Italy
14 Days of Ancient Cities, Coastlines & Sicilian Soul
Rome • Palermo • Cefalù • Taormina • Mt. Etna • Siracusa/Ortigia
Italy’s heart and Sicily’s soul meet on this journey — where ancient cities, sun-soaked coastlines, vibrant markets, and volcanic landscapes come together in one unforgettable arc.
This trip blends:
Rome’s timeless icons & golden-hour streets
The Colosseum, Vatican, piazzas, and hidden corners that reveal the city’s layered history.Palermo’s mosaics, markets & multicultural energy
Cappella Palatina, lively street food culture (Wanderwell-curated GF options), and the city’s Arab–Norman heritage.Cefalù’s seaside charm
Medieval alleys, mosaic cathedrals, and a crescent coastline perfect for slow afternoons.Taormina’s elegance & Ionian views
Ancient theaters, terrace dinners, and cinematic Mediterranean scenery.Mt. Etna’s volcanic landscapes & wine country
Crater walks, lava fields, and vineyard tastings on some of Italy’s most dramatic terrain.Siracusa & Ortigia’s ancient Greek history
Archaeological marvels, waterfront promenades, and honey-colored baroque architecture.Wanderwell-curated gluten-aware dining throughout
From Rome’s celiac-safe pasta to Sicily’s seafood and street food, all thoughtfully vetted.Smooth, scenic connections across Italy’s most storied regions
A seamless route from capital city to coastline to island magic.
Itinerary
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• Private transfer into the city
• Settle into a boutique hotel in Trastevere, Monti, or the historic center
• Evening walk + GF gelato
• Dinner at a vetted celiac-safe trattoria -
• Colosseum & Roman Forum with skip-the-line entry
• GF lunch in Monti
• Afternoon walk: Capitoline Hill → Piazza Venezia
• Sunset in Piazza Navona & the Pantheon
• Dinner at a cozy osteria -
• Vatican Museums, Sistine Chapel, St. Peter’s Basilica
• GF lunch in Prati
• Afternoon options: Castel Sant’Angelo, Trastevere, or Villa Borghese
• Aperitivo along the Tiber
• Dinner in Trastevere -
• Slow morning: Campo de’ Fiori market or Jewish Ghetto
• Lunch at a GF-safe spot
• Transfer to airport → Flight to Palermo
• Evening stroll in the historic center
• Dinner at a Wanderwell-vetted seafood spot -
• Palazzo dei Normanni + Cappella Palatina (gold mosaics)
• Explore the Quattro Canti + Piazza Pretoria
• Street food tasting (GF-aware options available)
• Sunset rooftop aperitivo
• Optional: Teatro Massimo tour -
• Explore Ballarò or Il Capo markets
• Wander Kalsa district’s art and gardens
• Afternoon coastal stroll to Foro Italico
• GF dinner featuring Sicilian specialties -
• Train to Cefalù (1 hr)
• Visit the Norman Cathedral & mosaic Christ Pantocrator
• Beach time on Cefalù’s picturesque shoreline
• GF lunch overlooking the sea
• Return to Palermo -
• Scenic train along Sicily’s eastern coast
• Check into hotel with Etna or sea views
• Wander Taormina’s boutiques, alleys, and piazzas
• Golden-hour visit to the Ancient Greek Theatre
• Terrace dinner overlooking the Ionian Sea -
• Slow morning in town or by the pool
• Optional beach time at Isola Bella
• Visit Villa Comunale gardens
• GF dinner in the old town -
• Guided excursion to Mt. Etna’s craters and lava fields
• Wine tasting + GF lunch at an Etna Rosso vineyard
• Return to Taormina for sunset -
Choose your style:
• Isola Bella Marine Reserve — rocky coves, snorkeling
• Giardini Naxos — sandy beach clubs & relaxed seaside bars
• Optional boat day along the coast
• Dinner in Taormina’s old town -
• Train or private car to Siracusa
• Check into a boutique stay on Ortigia Island
• Evening walk through golden-hued alleys
• Dinner overlooking the harbor (GF-aware) -
• Guided visit: Greek Theatre, Ear of Dionysius, archaeological park
• Explore Ortigia’s food market
• Afternoon at the Duomo & seaside promenade
• Optional boat tour around Ortigia
• Final Sicilian dinner on the water -
• Private transfer to Catania Airport (CTA)
• Depart Sicily filled with coastlines, culture, and slow-travel magic
