Italy

Paper Plane can help with any type of Italian holiday, be it a city break, a road trip through the country or a week by the beach. Get in touch to start planning your tailor-made trip.

All itineraries can be tailor-made to suit your preferences

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Featured Itineraries

The Cities

Train hop around the Italian cities.

DAYS 1 - 2 Fly into Milan to start your city hopping. A few nights at Palazzo Parigi puts you in a great location to explore this fashion filled city.

DAYS 3 - 5 In less than 3 hours, you’ll reach Venice to spend your days wandering the canal lined streets and sipping cocktails at Il Palazzo Experimental.

DAYS 6 - 8 Start your journey south to hit Florence next. Stay at Portrait Firenze for an enviable location overlooking the Ponte Vecchio. A busy 3 days to fit in wine tasting, a tour of the Duomo, biking around the city, walking through Boboli Gardens and more.

DAYS 9 - 11 A very different city but again, plenty to see as you head to Rome. Once you’ve visited the Colosseum, Pantheon and Trevi Fountain, let us arrange the best vespa tour of the city for you to touch some less-known places.

DAY 12 One night only and it’s time to eat pizza in Naples (we know the best place in town).

Como to Capri road trip

Cover the country.

DAYS 1 - 3 Fly into Milan and be whisked off to Lake Como to start your trip in the grandest way possible at Grand Hotel Tremezzo. A day on the Lake in Ruy or Batt, the hotel's Venetian motor boats is a must whilst here.

DAYS 4 - 6 A city stay next at Portrait Firenze in Florence. We can organise private viewings, a city cycling tour and a spot at the best bar in town whilst you're here.

DAYS 7 - 10 Pick up your wheels and drive into the Tuscan sunset for 4 nights of wine tasting, spa treatments and cooking classes (inc. plenty of eating) at Monteverdi.

DAYS 10 - 14 Next, head South (via Rome if you wish) to the Amalfi Coast. Your fix of perfect sunsets and Italian winding roads will be fulfilled with a stay at Monastero Santa Rosa before hopping over to Capri for a few nights at JK Place Capri to finish just as grand as you started.

Puglia

Head to the heel.

DAYS 1 - 3 A city less visited than other Italian cities and in turn, beautifully local. Spend a few nights at La Fiermontina in Lecce with days by the pool and evenings wandering around this walkable city.

DAYS 4 - 6 Jump back in your car to head even further south to Palazzo Daniele. If you can drag yourself away from this beautiful Palazzo, take the opportunity to visit nearby bays, spend a day out on the boat with a local fisherman or learn to make Puglia’s pasta Orecchiette with the house chef Donata.

DAYS 7 - 10 As you make your way to La Peschiera, be sure to stop in the whitewashed Puglian town of Ostuni for lunch. When you reach the coast, it’s time for relaxation, seafood and days at one of the many pools.