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    The Ultimate Italian Road Trip Escape: What You Should Do If You Win

    What would you do and what would you see if you won a free road trip in Italy?! Well in this post you'll find out where our guest blog contributor and avid traveler Diana Russler &  her husband Bill visited when she won our 7 Night Italian Road Trip Escape sweepstakes last year. Ya, we're jealous too! Read on to find out where you should go if you win the ultimate Italian road trip!

    There's nothing quite like the freedom of a road trip, trundling along wherever serendipity takes you. Driving across Italy in a rental car lends itself well to this type of exploring. The ever-changing succession of remote hill towns, winding mountain roads, coastlines, and castles ensures that there is always something new to see.

    As winners of a seven-day Italian road trip sweepstakes (which is part of this itinerary), there were three specific locations we were scheduled to visit - Rome, Camogli and Puglia. For the rest of our time, we wandered freely, visiting iconic landmarks and unknown corners, sampling the various regional cuisines and enjoying life on the road for a whole month.

    Looking for other things to do in Italy? Check out our other Drive to Discover guides where we explore the best road trips in Italy including a Road Trip through Tuscany for Food & Wine Lovers, an Amalfi Coast itinerary and a guide to UNESCO sites surrounding Venice.
    Driving Itinerary Distance Driving Time
    Rome to Monteriggioni 155 miles  2 hours 45 minutes
    Monteriggioni to Camogli 165 miles 2 hours 50 minutes
    Camogli to Monterosso al Mare 46 miles 1 hour 12 minutes
    Monterosso al Mare to Civitella del Tronto 356 miles 5 hours 51 minutes
    Civitella del Tronto to Vieste 186 miles 3 hours 41 minutes
    Vieste to Ostuni 169 miles 3 hours 21 minutes
    Ostuni to Rome 317 miles 5 hours 22 minutes
    Total Distance Covered: 1,396 miles 24h 52m

    Read on to Drive to Discover the adventures that await you in Italy!

    1. Rome

    Rome, Italy Rome, Italy
    The adventure starts in Rome on a beautiful sunny autumn day. No matter how many times we visit the city, there is always something new to discover or revisit. This time, recent renovations to the Trevi Fountain, Spanish Steps, Circus Maximus and other iconic treasures make Rome shine.

    Our hotel, the ultra-luxurious Palazzo Manfredi, overlooks the newly restored Colosseum. From its rooftop Michelin-starred restaurant, Aroma, spectacular sunrise and sunsets over the ancient arena, as well as mouthwatering cuisine, are a treat.

    A food walking tour of Trastevere (part of the prize) takes us through cobblestone streets with ivy-covered buildings to the neighborhood where the traditions of Roman cuisine are still preserved. Along the way, we stop at a restaurant/wine bar with a cellar that is 150 years older than the Colosseum, a trattoria with an eclectic menu and mismatched chairs, a shop specializing in pork sausages and a hole-in-the-wall selling Roman street food; fried rice balls and pizza! A cookie bakery and a gelateria round out the walk and our “meal.”


    Next stop: 2 hours & 45 minutes

    2. Montegriggioni

    Montegriggioni, Italy Montegriggioni, Italy
    Driving out of Rome is an adventure all on its own; however, we eventually find ourselves heading north to Monteriggioni. This spectacular Tuscan hill town near Siena is entirely surrounded by a wall, protected with 14 watchtowers. We make this our base for a week exploring the iconic areas of the Crete Senesi and Val d’Orcia, the wine country around Montepulciano and the Strada Chiantigiana between Siena and Florence, including a stop at the Castello di Verrazzano (home of the famous explorer) near Greve.

    Day trip ideas from Monteriggioni:
    • Greve and Castello di Verrazzano
    • Strada Chiantigiana
    • Pienza
    • Montepulciano
    • Val d’Orcia
    • Crete Senesi

    Next stop: 2 hours & 50 minutes

    3. Camogli

    Camogli, Italy Camogli, Italy
    From Monteriggioni the road takes us northwest towards Genoa. South of the city, the Riviera di Levante (Sunrise Coast) with its cliffs and bays is home to picturesque towns and villages. A hair-raising drive down the cliff road leads to the charming Cenobio Dei Dogi Hotel in Camogli. Its terrace overlooking the sea is the perfect spot to enjoy an evening aperitivo as the sun dips into the Mediterranean. Steps lead down to the beach where the water is warm enough to swim, even in October.

    From here, a short walk along the colorful seafront promenade takes us to the harbor where ferries leave for Portofino, the quintessential, most luxurious, coastal village favored by the rich and famous, whose super yachts dot the harbor.

    Day trip ideas from Camogli:
    • Genoa
    • Portofino

    Next stop: 1 hour & 12 Minutes

    4. Monterosso al Mare

    Monterosso al Mare, Italy Monterosso al Mare, Italy
    Just south of Camogli are the legendary Cinque Terre – five dramatic medieval cliff-top villages accessible only by train, ferry or on foot. Basing ourselves at the Hotel Pasquale, a delightful family-run residence on the edge of the harbor in Monterosso al Mare, we hike to the village of Vernazza and take the train to Manarola, Riomaggiore and Corniglia. Each has its special charms, and it is difficult to tear oneself away from the magnificent vistas

    Tip: This is the only village in the Cinque Terre where you can park. Many hotels in Monterosso al Mare have parking available (for a fee) but you must be sure to reserve your spot when you book your room as they go very quickly!


    Next stop: 5 hours & 51 minutes

    5. Civitella del Tronto

    Civitella del Tronto, Italy Civitella del Tronto, Italy
    In the mountaintop village of Civitella del Tronto, we are the only guests at the Hotel Zunica, housed in a 17th-century building under the brooding walls of the Fortezza, the largest medieval fortified castle in Europe. The views from our room extend from the Grand Sasso Mountain to the blue Adriatic coastline, shimmering in the morning sunlight. Considered to be one of the best in the province, the hotel restaurant serves a menu that changes with the seasons. A private three-day cooking school provides a hands-on experience shopping for fresh ingredients and then working with the chef to prepare dinner.

    Day trip ideas from Civitella del Tronto:
    • Ascoli Piceno in Le Marche
    • Gran Sasso National Park Abruzzo
    • Santo Stefano di Sessanio Abruzzo
    • Atri Abruzzo
    • Vasto Abruzzo

    Next stop: 3 hours & 41 minutes

    6. Vieste

    Vieste, Italy Vieste, Italy
    Our first stop is Vieste on the Gargano Peninsula, the spur on Italy’s boot. Built on top of the steep Pizzomunno cliffs, the city perches on a promontory jutting into the azure Adriatic.

    Basing ourselves here, we explore the area with a number of day trips, including to the magnificent Castel del Monte, a 13th century citadel and castle built by Emperor Frederick II. Trabucchi, the old, traditional, fishing contraptions dot the coastline, while the rarely visited Tremiti Islands sit a few miles offshore in the Adriatic.

    Tip: Viste is a resort town with many luxury hotels but accommodations are limited in the off-season.

    Day trip ideas from Vieste:
    • Peschici
    • Isole Tremiti - this would be a boat trip
    • Foresta Umbra
    • Mattinata
    • Trani
    • Bari
    • Castel del Monte

    Next stop: 3 hours & 21 minutes

    7. Ostuni

    Ostuni, Italy Ostuni, Italy
    Our last stop in Puglia is the fantastic Masseria Il Frantoio near the so-called “White City” of Ostuni (in the Salento region). The region is filled with fantastical, conical, stone Trulli structures, medieval castles, and beautiful white sand beaches. Olive trees, some over a thousand years old, stretch to the horizon between ancient stone walls. From here you can explore the iconic towns of Alberobello and Locorotondo as well as several coastal towns, including Ostuni.

    The Masseria is a 500-year old fortified farm, its unique rooms decorated with some of the artifacts that Armando Balestrazzi and his wife, Rosalba, found when they bought the property some years ago.

    The Masseria is a 500-year old fortified farm, its unique rooms decorated with some of the artifacts that Armando Balestrazzi and his wife, Rosalba, found when they bought the property some years ago.

    Day trip ideas from Ostuni:
    • Alberobello
    • Locorotondo
    • Martina Franca
    • Brindisi
    • Polignano a Mare
    • Monopoli
    • Lecce

    Next stop: 5 hours & 22 minutes back to Florence-Peretola Airport.

    About Diana & Bill

    Diana & BillNew York-based adventurers, writers and photographers Diana Russler and Bill Gent, delight in sharing their discoveries, especially from lesser-known parts of the world. You can follow their adventures on their blog The Winged Sandles and on their photography website Allegria Photos.


    Take the Ultimate Italian Road Trip with Auto Europe

    20000 pickups locations worldwideIf you’d like other things to do in Italy, check out our Road Trips in Italy, and if you’d like to see how much you can save on your next trip by bundling your hotel reservation and car rental, give our travel specialists a call toll-free at 1-888-223-5555. We look forward to helping you plan the ultimate trip to France, or wherever your travels take you.


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