Can we extend the trip?

Absolutely. Common extensions include the Baroque towns of Noto and Ragusa (2 nights), the Aeolian Islands (2–3 nights), or a few days on the mainland — the Amalfi Coast or Rome are easy connections from Catania. We'll build the extension seamlessly.

How does this differ from the Essence of Sicily 7-day tour?

The 9-day version adds the full Segesta and Erice day trip, plus an extra day in Taormina with the Mount Etna wine adventure. It's the more complete Sicily experience with more breathing room.

What happens after I request this trip?

You'll complete a short planning form with your dates, group size, and any preferences. A travel specialist will respond within one business day with a personalised proposal and exact pricing. No obligation — it's a conversation.

9-Day Private Package Journey

Best of Sicily

Palermo, Segesta, Agrigento, Taormina & Mount Etna — the complete Sicilian journey.

Available as Private Semi-Private Self-Guided

From €3,110 per person 9 days / 8 nights

View Itinerary

Tour Overview

9 days across Sicily.

Nine days tracing Sicily's extraordinary arc — from the Arab-Norman palaces of Palermo to the ancient temples of Agrigento and the dramatic volcanic coastline of Taormina. This private journey puts you in the hands of local guides who know every chapel, every trattoria, and every back road through the island's layered history. Greek, Roman, Arab, Norman, Baroque — Sicily has been conquered by everyone and absorbed them all, producing a culture and a cuisine unlike anywhere else in the Mediterranean.

Detailed Itinerary

Your journey, day by day.

Every day is designed with breathing room. Sleep in, take a detour, linger at lunch — the itinerary flexes around you, not the other way around.

Day 1

Arrival in Palermo

Where every street corner tells a thousand years of stories.

Your private driver meets you at Palermo Falcone Borsellino Airport and delivers you to your hotel in the historic centre — a city where Arab domes sit beside Norman towers and Baroque churches open onto markets that haven't changed in centuries. After check-in, the rest of the day is yours to absorb Palermo at your own pace: wander through the Vucciria or Ballarò street markets where vendors shout over mountains of swordfish and blood oranges, find a café in the Quattro Canti, or simply sit on your terrace and watch the rooftops turn pink as the sun sets behind Monte Pellegrino. We'll share our curated list of favourite restaurants for your first Sicilian evening.

Private airport transfer to central Palermo
Curated restaurant recommendations for your first evening

4–5★ centrally located hotel, Palermo

Day 2

Palermo Highlights

Arab-Norman splendour and the chaos that makes it beautiful.

Your private guide meets you after breakfast for a morning that reveals Palermo's extraordinary layered history. Begin at the Norman Palace — the seat of Sicilian power for nine centuries — and step inside the Cappella Palatina, where every surface blazes with Byzantine gold mosaics so fine they take your breath away. From there, walk through the historic centre: the Cathedral with its mix of Arab, Norman, and Gothic architecture, the elegant Quattro Canti crossroads, Piazza Pretoria with its monumental Renaissance fountain, and the twin Arabo-Norman churches of La Martorana and San Cataldo. The afternoon is free to explore at your own pace — the Kalsa quarter, the puppet theatre tradition, or the street food that Palermo does better than anywhere in Italy: arancini, panelle, and sfincione from vendors who've been at it for generations.

Norman Palace and Cappella Palatina gold mosaics
Palermo Cathedral and Quattro Canti
Piazza Pretoria, La Martorana and San Cataldo churches
Free afternoon for Palermo street food and markets

Meals: Breakfast 4–5★ centrally located hotel, Palermo

Day 3

Segesta & Erice

A Greek temple in a green valley, a medieval town in the clouds.

Your private driver takes you west into the rolling countryside of western Sicily. First stop: the ancient site of Segesta, where a magnificent Doric temple — never finished, never roofed, but perfectly proportioned — stands alone in a green valley with sheep grazing around its columns. Above it, a Greek theatre carved into the hillside commands views that stretch to the sea. From Segesta, the road climbs to Erice — a medieval hilltop town perched at 750 metres, wreathed in mist and filled with more than sixty churches dating to the 1300s. Wander the cobblestone streets past the Pepoli Castle, the Venus Castle on its clifftop, and the Chiesa Matrice with its detached bell tower. Before leaving, stop at one of Erice's legendary pasticcerias for traditional cannoli, Sicilian cassata, and almond pastries that are reason enough to make the climb. Return to Palermo in the late afternoon.

Segesta's Doric Temple and Greek theatre
Medieval Erice — hilltop town at 750 metres
Pepoli Castle, Venus Castle and Chiesa Matrice
Pasticceria tasting: cannoli, cassata and almond pastries

Meals: Breakfast 4–5★ centrally located hotel, Palermo

Day 4

Palermo to Agrigento

Crossing the Sicilian heartland to the temple coast.

A leisurely final morning in Palermo — perhaps a last visit to the Ballarò market, a coffee in the Kalsa quarter, or a walk along the waterfront. Late morning, your private driver takes you south through the Sicilian interior — a landscape of golden wheat fields, hilltop villages, and almond groves that unfolds like a Renaissance painting. The drive takes roughly two and a half hours, with the landscape growing more dramatic as you approach the southern coast. Arrive in Agrigento by mid-afternoon and check into your hotel. The rest of the day is yours to explore the charming old town, with its narrow streets, Baroque churches, and terraces overlooking the Valley of the Temples below — spectacular at sunset when the ancient stones turn the colour of honey.

Scenic drive through the Sicilian interior
Afternoon arrival in Agrigento
Optional sunset views over the Valley of the Temples

Meals: Breakfast 4–5★ centrally located hotel, Agrigento

Day 5

Valley of the Temples & Scala dei Turchi

Two and a half thousand years of stone, and a cliff carved by the sea.

The morning belongs to one of the most extraordinary archaeological sites in the world. Your private guide leads you through the Valley of the Temples — a ridge-top sanctuary where eight Greek temples stand against the Sicilian sky, the Mediterranean shimmering below. The Temple of Concordia, remarkably intact after twenty-five centuries, is considered the best-preserved Greek temple in existence. Your guide brings the ancient colony of Akragas to life: the politics, the rituals, the sheer ambition of a city that rivalled Athens. After the temples, your driver takes you to the Scala dei Turchi — a dramatic staircase of white chalk cliffs rising fifty metres from a turquoise sea, sculpted by wind and waves into something that looks more like a work of art than a geological formation. The afternoon is free to explore Agrigento's old town or simply rest at the hotel.

Private guided tour of the Valley of the Temples (UNESCO)
Temple of Concordia — world's best-preserved Greek temple
Scala dei Turchi white chalk cliffs
Free afternoon in Agrigento

Meals: Breakfast 4–5★ centrally located hotel, Agrigento

Day 6

Agrigento to Taormina

From the temple coast to the volcano's doorstep.

After breakfast, your private driver takes you east across Sicily toward the Ionian coast — a drive of roughly three hours through the island's agricultural heartland, past pistachio groves, citrus orchards, and the occasional glimpse of Mount Etna's snow-capped summit growing larger on the horizon. Arrive in Taormina by early afternoon — a town perched on a cliff above the sea, with views so beautiful that writers from Goethe to D.H. Lawrence chose to live here. Check into your hotel and spend the afternoon getting your bearings: the main street of Corso Umberto I, the public gardens with their Mediterranean plants and sea views, or simply a table at a café in Piazza IX Aprile where the terrace hangs above the coast and Etna smokes quietly in the background.

Scenic drive across Sicily with Etna views
Afternoon arrival in clifftop Taormina
Corso Umberto I and Piazza IX Aprile at leisure

Meals: Breakfast 4–5★ centrally located hotel, Taormina

Day 7

Taormina Highlights

Where Greek theatre meets volcanic drama.

Your private guide meets you after breakfast for a walking tour of Taormina — a town that packs an extraordinary amount of beauty into a very small space. The morning centres on the Greco-Roman Theatre, one of the most dramatically sited ancient theatres in the world: the stage frames Mount Etna on one side and the Ionian Sea on the other, and on a clear day the combination is genuinely staggering. Your guide explains the theatre's Greek origins and Roman modifications before leading you through the winding lanes of the historic centre — medieval palaces, hidden courtyards, and the small piazzas where Taormina's social life plays out. The afternoon and evening are entirely free: descend to the beach at Isola Bella, a tiny island connected to the shore by a narrow sandbar, explore the boutiques along Corso Umberto, or find a restaurant where the seafood is as fresh as the view.

Greco-Roman Theatre with Etna and sea views
Walking tour of Taormina's historic lanes
Free afternoon: Isola Bella beach or Corso Umberto shopping

Meals: Breakfast 4–5★ centrally located hotel, Taormina

Day 8

Mount Etna Wine Adventure

Europe's most active volcano — and the wine it nurtures.

Today you trade the coast for the mountain. Your private driver takes you up the slopes of Mount Etna — Europe's tallest and most active volcano, a vast presence that dominates eastern Sicily. The road climbs through lemon groves and lava-stone villages to Rifugio Sapienza at 2,000 metres, where the air is thin and the landscape turns lunar: the Silvestri craters and the hardened lava flows from 2001 and 2003 erupt from the black volcanic soil like something from another planet. Walk the crater rims with your guide, who explains the geology and the ongoing eruptions that have shaped Sicilian life for millennia. After descending, visit a local winery on Etna's fertile lower slopes — the volcanic soil produces some of Sicily's most distinctive wines, and the tasting comes with views of the vineyards cascading down toward the coast. Return to Taormina in the late afternoon with the evening free for your final Sicilian dinner.

Mount Etna ascent to Rifugio Sapienza (2,000m)
Silvestri craters and recent lava flows
Etna winery tasting on the volcano's slopes
Free evening for a farewell dinner in Taormina

Meals: Breakfast 4–5★ centrally located hotel, Taormina

Day 9

Departure

Arrivederci, Sicilia — the island stays with you.

A final Sicilian breakfast on the terrace, a last look at the sea from your hotel, and perhaps a quick walk through Taormina's quiet morning streets before the town wakes up. Your private driver will collect you from the hotel and transfer you to Catania Airport in plenty of time for your flight. If your departure is later in the day, we can arrange a morning visit to the fish market in Catania — one of the most theatrical in the Mediterranean — or simply a late checkout to savour the last unhurried hours. Your travel specialist remains on call until you're home.

Private transfer to Catania Airport
Optional morning visit to Catania's fish market

Meals: Breakfast

Where You'll Stay

Hand-picked hotels, every night.

We choose properties for character, location, and the kind of service that makes you feel looked after — not just checked in. Every hotel can be swapped for an alternative if you prefer.

Palermo

3 nights

4–5★ centrally located hotel

Historic centre

Walking distance to the Norman Palace, Cathedral, and street markets

Agrigento

2 nights

4–5★ centrally located hotel

Old town / temple district

Views over the Valley of the Temples, walking distance to the old town

Taormina

3 nights

4–5★ centrally located hotel

Historic centre

Clifftop setting with sea and Etna views, steps from Corso Umberto

Hotels shown are indicative of the standard we book. Upon request, we will provide a detailed itinerary with specific hotel options tailored to your preferences and budget.

What's in the Price

Included

8 nights in 4–5★ centrally located hotels (double occupancy)
Daily breakfast at each hotel
Airport meet & greet on arrival
Private airport transfers in Palermo and Catania
Private driver for all excursions and inter-city transfers
Private expert guides in Palermo, Valley of the Temples, Taormina, and Mount Etna
Skip-the-line access at major sites
Valley of the Temples guided tour
Segesta and Erice full-day excursion
Mount Etna excursion with Etna winery tasting
All entrance fees and museum tickets
24/7 travel specialist support throughout your trip
Hamilton & Chase digital travel booklet with restaurant & local recommendations

Not Included

International flights to Palermo / from Catania
Travel insurance (required — we can arrange coverage on request)
Lunches and dinners
Personal expenses (shopping, additional tastings, spa treatments)
Gratuities for guides and drivers (optional but appreciated)
City tax (collected directly by hotels, typically €1–4 per person per night)

Good to Know

This itinerary is a starting point — days can be reordered, towns swapped, and the pace adjusted to suit your group.
Sicily is best explored by private vehicle. Your driver handles all the driving so you can enjoy the scenery.
All guides and experiences are arranged exclusively for your group — never shared with other travellers.
Comfortable walking shoes are essential — archaeological sites and hilltop towns involve uneven terrain.
Flexible booking: adjust or postpone your dates up to 60 days before departure at no charge.

Make It Yours

Optional add-ons & upgrades.

Every trip is different. These extras can be woven into your itinerary — just let your travel specialist know what catches your eye.

Sicilian cooking class

Market visit and hands-on cooking with a local chef — pasta alla Norma, caponata, and cannoli

From €120 pp

Monreale Cathedral excursion

Half-day trip from Palermo to see the finest Norman mosaics in Sicily — 6,340 square metres of gold

From €95 pp

Cefalù beach & old town

Half-day excursion to the charming coastal town with its Norman cathedral and sandy beach

From €110 pp

Etna summit crater hike

Guided ascent to the summit craters at 3,300m with certified volcanologist (weather permitting)

From €180 pp

Godfather filming locations tour

Visit the villages of Savoca and Forza d'Agrò where the iconic film scenes were shot

From €140 pp

Professional photo session

1-hour portrait session at iconic Sicilian locations with a local photographer

From €350

"Sicily was a revelation — the Valley of the Temples at golden hour, the street food in Palermo, and that view from the Greek theatre in Taormina with Etna smoking behind it. Hamilton & Chase found the perfect balance between guided days and free time to wander."

Sarah & Mark T.

Boston, MA · Best of Sicily, September 2025

Common Questions

Questions about this trip.

When is the best time to visit Sicily?

April–June and September–October are ideal — warm, sunny, and without the intense heat of July–August. Spring brings wildflowers to the temple sites, and autumn is perfect for the grape and olive harvests. Winter is mild and uncrowded, especially along the coast.

Is this trip suitable for children?

Yes. Sicily's beaches, street food, and Mount Etna are natural hits with families. We'll adjust the pacing and add age-appropriate activities — the Godfather filming locations tour and Isola Bella beach are particular favourites with older kids.

Private Package Journey

Best of Sicily

9 days / 8 nights

From €3,110

per person

Ready to go?

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More Sicily Tours

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+1 646-466-6841 explore@hamiltonandchase.com

Available Mon–Fri 9am–6pm CET.
On-trip support is 24/7.

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