Two-week Italy itinerary from Tuscany to Amalfi

Millions of people visit Italy each year from around the world. North Americans travel there for food and culture while the neighbouring countries escape to the coast for the summer break. Admittedly as a destination Italy has become significantly more popular over the last few years making some of its capital cities overwhelmed with tourism. But we won’t go there. Not exactly. We spent weeks planning this itinerary taking into consideration transportation modes, activities, and wish list stops. At least once in each location, my heart skipped a beat looking out in the distance, at the setting sun, green vineyards, or the deep blue sea. 

This Italy travel itinerary took us about two weeks, you can do it a bit faster (though not recommended), or stretch it out with more day trips and relaxing days at the beach.  Alternatively, if you are only visiting one of these destinations (Tuscany, Puglia, Naples, Amalfi), skip ahead to that guide using the table of contents.

This blog post uses affiliate links denoted by ( * ).
Read the disclaimer about affiliate links & PR gifting here. 

Stop One: Tuscany

Florence is the closest international airport for Tuscany. Here you can pick up the car and begin your journey to the Italian wine country. The drive from the airport to our chosen hotel is about an hour. Alternatively you can lend in Pisa which will make this drive about two hours. In this case, if you start to feel peckish, Restorante Il Convio in San Miniato is a good stop (Google, Instagram). Have your first spritz, order a coccoli starter (bite-sized fried dough balls with accoutrements), and one of their signature house-made pastas to enjoy in a serine garden environment. 

Tuscany will be the only stop where we rent a car or fly. Once we leave Tuscany we will move across the country by trains and ferries.

Simple planning tip: Add places you’d like to visit on the map and break up the days based on the regional clusters created on that map. For example, a few of the wineries on this list are near Siena so the day would be Siena plus those wineries.

Above: Restorante Il Convio in San Miniato

Where to stay in Tuscany

We had a vision of a remote historic stay which led us to Relais La Costa. This is a small boutique hotel recently renovated to preserve all of its historic elements. The rooms are spread out across multiple floors each with their own door and access to a shared or private terrace. We had a slow daily breakfast in the garden (included) while planning the day ahead. The hotel offers dinner service as well which you need to prebook because each meal is quite unique. It is worth noting that a few of the ingredients are grown here on the property. There is also a rooftop-style pool and a spa where guests can get a mix of services including manicures and pedicures. 

The location of this stay was very strategic: to be close to other towns without having to drive for over an hour in each direction. 

Book directly on relaislacosta.it or your favourite booking site: booking.com | Expedia | TripAdvisor* | Hotels*

Quick Tip: Stay connected with an eSIM, my go-to are AirAlo* $24 USD for 10GB, 30 days (more on that here).

Below: Relais La Costa Hotel building, chef’s garden, and inclusive breakfast.

Above and below: San Giorgio a Lapi winery, Siena, Italy.

Wineries to visit in Tuscany

San Giorgio a Lapi was perhaps my favourite stop in this region (Website, Google, Instagram). This family-owned production is known for its wonderful wines and olive oil, all of which are grown around the tasting room. The wine flight comes with a small snack, a delicious baguette bite with olive oil. Their pink Sangiovese is a chef’s kiss. Next is Loacker Wines, which has a breathtaking Corte Pavone Winery estate elevated above the region offering a wonderful view of Tuscany (Website, Google, Instagram). 

Arrigoni Pietraserena winery has a scenic terrace and does frequent tours which you might even be able to book the same day (Website, Google, Instagram). The tour includes a walk through the winemaking facilities, the vineyard, and a guided tasting. In your free time, you can walk around the property where horses and a lama live. Cantinale’s Castello di Monteriggioni Farm Restaurant is located in Monteriggioni fairly close to the hotel so that stop can be made at any time (Website, Google, Instagram). 

Above and below: Corte Pavone Winery estate. The standard tasting doesn’t come with snacks but the wines by the glass does.

Above and below: Arrigoni Pietraserena winery.

Below: Cantinale’s Castello di Monteriggioni Farm Restaurant.

If time permits before your departure flight visit the Ruffino 1877 Estate just outside of Florence (Website, Google, Instagram). This property is immense: there are two restaurants, a garden terrace (where the tastings take place), on-site lodging, and even a garden maze. If you choose to stay in Casa Ruffino the daily journey into the wine country will be longer. 

Wine tastings in the region start at €30+ or €5 by the glass; tour and tasting €40+ and from there you can elevate these experiences with meals, picnics, and rare wines.

Ruffino 1877 Estate, Florence, below is the garden terrace where the tastings take place in the summer.

*** Learn Italian with italki* one-on-one with a real teacher. In most places people speak at least some English but a common courtesy is to at least try 🙂 This link* will offer you $5 off. 

Towns to visit in Tuscany

San Gimignano: A gorgeous Italian hill town with many shops, historic monuments, and medieval architecture. In the heart of it is a square plaza, Piazza della Cisterna, where everyone gathers and enjoys their ice cream. Go on a little walking tour, pop into a few shops, and enjoy the elevated views. The historic center of San Gimignano is a recognized UNESCO World Heritage Site.

Below: Siena at night, we got there fairly late and I took very few photos.

Siena: One of the largest cities in Italy and the heart of Tuscany this town is a popular stop and for many reasons. Siena also has a UNESCO-listed historic center, Piazza del Campo. Il Campo is a one-of-a-kind structure angled towards the center facilitating great views for all in attendance for various public performances. Even today all public and civic holidays are celebrated in the piazza. 

Quick note: The parking in Siena can be tricky and is illegal in most places unless you are a local. Find more about parking in Siena on discovertuscany.com.

Montalcino: another hilltop medieval town, some would say a village, with a vibrant community spread across its many restaurants and patios. Montalcino region is well known for its production of Brunello so you will see plenty of wine shops and tasting rooms. Architecturally speaking this town is perhaps best known for its clock tower at the top of Palazzo dei Priori. A must-stop in Montalcino is Il Gallo Stuzzicheria for its warm toast sandwiches and local wine (Google Map, TripAdvsior*)

Don’t feel like driving? Here are a few tour options

• Book a private wine tour from wherever you are staying through local guides: tuscanwinetastingtours.com, scenicwinetoursintuscany.com, or tuscandrivers.com/wine-tours. There are others as well but these promise private custom itineraries. 
• From Siena: Chianti and Castles Tour with Wine Tastings* 
• From Siena: Brunello di Montalcino Guided Wine Tour w/ Lunch* 
• Siena: Tuk Tuk Tour with Wine Tasting* 

Above: Il Gallo Stuzzicheria cafe and one of their warm sandwiches.
Below: Some views of Montalcino and the infamous tower clock.

Transit day: Tuscany to Puglia

Our next stop is Puglia and while there are trains that go there they take 8+ hours, at least one change, and can involve a bus. So to save time we opt for a short flight. Florence to Bari journey by air takes about 1 hour and 15 minutes non-stop with Ryanair.

From Bari to Monopoli there are a few travel options. There is a +/- 30-minute train however, you will need to travel to that train from the airport by bus which will increase the time to over an hour and a half. It’s also worth mentioning that this specific train line does not go all night so depending on when your flight lands you might miss the last train. This was the case for us so we pre-booked a transfer securely on the airport’s website (~€128 for 2 passages and 2 bags). Monopoli Historic Center is car-free so you will be dropped off at the border and will need to travel on foot. The town is quite small though, so don’t panic 🙂

Stop Two: Monopoli

Welcome to Monopoli, Metropolitan City of Bari located on the Adriatic Sea. This charming white town has a vibrant culture, beautiful architecture, a great culinary scene, and a generally relaxed atmosphere. Monopoly, Italy, is absolutely worth visiting and if you are anything like me you just might fall a little bit in love with it. Puglia itself is quite large but Monopoli is a good base for Puglia, especially if you are planning to visit Alberobello, The Home Of Trulli.

Where to stay in Monopoli, Italy

The town is small and there aren’t many hotels but there are a few nice AirBNBs and we chose Pusa Mare Suite. This rental is located on the second floor (no lift) and has a unique one-bedroom design. There is also a fully private terrace one floor up with two sunbeds, a dining table, and a jacuzzi. We absolutely loved having slow mornings and aperitivo hour on this roof. 

Alternatively here are a few hotels and suites:

• Palazzo Indelli hotel in the city center, breakfast included 
• Suite1212 Pirrelli townhouse rental in the city center, with a rooftop terrace 
• Al Console Luxury Suite in the city center, with a pool, hot tub, and included breakfast

What to do in Monopoli

Slowly stroll the city streets bopping into its many shops and historic buildings. Take a walk along the town walls where the rugged sea waves occasionally splash over leaving behind speckles of white sand. Sit back and enjoy the early morning fisherman activities or take a walk down to the rocky beach and join the locals in the sun. 

There are quite a few festivals in Monopoli one of which is PhEST, a major art and photography festival that takes over the city at the end of August. In June the city hosts a literature festival called Prospero Fest and Ritratti music festival is on from mid-July to early August. See the complete events list on monopolitourism.com. 

A few organized tours and excursions:

• 2.5-hour Guided Boat Tour to Polignano a Mare Caves*
• Walking Street Food Tour*
• Snorkeling Tour in Cala Incina or Porto Alga*
• Tour of the beaches of Monopoli and Polignano a Mare* 
• Discover Scuba Diving in the Apulian Riviera*

Where to eat in Monopoli

Monopoli is where you come for the wine and the seafood. Baldovino Wine Bar seems to be a local favourite (Google, Instagram). Here in a casual atmosphere, you will enjoy fresh, uniquely prepared local dishes paired with delicious natural wines. There are very few tables but the sitting area, in true European nature, is extended to the nearby building steps. For the sea view head to Portavecchia Terrazza  (Google, Instagram) while a more mixology-forward menu can be found at Alchemy Bar and Things (Google, Instagram). For an elevated dinner, there is Condominio 60 (Website, Google, Instagram) and Room 21 (Website, Google, Instagram).

Generally speaking, you will see menu fun terraces, appetizing menus, and casual bodegas with tables out front. Most of these vendors will at minimum offer you a good glass of wine and a cold beer. So take a seat and enjoy the people-watching, there is always music to make the experience more fun.

Above: Portavecchia Terrazza, Monopoli

Day trip to Alberobello, The Home Of Trulli

Puglia is known for its cheese but over the last few years, its most popular images are from Alberobello, The Home Of Trulli.

How to get to Alberobello from Monopoli:

There is a bus that goes from Monopoli to Alberobello, the stop is called Monopoli Station and is located on the outskirts of the city (walkable). This journey will take about an hour and cost ~€2/person each way. The bus tickets must be purchased ahead of time for a specific time (at least 5min before departure). To purchase the tickets, head to trenitalia.com and choose “regional” from the dropdown menu. The bus stop is a short walk from the center and isn’t actually a station but just a street stop, unless it moved, which is entirely possible. According to the TrenItalia website, it is also possible to purchase a ticket using the “Trenitalia app, by contacting the call centre: +39.06.5210550 (premium-rate number), at the ticket offices in the station, from the Self-service machines and affiliated travel agencies”. You can also take a taxi (hard to find, $$) or book a transfer vehicle ($$-$$$ in season), there is an updated list of both on TripAdvisor here.

When in Alberobello…

Once in town, take slow, leisurely strolls up and down the city streets, visit the small vendor shops, and get the ultimate panoramic view from the elevated balcony up a few steps from the main street. If you are looking for a more informative experience, join the Alberobello: 2-Hour Guided Trulli Tour*, this tour is approved by the local tourism board.

There are naturally quite a few restaurants and bars in the village but I was looking for a wine bar with a local cheese selection. The two best spots to satisfy that craving are Trulli e Puglia Wine Bar and Vino & Amore which is where we had lunch. Vino & Amore (Instagram) is a lovely family-run lunch spot with an impressive selection of local wines and all kinds of homemade deliciousness (they don’t do takeout). What was meant to be a quick pit stop turned into a fun lunch and a hang-out with the kind people who work there.

Above: A few photos from Alberobello, The Home of the Trulli, Puglia
Below: Images from Vino & Amore, Alberobello, Puglia

Given the distance from Monopoli, we combined this journey with a wine-tasting experience below. There was no bus available to get to the winery so the folks at Vino & Amore recommended a driver who then ended up taking us back to Monopoli after.

Alberobello transfers: togotopuglia.it, you can call or use WhatsApp to schedule as well: 377-341-6385

Sunset wine-tasting experience trip

The vision was rural Puglia, a harvest table, and endless rows of vines. This vision came to fruition with Puglia del Trulli, a small family owner winery that up until this current generation of children (2 sons) only produced wine and olive oil for themselves (Website, Instagram). The family offers a few different experiences from cooking lessons to dinners and tastings in the vineyard. You can also stay here in a Trulli overnight, there are three available for flexible booking.

At the wine tasting, a small group of us strolled the vineyard, tasted the grapes, and learned about regional varietals before sitting down for a communal tasting with snack pairings. Book directly on pugliadeitrulli.com/en/experiences, transfer can be arranged with them if desired. 

*** Find a set of postcards from Italy, Amalfi Beach, and Atrani Artchitecture prints in my Gift Shop.

Transit day: Monopoli to Naples

This journey is about 5 hours and will have up to two transfers: Bari Central (regional) and then likely Caserta, though there are other routes this one is the fastest option to Naples Centrale. The longer trains include snack boxes with water and most changes were on the same platform but do pay attention.  Book with RailErope* or trenitalia.com which, in full transparency, I found extremely frustrating to use. 

The safest transfer option from the train station to the hotel is one booked with the hotel. The hotel will make sure the rate is fair and the driver won’t take you on a ride around town, like it used to be in New York ;).

Stop Three: Naples

Naples is the third largest city in Italy. It is a large urban center with a unique culture, architecture, and history. The city is a bit messy, raw in its appearance but vibrant, exciting, and beautiful at the same time. It is a safe city to travel to but you should pay attention to your surroundings and belonging here just as much as anywhere else. Napoli, as the locals call it, will take you on adventures, feed you great food, and show you art and literature beyond what you could’ve imagined.

Where to stay in Naples, Italy

Stay in the historic heart of Naples at the Rinuccini Relais Hotel, I wrote a separate piece on that, please see that article here. This property is directly in the center with spectacular views and multiple added safety measures for that piece of mind.

What to do in Naples  

Food is a huge part of Italian culture, especially here in Naples so head out on a walking food tour. My choice is Secret Food Tours*, ever since I did their tour in Paris they have been my go-to. This walking tour will begin near the hotel, take you through the main streets, and between the bites speak about the historic development of this great city in an informative and often entertaining manner. Your guide will communicate using WhatsApp.

Explore on foot on your own. Visit the breathtaking Duomo di Napoli (Naples Cathedral) and the city’s many other churches like The Sansevero Chapel and San Domenico Maggiore. Dedicate at least an hour to Complesso Monumentale di Santa Chiara, a stunningly ornate and colourful majolica-tiled museum. Learn about the city’s history through its medieval fortress Castel Nuovo or head further out to the Catacombs of San Gennaro and Certosa e Museo di San Martino monastery. 

If you have enough time for day tours Naples is 30 minutes away from Pompeii and close to a famous diving center, Centro Sub Campi Flegrei Srl. The diving center offers a range of certifications and recreational courses and is located on a private beach on the shore of the Underwater Archaeology Park of Baia. Yet another unique experience.

A few other tours to consider: 

• Pompeii Ruins & Mount Vesuvius Day Tour*
• Wine Tasting Tour on Vesuvius Slopes with Lunch*
• Neapolitan Pizza Making Class* 
• Pasta-making class in a private garden*

Above and below: Complesso Monumentale di Santa Chiara

Where to eat & drink in Naples

Naples is the birthplace of the infamous Neapolitan Pizza and the people who have made it the longest are Di Matteo (Website, Google, Instagram), the food tour will stop here. Located on one of the busiest city streets surrounded by many other food vendors Di Matteo is not just a street window, there is an entire restaurant on the higher floor with a nice city view. This Neapolitan pizza is traditionally made with mouthwatering local tomatoes and soft salty cheese. 

While in Naples, get a giant pizza pocket at Caffè del Professore (Google). And when I say giant I’m not exaggerating, this is not a small snack. Down the street is a great seafood spot, Ristopescheria la Tana Della Sirena (Google), order one of their fried seafood dishes like sardines, cod, or calamari to enjoy on the side terrace or take away. 

Back in the plaza near the hotel is a great traditional Neapolitan spot called Ristorante 53 (Google). The kitchen team at his restaurant are members of the Slow Food Network working with small, quality producers. Tandem Via Paladino has a similar menu and casual atmosphere (Google). For more wine bar feels check out Vineria Bandita (Google, Instagram) and JUS (Google, Instagram). On the beverages side, Naples is home to L’Antiquario, one of the World’s 50 Best Bars (Website, Google, Instagram). Reservations are required, the drinks are expertly mixed, and a small food menu is available. Archivio Storico also comes with high promises and looks like a cool experience (Google, Instagram). 

Transit day: Naples to Amalfi

For this last leg of the journey take a taxi to the ferry terminal and enjoy a scenic ferry ride to Amalfi. This ride is about 2 hours long and costs roughly $55/per person, book on directferries.com. You will need to arrive at least 30 minutes early for check-in. This terminal gets very busy and crowded so make sure you have time for emergencies or to accommodate for various potential confusions. If you are staying in Amalfi, most hotels are pretty high up, you can hire a porter to drag your luggage up the hill. If you are staying in Atrani or along the coast, it’s a nice and scenic walk but will not be fun with bags, get a taxi. 

Stop Four: Amalfi & Atrani

The town of Amalfi is the port for the Amalfi coast. It’s a fairly small town with lots of shops, lemon gelaterias, and other souvenir vendors. Atrani is a small city commune nearby and is quite a bit less touristy. The two are connected by a coastal road which makes for a lovely walk along the shore and through the interior passages. There is an elevator that will take you to the scenic lookout in Amalfi and then you can walk down through the residential neighbourhood, a cluster of tightly woven white houses nested up the hill. 

Where to stay in Amalfi, Italy

Hotel Luna Convento is where I would like to stay for my next visit. This hotel has a private pool and access to the water as well as a beautiful scenic restaurant. La Scogliera is a bit further up closer to Atrani. This hotel has colourful rooms, scenic windows, a pool, and a restaurant with quick access to Citara Beach. For a more luxurious experience have a look at the beautiful Santa Caterina Hotel with direct access to Amalfi Beach and Anantara Convento di Amalfi Grand Hotel where some suites have private pools.

Personal note: We stayed at the Amalfi Resort which I strongly recommend against – one of those situations where it looks much better online than in person and then some. While the rooms are nice the rest of the property could use an update, the stay came with extra fees, and the only nice team member was the sweet lady serving breakfast.

Above: Collegiate Santa Maria Maddalena, Amalfi, interior and gardens, and the cathedral on the right.
Below: A few shots from Atrani including Restorante Savo on the right.

Below: Views from the observation platform.

What to do in Amalfi & Atrani

One of the main attractions in Amalfi are Chiostro del Paradiso, a Moorish-style cloister and garden (Google), and the Amalfi Cathedral (Google), both are absolutely stunning examples of Italian architecture. Note, you will need to cover your bare shoulders at the cathedral and if you don’t have something to do so they’ll give you a paper shawl.

Atrani, located just 15 minutes away walking, also has a lot of colourful historic architecture, like Collegiate Santa Maria Maddalena and the pink castle-like building near it. From the seaside, you will enter into the small public square called Piazza Umberto where you will also find the public bathroom for the nearby beach. Atrani Beach is sandy and has a beach bar, changing room amenities, and sunbeds for rent. The beach stretches all the way back to the Amalfi port broken up into different beach club businesses. Beaches in Amalfi get a bit more rocky but are still nice and all have the same amenities. All the beach images are below.

Accessing the Amalfi scenic lift/elevator

To get to the scenic lift can be tricky. First, you need to enter a parking lot and pay a small fee, here is a Google map pin from which you will see the said parking lot. The walk from the viewing platform to Atrani is really nice, but be mindful of the fact that people live there and refrain from entering their yards. 

The many regional festivals

Quite a few different festivals occur here during the warm summer season. Rome Chamber Music Festival takes place in June, in August there is Atrani’s Festa del Pesce Azzurro music and culinary festival, and in September there is a theatre festival called Teatro Regio Parma. Last year on September 9th we stumbled into a very local event based on a mythological story about water and fire, folks from across the region were out on the beach after dark celebrating, it was wonderful.

Abeove: Scene from a local Atrani festival. Below: Atrani as seen from the interior passages.

A few tours for consideration:

• Amalfi Organic Lemon Tour & Tasting: Private* or Group Tour*
• Amalfi Coast: Boat and Snorkeling Tour with a Captain*
• Amalfi Coast Sunset Small-Group Boat Tour*
• Capri Island Boat Tour with Snorkeling & Drinks*

Where to eat in Amalfi

So fun fact, the latest Equalizer was filmed in Atrani and the cafe where he spends time is Ristorante Savò Quality Food (Website, Google). Their menu is simple yet delicious. Get the pasta, get the seafood, leave room for a lemon dessert; make a reservation on WhatsApp. Back in Amalfi, there is the beachside Marina Grande (listed in the Michelin Guide) with a dining room overlooking the sea (Website, Google, Instagram). Have a glass of sparkling wine and one of the local signature dishes garlic, lemon, and clam pasta. Pizzeria Donna Stella is another well-known casual spot up a few stairs located inside an enclosed lemon garden (Google, Instagram).

Amalfi Coast is famous for its lemon desserts, both cold, like gelato, and the infamous baked Lemon Delight. Pasticceria Savoia is located in the Amalfi public square, has coffee and wine, and is a great spot for people-watching (Website, Google, Instagram).

***

At this point, our journey through Italy comes to an end. Hope you enjoyed your adventures.

In the gear bag: Fujifilm X-H2S with an XF50mmF2 R WR lens* and Fuji XF 23MM F2 R WR lens* plus DJI Mavic Mini* drone. To see the trip on Instagram look up #xoitaly23.