Splendors of Sicily – Fall 2025

The allure of Sicily lies in its contrasts. We start in Palermo, cradle of the Mediterranean and “a city of extremes, a mixture of panache and poverty.” Filled with hints of powerful Arab influence, the city teems with the languid air of Eastern sensuality and mystery. Over-the-top Byzantine and Baroque architecture, centuries of noble rule, imprints left by dozens of invaders, reserved yet courteous people – this is Palermo. Agrigento’s Greek temples follow, seen both up close and by candlelight from our 5-star hotel balcony …  completely magical. Traveling eastward along the island’s interior route, we stop at one of Sicily’s top sites: Villa del Casale in Piazza Armerina. Here we’ll encounter the world’s most impressive collection of Roman mosaics in situ.   Our adventure finishes in the east, once the center of Magna Graecia, where its dazzling coastal towns of Ragusa, Catania, and Siracusa have a refreshingly different flavor. 11,000-foot Mount Etna majestically dominates the eastern skyline of the island. Sicily’s multi-cultural experience continues at the table. Each meal is a tantalizing cultural mosaic crafted with elements left by sea-faring Phoenicians, Greeks, Normans, Arabs and others.

Sicily is like a sweater woven with multi-colored yarn. In order to capture the yin-yang essence of its micro-cultures, we’ve packed a lot into ten days. Where we normally stay in no more than three hotels during our journeys, we’ve found four wonderful realities to welcome us along the way for this trip. In order to flatten the learning curve, we’ll have the benefit of a local guide in virtually every place visited. And we never forget — this is a vacation, so we’ve included some free time each day and have purposely avoided early departures. Come discover with us, for ten magical days….

DAY 1 – Island Welcome

Independent arrival to our 4-star boutique hotel, centrally located in colorful Palermo.  We’ll help you ease into Sicily’s frenetic capital with an early evening cocktail in the garden of a chic wine bar. Dinner follows at a nearby romantic restaurant, sophisticated yet still frequented by locals. Welcome drink, D

Lodging for the next 3 nights: Grand Hotel Piazza Borsa 4* or similar

DAY 2 – Palermo

One of the Mediterranean’s great unsung destinations, Palermo is a magnificent jumble of exquisite beauty and decay, abundance and austerity, and organized chaos. If you take a short walk through the center of town, you’ll pass, in moments, sumptuous palazzos, elegant squares, chic restaurants, immaculate pastry shops, and enough artifacts left over from the various foreign invaders to keep a voracious traveler occupied for weeks. But the city still has an unruly side. The traffic is appalling, certain neighborhoods are seedy, and for every newly spiffed-up Baroque fountain there’s a centuries-old building caked in grime or still in ruins thanks to an Allied bomb.

A guide is an absolute must in a city this dense. Ours will show us the city’s highlights this morning, starting with the Norman Palace (Palazzo Normanni). This repurposed Arab fortress, with a few stone walls built by the Phoenicians and a chapel blanketed in glittering mosaics by the Byzantine Greeks, is Palermo’s most popular attraction and you’ll see why. We’ll take in the Duomo, the octagonal Quattro Canti, and the wildly Baroque Chiesa di Gesu.

Afternoon is free to shop and/or enjoy some local specialties for lunch. Free afternoon, followed by an al fresco (weather permitting) dinner in an elegant nearby seaside restaurant. B, D

DAY 3 — Northwestern Sicily – Erice, Couscous, OMG Panoramas

Today we explore the northwestern coastline of Sicily. First stop is Monreale Cathedral. The interior of this World Heritage Site is covered with over 6,000 square meters of mosaics (surpassed only by Istanbul’s Cathedral of Santa Sofia). Then we’ll ride along the island’s northern shore, where olive groves and vineyards are juxtaposed with creamy white marble quarries, jutting rock formations and cerulean sea. Suddenly, we’ll start a 2,300 foot ascent to the medieval hilltop town of Erice, arriving just in time for lunch. We’ve snagged the perfect option, a room with a view where multiple tastings of food with an Eastern flair just keep arriving!  You might want to follow with frutta di martorana at one of several pastry shops, including that of Maria Grammatico (of Bitter Almond fame). Afternoon options include time on your own to enjoy a walk through the public gardens and the boutiques (we found some particularly nice pottery shops). Those who are interested can stroll the city with our local guide, who ties together the origins of these blue-eyed people with works dating as far back as The Illiad, Back to Palermo in the late afternoon, where you can relax before exploring the many food options offered by this vibrant city. B, L

DAY 4 – Planeta Winery; Agrigento by Night in a 5-Star Hotel 

We’ll begin our cross-island sojourn today, stopping on the way at Planeta in Sambuca for a wine tasting and lunch. Established in 1990, this is the family’s first wine making facility and surrounds the beautiful ancestral home located on Arancio Lake.  Your visit includes a walk in the vineyards and a tasting of 4 wines paired with a traditional Planeta family lunch including a tasting of their olive-oils.

We’ll continue on to Agrigento. Established as a Greek colony in 580 BC on a ridge above Sicily’s southwest, the city grew into one of the most important commercial centers in the Mediterranean. The remains, including the soaring columns of the Temple of Concordia, rival the temple ruins in Greece. Agrigento’s archaeological park—with its irresistible sobriquet, Valley of the Temples—spreads over 3,000 acres bordered by a grove of olive and almond trees. Rather than just wandering about, you’ll have a superb guide to put all those stones in context.

Overnight stay at 5-star Hotel Athena. A slice of heaven, Villa Athena is a restored 18^th century residence, now a boutique hotel that’s alluring both inside and out. Dinner in house tonight, offering more time to enjoy the view of the Concordia Temple (only 200 yards away) in the luxury of this splendid property. B,  light L and wine pairing, D

DAY 5 – From Agrigento to Siracusa with stop in Piazza Armerina 

After a leisurely breakfast we’ll travel along an inland route, stopping at midday at the phenomenal Villa del Casale in Piazza Armerina. This site boasts the largest and best-preserved collection of Roman mosaics in the world.

After a delicious lunch in a local agriturismo we continue to Ortigia, where 3000 years of Sicilian history are written. We’ll offer a guided orientation walk which will include a visit to the magnificent Cathedral. Ortigia is small (you can cover all of its tiny streets during our time here) but chock full of boutiques and restaurants. Choose one of them for dinner on your own tonight.

Accommodation for the next 3 nights: G.H. Ortigia 5*, Siracusa  B, L

“The richness of [southern Italian food] is most visible in Sicily, where succeeding waves of occupation—Greek Byzantine, Arab, Norman and even Swedish—have combined with local imagination to produce a stunningly inventive cuisine. In Sicily the great family cooks were men trained in France; some of these monzus are still cooking…” Jo Bettoja, Southern Italian Cooking

DAY 6 – An Island’s Island: Ortigia

Sleep in. Then, choose your breakfast pleasure before setting off to discover. Today day is yours. Eminently walkable and achingly charming (and touristy, yes, but even so…), Ortigia is connected to the mainland by short bridges and otherwise surrounded by ancient seawalls. Within those walls is a tangle of cobblestone streets with numerous candlelit wine bars and boisterous trattorias, echoing piazzas paved in pearlescent stones, grand Baroque palaces from the 18th century, Spanish palaces from the 15th century, and Greek ruins from the time of Plato. Cicero extolled the beauties of Ortigia, and he clearly wasn’t the only one smitten. Look hard enough and you’ll find remnants of nearly all the factions that have seized control of Sicily over the years, from the Byzantine Greeks to the Normans.

Today is your day. Enjoy. B

Day 7 : Noto

Transfer after breakfast to the nearby town of Noto, renowned for its splendid Sicilian Baroque architecture. Noto was rebuilt after the earthquake of 1693, and has been recognized by the UNESCO World Heritage as an “outstanding testimony to the exuberant genius of late Baroque art and architecture.” Around noon we’ll  drive through the dreamy countryside where “Inspector Montalbano” episodes were filmed. Lunch will be a leisurely affair, taken al fresco (weather permitting) at the stunning Masseria delle Volpe.  Back to Ortigia in mid-afternoon.B, L

DAY 8 – Our final stop: Mt. Etna 

Can’t leave Siracusa before visiting the huge archaeological area of the Neapolis Park where our guide will show us the Greek Theater and the Ear of Dionisio. Then it’s time to drive north and discover the tremendous volcano that we’ve seen from afar for days now.

Wines coming out of Mount Etna are considered today among the finest in Italy and you’ll taste some of the most exciting during your lunch at Benanti Winery. Considered trailblazers in the emergence of quality Sicilian wines, Benanti produces award-winning wines. Your visit begins in the vineyards where Nerello Mascalese and Nerello Capuccio grow, ungrafted vines aged 20 – 100 years. Continue in the 18th century lava stone Palmento where you will taste Benanti’s best labels paired with Sicilian specialties.

Accommodation for the last 2 nights: Relais San Giuliano – Mt Etna  B, wine tasting & light lunch

Day 9 — Mt. Etna

Today it’s time to explore Mount Etna, Europe’s highest and most active volcano. You’ll traverse spectacular landscapes through the lava fields and the craters of ancient and recent eruptions. You will pass over pleasant villages, winding little black lava-stone roads, vineyards, orange tree groves stopping to visit local producers and taste local specialties.

In the afternoon you might want to go to Taormina for a leisurely walk in this lovely resort town or to Catania to visit this elegant Baroque town on the slopes of the volcano. Perhaps a spa experience calls you back at the hotel. Whatever you choose, we’ll enjoy a gorgeous dinner together at day’s end.  B, Farewell dinner.

DAY 10 – Departure … or consider a couple more days in Taormina (see Special Features)

Transfer to Catania’s Fontanarossa airport and departure (please schedule flights AFTER 11am). Arrivederci! B

*B=Breakfast, L=Lunch, D=Dinner provided

Taormina © Page Dowdy Photography

STAY ON IN SICILY: TAORMINA

Less than an hour north of our last hotel lies magical Taormina. Sprawling on a hillside above the Ionian Sea, Taormina is a walkable assemblage of crooked alleyways and Gothic churches looming over grand piazzas—an iconic playground for the elite of yesteryear. The Greeks built a clifftop theater here in the 3rd century BC, and the Romans later supersized it. From the late 1880s for nearly 100 years, the town attracted an international set of the rich, the famous, and the famously scandalous (Greta Garbo, Picasso, Hemingway, D.H. Lawrence, Truman Capote—a stunning list). It’s now the most popular spot on the island, so start early by strolling around the Greek Theater and the gardens of the 19th-century Villa Comunale; both have stunning views of the sea and the often snowcapped Mount Etna.

As the main street fills toward midday, climb up the stone steps that splinter off to narrow alleys hemmed in by balconies draped with bougainvillea and lace tablecloths. Or consider an afternoon (or splurge on a full-day) boating trip around Naxos Bay, which is known for its electric blue grottoes and neon orange coral. Explore the small, pebbly beach and lush vegetation of craggy Isola Bella. This is a great area for snorkeling.

Contact Adagio for hotel options in Taormina.