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Begin your Emilia-Romagna adventure by stepping into Bologna’s monumental Piazza Maggiore, the pulsating heart of the city. Spend the morning marveling at the Basilica di San Petronio’s imposing Gothic facade, its intricate brickwork glowing warmly in September’s gentle sun. Wander through the square as local vendors arrange fresh produce and cheese, absorbing the city’s rhythms and perhaps savoring a cup of rich Italian espresso at one of the historic cafés overlooking the piazza. The lingering scent of freshly baked crescentine bread draws you along shaded porticoes towards medieval landmarks.

Continue to the iconic Due Torri — Torre degli Asinelli and Torre Garisenda — symbols of Bologna’s medieval strength and ambition. Ascend the Torre degli Asinelli’s 498 steps for a breathtaking panorama of red rooftops stretching to the distant Apennines; the crisp September air enhances visibility, letting you see rolling hills beyond the city limits. Descending, delve into the labyrinthine streets beneath the porticoes visiting small artisan shops where you might pick up handmade ceramics or local balsamic vinegar as souvenirs.

As the afternoon light softens, meander to the Quadrilatero Market district, a bustling maze of alleyways rich with culinary treasures. Here you can sample Parmigiano-Reggiano cheeses matured in nearby dairies and succulent mortadella, an Emilia-Romagna specialty. A stop at Tamburini, a historic gastronomia, offers the opportunity to revel in traditional coppa and fresh pasta. End your day with an aperitivo in a lively piazza bar, watching the city’s evening transformation as the streets fill with locals and travelers alike.

Start your morning in Modena’s historic center wandering the Piazza Grande, a UNESCO World Heritage Site framed by the Romanesque Cathedral of Modena. Allow yourself to be captivated by the intricate stone carvings and sculptures on the cathedral’s facade as the sunlight filters through the surrounding arcades. From the square, stroll to the adjacent Ghirlandina Tower, climbing its steps to take in the quiet city streets before the day crowds gather.

Next, dive into Modena’s culinary heritage with a visit to Acetaia Pedroni, an artisan balsamic vinegar producer located just a short 15-minute taxi ride from the city center. Here, you’ll learn about the century-old process of creating traditional balsamic vinegar, tasting varieties aged from 12 to over 25 years. The rich, complex flavors provide a sensual connection to the region’s land and tradition that is uniquely Modenese.

In the afternoon, shift gears entirely toward adrenaline with a visit to the Ferrari Museum at Maranello, a 20-minute drive from Modena. The museum presents a stunning collection of iconic Ferrari cars and chronicles the innovation and passion behind Italy’s legendary supercar brand. Engage with interactive exhibits and soak in the atmosphere of speed and precision engineering. After your visit, consider taking a short scenic drive through the Emilian countryside, where vineyards and rolling hills spill color under the warm September sun, perfect for a sunset photo moment.

Return to Modena’s city center in the evening to enjoy its intimate Trattorias and small piazzas filled with local warmth and lively conversation, relishing the perfectly balanced Emilia-Romagna cuisine.

Begin your day at the UNESCO-listed Basilica di San Vitale, where the dazzling mosaics depict biblical scenes in vivid jewel tones, preserved perfectly across centuries. The morning light enhances the shimmering gold tesserae creating an almost otherworldly glow that envelopes the interior. Interior silence invites contemplation, as your eyes trace the intricate artistry telling sacred stories in mosaic symbolism unique to Ravenna.

Just a short five-minute walk leads you to the Mausoleum of Galla Placidia, a more intimate jewel box covered in breathtaking mosaic patterns. Its jewel-like ceiling illuminates with sunlight filtering through the clerestory windows, inviting you to absorb this jewel of early Christian art in serene stillness. Then explore the Basilica di Sant’Apollinare Nuovo, another gem showcasing Ravenna’s mosaic mastery in frescoed narrative scenes of saints and martyrs.

For lunch, find a local Osteria in the historic center that serves piadina romagnola, a traditional thin flatbread stuffed with local meats and cheeses, perfect for filling up after morning explorations. In the afternoon, stroll through the narrow lanes toward the Dante Alighieri Tomb and the nearby Piazza del Popolo, absorbing the relaxed charm of Ravenna, including stops at specialized artisan shops where you can discover handcrafted mosaics or local ceramics.

As the day winds down, visit the tranquil Parco della Resistenza, a green refuge perfect for a leisurely walk or a peaceful rest, surrounded by foliage slowly transitioning into autumnal hues in September.

Kick off your day with a refreshing morning walk along Rimini’s famous beachfront, where the Adriatic waves lap softly onto golden sands and charming wooden piers stretch into the sea. September offers pleasantly warm weather and lighter crowds, perfect for a peaceful seaside escape while watching local fishermen cast their nets or early risers jogging along the shore.

Walk into Rimini’s historic heart to visit the Arch of Augustus, an imposing Roman triumphal arch built in 27 BC and the oldest surviving Roman arch in Italy. Surrounding it, cobbled streets open to Piazza Cavour, where you can pause for coffee at a café terrace brimming with local life and observe the architectural blend of Renaissance and Baroque buildings.

Head to the nearby Tempio Malatestiano, a Renaissance cathedral designed by Leon Battista Alberti that harmonizes medieval elements with Renaissance humanism. Admire the unfinished marble façade and explore the interior art commissioned by the Malatesta family, discovering frescoes by Rimini’s own Piero della Francesca.

In the late afternoon, venture out to the scenic Borgo San Giuliano district. Once a fishermen’s neighborhood, its alleys are now vibrantly painted with murals that capture Rimini’s culture and history, offering a perfect backdrop for photography or romantic exploration. As evening falls, consider indulging in local Romagna seafood specialties at a nearby trattoria, with views of the illuminated harbor making for an unforgettable dining experience.

Begin your day with a peaceful visit to the Parco Ducale, a vast green expanse perfect for wandering amid sculpted gardens and tree-lined paths where the autumn light casts long shadows. Adjacent is Palazzo della Pilotta, an imposing Renaissance palace housing the National Gallery, Teatro Farnese, and the Teatro Regio, showcasing Parma’s artistic grandeur and history. Absorb art and architecture at your own pace, letting the quiet resonate.

Afterwards, move on to visit a nearby Parmigiano-Reggiano cheese dairy such as Caseificio San Pier Damiani, located a scenic 20-minute drive from Parma’s center. Experience firsthand the traditional cheese-making process that crafts the world-famous Parmesan, complete with tastings that celebrate the complex nuttiness and crystalline texture of this emblem of Emilia-Romagna’s culinary pride.

Return to the historic center for a relaxed afternoon exploring Parma Cathedral and the Baptistery with their stunning medieval frescoes and pink Verona marble architecture. The ornate interior details invite you to linger, appreciating the intertwining of spirituality and artistic mastery typical of the city.

Conclude your day in the aromatic embrace of Parma’s local trattorias, where farms-to-table practices shine through fresh pasta dishes like tortelli d’erbetta, making for an unforgettable gastronomic farewell to the city.

Depart from Bologna in the morning for a 45-minute drive to the village of Brisighella, a picture-perfect medieval town known for its three distinctive towers and charming pastel houses. Meander through cobbled lanes beneath ancient porticoes, absorbing the timeless atmosphere and stopping at local shops selling olive oil and handmade ceramics. Climb to the Via degli Asini, a captivating elevated path offering stunning views over the lush hills and vineyards.

Next, continue a short 20-minute drive to a family-run winery in the Colli Bolognesi region, such as Fattoria Zerbina. Here, engage in a warm and authentic wine tasting experience featuring Sangiovese and Pignoletto wines, complemented by local salumi and focaccia. The winemakers’ stories infuse the tasting with deeper appreciation, and the rustic cellar setting immerses you in the region’s viticultural traditions dating back centuries.

Spend the afternoon exploring the gentle hills by hiking or renting bicycles with routes that meander past olive groves, sunflower fields, and quaint farmhouses. Pause atop panoramic lookouts to absorb views of the verdant landscape under the soft September sun, where the golden light makes the vines glow and invites cherished moments of contemplation and shared wonder.

Return to Bologna in the early evening, concluding your trip with a relaxed dinner in a cozy trattoria near your accommodation, reminiscing about the elegance, history, flavors, and adventures that have made your Emilia-Romagna escape truly unforgettable.