Small Group · Sicily

The Soul of Sicily® An Intimate 10 Day Journey Through Sicily

10 Days Sicily

The Journey

Ten days, two coasts, and never more than ten guests.

Sicily has been conquered, rebuilt and loved by Greeks, Romans, Arabs, Normans and Spaniards, and every one of them left something behind. A temple inside a cathedral. A market that still sounds like North Africa. A pastry recipe that nuns kept to themselves for centuries.

The Soul of Sicily® was built for travellers who want to feel all of that without spending their holiday in a coach. Small numbers, local guides who live here, and enough time between the highlights to sit down, order another coffee and watch the island go about its day.

The Overview

Overview

Most visitors see Sicily in a hurry: a morning in Taormina, a photo at Mount Etna, then back on the road. This journey was built the other way around. The Soul of Sicily® is an intimate 10-day small group tour of Sicily for no more than 10 guests, with private local guides, 4-star boutique hotels and just two bases, so you unpack once on the east coast, once on the west, and spend your time living the island rather than chasing it.

You begin in Ortigia, the ancient heart of Syracuse, where a Baroque cathedral is built around the columns of a Greek temple and the sea is never more than a few streets away. A morning boat ride takes you past sea caves for a swim in clear water, and in the afternoon your local guide, Carlo, walks you through centuries of history in the old town. From here you explore the UNESCO Baroque towns of Modica, famous for its chocolate, and Noto, then spend a full day on Mount Etna, walking the Silvestri Craters before a tasting of volcanic wines and a light lunch at an Etna winery. The day ends in Taormina at the ancient Greek Theatre, with the sea on one side and the volcano on the other.

Crossing to the west, you stop at the Valley of the Temples in Agrigento, home to some of the best preserved Greek monuments in the world, before settling into Castellammare del Golfo. The west feels different, wilder and more rugged. A catamaran carries you along the Riserva dello Zingaro to swim in turquoise coves. In Palermo, a local guide leads you through the Capo and Ballarò markets for panelle, arancine and fresh cannoli, then into the convent bakery of Santa Caterina for pastries made from recipes the nuns kept to themselves for generations. On the way back, you wander the colourful artisan lanes of Borgo Parrini.

Some of the best moments are the simplest. Lunch at a family-run winery, where you see how the wine is made and finish by filling your own cannoli. The medieval hilltop village of Erice, and at the right time of year, sunset over the Egadi Islands. A slow day at your hotel with the wellness path included. Then a farewell dinner together, the kind of evening where the strangers you met on day one feel like old friends.

Airport transfers, drivers, three group dinners, two wine tastings and two boat excursions are all arranged for you. What is left is the part that matters: good food, good company, and the chance to see Sicily the way the people who live here do.

Duration

10 days

9 nights

Pricing

On request

Tailored to your dates and group.

Discover Sicily on an intimate 10-day adventure combining UNESCO heritage, coastal beauty, exceptional food and wine, and authentic local experiences. From Ortigia and Noto to Mount Etna, Taormina, Palermo and Erice, enjoy private guides, leisurely boat excursions, family-run wineries, elegant accommodations and carefully chosen experiences with a maximum of 10 guests.

Regions
Sicily
Tour Style
Small Group
Departs From
Sicily
Included Meals
Daily breakfast · 3 dinners · 2 wine tastings · 2 lunches · 1 cooking class
Day by day

Itinerary

Follow the route as you read. The map traces each day of the journey, moving with you from place to place.

Sicily

Chapter 1 · Days 1–10

Welcome to Sicily

Italy’s historic and cultural diversity is perfectly expressed in Sicily, an island rich in history and overflowing with scenic beauty. A visit to Taormina, 200 meters above sea level and looking down onto the Ionian Sea like a terrace, will deliver a calm to the soul, a must see while visiting this island.   From the breathtaking beauty and vantage point…

Explore Sicily
Day 1

Sicily, Siracusa

Arrive in Sicily & Welcome to Ortigia

  • Dinner
Arrive in Sicily & Welcome to Ortigia — photo 1 Arrive in Sicily & Welcome to Ortigia — photo 2 Arrive in Sicily & Welcome to Ortigia — photo 3 Arrive in Sicily & Welcome to Ortigia — photo 4 Arrive in Sicily & Welcome to Ortigia — photo 5

Arrive at Catania Airport, where your private driver will meet you for a comfortable transfer to the enchanting island of Ortigia, the historic heart of Syracuse. Settle into your hotel and enjoy some time to relax and begin discovering your surroundings at your own pace.

This evening, come together with your fellow travellers for your first taste of Sicily. Enjoy a welcome dinner at a lovely local restaurant, where you can settle into the relaxed rhythm of island life and get to know the group.

Where we collect you At your hotel
Day 2

Sicily, Siracusa

Deep-dive into the Island of Ortigia

  • Breakfast
Deep-dive into the Island of Ortigia — photo 1 Deep-dive into the Island of Ortigia — photo 2 Deep-dive into the Island of Ortigia — photo 3 Deep-dive into the Island of Ortigia — photo 4 Deep-dive into the Island of Ortigia — photo 5

Start your morning with a relaxed 2-hour boat ride around the Island of Ortigia with a personal local skipper! Enjoy a swim, admire the Sea caves, and the protected Marine zone of Plemmirio!    Ending at roughly 1230, take this time at leisure to browse the nearby market and have lunch. Once rested and recharged, you will meet your Private local guide, Carlo, in the afternoon for an enchanting walking tour together!    Step into a living museum on an exclusive 2.5-hour private walking tour of Ortigia, the sun-drenched ancient heart of Syracuse. Guided by a passionate local expert, you will trace the footsteps of the legendary genius Archimedes, discovering how his brilliant engineering shaped this vital Mediterranean stronghold.   Explore the fascinating layers of the original Greek and Roman city layout, where grand classical colonnades still stand beneath elegant Baroque facades. The highlight of your VIP journey is the breathtaking Piazza Duomo, where you will step inside the magnificent Cathedral - a stunning masterpiece uniquely built directly into the towering stone pillars of an ancient Greek Temple of Athena. Blending brilliant history, timeless mythology, and insider tips on the island's best seaside dining, this perfectly paced tour offers an intimate look at the true jewel of Sicily.  

Day 3

Sicily, Modica Sicily, Noto

Modica & the Baroque Beauty of Noto

  • Breakfast
Modica & the Baroque Beauty of Noto — photo 1 Modica & the Baroque Beauty of Noto — photo 2 Modica & the Baroque Beauty of Noto — photo 3 Modica & the Baroque Beauty of Noto — photo 4 Modica & the Baroque Beauty of Noto — photo 5

After breakfast, depart Ortigia with your private driver for the beautiful town of Modica, dramatically set among the hills of southeastern Sicily. Meet your private guide for an introduction to this UNESCO World Heritage town, celebrated for its spectacular Baroque architecture and long tradition of chocolate making.

Discover the historic centre before enjoying an explanation and tasting of Modica's famous local chocolate. Following your visit, enjoy time at leisure for lunch.

In the afternoon, continue to Noto, often referred to as the "Capital of Baroque." With your private guide, explore the historic centre along Corso Vittorio Emanuele and its elegant piazzas, where magnificent buildings create what is often described as an open-air theatre.

Return to your hotel in the early evening and enjoy a relaxed evening at leisure.

Day 4

Sicily, Mt. Etna Sicily, Taormina

Mount Etna Volcano Winery and Taormina Private tour

  • Breakfast
  • Wine Tasting
Mount Etna Volcano Winery and Taormina Private tour — photo 1 Mount Etna Volcano Winery and Taormina Private tour — photo 2 Mount Etna Volcano Winery and Taormina Private tour — photo 3 Mount Etna Volcano Winery and Taormina Private tour — photo 4 Mount Etna Volcano Winery and Taormina Private tour — photo 5

Experience the ultimate Sicilian bucket-list day with a private tour from your Ortigia hotel to Mt. Etna and Taormina. Your personal driver will whisk you up the volcanic slopes to explore the dramatic, otherworldly Silvestri Craters of Mt. Etna, standing 6,000 feet above sea level. Afterwards, unwind at an exclusive Etna winery for a premium tasting of volcanic wines paired with a delicious, authentic Sicilian light lunch.

Your journey continues to the cliffside paradise of Taormina, where you will enjoy a 2-hour guided stroll of its glamorous highlights and use included, skip-the-line tickets to explore the breathtaking ancient Greek Theatre, framed by postcard-perfect views of the sea and volcano. After a seamless day of history, wine, and scenery, sit back and relax as your driver brings you right back to your hotel doorstep in Ortigia to enjoy your last night there. 

Day 5

Sicily, Agrigento Sicily, Castellammare del Golfo

From East to West - Private driver service and Valley of the Temples tour

  • Breakfast
  • Dinner
From East to West - Private driver service and Valley of the Temples tour — photo 1 From East to West - Private driver service and Valley of the Temples tour — photo 2 From East to West - Private driver service and Valley of the Temples tour — photo 3 From East to West - Private driver service and Valley of the Temples tour — photo 4 From East to West - Private driver service and Valley of the Temples tour — photo 5

Enjoy your last breakfast in Ortigia and check out of the hotel. Private transfer to your new hotel, based in the North West island of Sicily, the beautiful Castellammare del Golfo.   Break up the drive with a seamless, skip-the-line stop at the spectacular Valley of the Temples in Agrigento. Here, your private expert guide will lead you through some of the world’s best-preserved ancient Greek monuments. After exploring these majestic, sun-drenched ruins, sit back and relax as your personal chauffeur handles all the driving and luggage, delivering you directly to your Castellammare del Golfo hotel in absolute comfort and style.   Enjoy our Group dinner in Castellammare del Golfo tonight! 

Day 6

Sicily, Castellammare del Golfo

Sicilian Catamaran boat tour!

  • Breakfast
Sicilian Catamaran boat tour! — photo 1 Sicilian Catamaran boat tour! — photo 2 Sicilian Catamaran boat tour! — photo 3 Sicilian Catamaran boat tour! — photo 4 Sicilian Catamaran boat tour! — photo 5

Set sail on the ultimate morning Catamaran adventure to the breathtaking Riserva dello Zingaro, departing directly from Castellammare del Golfo.   This exclusive, small-group boat tour offers a relaxed, intimate vibe away from the crowds as you glide along Sicily’s most pristine coastline. You will marvel at dramatic cliffs, discover hidden sea caves, and dive into the crystal-clear, turquoise waters of untouched coves for unforgettable swimming and snorkelling. After the 4-hour experience, you will have the rest of the day at leisure to relax.     

Day 7

Sicily, Palermo

World Class Street food of Palermo with Hidden Gem village

  • Breakfast
  • Lunch
World Class Street food of Palermo with Hidden Gem village — photo 1 World Class Street food of Palermo with Hidden Gem village — photo 2 World Class Street food of Palermo with Hidden Gem village — photo 3 World Class Street food of Palermo with Hidden Gem village — photo 4 World Class Street food of Palermo with Hidden Gem village — photo 5

Dive into the vibrant heart of Sicily’s capital on an exclusive, private morning street food and cultural tour of Palermo. Led by your personal local guide, you will weave through bustling historical markets like Capo or Ballarò just as the city comes alive, skipping the tourist traps to sample authentic morning specialities like panelle, arancine, and fresh cannoli.

The highlight of your VIP experience includes skip-the-line entry to the spectacular Church of Santa Caterina, where you will marvel at breathtaking Baroque interiors and visit the famous convent bakery to taste legendary pastries made from secret cloistered recipes. It is the ultimate blend of rich history, architectural beauty, and world-class street food, tailored entirely to your pace. After this lovely 3-hour walking tour, you will meet back with your driver and head to a real-life fairy tale village on the way back to your hotel. 

Borgo Parrini, Sicily’s most colourful and artistic hidden gem. Often called western Sicily’s "Little Barcelona," this charming, historic village has been reimagined into a living open-air gallery, featuring cobblestone alleys and vibrant house facades inspired by the surrealist style of Antoni Gaudí. You will have 45 minutes here to leisurely walk the picturesque streets and enter the Artisan houses. Meet back with your driver for the return hotel transfer.    Evening at leisure in Castellammare del Golfo 
Day 8

Sicily, Erice

Medieval Mountain Top Erice and Family Winery!

  • Breakfast
  • Lunch
  • Wine Tasting
  • Cooking Class
Medieval Mountain Top Erice and Family Winery! — photo 1 Medieval Mountain Top Erice and Family Winery! — photo 2 Medieval Mountain Top Erice and Family Winery! — photo 3 Medieval Mountain Top Erice and Family Winery! — photo 4 Medieval Mountain Top Erice and Family Winery! — photo 5

Meet your Private driver and head straight for an off the beaten track family run winery in Sicily! Here, you will be shown how their wine is made and visit the vineyards before sitting down for a traditional full lunch and ending with a very fun cannolo-making session with coffee!    Following lunch and a quick group photo, we will head to the Mountain top Medieval village of Erice!    During this two-hour private afternoon walking tour, you will be guided by a local expert through atmospheric, cobblestone alleyways and past ancient stone castles as the daytime crowds disappear. Watch a breathtaking sunset (season-dependent) over the Mediterranean and the Egadi Islands for a truly spectacular experience and sweeping views. The tour will end by meeting with your driver for the return hotel transfer. 

Day 9

Sicily, Castellammare del Golfo

A Day to Relax & Enjoy Sicily

  • Breakfast
  • Dinner
A Day to Relax & Enjoy Sicily — photo 1 A Day to Relax & Enjoy Sicily — photo 2 A Day to Relax & Enjoy Sicily — photo 3 A Day to Relax & Enjoy Sicily — photo 4 A Day to Relax & Enjoy Sicily — photo 5

After several days of exploring Sicily's historic towns, archaeological treasures, vineyards and coastline, today is yours to enjoy at a more leisurely pace.

Spend the day relaxing in Castellammare del Golfo and making the most of your hotel and its surroundings. Your hotel wellness path is included, offering the perfect opportunity to slow down and recharge.

The evening brings one final special moment together as the group gathers for a farewell dinner at a lovely local restaurant. Raise a glass to the experiences, flavors and memories shared throughout your Sicilian adventure.

Day 10

Sicily, Castellammare del Golfo Sicily, Palermo

Departure from Sicily

  • Breakfast
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Enjoy your final morning in Sicily before your private driver transfers you from Castellammare del Golfo to Palermo Airport for your departure.

For those wishing to continue their Italian adventure, your journey can also be extended into mainland Italy. With convenient flights of approximately one hour, you can continue privately to destinations such as Rome, Puglia or Naples.

Pre-itinerary options in Malta are also available for travelers wishing to add another Mediterranean destination to their journey.

In the press

Where this journey has been featured

Italy Places Change Us, On Page One of National Geographic Traveller (UK), September 2026 National Geographic Traveller (UK) On Page One of National Geographic Traveller (UK), September 2026 September 2026 Open the September 2026 Italy issue of National Geographic Traveller (UK) and you will find us on page one, with three words that sum up why we plan journeys: places change us. Read the story

All press & recognition

Why choose this tour

Why Choose This Tour

Ten guests, never more. Small enough to fit around one table at dinner, to slip into a convent bakery or a family winery without a crowd, and to actually get to know the people you travel with.

You unpack twice. Four nights in Ortigia, five in Castellammare del Golfo. No new hotel every morning, no living out of a suitcase.

Local guides, private drivers. Carlo in Ortigia, experts at the Valley of the Temples, Erice and Palermo. Your driver handles the luggage and the roads, so you look out of the window instead of at a map.

Boutique hotels in the historic centres. Algilà sits inside two restored Baroque palaces in Ortigia. Costamante Suites has just seven suites in the old heart of Castellammare. You step out of the door and you are already there.

A pace that leaves room to breathe. Free afternoons, a full day to relax near the end, and evenings that are yours. We planned the days so you come home rested, not needing another holiday.

Why Choose This Tour, The Soul of Sicily® An Intimate 10 Day Journey Through Sicily
Who this tour is for

Who This Tour Is For

This journey is for travellers who love history but would rather hear it from a local than read it off a sign. For people who plan their day around lunch. For couples, friends and solo travellers who enjoy good company but do not want to be one of forty people following a flag.

You should be comfortable walking for two to three hours on cobblestones and uneven streets, including at the Silvestri Craters on Mount Etna. Swimming on the boat days is a pleasure, never a requirement.

If you want to see every corner of Sicily in a week, this is not that trip. If you want to travel with complete privacy and set every detail yourself, we would suggest one of our private Sicily journeys instead. But if you want the island at a human pace, with a small group and people who know it well, you will feel at home here.

Who This Tour Is For, The Soul of Sicily® An Intimate 10 Day Journey Through Sicily
Best time to visit

Best Time to Visit

This journey is designed for the warmer months, when Sicily is at its most generous. The sea is inviting, the evenings are long, and days built around boat trips, hilltop villages and long lunches at family wineries feel exactly as they should.

Spring (April to early June)
Spring is the gentlest time to travel. Days are warm but comfortable, which makes the walking tours through Ortigia, Noto and the markets of Palermo a real pleasure. The countryside is still green, wildflowers brighten the hills, and the major sites, from the Valley of the Temples to the Greek Theatre in Taormina, are noticeably quieter than in high summer. By late May the sea begins to warm, and a morning on the water around Ortigia or along the Zingaro coastline is already a highlight.

Summer (mid June to August)
Summer is Sicily in full colour. The water around Ortigia and the Riserva dello Zingaro is warm and crystal clear, perfect for swimming and snorkelling from the catamaran. Evenings stretch late, so dinners outdoors and golden light over Erice and the Egadi Islands become part of the experience. July and August are hot, especially inland at Agrigento, and the most popular sites are busier. The itinerary is paced with this in mind, with boat excursions in the morning, afternoons at leisure, and a full day to unwind at your hotel in Castellammare del Golfo.

Best Time to Visit, The Soul of Sicily® An Intimate 10 Day Journey Through Sicily
Food & the table

Food & The Table

In Sicily, food is not a break from sightseeing. It is the sightseeing.

It starts on your first evening with a welcome dinner in Ortigia, and continues the next day when you wander the market for lunch after your morning on the water. In Modica you taste chocolate made the old way, grainy and rich. On Mount Etna, volcanic wines are poured with a light Sicilian lunch, grown in soil that the mountain itself created.

On the west coast, Palermo feeds you standing up: panelle, arancine and fresh cannoli from the stalls of the old markets, then pastries from the convent bakery of Santa Caterina, made from recipes the nuns guarded for generations. At a family-run winery you sit down to a traditional full lunch, then roll up your sleeves and fill your own cannoli.

Three group dinners bring everyone together, at the beginning, the middle and the end. The other evenings are yours, and your guides will happily point you to the places they eat themselves.

Food & The Table, The Soul of Sicily® An Intimate 10 Day Journey Through Sicily
The details

Inclusions & Exclusions

What's Included

  • All mentioned Private guided tours for your group
  • Private driver where mentioned for your group
  • Arrival and Departure airport transfers
  • Transport between hotels
  • Transport where mentioned during tour days
  • High-end 4-star boutique hotels
  • 2 boat tours
  • Daily breakfasts
  • 3 Full Group dinners
  • 2 Wine tastings

What's Not Included

  • Hotel city taxes
  • Travel insurance
  • Flights to/from Sicily
  • Anything not clearly mentioned in the itinerary
Your rooms

Where You'll Stay

Hotels are subject to availability and may be replaced with a property of similar standard.

Algilà Ortigia Charme Hotel

Algilà Ortigia Charme Hotel

Sicily, Siracusa

Set within two beautifully restored Baroque palaces in the heart of Ortigia, Algilà Ortigia Charme Hotel is a 4-star superior boutique retreat just st...

Discover Property
Costamante Suites

Costamante Suites

Sicily, Castellammare del Golfo

A refined 4-star boutique hotel in historic Castellammare del Golfo, offering seven individually designed suites, selected sea-view terraces and an at...

Discover Property
In their words

Traveler Reviews

Emily and David Davison Travelled with us

My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She planned the perfect trip with excellent private guides at all of our sites, professional drivers and lovely hotels. We arrived in Italy with all of our train and ferry reservations made by Ele, with tickets in hand. She was in touch with us daily throughout our trip to make sure that things were going smoothly. She was able to make a few changes to our itinerary as needed. We look forward to working with Ele again on our next trip and have put her in touch with another family member to help plan their trip as well.

Ron and Deb Crosby Travelled with us

Dear Guiseppe and Jesse,

We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future.

Hotels

1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were part of their family. I would recommend it to anyone and would specifically ask for it if we were to make a return visit.

2. Hotel La Baia in Monterosso was nice and it's location was very good especially for us older folks humping luggage from/to the train station.

3. Hotel Lucchesi in Florence- what can I say expect FANTASTIC. The rooftop view at sunset is well worth it. Again very friendly and helpful staff. Would recommend it to everyone.

Wine Tour

Money well spent. We had a great time overall. The driver Mario was OUTSTANDING. He had lots of local knowledge as well as about winemaking. USE HIM AGAIN!!!

The various wineries we visited on tour:

Altesino- fantastic and they were not cheap on their pouring. Great experience.

Azienda Agricola Patrizia Cencion Sloaria- Again a great tour by one of the owner's daughters. We felt like we were the only thing on their mind although there were other customers there. A great way to complete the day.

Again we had a fantastic time and are very appreciative of everything you booked for us. We wish you continued success and if our travels should bring us back to Italy, we know who to call.

Leon and Michele Travelled with us

The trip was great we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.

Bob & Sandy Travelled with us

Jesse & Giuseppe,

Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.

Good to know

Frequently Asked Questions

Is this a private tour, or will we join a group?

Private. You travel with your own guide and driver, and the only people on the itinerary are the ones you bring with you. Nothing is shared with strangers, and the pace of each day is yours to set.

Can the itinerary be changed to suit us?

Yes. What you see here is a starting point, not a fixed departure. Tell us how long you have, what you love and what you would rather skip, and we will reshape it around you. A slower morning, an extra night somewhere you fell for, a different region entirely.

How do we start planning?

Send us a note using the form on this page, or call us on 1-866-779-2565. A travel specialist replies within one business day, usually with a few questions of their own. There is no cost and no obligation in asking.

Are the hotels shown the ones we will stay in?

Usually, yes. Hotels are subject to availability, and if one is full on your dates we will replace it with a property of a similar standard and tell you before you book. Never a surprise on arrival.

When should we book?

The earlier the better, particularly for travel between May and September, when the best small hotels and the guides worth having are taken first. That said, we have put together beautiful trips at short notice, so ask and we will tell you honestly what is still possible for your dates.

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