departure info pack Everything you need before you arrive

Find Your Fit

Is This Trip For You?

An honest look at who this journey is designed for.

Perfect Match You'll love this trip

You like seeing and doing things, not just skimming highlights
You appreciate good organisation and thoughtful pacing
You enjoy learning about a place through its landscape, history, food and daily life
You want the confidence of travelling with someone who knows Sicily from the inside out

Not the Best Fit This may not suit you

You're looking for a slow, wellness-focused retreat
You prefer lots of unstructured free time
You're travelling mainly for luxury or downtime

Elements of Sicily is designed for women who are curious, capable, have a sense of adventure and enjoy experiencing a place fully.

Pricing & Booking

Transparent pricing with flexible payment options.

£ 3,200 per person

Early booking rate: £2,900 — limited places

Early rate places are limited and confirmed on receipt of deposit.

Payment Structure

Spread the cost across three simple payments

Step 1

£800

Deposit to secure your place

Due at booking

Step 2

£1,200

First instalment

Due on April 1, 2027

Step 3

£1,200

Second instalment

Due on July 1, 2027

ALTERNATIVE PAYMENT PLANS ARE AVAILABLE. Alternatively, pay in full at booking and receive a 3% reduction on the total price. Must be selected at booking — cannot be applied retrospectively.

Payment Methods

Choose what works best for you

Card Payment Via Stripe — secure & instant

UK Bank Transfer Available on request

International Transfer Handled securely via Wise

Once you're ready to proceed, get in touch and we'll arrange the most convenient payment for you. An invoice and booking confirmation will be issued on receipt of payment.

Your Host

Meet Chloe

Hi, I am Chloe, the founder of Chloe Keeps Travelling and your host for this journey. Sicily has been my home for the past 7 years, and I have fallen deeply in love with this island's beauty, culture, and people.

I created Elements of Sicily because I believe travel is about more than ticking off sights, it is about connection, curiosity, and creating space for wonder. I have curated every detail of this trip to give you an authentic, joyful, and deeply personal experience of the Sicily I know and love.

Whether you are travelling solo or with a friend, you will be welcomed into a small group of like-minded women who share your love of adventure, good food, and beautiful moments.

Stories

What Past Travellers Say

Real words from women who have experienced Elements of Sicily.

"I loved it all. The place, the ladies and most of all the energy you brought to it all. Always smiling and nothing was too much trouble. I felt like I could breathe again."

Julie, UK

"Chloe created such a thoughtful and grounding experience for our time in Ortigia. She has a natural ability to make everyone feel comfortable and taken care of while still giving us space to explore. Everything felt intentional from the pacing of the days to the overall atmosphere she created. I left feeling reset, inspired and really grateful for the experience. I would absolutely recommend a retreat with her."

Jane, USA.

"Thank you for being such a great host. You made everything so fun and enjoyable. I am truly happy to have met you."

Meggy, USA

Questions

Frequently Asked Questions

Everything you need to know before booking your spot.

What is the group size?

We keep our groups intentionally small, maximum 12 women. This allows us to stay in boutique accommodations, get to know each other properly, and have a more intimate, personalised experience.

Are flights included?

Flights to and from Catania (CTA) are not included. This gives you flexibility to use points, fly from your preferred airport, or extend your trip. We will provide guidance on the best flight options once you book.

What is the fitness level required?

This trip is suitable for women with a moderate fitness level. We do a fair amount of walking on cobblestones and some uneven terrain (especially on Mount Etna). Everything is at a relaxed pace with plenty of breaks. If you have any concerns, please reach out and we can chat.

What should I pack?

Once you book, we will send you a detailed packing list. In general: comfortable walking shoes, layers for October weather (warm days, cooler evenings), a swimsuit for boat trips, and something nice for our welcome and farewell dinners. Sicily in October is beautiful and mild.

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