An Italian Destination for Every Month of 2019

~ A Guide on where to go in Italy in 2019 ~

Happy New Year! 2019 is here and I couldn’t be more excited because a new year means new adventures! If you’re anything like me, then the second the new year celebrations are over, you’re madly plotting sunny escapes and googling travel options for the coming year. To assist you in this quest, I’ve done all the homework and found the most perfect Italian destination for every month of the year. Because it’s always a good time to go to Italy, right? Right! Happy travels!

January: Rome

G Rough Rome What to do in Italy every month of the Year
G Rough Rome What to do in Italy every month of the year
Images:  G Rough

Images: G Rough

January is a time for fresh starts and good intentions, and this means throwing some coins in the Trevi Fountain. In summer, Rome can be unbearably hot, crowded and chaotic. But in January, it’s much calmer, and you might actually get close enough to the fountain to ensure those coins land in the water!

A January visit to Rome actually played a big part in my falling in love with Italy. I have such fond memories of wandering around the city in a coat, shiny boots and a cashmere scarf, being completely mesmerised with every turn of a corner.

Where to stay: G Rough

February: Dolomites

Image:  Rosa Alpina

February is all about powder in Europe! Before I had children, you could find me on the slopes this time every year, sometimes even two or three times. Life is not quite the same these days, but I am plotting a return nonetheless. As soon as possible I’ll be heading straight to the village of San Cassiano in Badia in the Italian Dolomites - the best place for fresh snow and amazing pasta!

Where to stay: Rosa Alpina

March: Puglia

Puglia Where to visit in Italy every month of the year

By March, I am dreaming of summer - of warm feet in the sand, gelato and picnics. It is also my birthday month, so the question I often find myself asking is where to go in Italy for some sun?

Two years ago, I was fortunate to go to Puglia at the end of March, and this sunflower felt like she was waking up from a long hibernation. I wore white sundresses for three days straight and we actually ended up moving inside at a restaurant in Polignano A Mare as it was too hot without shade! Needless to say, if you're starved for the sun’s warmth on your skin by March like me, this is the place to go.

Where to stay: Castello di Ugento

April: Noto Sicily

In April I ask myself exactly the same question: Where is the sun? The answer is always, “Go south”! You cannot get much further south in Italy than wonderful Sicily, and the baroque towns of South East Sicily are so hot right now… both metaphorically and temperature wise! Noto is an absolute jewel and a UNESCO World Heritage Site. Oh, and you’re just down the road from the wonderful village of Marzamemi and a table in the piazza at Taverna La Cialoma, which has my Dad’s seal of approval (this isn’t easily earned, by the way).

Where to stay: Seven Rooms Villadorata

May: Ponza

May is pure gold in Italy! My favourite month - no contest! It’s lying by the pool drinking spritz weather. It’s playing on boats weather, and it’s eating every single course of every meal outside in the sunshine weather but without the crowds!

Last May, I spent five dreamy days on Ponza with my husband. There were dolphins, boats, Negronis and many scoops of gelato. Ponza is one of my favourite Italian islands. It has the beauty and drama of Capri but without the bling, price tag or paparazzi.

Where to stay: Hotel Chiaia di Luna

June: Positano

Images:  Villa Tre Ville
A Guide to 12 months in Italy Positano

June is when you want to visit Positano. The weather is glorious and the crowds that clog the narrow streets in July and August are manageable. Positano is one of the few places that, despite its overwhelming popularity and iconic vistas, manages to stay strongly in one's heart because it is so damn pretty. It’s simply a must-visit kind of place - there’s just nothing like it.

In recent years, there is one hotel that I have seen in my Instagram feed and on the pages of Pinterest more than any other, Villa Tre Ville. From the likes of Zimmermann to Sarah Harris to that amazing wedding of Kristin O’Neill and Brett Shapiro captured in Vogue, this hotel terrace just keeps popping up and calling my name!

Where to stay: Villa Tre Ville

July: Stromboli

Ginostra, Stromboli, May 2016

Ginostra, Stromboli, May 2016


My other favourite Italian island is volcanic Stromboli. It’s a stunning, secret island. An entire week on Stromboli with my 10 favourite people was one of the best weeks of my life. I love Stromboli for its magic - incandescent lava at sunset and jet black sand. I love it for the dramatic views, uphill walks and the fact that you can walk past the house where Ingrid Bergman stayed whilst filming, and falling in love, with Roberto Rossellini. Oh, and there is Ginostra - a cliffside village only accessible by boat with the best spritz I’ve ever had!

Where to stay: Stromboli is not a luxury destination in the traditional sense, but that hasn’t stopped the fashion set rocking up to party every summer. If you don’t fancy the rustic chic hotels on offer, then do as Giorgio Armani does and bring your own yacht! Otherwise stay at Il Gabbiano Relais.

August: Lake Como

A Guide to Italy Lake Como
Images:  Villa Derriere

A few years ago in August, my husband and I had one of those dreamy, perfect trips to Lake Como. We stayed in Relais Villa Vittoria in the village of Laglio (yes, that is the village where George Clooney has a home). We spent most of our stay lying by the pool reading, but we did manage to visit the famous island of Locanda dell'isola Comacina for lunch. The classical beauty of Lake Como should be on every bucket list.

Where to stay: When I return, I plan to stay at Villa Derrière in Cernobbio. This delightful bed and breakfast first came to my attention after travel writer and photographer Lucy Laucht (see our interview with her here) visited on her honeymoon. It’s a sweet B&B with only two rooms and a lovely garden.

September: Tuscan Coast

Tuscan Coast A Guide to 12 months in Italy
Tuscan Coast A Guide to 12 months in Italy
Images:  Casa Iris

Images: Casa Iris


Oh, September! You are such a lovely month in Italy. The crowds have left to return to everyday life but there is still so much more summer to be had all month long.

The Tuscan coast and the surrounding towns are much calmer in September. For years most people travelled to Porto Ercole to visit Il Pellicano, but now there is another gem on the radar just down the road in lovely Orbetello - the recently opened and charming Casa Iris. It’s perfectly located for wildlife spotting or beach clubs depending on the type of holiday you want.

Where to stay: Casa Iris

October: Ravello

A Guide to 12 months in Italy Ravello
A Guide to 12 months in Italy Ravello

The last of the summer sun can be found on the Amalfi Coast well into the month of October. Romantic Ravello is quite possibly the most beautiful village I have ever seen. It’s set high above the Amalfi Coast with spectacular cliffs and enchanting views out to sea.

This tiny village has a surprising number of luxury hotels with infinity swimming pools. Go old-school glamour and stay at the intimate Belmond Villa Margherita where the two suites are filled with antiques and lying by the infinity pool will make you feel like a 1950s movie star. The bigger your sunglasses, the better!

Where to stay: Belmond Villa Margherita

November: Florence

Florence A Guide to 12 months in Italy
Florence A Guide to 12 months in Italy
Images:  Ad Astra

Images: Ad Astra


I wrote recently about why I think Florence is an autumn destination after spending time there with my Dad. It’s the palette of the architecture - all those golden buildings, the terracotta - it just screams to be seen at this time of year. Of course it’s dependent on the weather, but it’s usually still nice enough to wander the streets in Florence during November, so don’t miss everything this city has to offer.

Where to stay: The elegant Ad Astra is like staying in a beautiful museum and should definitely be on your radar if you are looking for a memorable stay.

December: Venice

Venice What to do in Italy in every month of the year
Venice What to do in Italy every month of the year
Images:  Hotel Heureka

Venice really is a fairytale at Christmas with all its twinkly lights and misty canals. Winter is not too busy and it’s easy to find a canal or alleyway in which you don’t have to share. Make sure you wrap up warm, though, as it does get chilly.

Speaking of chilly, there are plenty of cosy places to retreat when that bitter wind blows in from the Dolomites. You can choose between hot chocolate at the insta-famous Café Florian or an opera at Teatro La Fenice. Or maybe the amazing collection of art at the Peggy Guggenheim Collection on the Grand Canal.

Where to stay: Hotel Heureka

What do you think? Are you going to book a holiday to Italy every month of 2019? If I had my way, I certainly would. If nothing else, I hope this guide provided you with some fabulous daydreaming.