17 days in Italy Itinerary

17 days in Italy Itinerary

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Route & dates

17 days in Italy Itinerary

Start: George Town, Grand Cayman
Fly + Drive:  19​h 45​min
1
Positano
— 3 nights
Drive:  3​h 15​min
2
Capri
— 3 nights
+4
Ferry + Shuttle + Fly + Foot + Train:  6​h 15​min
3
Portofino
— 3 nights
Drive:  3​h 15​min
4
Bellagio
— 3 nights
Drive + Fly:  20​h 30​min
End: George Town, Grand Cayman

3
nights
Positano

Positano ©
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Change things up with these side-trips from Positano: Amalfi (Duomo di Sant'Andrea, Wine Tours & Tastings, & more) and Ravello (Villa Rufolo, Villa Cimbrone Gardens, & more). Next up on the itinerary: get great views at Il Sentiero Degli Dei, make a trip to Parrocchia Di San Gennaro, brush up on your knowledge of spirits at Il Gusto della Costa, and get outside with Walk of the Gods.

To see other places to visit, maps, traveler tips, and other tourist information, you can read our Positano holiday planner.

George Town, Cayman Islands to Positano is an approximately 20-hour combination of flight and car. Traveling from George Town to Positano, you'll lose 6 hours due to the time zone difference. Traveling from George Town in May, expect Positano to be slightly colder, temps between 27°C and 18°C. Finish your sightseeing early on the 20th (Wed) to allow enough time to drive to Capri.

Things to do in Positano

Outdoors Historic Sites Parks

Side Trips

Amalfi, Ravello, Praiano
Find places to stay May 17 — 20:
Highlights from your plan
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Villa Rufolo ©
Villa Rufolo

3
nights
Capri

Capri
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Capri is known for nature, parks, historic sites, beaches, and scenic drive. Your plan includes some of its best attractions: take in the dramatic natural features at I Faraglioni, take in nature's colorful creations at Giardini di Augusto, stroll through Marina Grande Public Beach, and don't miss a visit to Belvedere Cannone.

To find more things to do, reviews, photos, and more tourist information, refer to the Capri trip maker app .

You can drive from Positano to Capri in 3.5 hours. Expect a daytime high around 27°C in May, and nighttime lows around 18°C. Finish up your sightseeing early on the 23rd (Sat) so you can travel to Portofino.

Things to do in Capri

Outdoors Parks Tours

Side Trip

Anacapri
Find places to stay May 20 — 23:
Highlights from your plan
I Faraglioni
I Faraglioni
Giardini di Augusto ©
Giardini di Augusto
Blue Grotto ©
Blue Grotto

3
nights
Portofino

Portofino ©
Portofino is an Italian fishing village and holiday resort famous for its picturesque harbour and historical association with celebrity and artistic visitors. You'll find plenty of places to visit near Portofino: Santuario della Madonna dell'Olivo (in Chiavari), Serravalle Designer Outlet (in Serravalle Scrivia) and Baia del Silenzio (in Sestri Levante). Next up on the itinerary: wander the streets of Santa Margherita Ligure, step into the grandiose world of Castello Brown, visit a coastal fixture at Faro di Portofino, and contemplate in the serene atmosphere at Santuario di Montallegro.

For reviews, maps, ratings, and more tourist information, refer to the Portofino online route planner .

You can do a combination of ferry, flight, and train from Capri to Portofino in 6.5 hours. Other options are to do a combination of ferry and car; or do a combination of ferry and train. When traveling from Capri in May, plan for a bit cooler days and about the same nights in Portofino: temperatures range from 24°C by day to 17°C at night. Finish up your sightseeing early on the 27th (Wed) so you can go by car to Bellagio.

Things to do in Portofino

Parks Historic Sites Wildlife

Side Trips

Santa Margherita Ligure, Santuario della Madonna dell'Olivo, Abbazia di San Fruttuoso, Baia del Silenzio, Santuario di Montallegro
Find places to stay May 24 — 27:
Highlights from your plan
Area Marina Protetta Portofino ©
Area Marina Protetta Portofino
Baia del Silenzio ©
Baia del Silenzio
Santa Margherita Ligure ©
Santa Margherita Ligure

3
nights
Bellagio

Bellagio ©
Known as the pearl of Lake Como for its luxury accommodations, high-end shops, and fine dining options, Bellagio serves as the lake's premiere resort town.
Venture out of the city with trips to Cathedral of Como (Duomo) (in Como), Tremezzina (Villa del Balbianello & Villa Carlotta) and Varenna (Villa Monastero & Chiesa di San Giorgio). There's lots more to do: admire the natural beauty at i Giardini di Villa Melzi, look for gifts at La Cantina, stroll around La Punta Spartivento, and explore the historical opulence of Castello di Vezio.

To find other places to visit, reviews, ratings, and more tourist information, use the Bellagio trip itinerary website .

Drive from Portofino to Bellagio in 3.5 hours. Alternatively, you can take a train; or do a combination of train and bus. Traveling from Portofino in May, plan for a bit cooler nights in Bellagio, with lows around 13°C. On the 31st (Sun), you'll have the morning to explore before heading back home.

Things to do in Bellagio

Parks Nature Museums

Side Trips

Tremezzina, Varenna, Castello di Vezio, Lago di Como, Chiesa di S. Leonardo
Find places to stay May 27 — 31:
Highlights from your plan
i Giardini di Villa Melzi ©
i Giardini di Villa Melzi
Villa del Balbianello ©
Villa del Balbianello
Villa Carlotta ©
Villa Carlotta

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