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Italian Road Tripping

The Real Holidays team have been exploring an Italy less travelled to bring you this brilliant road trip which starts in Bologna and finishes in Tuscany.

Coast to Coast in Italy

You will discover its two coastlines, spend time at lesser-seen hilltop towns and enjoy locally produced food and wine. We’ve sought out off-the-radar family-run places to stay where owners go the extra mile to show you the best of Italy.

The Lowdown

  • Travel

    This self-guided fly-drive trip offers you the independence to enjoy the freedom of the open road.

  • Itinerary

    You’ll have detailed maps and routes of your journey, and we will plan your itinerary with stays in small properties whose owners are passionate about showcasing their region.

  • Discover hidden spots

    We have over 20 years of planning our famous fly-drives, and our first-hand experience allows us to take you to some lesser known spots.


Many aren’t well acquainted with the Emilia-Romagna region known by Italians for its medieval cities and seaside resorts.
But this area is also considered to be Italy’s culinary heartland, with capital Bologna a veritable foodie city and the birthplace of ragu, lasagne and tortellini. Beyond the restaurants are architectural highlights including the striking medieval towers of La Due Torri and Basilica di San Petronio which dominates Piazza Maggiore.

Make smart and centrally located Al Capello Rosso your base for further explorations around Emilia-Romagna. Easy day trips can take you to Ravenna to visit the beautiful Byzantine frescos that adorn the interior of many of the honeyed 6th century buildings. Epicureans may like to visit other foodie centres in the region such as Modena for its famed balsamic vinegar, and to sample prosciutto and parmigiana in Parma.

Emilia Romagna, Italy:

    Le Marche

    We think the region of Le Marche, that stretches for 100 miles alongside the Adriatic Sea is often unfairly overlooked.
    Yet it has rolling hills topped with picturesque towns that rival any Umbrian counterpart, plus a coastline littered with sandy coves backed by arresting limestone cliffs. Even more appealing is the lack of tourists, you’re unlikely to hear British spoken. Art aficionados can have their fill in hidden-away Urbino which packs a punch with its Renaissance art.

    The National Gallery features paintings by masters Titian and Raphael, who was born in Urbino in 1483. Laid-back Senigallia is a seaside town where you can find great value, freshly caught seafood. We recommend staying in one of our new discoveries: Castello di Monterado. This hilltop castle retreat, once owned by a relative of Napoleon, is grand but extremely comfortable and current owners Orlando and Kira are wonderful, warm hosts happy to share their ancestral home.

    North Umbria

    This is classic Italy at its very best. Here’s the place to soak up those hilltop towns whose names roll off your tongue as smoothly as the red wine you’ll be drinking. In the north of Umbria, be entranced by medieval town Gubbio located on the foothills of Mount Ingino where an open-air lift whisks daring travellers up the slopes for heart-quickening views. Assisi lures visitors to the Basilica di San Francesco where you can learn all about famed Saint Francis.

    Umbria’s charming capital is Perugia, a university town with a thriving culinary scene, where summer sees the annual jazz festival filling the historic squares with melodic notes. For an antidote to Umbria’s enveloping culture, spend time at Lake Trasimeno – swim, cycle and hike around the shimmering waters. Stay at Locanda del Gallo, another recent Real Holidays’ find, which has a calm, do-as-you-please vibe and tempting honesty bar.

    South Umbria

    Southern Umbria is all about the fairy-tale towns of Todi and Orvieto, the former is the kind of jaw-slackeningly beautiful place that will have you daydreaming about relocation in seconds. Orvieto has a golden-hued Gothic cathedral and a crisp white wine that you drink in atmospheric enotecas alongside cheese and meat platters. For more wine quaffing, stay at winery Locanda Palazzone – which has very stylish suites and excellent fine dining, perfect after a day’s sightseeing.


    Your trip comes to an end in Tuscany, but you can decide how long you’d like on the beach at the end of your driving holiday. You won’t be joining the masses at a crammed beach club though. Our recommendation is located near a quiet sandy cove of the Tuscan coastline. Relais Poggio Ai Santi is a rural den of tranquillity with home-grown produce forming the base of delicious meals, where views stretch to Elba and relaxation is the only order of the day.


    Speak to the team about how to start planning your own ‘coast to coast in Italy’ trip.