Grand Italy with Amalfi

Italy14 days$$SpringFall

About This Trip

Footsteps tap softly on worn cobblestones as twilight settles over Piazza Navona. Street artists pack away their easels, café lights flicker on, and the first notes of a violin drift under the baroque fountains. You fall into the slow tide of the evening passeggiata, following locals past shuttered palazzi and glowing trattorias, down narrow lanes that spill out at last into the rush of the Trevi Fountain, where water pounds stone and wishes are whispered with the toss of a coin. Mornings in Rome begin early, while the city is still rubbing its eyes. The Colosseum rises pale against the sky, its arches empty of crowds for a brief, precious hour. A guide brings the arena back to life—gladiators, emperors, roaring spectators—before you move on to the Roman Forum, where fragments of columns and temples line the ancient Via Sacra. Later, an espresso at a standing bar, the clatter of cups, and a plate of cacio e pepe remind you that here, history and daily life share the same streets. North in Florence, stone towers give way to Renaissance grace. Days unfold at a gentler rhythm: frescoed chapels in the morning, the curve of Brunelleschi’s dome above terracotta roofs by midday. One afternoon, you leave the city behind for Chianti, where vines stripe the hills and cypress trees mark the ridgelines. A wine-tasting lunch stretches long—Chianti Classico in your glass, olive oil pressed from the grove outside, simple grilled meats and ribollita served at a farmhouse table overlooking the vineyards. By the time you reach Venice, the soundscape has changed. No engines, just the slap of water against brick and the creak of mooring ropes. As the sun sinks, you cradle a spritz at a canalside bacaro, watching the buildings blush gold. A gondola glides into view, and soon you’re aboard, drifting under low bridges and past crumbling facades, the city’s reflections quivering in the wake. The finale comes on the Amalfi Coast, where terraces cling to cliffs and lemon trees lean toward the sea. From Ravello’s Villa Cimbrone gardens, the Tyrrhenian stretches out in layered blues, silent and immense. Another day, a boat cuts across the water to Capri, circling limestone cliffs before slipping into the shadowed hush of the Blue Grotto, where the sea glows an electric, impossible blue. On your last evening, the coast is quiet. Lights dot the shoreline, a faint curve against the dark. From your balcony, glass in hand, you listen to the waves below and the distant hum of a passing boat, letting the days just lived settle into memory.

Trip at a glance

See the route before diving into daily details.

Arrival and Rome Passeggiata
Day 1
Arrival and Rome Passeggiata
Rome Historic Center
First espresso and lunch near Piazza Navona
Colosseum and Ancient Rome
Day 2
Colosseum and Ancient Rome
Colosseum & Roman Forum
Guided Colosseum exploration before crowds
Vatican Art and Trastevere Night
Day 3
Vatican Art and Trastevere Night
Vatican City & Trastevere
Early-entry visit to the Vatican Museums
Campo de’ Fiori and Train to Florence
Day 4
Campo de’ Fiori and Train to Florence
Florence Historic Center
Morning market atmosphere at Campo de’ Fiori
Florence Art and Duomo Views
Day 5
Florence Art and Duomo Views
Florence Historic Center
Masterpieces and corridors in the Uffizi Galleries
Chianti Vineyards and Castle Lunch
Day 6
Chianti Vineyards and Castle Lunch
Greve in Chianti
Scenic drive through the Chianti hills
Oltrarno Morning and Train to Venice
Day 7
Oltrarno Morning and Train to Venice
Venice Historic Center
Browsing artisan workshops in Florence’s Oltrarno
San Marco, Basilica, and Palace
Day 8
San Marco, Basilica, and Palace
San Marco, Venice
Morning in Piazza San Marco
Rialto Market, Spritz, and Gondola
Day 9
Rialto Market, Spritz, and Gondola
Venice Canals
Morning bustle at the Rialto Market
Across Italy to Positano
Day 10
Across Italy to Positano
Positano
Long-distance train from Venice to Naples
Positano Beach and Coastal Lanes
Day 11
Positano Beach and Coastal Lanes
Positano
Unhurried morning on Positano’s main beach
Ravello and Villa Cimbrone Gardens
Day 12
Ravello and Villa Cimbrone Gardens
Ravello
Scenic drive up from Positano to Ravello
Capri and the Blue Grotto
Day 13
Capri and the Blue Grotto
Capri
Ferry ride from Positano to Capri
Naples Flavor and Departure
Day 14
Naples Flavor and Departure
Naples
Scenic drive from Positano to Naples

Trip Highlights

Evening passeggiata from Piazza Navona to Trevi FountainGuided exploration of the Colosseum and Roman ForumWine-tasting lunch among rolling Chianti vineyardsSunset spritz and gondola ride on Venice’s canalsClifftop panoramas from Ravello’s Villa Cimbrone gardensBoat excursion to Capri and the Blue Grotto

Trip Impressions

Your Journey — Preview

14 Days
31 Activities
6 Signature Experiences
Day 1
Signature Day
Arrival and Rome Passeggiata

Arrival and Rome Passeggiata

Rome Historic Center
Rome
City Life
Romance

You land in Rome and head into the historic center, where baroque domes and narrow alleys immediately set the tone. After settling in, you ease into Italy with a quick espresso and a light lunch near Piazza Navona. As afternoon light softens, you wander the square’s fountains and street artists. After dusk, an unhurried evening passeggiata links Piazza Navona to the roar of the Trevi Fountain, where you toss your first coin before a late trattoria dinner nearby.

First espresso and lunch near Piazza NavonaGolden-hour stroll through Piazza NavonaEvening walk from Navona to Trevi Fountain
Evening Passeggiata Navona to Trevi
2 activities · afternoon–evening
Walk
Day 2
Signature Day
Colosseum and Ancient Rome

Colosseum and Ancient Rome

Colosseum & Roman Forum
Rome
Culture History

You’re out early, when the stone of the Colosseum is still pale and the tour groups thin. With a guide, the arena’s arches, underground passages, and seating tiers turn back into a roaring amphitheater. From there, you follow the line of the Via Sacra through the Roman Forum’s temples and basilicas, piecing together the city’s imperial heart. A hearty lunch near the ruins fuels a slower afternoon in the Monti district, before a classic Roman dinner close to your hotel.

Guided Colosseum exploration before crowdsStrolling the Via Sacra through the Roman ForumSlow afternoon wandering Monti’s side streets
Colosseum & Forum Through Time
3 activities · morning–afternoon
Guided TourSightseeingWalk
Day 3
Vatican Art and Trastevere Night

Vatican Art and Trastevere Night

Vatican City & Trastevere
Rome
Culture History
Romance

This morning you cross the Tiber toward the Vatican, joining an early entry into the Vatican Museums before the corridors fill. The galleries, Raphael Rooms, and finally the Sistine Chapel unfold as one long story of Renaissance ambition. After a simple lunch nearby, you step into the cool vastness of St. Peter’s Basilica, perhaps climbing to the dome for a view over Rome’s terracotta roofs. Evening belongs to Trastevere: cobbled streets, a beloved trattoria, and a relaxed wander under washing lines and lanterns.

Early-entry visit to the Vatican MuseumsQuiet time under Michelangelo’s Sistine Chapel ceilingSt. Peter’s Basilica and dome views
3 activities · morning–evening
MuseumCulturalWalk

Days 414 await in the full itinerary

Day-by-day schedules, places, and insider tips — personalized to you.