Ravenna

Sure, Italy may overflow with glamorous Renaissance tombs and gilded monuments, but Dante Alighieri-chronicler of Hell itself-rests modestly in Ravenna's city center, exiled even in death from his beloved Florence. His humble tomb-surprisingly understated for a poet who dared to imprison popes, royalty, and enemies in eternal torment-is tucked into a quiet corner where tourists often stumble upon it accidentally, distracted by gelato shops and souvenir stands hawking dubious Inferno fridge magnets nearby. Swing by early-ish in the morning-preferably before caffeinated tour buses disgorge selfie-stick-wielding pilgrims-in order to savor a few uncrowded moments of literary contemplation (or irreverently wonder why Florence, after seven centuries, still can't convince Ravenna to hand Dante back). No ticket cost means budgeting is minimal, but leave yourself enough euros for a suitably decadent espresso afterward. Bring a copy of the Divine Comedy if you're feeling theatrical, sunscreen if your sins lean toward vanity, and an ironic smile considering Dante spent half his career skewering human vanity in verse. Even if your literary appreciation begins and ends with Dan Brown's pop-culture puzzles, visiting Dante's tomb provides priceless bragging rights: after all, how often can you casually mention you've visited the guy who's given generations nightmares and genius metaphors for life's daily humiliations?

If your idea of celebrating the sea involves slurping briny mollusks, sipping wine served by sun-baked fishermen who boast epic tales (half of which might be true), and navigating lively throngs of decidedly enthusiastic Italians, then the Festa del Mare in Marina di Ravenna is your seafood-soaked paradise. Held each July in this breezy Adriatic neighborhood, the event is part gastronomic carnival, part salty maritime homage-imagine Hemingway throwing a party for Poseidon, all orchestrated by jovial Emilia-Romagna locals obsessed with the freshest catch. Show up in the early evening-around sunset-when the sardines hit the grill and the crowds start swelling like waves at high tide. Plan a couple weeks ahead, since even spontaneous Italians prefer their seafood sprees organized, and bring along €30-50 to indulge properly in fried calamari, grilled skewers, and crisp local whites that flow freely into cheerful cups. A healthy appreciation for chaos-and some wet wipes-is highly recommended. Even if your shoes end up soaked in sea spray or dripping with clam juices, the Festa del Mare is worth every messy moment, if only to gleefully recount the night you feasted like Neptune, elbow-to-elbow with tipsy sailors, beneath the glowing lights of a salty Italian summer.

Nestled stubbornly atop Monte Titano like a medieval exclamation mark, San Marino-one of Europe's oldest, tiniest, and most fiercely independent microstates-is the kind of absurdly picturesque place that makes you wonder if you've accidentally wandered onto a very elaborate movie set. Spending the night here feels slightly rebellious, like sneaking backstage at history's most charming theme park after closing hours. Arrive by late afternoon when day-trippers scuttle away, leaving cobblestone streets blessedly quiet, illuminated only by warm lamps, murmured laughter from cozy trattorias, and the occasional local cat giving you a judgmental stare. Book your stay a month or two ahead to snag accommodations with unbeatable views that won't drain your wallet-around 80 to 150 euros should secure you comfort and subtle charm. Pack comfortable shoes (those alleyways were designed well before any ideas about urban comfort arose), layers for the unpredictable hilltop breezes, and your curiosity for the quirky museums dedicated bizarrely and unapologetically to torture instruments and ancient armaments. At sunrise, drag yourself awake for a solitary stroll along the ramparts; you'll feel as though you've stumbled upon Europe's best-kept medieval secret, though your Instagram followers definitely need to know. Even if tiny nations perched improbably on rocky crags aren't your usual vacation choice, San Marino is worth it-because how many people can casually drop "overnighted in a microstate" into conversation at next week's dinner party?