When I think about Italy, I dream of sunny days spent by the sea, glasses of white wine sweating in the summer heat. Of looking out into the rolling hills of Tuscany in awe. Of walking through the busy streets of Venice and feeling the magic around me.
I spent two weeks on my honeymoon in Italy, and just got back from my second trip (more to come on that soon…)
If you’re looking for a romantic trip that gives an overview of Italy’s best spots, you’re in the right place! Here, you’ll find my dynamic itinerary travelling by train, and experiencing luxury for less.
Trip overview
- Start in Praiano, a small town on the Amalfi Coast for a romantic and relaxing few days listening to the sounds of the ocean, eating seafood pasta, and sipping Aperol Spritz on a beach chair
- Enjoy a couple of hot, bustling days immersing yourself in the history of Rome
- Visit Italy’s famous wine region of Tuscany, where you’ll explore beautiful vineyards and relax with the rolling hills all around you, with a stop in Florence for beautiful views, churches and art
- Wrap up your trip with a trip to Venice, where you’ll get lost wandering through the canal streets
My travel style
Days in Italy spent exploring the history baked into every city, or relaxing by a body of water with an Aperol spritz. Nights spent lingering over dinner with a glass of wine in hand.
I set an intention to get a taste of what the country has to offer, and build in more relaxation time than I might normally. It was a honeymoon, after all!
If you want a romantic, relaxing couples trip that doesn’t skip out on the sights, this itinerary is for you.
Day 1-4: Praiano, Amalfi Coast
Welcome to Italy!
Picture this: you wake up overlooking the ocean, where you’re brought breakfast on a balcony and spend the morning reading with the sun on your face. You then spend the day by the water, walk through the winding streets and staircases, and have a beautiful dinner overlooking the hills of Praiano.
The first leg of our trip was on the beautiful Amalfi Coast, where we chose to stay in Praiano for a quieter experience. We were looking for beaches, good restaurants and a walkable town, and that’s exactly what we found.a
Keep reading for details on the dreamy first leg of our honeymoon.
Take a detour to visit Pompeii on your first day
After a long day of travel, I bet you want to go straight to bed – but you’re in Italy! The best way to beat jet lag is to have an active first day, so I suggest a stop in the ancient ruins of Pompeii before you head to the Amalfi Coast to relax.
We booked a private transfer from Naples train station to our accommodations, and planned for our driver to take us to Pompeii on the way. Plan for a 2 hour stop.
Walk around the archaeological site, imagining the way of life before the volcano erupted. Make sure to bring earphones for your audio guide – it comes through your phone, and is worth listening to for the added context.
Visit a beautiful beach club with a Positano view
There aren’t many public beaches in this area of the Amalfi Coast – renting a chair at a beach club is the way to go.
After our wedding, we knew we’d want some relaxation time, and La Gavitella was truly magical. We spent our first full day on our beach chairs, reading books to the soundtrack of waves against the shore. When it was time for lunch, they had fantastic seafood and wine just up the staircase.
It’s also right beside One Fire Beach Club, which attracts many visitors and has more of a party vibe. For chairs close to the water, lunch on site and a spot to read and relax, this would be my choice!
Take a boat trip to Capri
We booked a day tour leaving from Praiano, stopping in Positano, and giving you a few hours on the luxurious island of Capri.
The crew on the boat was lovely, and took us on a couple stops, including beautiful rock formations. If kiss under the Faglioni rocks, it means you’ll be together forever.
Walking through the small cobblestone streets, there are so many flowers, lemon themed souvenirs everywhere and designer shops lining the streets.
For a special experience, check out the restaurant that makes picnics to go for your Capri adventure – Giardino di Capri.
We met them in the square at the top of the funicular, and took the picnic on our walk to Belvedere Cannon. This made the perfect day in Capri, after boating back with a swim stop.
Disclaimer:
On our trip, the waves were high and there was lots of seasickness, but even so, the boat crew took care of us and the experience was worth it. I’d suggest checking out the wind forecast if you’re prone to seasickness.
Spend another beach day in a cove
We spent our last day lounging by the sea on the other side of Praiano, at Il Pirata, reading books and enjoying the food and drinks.
The sun was glittering off the ocean, with a cloudless sky and a beautiful breeze to cool us down. We ordered spritzes and Peroni, and had a break from the sun at their restaurant for lunch.
I’d considered the Path of the Gods hike, but ended up pivoting based on how much exercise we were already getting walking the stairs of Praiano, and the heat. We just wanted another beautiful beach day.
Eat all the seafood you can!
Oh my goodness, the seafood was the highlight of my time in Praiano. After every long day in the sun, we went home for a rest and headed out for an outdoor dinner with a view. I had 3 variations of seafood pasta, lobster and fresh tomatoes in every meal.
For more details on the restaurants I went to in Praiano, check out my guide to Praiano, coming soon!
How to get to Praiano
From the airport in Rome, we took a train to Naples, and get picked up by our driver. The streets are windy and narrow, and we were really glad that we didn’t drive ourselves.
Cutting the trip to be picked up in Naples saves a great deal of money, and makes it much more affordable to visit.
Now it’s time for the next leg of the trip – Rome!
Day 5-6: Rome highlights
We left the morning of Day 5 to continue our journey to Rome, arriving mid-afternoon. After grabbing a slice of pizza, we strolled through the streets and stumbled upon ruins and many formidable sights along the way.
Here’s how I think you should spend a quick visit to Rome, experiencing the city highlights and the food.
Visit the Pantheon
Our first stop was a visit to the Pantheon, where we used Rick Steves’ audioguide app to learn more about what we were experiencing. There was stained glass and so much history in this beautiful monument. It’s HOT in the summer, so ducking into stops like these make sightseeing that much more enjoyable.
Next: a stop for gelato of course!
Take a food tour through Trastevere
One of my favourite parts of Rome was our Secret Food Tour in the hip neighbourhood of Trastevere. We tasted wine, cheese, street foods, and ended with famous gelato from a bar.
Secret Food Tours always has a local guide that mixes in history and a walking tour with your food stops. I would strongly recommend!
Book a morning Colosseum & Roman Forum tour
The easiest way to see the Colosseum in busy season is through a pre-booked tour. I loved our joint tour that included the Roman Forum, and our excellent guide (with a history degree!) that taught us so much. This was our main historical stop in Rome so we had to do it right.
Throw a coin into the Trevi Fountain
Of course you need to see it! It’s as busy as they say, but throwing a coin in for my Lizzie McGuire moment was a highlight.
Something else I found online was the Fountain of the Lovers, hidden over on the right side. We had to be romantic and drink from it, too.
Eat carbonara!
Created in Rome, carbonara and cacio e pepe are some of my favourite dishes. The famous Roscioli restaurants are worth a visit, and Gli Angeletti near the Colosseum had our favourite carbonara.
Day 7-9: Tuscany
Tuscany is a place I could go back to again and again. The rolling hills span all around you, so far into the distance you can’t even capture it in a picture. It’s so dreamy.
Spend a couple days wine tasting and relaxing on an agriturismo, before finishing this leg in Florence.
Visit an organic winery for lunch
I will never stop thinking about the zucchini and ricotta ravioli that I had at La Lastra, a beautiful and rustic organic winery.
We took a walking tour that we booked last minute, learning about the winemaking process and walking through the vines, before sitting down for a tasting lunch. We were lucky enough to have the owner with us for the whole experience.
Next, we moved on to a beautiful place I’d go back to again and again.
Stay at an agriturismo to relax
I will always recommend my agriturismo, Villa il Castagno. Sitting in the rolling hills of a vineyard, poolside, with a glass of wine made from those vines? It can’t be matched.
An agriturismo is a working farm that has rooms for guests – similar to a bed and breakfast, but authentic and Italian. They’re a popular vacation accommodation for Italians and tourists alike, and you can find them on agriturismo.it, or your usual travel booking sites.
I suggest booking one with a pool and a restaurant on site so you can use it as your base and spend lots of time there. I actually would’ve spent more than 2 nights, had I known how much I would love it there.
Take a wine tour in the Chianti region
After this trip, my husband and I signed up for wine classes. We learned so much from the winemakers in Italy that we knew we wanted to get deeper into wine culture.
Our Chianti wine tour travelled to Lornano, Tenuta Torciano, and stopped in San Gimignano for a quick walk.
We learned about the different expressions of Sangiovese.
I booked online on Viator, and GetYourGuide had a lot of the same options. Make sure to read where you can get picked up and dropped off, and focus on catching a couple different wineries. I’d also suggest doing one with lunch included.
Spend the day in Florence
Book a morning time slot to climb the bell tower at the Duomo (Cattedrale di Santa Maria del Fiore), watch the sunset at Michelangelo square, and visit La Giostra for a Florentine steak.
Florence is lively, historic and genuinely fun to explore without an itinerary.
If you want to visit museums, maybe build in an extra day, but one was enough for a quick exploration.
Day 10-11: Venice
Ah, Venice. The land of cicchetti, spritzes, and tiramisù. A perfect place to wander the canals and take a romantic gondola ride, while also learning the history.
You could spend longer here, but with the amount of people, 2 days was perfect for me.
Get lost wandering the streets
The best advice I was given when visiting Venice: get lost. We spent our entire last day in the canal city walking between bars and restaurants and enjoying the streets we walked on the way.
Visit historical monuments
Use the Rick Steves guide to learn. Starting in Piazza San Marco, we went into the Correr Museum, and through Doge’s Palace. A historical highlight for us was learning about the last taste of freedom prisoner’s would get before walking into the jail.
Take a romantic gondola ride
Yes, this is a touristy thing to do in Venice. Yes, you have to do it!
We got some great advice for our gondola ride: go early in the morning to avoid having company, and barter.
It was a perfect morning activity to go through the canals and experience the bustling city from the outside in. We did it early, so we could note down the pretty spots we wanted to go back to, and it was perfect.
How to get around Italy
Trains
We travelled between towns primarily by train. To save money, book (very far) in advance if you can!
Make sure to download the Trainline app to keep it simple.
Car – with a driver!
For the Amalfi Coast, I suggest hiring a driver to take you to your accommodations. You won’t need to drive in Praiano, as you can walk to any beaches and restaurants you want to visit.
Though we didn’t end up visiting Positano, driving through was chaotic and overwhelming. It made us glad that we weren’t driving ourselves.
Boat
We took a day trip to Capri via boat, starting in Praiano.
You can also use the ferries in Venice to get to your accommodations.
I hope you enjoyed your time in Italy with me – I can’t wait to go back!
Love,
Cayley
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