14 Day Romantic Italy

After arriving in Venice, you’ll be met by your private guide and brought into the city by private boat along the Grand Canal. Arriving by water is one of the best ways to experience Venice for the first time, passing palaces, churches, bridges, and boats moving through the canals as you enter the historic center.

After checking into your accommodation, head out on foot with your guide to begin exploring the city. Walk through narrow streets and small squares before reaching the Rialto Bridge, one of Venice’s best-known landmarks and one of the main crossing points over the Grand Canal.

Spend the evening walking beside the canals or stopping for dinner at a local restaurant overlooking the water. Venice is especially enjoyable in the evening once many of the daytime crowds begin to disappear.

This morning, head out with your private guide to explore the area around St Mark’s Square, the main center of Venice. Spend time in the square before visiting St Mark’s Basilica, where you’ll see the mosaics, domed ceilings, and detailed interior that made it one of the most important churches in Venice. 

Continue next door into Doge’s Palace, where your guide will explain how Venice was governed during the height of the Venetian Republic. You’ll also pass through the Bridge of Sighs, connecting the palace to the old prison.

The rest of the afternoon is spent walking through central Venice, crossing small bridges, following canals, and stopping at cafés or wine bars along the way before returning to your accommodation later in the day.

Leave Venice by private boat and head into the Venetian Lagoon to visit two of the area’s best-known islands.

Your first stop is Murano, where you’ll visit a working glass workshop to see traditional Venetian glassmaking still carried out by hand. Afterward, spend time walking through the quieter streets and canals around the island.

Continue by boat to Burano, one of the most recognizable islands in the Venetian Lagoon because of its brightly painted houses and small canals running through the village. Walk around the island with your guide, passing local homes, fishing boats, bakeries, and small cafés before returning to Venice later in the afternoon. 

This morning, your private guide will drive you from Venice to Verona. After arriving, head into the center of the city to explore the old town on foot, walking through historic streets, open piazzas, shopping areas, and café-lined squares around the center of Verona. 

Visit Juliet’s Balcony, one of the city’s most famous landmarks, before continuing through Piazza delle Erbe and nearby streets filled with cafés and restaurants. Verona works especially well as part of a romantic Italy itinerary because the city feels smaller and quieter than Venice, Florence, or Rome while still having plenty to explore.

Spend the evening enjoying dinner in the center of Verona before returning to your accommodation.

Today, your private guide will take you south into Tuscany toward Florence. After arriving and checking into your accommodation, head into the historic center to begin exploring the city on foot.

Begin in the center of Florence around the Duomo, where your guide will show you the cathedral, the Baptistery, and the surrounding streets and piazzas around the heart of the city. From here, continue on foot toward Piazza della Signoria and Palazzo Vecchio before walking through the nearby streets around the Uffizi Gallery. 

Later in the day, cross the Ponte Vecchio and spend time walking along the Arno River before stopping for dinner in one of Florence’s local neighborhoods.

Today, your private guide will take you to some of Florence’s best-known galleries and food areas. Begin at the Accademia Gallery to see Michelangelo’s David before continuing through the historic center on foot.

Along the way, stop at local food markets, bakeries, wine bars, and cafés spread throughout Florence’s older streets. Compared with some of Italy’s larger cities, Florence is easy to explore slowly on foot, with many of the main landmarks sitting close together.

The afternoon stays flexible depending on your interests, whether you’d prefer more galleries, shopping, or time sitting in one of the city’s piazzas with wine or coffee.

Today, leave Florence behind for the day and head into the Tuscan countryside with your private guide. The drive takes you through vineyard areas, olive groves, and smaller hill towns spread across the region before arriving in Siena.

After arriving, explore Siena on foot with your guide. Walk through the old streets toward Piazza del Campo, the large square at the center of the city, before continuing past local cafés, bakeries, and small shops around the historic center. You’ll also see Siena Cathedral and some of the smaller streets branching away from the main piazzas.

Later in the afternoon, continue through the countryside with stops in smaller Tuscan towns or at a local winery before returning to Florence in the evening.

Today you’ll leave Florence behind and continue south toward Rome with your private guide. After arriving and checking into your accommodation, begin exploring the historic center on foot.

Walk between some of Rome’s best-known landmarks, including the Spanish Steps, Trevi Fountain, and Piazza Navona, while your guide explains the history behind the city’s streets and buildings.

In the evening, spend time walking through Rome after dark, when many of the piazzas and monuments become quieter and more atmospheric.

This morning, visit Vatican City with your private guide, starting at St Peter’s Basilica before continuing into the Vatican Museums and Sistine Chapel. As you move through the museums, you’ll see famous paintings, sculptures, ceiling frescoes, tapestries, and long gallery halls leading toward Michelangelo’s Sistine Chapel ceiling. 

Later in the day, head across the city toward the Colosseum for a guided visit inside one of the most famous landmarks in the world. Your guide will explain how gladiator events once took place here and how the structure was built during the Roman Empire.

After the tour, continue through the surrounding streets with views across the Roman Forum before returning to your accommodation later in the evening.

This morning, your private guide will drive you south from Rome toward the Amalfi Coast. On the way, stop in Naples to spend some time around the historic center and waterfront areas before continuing along the coast toward Sorrento later in the day. 

The drive becomes more scenic as you approach the coastline around Sorrento, with sea views, cliffs, and smaller coastal towns appearing along the route.

After arriving in Sorrento, spend the evening walking around the town center or having dinner overlooking the Bay of Naples.

Today, your private guide takes you along the Amalfi Coast, following one of Italy’s most famous coastal roads. The route passes cliffside villages, beaches, viewpoints, lemon groves, and marinas overlooking the Mediterranean.

Stop first in Positano, where steep streets lead down toward the beach and waterfront cafés. Spend time walking through the town before continuing onward to Amalfi later in the day.

In Amalfi, explore the town center, cathedral area, and waterfront before stopping for lunch beside the sea.

Today, your private guide will drive you up from the coastline to Ravello, a small town high above the Amalfi Coast known for its gardens, quiet streets, and views back across the sea. After arriving, spend time exploring the town center on foot before visiting some of Ravello’s historic villas and garden terraces. 

Visit Villa Rufolo and its gardens before spending time walking through Ravello’s quieter streets, small piazzas, and cafés overlooking the coastline below.

The rest of the afternoon stays flexible depending on your interests, with time for lunch, more coastal stops, or additional time around the Amalfi Coast.

This morning, take a boat across to Capri with your private guide. After arriving on the island, spend the day exploring different parts of Capri, including the marina area, the main town, local cafés, shopping streets, and viewpoints looking back across the coastline and surrounding sea. 

Depending on the weather and timing, there may also be opportunities for short boat rides around parts of the island to see cliffs, caves, and smaller beaches from the water.

Return to the Amalfi Coast later in the afternoon for your final evening in southern Italy.

Before leaving the Amalfi Coast, spend some final time in Sorrento with your private guide, walking through the town center, stopping at local cafés or shops, and enjoying the waterfront before your departure transfer later in the day. 

Walk through the town center, stop at cafés or local shops, and enjoy some final time beside the sea before leaving the Amalfi Coast behind.

After your time in Sorrento, your private guide will transfer you to the airport or onward destination, bringing your romantic Italy journey to a close.