STAY

Begin your vacation with a stay at the Palazzo Portinari Salviati, an extravagantly beautiful hotel occupying a 15th-century palace in the heart of the city. The sumptuous décor of the guest suites echoes the opulence of the public spaces, with striking paintings, magnificent draperies and gilded mirrors. A night at this gracious mansion feels like an enchanting journey into the past.

DINE

Savor classic dishes in your hotel’s glassed-roofed courtyard restaurant (currently one of Florence’s most quietly beloved eateries), or try its beautiful Michelin-starred dining room, adorned with busts of Roman emperors. Nearby, several excellent wine bistros are within walking distance. These include the new Innocenti Wines Enoteca Ristorante, where you can dine in a cellar among ancient Roman foundations or on a mezzanine beneath 14th-century frescoes; La Tenda Rossa, known for contemporary Tuscan fare served in an intimate space; or Degusteria Italiana, a romantic gem of a restaurant with candlelit tables, wine-bottle-lined walls and elaborately painted ceilings.

EXPLORE

From its famed museums to its storied galleries, Florence brims with artistic treasures. For a more personal encounter with the city’s heritage, have your Andrew Harper travel advisor book a session at an artisan workshop (or two), where centuries-old crafts still thrive. Maybe observe the inner workings of a historic silk mill, concoct your own customized fragrance, or craft a bag at a leather school. When relaxation is in order, indulge in the serene luxury of your hotel’s subterranean spa.

STAY

Opened in mid-2024, in the majestic hill town of Orvieto, which is situated midway between Florence and Rome, the Palazzo Petrvs is one of the finest hotels in Umbria. The property is a designer’s paradise. The defining black and white exterior bands of Orvieto’s famed cathedral served as the inspiration behind the renovation of this 15th-century aristocratic residence. You’ll see these stripes on textiles, furniture and even the bathtubs fronting the beds in some rooms.

DINE

The hotel’s restaurant, Coro, housed within a deconsecrated church adjoining the palazzo, serves inventive seasonal menus that highlight local ingredients. The monastic vaulted dining room becomes incredibly romantic at dinner, lit by the soft flicker of candlelight. There are also several delightful establishments nearby, including Il Malandrino Bistrot and Trattoria dell’ Orso.

EXPLORE

Many travelers to Orvieto stop just long enough to visit its resplendent 14th-century cathedral, but this hill town offers much more, including a labyrinth of underground Etruscan tunnels, charming pedestrian-friendly lanes and sweeping views over the Umbrian countryside. The surrounding area is also home to first-rate wineries. The Orvieto Classico appellation excels in producing bright, textured whites rooted in traditions dating to the Etruscan era. Consider tastings at family-owned Cantine Neri and the historic Palazzone winery, housed within a handsome 13th-century stone villa.

STAY

Opened in August 2022 by a welcoming German couple, Vocabolo Moscatelli Boutique Hotel & Restaurant occupies the grounds of a 12th-century monastery. This intimate retreat, encompassing a former chapel, a piazzalike courtyard and the ancient monastery, evokes the charm of a small Italian village. Inside, the design blends the old with the new. Exposed terra-cotta bricks and timeworn beams contrast with contemporary artwork and bright color schemes, creating an ambience that feels both historic and fresh. Book a Terrace Junior Suite, for its outdoor tub and superior views.

DINE

Though there aren’t many dining options of note in the vicinity, Vocabolo’s own restaurant offers memorable tasting menus (one vegetarian, one not), plus tempting à la carte options that highlight produce sourced from the on-site kitchen garden and nearby farms. Evenings conclude around convivial nightly bonfires, where guests gather over glasses of limoncello.

EXPLORE

This peaceful estate is an ideal setting to simply unwind amid the understated beauty of the Umbrian countryside. Yet its location — less than an hour from Cortona, Perugia and Assisi — also suits those eager to discover the region. Vocabolo Moscatelli is a convenient base for visiting wineries in the Montefalco and Torgiano appellations, or for touring the fabrication workshop of Brunello Cucinelli, the “King of Cashmere.” Don’t miss a visit to his medieval hamlet, Solomeo, home to the Renaissance-style Teatro Cucinelli in the Forum of the Arts, the Church of Saint Bartholomew and an open-air amphitheater that hosts summer concerts. Truffle-hunting excursions, pottery classes in the renovated chapel at Vocabolo and horseback-riding outings can also be arranged.

STAY

For your final stop, head back toward Florence. While you could end your trip at a property downtown, consider instead a relaxing stay at the new Collegio alla Querce, Auberge Resorts Collection, set in a residential hilltop neighborhood 15 minutes northeast of Florence’s historic center. Occupying a 16th-century farmhouse-turned-boarding school, Collegio alla Querce offers majestic vistas of the city’s skyline and the Tuscan countryside beyond. Though just a short drive from the heart of town, this elegant hideaway feels far removed from the urban bustle and is utterly tranquil.

DINE

La Gamella, housed in the school’s former refectory, serves creatively presented Italian cuisine in a naturally lit dining room or on a sun-drenched garden terrace. A seasonal poolside grill specializes in pizzas and panini.

EXPLORE

Complimentary shuttle service to the Piazza della Santissima Annunziata puts the city within easy reach. But the elegant spa, inviting pool and peaceful grounds offer compelling reasons to linger.