27 days in Southern Italy Itinerary

27 days in Southern Italy Itinerary

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Route & dates

27 days in Southern Italy Itinerary

Start: Milan
+2
Fly + shuttle + ferry:  5​h
1
Capri, Island of Capri
— 6 nights
Drive:  3​h 15​min
2
Positano
— 8 nights
Drive:  1​h 15​min
3
Maiori
— 4 nights
Drive:  1​h 15​min
4
Naples
— 8 nights
Fly:  3​h 45​min
End: Milan

6
nights
Capri, Island of 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: explore the striking landscape at I Faraglioni, stroll through Pizzolungo, don't miss a visit to Villa Lysis, and Head underground at Blue Grotto.

To find maps, more things to do, photos, and tourist information, you can read our Capri trip app .

Milan to Capri is an approximately 5-hour combination of flight and ferry. You can also do a combination of train and ferry; or do a combination of car and ferry. Traveling from Milan in December, expect Capri to be a bit warmer, temps between 17°C and 12°C. Finish up your sightseeing early on the 21st (Sat) so you can go by car to Positano.

Things to do in Capri

Outdoors Parks Nature

Side Trip

Anacapri
Find places to stay Dec 15 — 21:
Highlights from your plan
Speed Boats Tours
I Faraglioni
I Faraglioni
Giardini di Augusto ©
Giardini di Augusto

8
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.
Venture out of the city with trips to Torre del Capo di Conca (in Conca dei Marini) and Wine Tours & Tastings (in Amalfi). And it doesn't end there: get great views at Il Sentiero Degli Dei, explore the fascinating underground world of Grotte di Suppraiano, make a trip to Chiesa di San Giovanni Battista, and stop by Theodora Moda Positano.

For other places to visit, photos, and other tourist information, you can read our Positano trip app .

Traveling by car from Capri to Positano takes 3.5 hours. In December, daily temperatures in Positano can reach 17°C, while at night they dip to 12°C. Finish up your sightseeing early on the 29th (Sun) so you can go by car to Maiori.

Things to do in Positano

Outdoors Tours Parks

Side Trips

Praiano, Torre del Capo di Conca
Find places to stay Dec 21 — 29:
Highlights from your plan
Fornillo ©
Fornillo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Tennis Al Settimo Piano ©
Tennis Al Settimo Piano

4
nights
Maiori

Maiori ©
Maiori is a town and comune on the Amalfi coast in the province of Salerno . You'll find plenty of places to visit near Maiori: Villa Cimbrone Gardens (in Ravello) and Villa Comunale (in Vietri sul Mare). The adventure continues: pause for some serene contemplation at Duomo di Sant'Andrea, admire the striking features of Villa Rufolo, contemplate in the serene atmosphere at Sanctuary of Our Lady of Sorrow (Sancturio Maria Santissima Addolorata), and steep yourself in history at Duomo di Ravello.

To find maps, where to stay, photos, and more tourist information, read Maiori itinerary app .

You can drive from Positano to Maiori in 1.5 hours. December in Maiori sees daily highs of 17°C and lows of 11°C at night. Wrap up your sightseeing on the 2nd (Thu) to allow time to drive to Naples.

Things to do in Maiori

Historic Sites Shopping Parks

Side Trips

Ravello, Amalfi, Minori, Atrani, Chiesa San Pietro Apostolo
Find places to stay Dec 29 — Jan 2:
Highlights from your plan
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Villa Rufolo ©
Villa Rufolo

8
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Venture out of the city with trips to Salerno (Giardino della Minerva, Palazzo Fruscione, & more) and Arciconfraternita della Santissima Annunziata e del Santissimo Rosario (in Vietri sul Mare). There's lots more to do: see the interesting displays at Museo Archeologico Nazionale di Napoli, pause for some serene contemplation at Cloister of Santa Chiara, don't miss a visit to Via San Gregorio Armeno, and admire the masterpieces at Museo e Real Bosco di Capodimonte.

To find ratings, reviews, other places to visit, and tourist information, read Naples tour itinerary planning app .

Drive from Maiori to Naples in 1.5 hours. Expect slightly colder evenings in Naples when traveling from Maiori in January, with lows around 6°C. Wrap up your sightseeing on the 10th (Fri) early enough to travel back home.

Things to do in Naples

Historic Sites Museums Parks

Side Trips

Salerno, Pompeii, Arciconfraternita della Santissima Annunziata e del Santissimo Rosario
Find places to stay Jan 2 — 10:
Highlights from your plan
Galleria Borbonica ©
Galleria Borbonica
Via San Gregorio Armeno ©
Via San Gregorio Armeno

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