Italy rewards fewer stops. A week split between a lake and the sea, with a few nights in Rome or the Tuscan hills at either end, almost always beats a different hotel every night. Here are the places we would stay on Lake Como, the Italian Riviera and the Amalfi Coast, two bookends in Rome and Tuscany, and how to join them up. All of them are on our Europe list.
The two hotels sit a few kilometers apart on the western shore, near Como itself, and they suit different people.
Villa d'Este in Cernobbio was built in the 1560s as a cardinal's summer residence and has been a hotel since 1873. It is the traditional choice: formal service, a large historic park climbing the hill behind, and the famous floating pool on the lake. It is a bigger hotel with more going on, which suits families and anyone who likes a full-service grand hotel. It is also the easiest of the great lake hotels to reach from Milan.
Passalacqua in Moltrasio is an 18th-century villa that opened as a hotel in 2022 with 24 rooms, run by the De Santis family of Grand Hotel Tremezzo. It feels like a private house, with frescoed rooms, terraced gardens running down to the water and the hotel's own boats at the dock. It suits couples and small groups who want quiet more than facilities. With so few rooms, it fills first.
If you want the classic lake hotel with everything on site, choose Villa d'Este. If you want to feel like a house guest, choose Passalacqua. Three nights is right for either, with a day on the water to Bellagio and the gardens of the central lake.
Splendido, A Belmond Hotel began as a 16th-century Benedictine monastery and sits on the hillside above Portofino's harbor. Most rooms and the terraces look straight down over the bay. Martin Brudnizki's studio recently redesigned the interiors, and a shuttle runs down to Splendido Mare on the piazzetta, so you get the quiet of the hill and the harbor at night. Days are for boat trips along the coast, walks on the Portofino headland and long lunches.
Portofino has no station of its own. The nearest is Santa Margherita Ligure, about five kilometers away, with a bus, taxi or, in the warmer months, a short boat ride into the village. Genoa airport is about an hour by car. Two or three nights here is plenty.
Le Sirenuse opened in 1951 with eight rooms in the Sersale family's villa in Positano and is still run by the family, now with 58 rooms. It sits in the middle of town, looking across the stacked houses to the sea, and the pool terrace is where everyone ends up in the afternoon. Days are for boats to Capri, the coast road to Amalfi and Ravello, or lunch at the family's new beach club, Le Sirenuse Mare in Nerano.
Positano is steep and full of steps, and it is crowded in July and August, so it is not ideal for anyone with limited mobility. The usual way in is by car from Naples, about an hour and ten minutes from the airport. Three or four nights is the right length.
Most trips to Italy start or finish in Rome. Hotel de Russie sits on Via del Babuino between Piazza del Popolo and the Spanish Steps, with a terraced garden climbing toward the Pincio. You can walk to Villa Borghese and the center, and lunch in the garden is the best way to recover from a morning of sightseeing. Two or three nights is enough for a first look.
Castello di Casole, A Belmond Hotel is a restored castle at the center of a large estate in the hills west of Siena, with vineyards, olive groves, a spa in the old wine cellar and room to spread out. Siena is about 40 minutes away and Florence about an hour, with San Gimignano and Volterra close by. It works best for three or four nights, with a car or a driver for day trips.
Pick two or three bases, not five. These are the combinations we suggest most often.
Italy's high-speed trains make the long legs easy. Rome to Naples takes about an hour and ten minutes, and Florence to Rome about an hour and a quarter. From Naples, a private car to Positano is far easier than juggling ferries and luggage. Milan to Como San Giovanni takes about 40 minutes on the regional train, though with luggage a car from the airport is simpler. Santa Margherita Ligure is about two hours from Milan by direct train. For Tuscany, plan on a driver or a rental car from Florence or Siena, since the castle is in open countryside.
Between the lake and Portofino, or Tuscany and the coast, we usually book a private driver. It costs more than the train, but it saves changes with bags and lets you stop for lunch on the way.
This matters more than people expect. Most of these hotels close for part of the year:
Exact dates change each year, so we confirm them before planning around a particular hotel. In practice, May, June and September are the sweet spot for a trip that includes the coast, when everything is open and the crowds and heat are lower than in July and August. For more on timing, read Europe in the Shoulder Season, and for why we plan around fewer bases, see why we build every trip from scratch.
If you would like help planning a trip to Italy, get in touch.
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