Amalfi Coast Beautiful Photo View

Itinerary: Solo Travel in Italy – La Dolce Vita from Naples to Milan

Posted on Posted in Italy, Itineraries
Amalfi Coast Ravello Villa Rufolo Solo Travel in Italy
Villa Rufolo in Ravello, a town along the Amalfi Coast

Italy is a country that every traveler should visit (a few times).  I was fortunate to begin my love affair with Italy, at the age of 22, on a memorable ten day bus tour with the local church group of senior citizens, a guide and a tight bus schedule (my version of solo travel in Italy with a safety net).  With so much time on the bus, I looked out the window and dreamt of just renting a villa (aka Italian mansion) for slow travel in Italy in the movie of my life. I wouldn’t recommend a bus tour of Italy anymore as its long days, multiple hotels and the same people day in and day out on a tight schedule.

Italy is meant to be savored through the seaside views, leisurely meals, local wines from each region and getting lost in the city (as much as you can in the age of Google Maps).   Unfortunately, when you are just out of college like I was, your funds are limited, however, now twenty (cough) plus years later, my budget is a bit bigger but my vacation time still American (aka limited 1-2 weeks at a time).  So how should you plan to solo travel in Italy (or family travel or even group travel)?

That’s easy – focus on food, fun and wine from Naples to Milan as you are surrounded by history.  Ok, it’s really not that easy because I’m sure you have a checklist of everything you must see and let me tell you – when that crazy schedule happens to collide with the Italian way of life, you’ll quickly learn the Italian way (and have a daily gelato habit like I did) so make a short list of “must see” and then if you find time, add some “would be nice to see”.

Tip: You’ll never have enough time on your first trip so be prepared to plan a second, third, etc. trip because you’ll need time to explore different regions, cities, towns and villages before you find a right fit to go back and leisurely explore some more. 

Italy Gelato in Florence Solo Travel in Italy
Gelato was a daily (or twice daily) habit during my visit in Italy – no calories on vacation was my motto!

For a first visit to Italy, I’d ideally allow at least two weeks (14 days) or more to visit from Naples to Milan to sample the highlights.  If you have only 7-10 days, you can mix and match the below.

Tip: Talk to your travel agent to book your airfare into one city and out of another to maximize your time.

Train Travel in Italy

The train is very easy to use in Italy to get between cities – I used Italio and Trenitalia.  The trains were on time but they were not announced so you had to keep checking the board. Buy tickets online in advance, if possible, for savings. Worth noting when traveling anywhere to be careful in and around train stations at all times because you are subject to pickpockets’. It’s your vacation and often the unfamiliar causes you to be distracted from your bags, luggage, souvenirs – Don’t be that tourist!

Tip: Carry a few coins as the public toilets in Italy as they charge an entrance fee (I call it the “pay to pee fee”. The fee can range from 50 cents to 2 Euros. 

Naples Train Station Bathroom Cost
Familiar view in Italy – pay to pee so have coins ready and budget for your bladder

Food in Italy

Sorrento Antipasti Sampler Solo Travel in Italy Food Plate
The antipasti sampler plate at lunch normally meant for more than one person in Sorrento

It’s not all pizza and pasta unless you want it to be.  Each region has specialties – fish, meats, pasta, etc.  I’ve even seen a few gluten free pasta options offered which was surprising but a sign of the times (and tourists). A few things to note:

  • Pizzas are generally one size (9-10”) for one person and eaten with a fork and knife.
  • If you ask for water, expect to be brought bottled water and charged accordingly.
  • Bread is not free (only in America are we carb happy free bread folks).
  • Look at the menus outside first (and the prices) before you sit – I just read a horror story of friends who were charged an outrageous amount for lunch in Venice (they could have avoided this)
  • Prices will vary at coffee bars/cafes – standing inside at the counter will be cheaper than sitting inside/outside.

The best foods I’ve found have been far from tourist areas – I’ve found slices of pizza in Venice (Dorsoduro) near the university, a multi course Italian feast in Florence and artesian gelato made in small batches in the maze of the cities.

Tip: Buy bottled water in the local supermarkets for less (go to the back of the store, not the easy to find cold water at the front which cost more)

Fun in Italy

While a wine tour is definitely a fun time, I’d save that for its own itinerary.  You can do day trips to winery or stay in the city and refill your glass (or bottle).  There are fun activities throughout the country from exhilarating car rides at Ferrari to flying through the air in Capri. Try something new and off the well-worn tourist path to see a different side of Italy and yourself! Maybe try to Row Venice?

Tip: I like the unique small group tours of Walks of Italy, Context Travel which use local guides and Row Venice which is an all women non-profit 

Row Venice Caroline
Row Venice with Caroline finishing up a lesson on the canal

Solo Travel in Italy Itinerary – 14 Days in Italy

Naples – Capri – Amalfi Coast (4 days)

Naples is a gritty city when compared with the other more touristy cities in Italy.  Cruise ships stop throughout the season (May-October) for one day and the city swells with people on tours.  But you can still find gems that the cruise ship folks haven’t found yet – the oldest Napoli pizza shop, Antica da Michelle, the Naples Underground Tour and a Bike Napoli tour. Note: Naples takes its pizza heritage quite seriously!

For history buffs, Pompeii and the lesser known Herculaneum is a must.  You can take the local train to each or join one of many tour options.  Seeing the ruins from the volcanic eruption is fascinating and having both locations to compare and contrast helps to understand even more.

Herculaneum Ruins at Ercolano solo train in italy
The view of Herculaneum from above – so many large and multi storied buildings

A ferry ride will transport you to the island of Capri, where the Blue Grotto and Limoncello are waiting for you.  The Blue Grotto experience involves laying down in a boat and going through a small opening (dependent on sea levels) to a magic blue cavern.  The sunlight hits the water and it glows blue, for me, this never gets old.  You can either travel to Anacapri to hire the local boat at the Anacapri landing or do an Blue Grotto tour from the ferry dock (note it takes time to unload all the boat passengers into the little boats so be prepared for that).

It's so blue at the Blue Grotto Capri solo travel in italy
It’s so blue inside the Blue Grotto

For the Amalfi Coast tour, hire a local guide (he’s worth the money) like I did. You’ll stop at scenic viewpoints, dine with amazing views and food and not worry about the narrow roads and tight corners. The Amalfi Coast is one place that I could really enjoy renting a villa for the whole time and relax with views of the sea.

Amalfi Coast Beautiful Photo View Solo Travel in Italy
Rugged cliffs, blue waters and greenery is wonderful combination along the Amalfi Coast

Rome (1-5 days)

Rome, for a first time visitor, is all about history, the Catholic Church and the Pope.  It’s hard not to visit The Sistine Chapel (go at night on a tour to avoid the crowds), Colosseum, Roman Forum, Pantheon, Trevi Fountain and Galleria Borghese.  For the most part you can do the Hop On/Hop Off bus and do drive by of the attractions.  Rome can really be one day or multiple days, it just depends on you and the rest of your “must see” itinerary.

The Trevi Fountain in Rome solo travel in italy
The Trevi Fountain in Rome – throw your coin in to ensure a return visit to the city

Florence (2 days)

Florence is a city with a mix of history, touches of modern and a whole lot of amazing food, wine and gelato to enjoy.  Come to the city hungry and leave satisfied.  With amazing views at sunset over the Ponte Vecchio Bridge, it’s hard to imagine anything more gorgeous in Italy. I’d suggest doing a Florence food tour before you start your Uffizi Gallery and/or church visits.

Tip: Have fun driving a Vintage Fiat500 (manual) or Vespa around the city and out to the nearby countryside

Florence Fiat 500 tour Tuscan Hills solo travel in italy
Driiving on the one lane roads through the villages outside of Florence

Venice (3-5 Days)

I won’t lie, Venice is my first love. The Venice of twenty years ago that is still there underneath a city teeming with tourists.  I prefer to visit in May or Fall months (Sept/Oct/Nov) when I can get lost in the maze of the city as if I have the city to myself.  The key to Venice is to do your list first (San Marco Square is always packed it seems) and then find the secret happy hour along the canals and try to fathom how long this city has existed and who has walked the streets before you.

Tip: For your gondola ride (expensive), try to find that lone gondolier on the canal for a more private ride rather than the central ride locations where you are on the assembly line.  

Venice Gondolas on Canal
The daily view of the gondolas on the canal from my amazing Venice Airbnb flat


Milan (1-2 days)

Milan is a business centre and it shows.  The historic Italy is mixed in with the modern Italy.  After visiting the Opera House and waiting for the light to change, a Ferrari drives by.  While touring the rooftop of the Duomo, I can look down at the shops inside the Galleria.  Milan mixes it up well throughout the city. Milan in one day can easily be done – the Last Supper with a city and Duomo walking tour and still have time for dinner in the Navilgli entertainment district along the canals.

Tip: The Duomo Rooftop is a must unless you are afraid of heights

Milan Duomo Arches
The Duomo rooftop walk over three levels provides so many great views


Overall – Solo Travel in Italy

You’ll notice I didn’t mention much about visiting all the wine regions of Italy (there are many) and that’s because for a first visit of Italy, especially solo travel in Italy, it’s best to visit the local wine shops for tastings.  In Venice, visit Vino Vino near Fenice Opera for a great wine list, including Barolo (a favorite). In Florence, you can do a day trip to Tuscany for a visit to the vines.

So this is just a start to your trip planning as Italy is a big country with so much to do, see, eat and drink that you can’t do it all in one short trip (please don’t try).  Learn to relax, take in a few sunsets and enjoy your solo travel in Italy –  La Dolce Vita!

Florence sunset Arno river Solo Travel in Italy
Sunset view in Florence over the Arno River

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