4 days, 3 nights · Best for Culture seekers and food lovers exploring lesser-known Italian regions
Emilia Romagna and Marche Semi-Escorted Tour
From Milan to Ravenna, discover Parma’s flavors, Bologna’s towers, San Marino’s history and Urbino’s Renaissance art on a journey through Italy’s culinary and cultural heart.
Your Adventure Starts Here
This is a starting point. Change the nights, choose the style of hotel, add the experiences you want. Your planner takes it from there.
Stop 1Bologna, Emilia Romagna
Bologna
Culinary capital and Renaissance art in Parma
Your escort meets the group in Milan at 8:30 AM for the drive into Emilia Romagna, where Ferrari engines roar and regional kitchens turn out Italy's most prized exports. The morning stop is Parma, a compact city known beyond Italy for prosciutto di Parma and wheels of Parmigiano Reggiano but rich enough in painting, theater and architecture to hold you longer. You walk the historic center, visit the Teatro Farnese, and find time for lunch among the porticoes before continuing east to Bologna for the night.
Arranged for you: We arrange your small-group tour with escort, private coach transport from Milan to Bologna via Parma, sightseeing in Parma's historic center including Teatro Farnese, and one night in Bologna.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Bologna
-
Private Parmigiano Reggiano and prosciutto tasting Day Trips · Half day
Visit a working dairy and curing house to see traditional production and taste the results.
-
Cooking class in a Bolognese kitchen Day Trips · Half day
Learn tagliatelle, tortellini and ragu under the guidance of a local cook.
-
Private visit to a Lambrusco cellar Day Trips · Half day
Tour a family winery in the hills and taste sparkling reds with the producer.
-
Bologna and Ducati Museum Shore Excursions · Tour in a DayFrom medieval Bologna to Ducati horsepower, an 8-hour day of history, local lunch, and Italian engineering legend.
-
Bologna and Maranello with Ferrari’s Museum Tour Shore Excursions · Tour in a Day
This tour of Bologna and Maranello with Ferrari’s Museum tour offers history, culture and racing history, it’s an ideal excursion for auto fans, as well as those who want to experience past and current Italian culture
Day by day in Bologna
Meet and greet with your tour group at 8.30 AM in a designated meeting point in Milan city center and depart to Emilia Romagna, famous for its breathtaking landscapes, artistic culture and culinary excellence, it is also where one of the most potent automobiles in the world comes from, the Ferrari. Arrival in Parma, most famous with foreigners for its delicious “prosciutto di Parma” and “parmigiano reggiano” cheese, its scenery is a jewel to discover marked by its remarkable artistic heritage. You will visit the historic center admiring the Teatro Regio (Royal Theater), the Cathedral and Palazzo del Governatore. Time at leisure for lunch before departing to Bologna. Capital of the region and synonym of art and culture, Bologna is recognized as a “UNESCO creative City of Music”. In the center surrounded by medieval palaces, you will visit the impressive Basilica of St. Petronius and Torri degli Asinelli harmoniously blending with the modernity of this fascinating city. Overnight at the hotel.
Stop 2Ancona, Marche
Ancona
Adriatic coast and the republic of San Marino
After breakfast the coach climbs inland to San Marino, the oldest surviving sovereign republic in Europe and an independent state within the Italian Peninsula. You visit La Rocca, the main defensive tower, and walk Mount Titano before breaking for lunch. The afternoon route descends to the Adriatic and Pesaro, a seaside city in Marche with a Renaissance core: Palazzo Ducale, Piazza del Popolo and other sites that reveal how coastal trade built inland taste. You overnight in Ancona, the regional capital founded by Greeks and later expanded by Rome.
Arranged for you: We arrange private coach transport from Bologna to Ancona via San Marino and Pesaro, sightseeing in San Marino including La Rocca and Mount Titano, a stop in Pesaro's historic center, and one night in Ancona.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Ancona
-
Private boat tour of the Conero coastline Day Trips · Half day
Cruise limestone cliffs and hidden coves with stops for swimming and lunch.
-
Wine tasting in the Verdicchio hills Day Trips · Half day
Visit a hillside estate to taste white Verdicchio dei Castelli di Jesi with the winemaker.
-
Market visit and cooking lesson in Ancona Day Trips · Half day
Shop with a local chef for Adriatic fish and vegetables, then prepare a regional lunch.
Day by day in Ancona
Breakfast at the hotel followed by departure to San Marino. The oldest surviving sovereign republic in Europe, it is an independent country within the Italian Peninsula. You will visit some of the capital’s most symbolic monuments such as La Rocca- the main defensive tower and Mount Titano. Time at leisure for lunch followed by afternoon departure to Pesaro. Located in one of Italy’s most geographically beautiful regions, Marche, the seaside city of Pesaro has a charming historic center with attractive Renaissance sites like the Palazzo Ducale, Piazza del Popolo and magnificent Rocca Costanza (Castle). Continue to Ancona for an overnight stay.
Stop 3Ravenna, Emilia Romagna
Ravenna
Byzantine mosaics and Renaissance Urbino before Milan
You drive north from Ancona into the morning, stopping first at the capital to see the Arch of Trajan, Piazza del Papa and the monumental Fontana delle Tredici Cannelle, a fountain cut with thirteen spouts. The route then climbs west to Urbino, where Renaissance architecture earned UNESCO recognition and Raphael was born. You walk the Palazzo Ducale and the painter's house, break for lunch, and continue to Ravenna for the night. The following morning brings a tour of the city's early Christian and Byzantine monuments: churches, baptisteries and mausoleums decorated with mosaic work so fine that UNESCO protects the ensemble. After lunch the coach returns to Milan, where the tour and our services end.
Arranged for you: We arrange private coach transport from Ancona to Ravenna via Urbino, sightseeing in Ancona and Urbino including Palazzo Ducale and the house of Raphael, one night in Ravenna, a morning tour of the city's Byzantine mosaics and UNESCO sites, and return transport to Milan.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Ravenna
-
Private mosaic workshop with a local artisan Day Trips · Half day
Learn Byzantine techniques and create a small piece to take home.
-
Dante walking tour in Ravenna Day Trips · Half day
Follow the poet's final years to his tomb and the places he frequented.
-
Piadina cooking class and market visit Day Trips · Half day
Master the flatbread of Romagna with a local cook after shopping for fillings.
-
Private visit to a traditional ceramics studio in Urbino Day Trips · Half day
See maiolica production and meet the painters who decorate each piece by hand.
-
Ravenna and Faenza Tour Shore Excursions · Tour in a Day
UNESCO mosaics in Ravenna, artisan ceramics in Faenza, an 8-hour deep dive into Emilia-Romagna’s most dazzling arts cities.
-
Ravenna City Tour Shore Excursions · Tour in a DayStep into a living mosaic, discover Ravenna’s UNESCO masterpieces and the dazzling Mausoleum of Galla Placidia in just four unforgettable hours.
Day by day in Ravenna
Breakfast at the hotel and departure to Ancona, capital of the Marche. This port city was first founded by the Greeks and later developed by the Romans is home to fascinating sites like the Arch of Trajan, Piazza del Papa and the monumental Fontana delle Tredici Cannelle (Fountain of the Thirteen Taps). Proceed to enchanting Urbino where you will have time at leisure for lunch. You will visit its historical center, a UNESCO world heritage site due to its impressive Renaissance architecture like the Palazzo Ducale, the house of Raphael- the famous painter, and the Cathedral. Continue to Ravenna for an overnight stay.
Day 4
Ravenna, Milan
Breakfast at the hotel followed by a tour of this beautiful city. Its ancient Eastern heritage has left its biggest mark in its churches, baptisteries and mausoleums decorated with the most impressive Byzantine mosaic art which collectively have been recognized as UNESCO heritage. Time at leisure for lunch. Proceed to Milan where the tour, and our services, will end.
Why plan with Trips 2 Italy?
Designed around you by Italian-born planners
Guides, drivers and boats for your party alone
Hand-selected hotels in every destination
Local English-speaking guides who know their city
Met at the airport, private transfers throughout
Testimonials
Hear from travelers who have planned Italy with us
They took the time to understand our preferences and designed an itinerary that was comfortable, personalized, and enjoyable. They offered thoughtful recommendations while never being pushy.
We missed our connecting flight in Munich. I had just got through customs and was looking up the number to call when Trips 2 Italy called me. They told me exactly what to do and they already knew what flight we had been rebooked on.
Ready to make it yours?
Send us this adventure with your changes. An Italian-born planner builds the first full draft and calls you to walk through it.
Or call 1-866-464-8259
Questions travelers ask
What destinations does this package visit?
Over 4 days this journey brings you to Bologna, Parma, Ravenna, Milan, Ancona, Pesaro, and San Marino. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How is transportation handled on this trip?
Transportation is arranged as part of the itinerary, with comfortable train segments between the cities and vehicle transfers where they serve you best. Every connection is planned for you, so you can focus on the scenery instead of the logistics.
Who will enjoy this itinerary most?
It suits travelers who enjoy the ease of an escorted experience, with sightseeing arranged and a group to share it with.
Can we tailor this trip to our wishes?
Yes. This sample itinerary is a starting point, and every Trips 2 Italy package is fully customizable. Your travel consultant will adjust the destinations, hotel category, pace, and experiences to fit your plans. A minimum of 2 travelers applies.
When is the best time to take this trip?
The package is available all year around on request. Spring and fall offer mild walking weather and lighter crowds at the major sights, summer brings long lively evenings, and winter rewards travelers with quieter museums and festive streets.