Top 5 Places to Stay in Italy (Lodging, Hotels, etc.)

“In America, one must be something, but in Italy, one can simply be.” – Pietros Maneos

The Grand Tour, Rome, Florence and Venice, is one way to experience Italy.  An alternative is to stray from the beaten path, far from the tour buses.  Taking time away from the big cities is sure to give a glimpse of the other Italy, the one described in books and movies from long ago, life at the pace and beauty of la dolce vita.  Here are our top five places to stay:

Relais Osteria dell’Orcia, Castiglione dell’Orcia (Southern Tuscany)

Along the Via Francigena pilgrimage route, this has been a place of rest for weary travelers for centuries.  From St. Catherine, to popes, to Chaucer, countless dignitaries have trod this trail to salvation, and many took time for the healing waters of the nearby thermal baths in Bagni Vignoni.  History only means so much when traveling.  The outstanding food, wine and service from our friends Silvano, Eliano and Antonio make this place magical.  Located between the great wine towns of Montalcino and Montepulciano, while just a stone’s throw from Pienza, this is a place to visit to experience rather than just see.

Hotel Cortina, Cortina d’Ampezzo (In the Dolomite mountains, north of Venice)

A four star hotel run by the same family for 150 years, located in the best village of the Dolomites, this place is a pearl of a find.  Dinner at the on-site restaurant is fantastic, and I always enjoy learning about the area from the owners, who have seen it all over the decades.  Situated in the heart of the pedestrian district, everything is nearby, including a wonderful rails-to-trails project.  The town of Cortina might be faintly familiar, as it was the home to the 1956 Winter Olympics, and will be co-host in 2026.  For history buffs, the area is steeped in WW I history.  I enjoy taking a gondola up Mt. Cristallo and having lunch and a bit of wine at Rifugio Faloria.  

Grand Hotel Tremezzo, Menaggio, (Lake Como, North of Milan)

Four generations of our family have stayed at this spectacular hotel, and someday we will share it with the next generation.  Liz’s grandparents honeymooned at the Grand, inspiring the rest of us to visit on several occasions.  The pool, which floats on Lake Como, is certainly a highlight, as is the location.  Adjacent to the Villa Carlotta with its magnificent gardens and ferry stop, the Grand Hotel offers serenity and timelessness, with a splash of panache.  For spectacular views coupled with amazing cooking, visit La Faguria.  (Talk about farm to table, you can meet some of their rabbits and quail before dinner.)

La Tavolazza, Positano, Amalfi Coast

If location is everything, this cannot be beat.  There is no need to describe the overwhelming beauty of Positano, as so many great writers have already done so.  The comment that sticks with me is by John Steinbeck.  “Positano bites deep.  It is a dream place that isn’t quite real when you are there, and becomes beckoning real after you have gone.”  So true.  Not willing to pay the stratospheric prices of the renowned Le Sirenuse, we stayed next door at La Tavolozza, offering the same view at a quarter the price.  My favorite memory is seeing our hostess in the local parade for the patron saint’s festival, part of the church band. She wasn’t in Positano for work, she was of the town, ensuring that Positano is more than just the Instagram version of itself.  Amazing.

U Catoiu, Scilla, at the tip of the boot, within view of Sicily

Looking for history?  Something older than Rome?  Homer wrote about this town, and it is just as beautiful today.  Want something close to the water?  The waves of the Tyrrhenian Sea lap up against the wall behind the bed all night.  The balcony is over the sea.  No need for artificial sound to be lulled to sleep here.  Looking for fresh seafood?  Walk 25 meters in either direction and talk to the fisherman while they unload.  Nothing in the local restaurants has been frozen and imported.  This little B&B is run by a wonderful woman.  Is her name Felicita (happiness)?  Or is it Fortuna (luck)?  Regardless, she is the type of inspiring person that makes a vacation memorable.