Messina Gate guards the northern end of Taormina’s historic center, a stone arch that has seen both armies and tourists step beneath it. The town’s medieval walls once tied it into a full defensive circuit, fragments of which still show near the Clock Tower and Catania Gate to the south. While that southern gate was last restored in the 15th century, Messina Gate is a later arrival in its current form, rebuilt in 1808 under the Bourbons. Its style is straightforward and stately, marked by the Bourbon coat of arms on the keystone. For a time it bore the name Ferdinand Gate in honor of Ferdinand IV, but after Italian unification locals quickly reverted to the older and more practical title, Messina Gate.

Historically, this was the threshold for anyone arriving from the north. The road from Messina funneled directly through the arch into Taormina, shifting the traveler from countryside quiet into the town’s civic and commercial stage. The arch itself, while simple, carried weight as a boundary marker, a reminder that one was now entering a community both ancient and guarded.

In the present day, Messina Gate frames a different kind of entry. Instead of knights or merchants, visitors stream into Umberto Street, a lively stretch of cafés, shops, and palaces. Just inside, Vittorio Emanuele Square sets the tone with the 17th-century Church of Saint Catherine and the Corvaja Palace rising nearby. The gate no longer needs to defend Taormina, but it still delivers a sense of arrival, the kind that bridges centuries in a single step.

The Four Fountains of Taormina play a small trick on the visitor: there is only one fountain, though its four spouting corners gave rise to the plural name. Standing in Cathedral Square before the Church of Saint Nicholas of Bari, the fountain was commissioned by the town in 1635, during the Baroque makeover of Sicily under Spanish rule. It was meant to quench the thirst of residents, livestock, and passing travelers, but at the same time to show that Taormina had taste-and funds-to spare.

Two stacked basins form the heart of the fountain, the smaller inscribed with the names of the town figures who paid for it. At each corner, a column sprouts a hippocampus, a strange hybrid of horse and fish, intended to pour water into small basins. Their plumbing is erratic now, but the creatures still stand guard, frozen in mid-spout.

The centerpiece is harder to overlook: a crowned centaur, long a symbol of Taormina, raised high on a pedestal. Here, though, tradition is bent-the figure is androgynous, orb and cross in one hand, scepter in the other, stomach spilling a little generously over its midsection. Far from the sleek warriors of myth, this centaur carries the airs of sovereignty with a human touch, an emblem both serious and sly.

Once the practical hub of Taormina’s public life, the Four Fountains now serve more as a stage set for the square. Encircled by narrow lanes and old palaces, they preserve the city’s mix of myth, Baroque style, and civic pride in stone and water.

Umberto Street may carry the name of a 19th-century king, but its roots run much deeper than royal vanity projects. It follows the line of the old Greco-Roman road, the Consular Valeria road, stretching neatly between Catania Gate on one side and Messina Gate on the other. For centuries it has served as Taormina’s backbone, first for soldiers and merchants, later for nobles and pilgrims, and now for anyone with a camera or an appetite for gelato.

In medieval times, this was the town’s central spine, with alleys leading to monasteries, chapels, and palaces that announced Taormina’s status under whichever ruler happened to hold Sicily. Its architecture still reads like a roll call of conquerors: Norman arches, Gothic tracery, Renaissance refinements, and Baroque flourishes. The Palace of the Corvaja family, a 15th-century residence that mixes Arab and Norman motifs, is a standout along the route. Look closer and you’ll spot the layers of antiquity as well-the Temple of Jupiter Serapis replaced by the Church of Saint Pancras, or the Roman Odeon now lying hidden beneath the Church of Saint Catherine.

Midway along, April 9th Square opens like a stage set, complete with checkerboard paving and a terrace that frames the Ionian Sea and Mount Etna as though they were painted backdrops. Overlooking it all is the Clock Tower, or Middle Gate, linking the Greco-Roman quarter to the medieval heart of the town.

Today, Umberto Street is equal parts history book and shop window. Designer stores rub shoulders with artisan workshops, while cafés and wine bars spill out onto the flagstones. From dawn until late, the street hums with life, reminding visitors that Taormina has always known how to turn a simple road into the grandest of stages.

The Clock Tower of Taormina, standing on Umberto Street, is less a simple landmark and more a time capsule of the town’s turbulent past. Once called the Middle Tower, it was planted on the remains of Taormina’s earliest defenses from the 4th century BC. The tower itself first rose in the 7th century AD, was rebuilt in the 12th, and later folded into the third ring of medieval walls protecting the Borgo quarter by the 15th century. As one of three gateways, it drew a line between Taormina’s Greco-Roman foundations and its medieval growth.

The tower’s life has been anything but calm. Its darkest moment came in 1676, when the forces of Louis XIV battered Taormina during a siege and left the structure in ruins. Locals, unwilling to let the gap stand, rebuilt it just three years later with some extra demands. They insisted on adding a clock and a carillon of bells, ensuring the tower no longer just guarded the town but also told it when to gather, worship, or celebrate. From mayoral elections to the July 9th feast of Saint Pancras, the bells marked out civic rhythms as clearly as any decree.

Visually, the tower is an exercise in layered strength and ceremony. Its square stone base supports a midsection with four rounded arches that hold the bells, all topped by a neat conical dome with windows looking out over the town. Flanking April 9th Square and close to the church of Saint Joseph, the tower anchors Taormina’s old center. Crossing its arch today still feels like a small act of arrival-into the bustle of Corso Umberto, framed by history and with Mount Etna waiting in the distance.

April 9th Square comes with a story that is part history, part blunder. On April 9, 1860, the congregation at Taormina’s Cathedral was told that Giuseppe Garibaldi had landed at Marsala to liberate Sicily from Bourbon rule. The preacher’s announcement sparked jubilation, even though it was completely wrong-Garibaldi would not arrive for another month. The error was so memorable that when Italy’s unification was complete, the square was renamed after the date, preserving the echo of that mistaken cheer.

Before the renaming, it was known as Sant’Agostino Square, after the small Church of Saint Augustine built in 1448. That church still stands, though today it holds books instead of worshippers, serving as the town’s public library. Across the square rises the Church of San Giuseppe, a Baroque confection from the 17th century with a staircase as theatrical as its façade. Completing the ensemble is the medieval Clock Tower, rebuilt in the 1600s after French troops leveled it, once marking the dividing line between Taormina’s Greco-Roman foundations and its medieval quarter.

The square unfolds directly off Umberto Street, halfway between the town’s two historic gates, and has always been a gathering place. Cafés and shops crowd its edges, with artists ready to sketch a visitor’s likeness for the price of a cappuccino. Yet the highlight is the terrace itself: its checkerboard paving leads to a panorama stretching from the Ionian Sea across the Bay of Naxos to Mount Etna’s volcanic peak. Few places capture Taormina’s mix of drama, history, and spectacle as vividly as this plaza.

The Odeon is a small-but historically rich-Roman theater constructed in the 2nd century AD under the reign of Emperor Augustus, likely built atop the remains of an earlier Greek temple, hinting at Taormina’s layered architectural past.

Unlike the larger Greek Theatre that looms over Taormina, this Odeon was a deliberately intimate venue-designed for musical performances and literary recitals enjoyed by the city’s elite. With a covered auditorium segmented into five seating areas and topped by a semicircular brick gallery, the space could host fewer than 200 people, creating a personal, exclusive experience.

The Odeon remained obscured until an 1892 archaeological excavation revealed its structure, requiring the removal of overlying buildings that had accumulated over centuries. Today, it enjoys a charming second life as the setting for Taormina’s live nativity scene during Christmas, bringing history and holiday spirit together in a unique way.

Greek Theatre Street is Taormina’s most theatrical approach, guiding visitors from Abbey Square straight to the town’s crown jewel, the Ancient Theatre. Its stones have carried generations of footsteps since Greek and Roman times, when crowds climbed this slope for tragedies, comedies, and later Roman spectacles. Even as centuries passed and rulers changed, the street kept its role as the artery leading into Taormina’s cultural life.

By the 18th and 19th centuries, it had gained a second life as part of the Grand Tour. Poets, painters, and aristocrats wandered here, with Goethe and D.H. Lawrence among those who praised both the ruins and the views that frame them. Their rapturous accounts gave the street an almost literary reputation, binding it to the romantic imagination of Europe.

Landmarks lend the walk its character. The staircase of Timoleon rises in honor of the Corinthian general who once defended the town, staged like a Sicilian answer to Rome’s Spanish Steps and dressed with azaleas each spring. Not far away are the legacies of Taormina’s more recent past: the villa of Lady Florence Trevelyan, who left the town its celebrated gardens; the medieval Corvaja Palace, now housing the Museum of Sicilian Art and Traditions; and Cuseni House, an Art Nouveau villa that hints at Gaudí in its curves. The Hotel Timeo, a 19th-century favorite of visiting elites, still watches over the street with quiet grandeur.

Today, Greek Theatre Street is more than a passage-it is an unfolding sequence of shops, cafés, and glimpses of sea and mountain, with the Ancient Theatre waiting at the end and the fortress of Mount Tauro towering above. It feels less like a walk and more like a rehearsal for the spectacle ahead.