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Beautiful seaside view of Cefalù, showcasing the charming town along the coast with its rocky hillt Panoramic view of the Piazza del Duomo in Catania, featuring the historical architecture and the Cat Catania city with the stunning backdrop of Mount Etna, with its volcanic peaks rising above the skyl Mount Etna spewing smoke, showcasing its active volcanic nature with the city of Catania below

Private · Catania

Harvest Time in Sicily: Experience a Sicilian Wine Journey - 7 Days of Vino, Volcanoes & Villages

7 Days Sicily

The Overview

Overview

Embark on a luxurious and immersive weeklong journey through Sicily’s most storied wine regions—where dramatic landscapes, timeworn villages, and volcanic terroir meet the warmth of southern Italian hospitality. From the fertile slopes of Mount Etna to the sun-drenched coastlines of Vittoria, Menfi, and Marsala, this curated itinerary blends premier wine tastings with breathtaking scenery and authentic culinary moments.

You’ll stay at exclusive wine estates and boutique agriturismos, meet pioneering winemakers, and taste Sicily’s most celebrated varietals—from crisp Carricante and structured Nerello Mascalese to the elegant Frappato, bold Cerasuolo di Vittoria, and Marsala’s iconic fortified wines. Guided vineyard walks, cellar tours, and chef-paired meals provide intimate insight into Sicily’s deep-rooted wine traditions, while optional cultural excursions add texture and depth to the experience.

Whether you’re admiring Baroque architecture in Ragusa, wandering Etna’s lava flows, or savoring seafood along the salt flats of the western coast, this journey is a celebration of Sicily’s soul—earthy, expressive, and unforgettable.

Optional Add-Ons to Enrich Your Journey:

Pre-Tour Experience in Taormina (2 nights / 3 days)

Begin your adventure early with a luxurious stay in the glamorous cliffside town of Taormina. Explore ancient ruins, sip aperitivi with sea views, and ease into island life before heading to Mount Etna.

Sicilian Cooking Class with Wine Pairings

Deepen your culinary connection to Sicily with a hands-on cooking class led by local chefs. Learn to prepare traditional dishes, then enjoy a meal paired with regional wines.

Sunset Boat Tour near Menfi or Marsala

End your day with a golden-hour cruise along the southwestern coast—perfect for a romantic interlude or a relaxed group moment with wine and sea breezes.

Private Photographer to Document the Journey

Capture the beauty of Sicily—and your time in it—with a professional photographer who discreetly joins for key moments, delivering a custom gallery of your trip.

Wine Shipping Assistance

Fallen in love with Sicilian wines? We’ll help arrange international shipping for bottles purchased along the way, so you can bring a taste of Sicily home without hassle.

Duration

7 days

6 nights

Pricing

On request

Tailored to your dates and group.

Autumn is when Sicily comes alive. The grapes are in, the volcano still breathes, and the villages fill with the smell of pressed fruit and slow cooking. Over seven days you follow the island through its harvest season, from the black slopes of Mount Etna, where vines grow in volcanic soil, to family cellars where the wine is poured by the people who made it. You walk medieval streets, sit at long tables with local hosts, and taste a Sicily that most visitors never reach. This is not a wine list on legs. It is an island in its richest season, felt from the inside.

Regions
Sicily
Tour Style
Private
Departs From
Catania
Meeting Point
Catania (CTA)
Included Meals
Daily breakfast · 5 wine tastings · 4 dinners · 3 lunches
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 1–7

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, Catania Sicily, Mt. Etna

Arrival in Catania & Transfer to Mount Etna

  • Dinner
  • Wine Tasting
Arrival in Catania & Transfer to Mount Etna — photo 1 Arrival in Catania & Transfer to Mount Etna — photo 2 Arrival in Catania & Transfer to Mount Etna — photo 3 Arrival in Catania & Transfer to Mount Etna — photo 4 Arrival in Catania & Transfer to Mount Etna — photo 5

Upon arrival at Catania Airport, a private transfer brings you to the slopes of Mount Etna, where you'll check into your wine resort-either the serene Monaci delle Terre Nere or the elegant Villa Neri. The afternoon is yours to relax, stroll through nearby Zafferana, or unwind at the spa. In the evening, enjoy a welcome aperitivo followed by a vineyard dinner featuring Etna DOC wine pairings, a perfect introduction to the region’s volcanic terroir.

Where we meet Catania (CTA)
Day 2

Sicily, Catania Sicily, Mt. Etna Sicily

Etna Wine Experience

  • Breakfast
  • Lunch
  • Dinner
Etna Wine Experience — photo 1 Etna Wine Experience — photo 2 Etna Wine Experience — photo 3 Etna Wine Experience — photo 4 Etna Wine Experience — photo 5

After breakfast, the day begins with a visit to a prestigious Etna winery like Barone di Villagrande or Tenuta delle Terre Nere. You’ll explore terraced vineyards and taste wines shaped by the mountain’s unique soils. Lunch is served at a winery, showcasing seasonal Sicilian fare. In the afternoon, a private guide leads you across Etna’s dramatic lava landscapes. Return to your resort for a light dinner or a relaxed meal at a local wine bar.

Day 3

Sicily, Ragusa Italy

Transfer to Vittoria (Frappato & Cerasuolo)

  • Breakfast
  • Dinner
  • Wine Tasting
Transfer to Vittoria (Frappato & Cerasuolo) — photo 1 Transfer to Vittoria (Frappato & Cerasuolo) — photo 2 Transfer to Vittoria (Frappato & Cerasuolo) — photo 3 Transfer to Vittoria (Frappato & Cerasuolo) — photo 4 Transfer to Vittoria (Frappato & Cerasuolo) — photo 5

Today you travel south through scenic countryside to Vittoria, checking in at the charming Baglio Occhipinti, a rustic-luxe vineyard estate. In the afternoon, visit COS Winery, pioneers of amphorae-aged and biodynamic wines. A guided tasting introduces you to Frappato and Cerasuolo di Vittoria. Dinner is a relaxed farm-to-table experience, either at the estate or a local wine-focused bistro.

Day 4

Sicily, Ragusa Sicily, Modica Sicily, Ragusa Ibla

Natural Wines & Baroque Towns

  • Breakfast
  • Lunch
  • Wine Tasting

Begin the day with a visit to Arianna Occhipinti’s winery, where her natural winemaking philosophy comes alive through elegant, expressive wines. Enjoy a picnic or tasting lunch among the vines. In the afternoon, take an optional trip to Modica or Ragusa Ibla to explore their stunning Baroque architecture and try the region’s famous chocolate. Return to the estate for a peaceful evening, perhaps with a sunset aperitivo by the pool.

Day 5

Sicily, Menfi Sicily, Agrigento

Menfi & Planeta Estate

  • Breakfast
  • Dinner
  • Wine Tasting
Menfi & Planeta Estate — photo 1 Menfi & Planeta Estate — photo 2 Menfi & Planeta Estate — photo 3 Menfi & Planeta Estate — photo 4 Menfi & Planeta Estate — photo 5

Travel west to Menfi and check in at La Foresteria Planeta, a sophisticated wine resort overlooking the Mediterranean. Spend the afternoon touring the estate and tasting Planeta’s acclaimed wines. In the evening, enjoy a gourmet dinner prepared by the in-house chef, with pairings that highlight the richness of the region’s ingredients and vintages.

Day 6

Sicily, Marsala Sicily Sicily

Marsala & Salt Flats

  • Breakfast
  • Lunch
  • Wine Tasting
Marsala & Salt Flats — photo 1 Marsala & Salt Flats — photo 2 Marsala & Salt Flats — photo 3 Marsala & Salt Flats — photo 4 Marsala & Salt Flats — photo 5

Embark on a day trip to Marsala, visiting Donnafugata Winery for Passito and signature reds, followed by a tasting at Florio Winery, known for its historic Marsala wines. Lunch is enjoyed near the picturesque salt flats of Stagnone, with fresh seafood and a glass of Grillo. Return to Menfi or opt to stay overnight in Marsala for a final night.

Day 7

Sicily, Segesta

Departure via Palermo

  • Breakfast
Departure via Palermo — photo 1 Departure via Palermo — photo 2 Departure via Palermo — photo 3 Departure via Palermo — photo 4 Departure via Palermo — photo 5

Depart via private transfer to Palermo Airport (approx. 2 hours). If time permits, stop to explore the ancient temple of Segesta or enjoy a quick stroll through Palermo’s historic streets. Reflect on a week rich with Sicilian wine, volcanic landscapes, and timeless village charm as you head home.

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

The details

Inclusions & Exclusions

What's Included

  • 6 nights of luxury accommodations
  • Private transportation with an English-speaking driver
  • Daily breakfast
  • Selected lunches and dinners (as specified in the itinerary)
  • Premium wine tastings
  • Private guided vineyard and cellar tours
  • Personalized 24/7 travel support
  • Local taxes and service charges

What's Not Included

  • International or domestic airfare
  • Meals not specified in the itinerary
  • Optional activities and add-ons (unless added by request):
  • Personal expenses
  • Travel insurance
  • Porterage & gratuities
  • Hotel City Taxes
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.

Where you are

Location

Italy Catania

Catania and beyond

7 days through Italy, with every stop chosen by the people who live here.

Where we meet

Catania (CTA)

Where it starts

Catania

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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.

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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7 days · Pricing on request

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