When planning a trip to Italy, most travelers gravitate toward the familiar: Naples, Rome, Florence, Venice. I explored those frontrunners, side-tripped to Pompeii, Siena and Pisa, and soaked up the entire Sicilian coastline from Cefalù to Catania. I thought I had tasted and wined my way through the best of Italy.
However, I had ignored its Adriatic Coast. A recent journey down the backside of the boot, from Venice to Italy’s easternmost point, Otranto, changed everything. These fresh experiences surpassed the old favorites.
We traveled the coastal route through seven personally undiscovered locations: medieval towns perched on craggy cliffs, picturesque fishing villages, and offshore islands. Along the way, we visited the Independent Republic of San Marino, tucked between Rimini and Pesaro. It earned its own pinpoint on my world travel map and its own stamp in my crammed passport.
I hiked up and down hills, uneven steps and cobblestoned streets, tasted the culinary delights of Puglia’s sweets, wine and olives, and lingered with the locals. Here is a glimpse of what waits along this historic slice of Italian heritage.
Burano Island
A 30-minute water taxi from Venice delivers you to Burano Island, one of the Venetian Lagoon’s main islands. Home to only 3,000 inhabitants, it offers a peaceful escape from Venice’s chaos. As we approached the main dock, color splashed across the landscape.
Brilliant pigments draped every building. Rainbow hues of turquoise, fuchsia, emerald, sunflower and violet exploded across the facades, no two adjacent buildings sharing the same color.
The island’s color-coding system dates to at least the 16th century. Fishermen, struggling against the relentless morning fog, used the beacon of color to guide them home. Even today, a request to repaint one’s house requires permission from the town council.
We strolled through the deserted kaleidoscope on a brisk October morning as the rising sun bounced off the cheerful buildings. Café owners moved tables to the sidewalk, inviting visitors to enjoy a robust cappuccino.
Burano has drawn celebrated visitors for centuries. Local legend holds that Leonardo da Vinci came here for the famed hand-stitched lace that women on the island have been producing since the 15th century, and that he purchased a piece for the altar of the Duomo di Milano.
I wandered into the intricate world of hand-stitched lace at Merletti dalla Olga on Plaza Galuppi. Mesmerized, I watched the shop owner, a master lace-maker of over 50 years, concentrate on every stitch while describing a process unchanged for 700 years.
The calm, colorful environs of Burano, topped with garlic-infused seafood cuisine, provided a welcome refresh from crowded Venice.
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Ravenna
Though not directly on the coast, this medieval city connects to the Adriatic via the Candiano Canal from Porto Corsini. The capital of Ravenna Province in the Emilia-Romagna region, the city is relatively flat, with vehicle traffic banned across much of the center.
Walkers must watch for bikes and scooters zipping through the streets; pedestrians seem an afterthought. My stroll turned into a harrowing dodge from two-wheelers.
Three things make a slight detour from the coast worthwhile. Ravenna is known for its well-preserved late Roman and Byzantine architecture, boasting eight UNESCO World Heritage sites. Among them, the Basilica of San Francesco hosted Dante’s funeral in 1321; his tomb stands in a small mausoleum directly beside it, and both travelers and locals flock here to reflect.
Since the 5th century, Ravenna has carried the title of Italy’s City of Mosaics. Visitors can explore the 1,400-year-old Basilica di San Vitale, where mosaic-tiled walls and floors remain magnificently intact. Mosaic workshops dot the city, where tiny shards of interlocking colored stone become commissioned masterpieces. The art form appears everywhere: on building facades, street signs, even house numbers.
The Independent Republic of San Marino
San Marino became my destination of superlatives. This smallest independent republic, an enclave of just 24 square miles sandwiched between two Adriatic coastal towns, is also the oldest, founded in 301 A.D., and ranks among the world’s wealthiest constitutional democracies.
You reach its lofty mountain perch by cable car. Its constitution has remained essentially unchanged since 1600. Governance falls to two coequal heads of state from opposing parties, each serving simultaneous six-month terms to ensure political balance.
I was delighted to pay five Euros for a silver national stamp glued into my passport rather than a smudged hand stamp. There is no flat land here; every step is either up or down, the ultimate goal being the summit of Mount Titano at 2,425 feet.
San Marino sits within Italy’s geographic borders, does not belong to the European Union, yet uses the Euro as currency. Its people speak and eat like Italians, but they will be quick to tell you they are not Italian.
My only recommendation: put this country on your must-go list.
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Urbino
A rival of Florence during the Renaissance and birthplace of Raphael, Urbino was a thriving hub for artists during the 15th century. Today, it is a city of contrasts.
The historic center, encircled by an expansive sandstone and brick wall, sits high above the surrounding slopes. Spectacular views unfold from atop the Albornoz Fortress and the Ducal Palace. You can walk up, though it is a steep climb. I sighed with relief to find an elevator that whisks visitors to the top for just one Euro.
Starting at the summit and walking downhill to the central car park is the only sensible way to explore without huffing and puffing.
A university town since the founding of the University of Urbino in 1506, it buzzes with the energy that only young, enthusiastic students can bring. Streets murmur with chatter as co-eds hang out at sidewalk cafés between classes.
Countless examples of Renaissance architecture dot the winding labyrinth of narrow alleys, many of those old structures now housing thousands of university students who glide up and down steep-sloped streets with ease despite book-loaded backpacks.
I loved the buzz of this medieval town, its center city very much alive.
Ortona
This small fishing village of 23,000 draws thousands of Italian summer visitors to its wide expanse of white sand beaches. For the international traveler passing through, the Battle of Ortona carries the greatest historical weight.
In December 1943, Allied troops and Nazi paratroopers fought fierce close-contact street battles here. Due to its deep port, Ortona was strategically vital to the Allied push north through Italy following the invasion of Sicily. Nearly 1,400 Canadian military casualties resulted from the fighting.
A Canadian Cemetery on the outskirts of town holds profound meaning for North American visitors. Beyond an impressive 15th-century Aragonese Castle, a 12th-century cathedral, and dramatic Adriatic views from the seafront promenade, a couple of hours is enough to take it all in.
The Tremiti Islands
A welcome stop at the archipelago of Tremiti Islands unfolded in the Adriatic. Eager to be with nature and explore coastal caves, we arrived in October when the summer throngs had gone. The shimmering, deserted waters and giant coastal pines swaying in offshore breezes felt like a reward.
The archipelago consists of five pieces of real estate, two of them merely rocks jutting from the sea. The remaining three, San Nicola, San Domino and Capraia, each deserve individual merit.
San Nicola, the second largest inhabited island accessible only by boat, offered dramatic arrival views. From shore, the eye is drawn straight up to the Abbey of St. Mary of the Sea, constructed in 1045. As we ascended, an outcropping of ancient buildings came into view. Stone fortifications have sheltered monks here since ancient times. Inside the church of Santa Maria, a wooden cross erected on mosaic-tiled floors remains the only Greek/Byzantine relic of its kind in Italy.
The cobalt sea below shimmered in the sun. A short distance away, uninhabited Capraia and its surrounding natural marine park serve scuba divers well. The wreck of a Roman ship from the 2nd century B.C. is visible from the surface through glass-clear water.
A short boat ride brought us to San Domino, the largest and most beautiful of the three. We walked through its forest of coastal pines, past deserted cottages and campsites, turquoise splashes peeking between the fir boughs at every turn. The beauty caught my breath. The privilege of travel humbled me.
Monopoli
There has to be a favorite, and Monopoli stole those honors and my heart. An important seaport on the heel of the boot dating to its Greek founding in 500 B.C., it delivered sun-kissed whitewashed buildings with clay-tiled roofs, fishermen mending their nets by the wharf, and a strolling musician playing the accordion.
Situated on the Adriatic shore in the beautiful region of Puglia, the level terrain and sandy beaches came as a delightful surprise. Secret winding alleyways begged me to get lost. Flowers tumbled from window boxes. The 1693 Cathedral urged me to linger, and I did, witnessing a local wedding.
The scenes had the hallmarks of a painting. The historic center opened to a grand piazza ringed by outdoor restaurants, cafes and trendy shops. Plates piled high with fresh seafood. The aroma of garlic and olives wafted through the air. It was my birthday, and Monopoli felt like the right place to celebrate.
The sights, sounds and tastes of that day will never wane.
Otranto
Our discovery journey ended in Otranto, the easternmost point on the Italian mainland, where the Adriatic joins the Ionian Sea and a strait separates Italy from Albania.
Its unique location made Otranto, originally a Roman city, a prize fought over for centuries by the Byzantine Empire, the Ottoman Turks, Spain and France. The Aragonese Castle and the Cathedral of Santa Maria Annunziata, consecrated in 1088, remain the historical highlights. The cathedral’s 12th-century mosaic floor, created between 1163 and 1165 by the monk Pantaleone, is one of the largest and most detailed in the world.
The city center feels vibrant with shops, restaurants and outdoor cafes, framed by views of unending sandy beaches. My favorite landscape emerged on the outskirts of town, where miles of ancient olive orchards stretched through the fertile hills.
The Road Less Traveled
Italy’s Adriatic coast rewards travelers willing to venture beyond the postcard circuit. From the painted facades of Burano to the olive-shaded outskirts of Otranto, this stretch of coastline offers a quieter, more layered Italy, one that most visitors never find.
The food is honest, the history is deep, and the towns feel genuinely lived in. If your next Italian itinerary leaves room for one detour from the familiar path, let it be this one.
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