Getaway Compass

One Week Italy Road Trip Itinerary (Coast, Wine, History)

Val D'Orcia Tuscany

Follow this guide for an incredible one week Italy road trip through Cinque Terre, Tuscany and the Amalfi Coast. This road trip can also be done the opposite way, starting in the Amalfi Coast and driving up to Cinque Terre. In one week in Italy you can get a taste of a variety of areas in Italy.

Early fall is the best time for this one week Italy road trip. Tuscany is beautiful during this time and often this is when grapes are picked. The Amalfi Coast starts to get less crowded in September and the weather is cooler than in the Summer.

One Week Italy Road Trip Itinerary

Best Sites for Booking Your Accommodations in Italy

The best sites to book your accommodation for your one week in Italy is through Airbnb or Airbnb offers many different options including apartments, houses, and single rooms. is a great option for booking hotels, guesthouses, or hostels in Italy.

Italy Road Trip Tips: Driving in Italy

  • Renting a manual car is significantly cheaper than an automatic car. Book your rental car on Discover Cars where you can compare rates to find the best fit for your Italy road trip.
  • There are a lot of highway fee stations so be ready to pay with cash or card.
  • The roads can be very narrow and steep in Tuscany and the Amalfi Coast.
  • You should get an Italian sim card so so that you can easily route to your next destination and keep in touch with your Airbnb hosts. The most common networks are TIM, Lycamobile, and Vodafone. Don’t buy the sim card at the airport because it will cost about twice as much. We purchased a TIM sim card from a technology store for 16 Euros that includes a prepaid plan with plenty of data for one month.
  • Carry enough cash and small change for parking (especially in Tuscan villages).

Travel Medical Insurance for Your Italy Road Trip

Don’t forget to get a travel insurance policy for your trip! SafetyWing offers affordable, flexible, and reliable travel medical insurance that can be purchased ahead of your travels or while you are already traveling.

Day 1: Arrive in Italy and Travel to Cinque Terre

Riomaggiore Above

Cinque Terre is about 3 hours from Milan Airport and 2 hours from Florence Airport. As there are not many parking options within Cinque Terre the best option would be to park the car in La Spezia or Levanto and take the Cinque Terre train from there to the villages. There is a parking garage at the La Spezia Centrale train station. If you are basing yourself in Florence and don’t plan to rent a car, you could book this organized tour to Cinque Terre.

Where to Stay in Cinque Terre

It is worth spending the money to stay in one of the villages for the experience and to save time. There are many Airbnb options in the villages where you can rent a room for a good price that only costs a little more than staying outside of Cinque Terre in La Spezia or Levanto.
All five villages are beautiful, but I would recommend staying in Manarola. There are less stairs here than some of the other villages which makes it easier if you have a lot of luggage. This village is stunning at night and enjoyable to walk around. It is not as expensive as Vernazza and there are many Airbnb options, just make sure to book early!

How to Get Around Cinque Terre

Cinque Terre has a train that runs between Levanto and La Spezia, stopping at each of the five villages. It is about five minutes between each village, and about ten minutes from Riomaggiore to La Spezia. You can ask for the Cinque Terre train schedule at the information centers at the train sations. Buy the Cinque Terre Card to use the trains freely throughout the day.
You can hike between some of the villages but note that not all of the trails are always open. To check which trails are open stop at the information centers at the train stations.

Another option is to explore Cinque Terre with a boat tour where you can enjoy great views of the villages without the crowds.

Day 2: Explore Cinque Terre

Hike from Corniglia to Vernazza

Vernazza View

Trailhead: The trail begins in Corniglia center next to the church
Time: 1.5-2 hours
Difficulty: Moderate
1. Take the shuttle from the train station to Corniglia to save time and energy. The hike up from the train station to Corniglia has a lot of stairs and is very strenuous.
2. Wear comfortable walking shoes, preferably sneakers or hiking shoes
3. Bring plenty of water as a majority of the trail is in the sun

Walk Around The Villages and Explore Different Viewpoints



This village has the most diverse colors. Most popular for its view from the harbor, this village is very enjoyable to walk around. This is the biggest village in Cinque Terre and has a lot of interesting streets and more to see and do.
Best Viewpoint:
1. Climb up the stairs to see a view of the village from above and get a different perspective.
2. Walk down to the harbor opposite the red house. Walk down to the rocks to get this well known view of the village.



Manarola is the most tranquil and romantic village. It is beautiful at all times of the day and night, especially during sunset. The village is small but has several restaurants and is nice to walk around. This was one of my favorite towns during our one week in Italy.
Best Viewpoint:
Walk along the trail on the west side of the village beside the water to see this view.


Corniglia Close

This is a small village nested on top of a cliff. It is a very steep hike to the village from the train stations, but there is a shuttle that runs from the train station to the village and back.
Best Viewpoint:
The trail from Corniglia to Vernazza offers many beautiful viewpoints of this village


Vernazza Above

This village is the most popular with pastel colored houses and a small beach. It is the most expensive village to stay and eat but definitely worth a visit.
Best Viewpoint:
Follow the hiking trail from Vernazza to Monterosso Al Mare. About 20 minutes into the hike you will see this view.

Monterosso al Mare

Monterosso al Mare

This village is very different from the other four villages in Cinque Terre. This village feels more like a small beach town with a large stretch of beach and great gelato. This is a great spot to relax, but expect the beach to be busy.
Best Viewpoint:
Walk towards the end of the beach in the direction of Vernazza and you will see stairs that lead up to this view.

Sunset Boat Tour

Finish your day in Cinque Terre with a sunset boat tour from Monterosso. Sail across the coast and enjoy the views of the villages with wine and snacks. If you want you also have the option to swim.

Day 3: Wine Taste in Chianti and Explore Tuscan Towns

On your third day of your one week Italy road trip, spend the day exploring Tuscany. If you don’t already have a car, rent a car outside of Cinque Terre in La Spezia in order to drive to Tuscany. If you are basing yourself in Florence for these days and don’t plan on renting a car, you could book an organized tour of Tuscany from Florence.

Albola Castle

Albola Castle Tuscany

Start the day by drinking a glass (or two) of wine at Albola Castle. They have a restaurant located in a courtyard in the castle which offers a relaxing place to try good food and Chianti Classico wine. You can then walk around and enjoy the vineyard surrounding the castle.
If you are looking for a tour they offer tours twice a day which include a wine and olive oil tasting. You can also do a wine tasting separately from the tour. Make sure to email the winery to get updated tour times.


Ridda Street

A quiet Tuscan town not far from Albola Castle and worth a quick stop. There is a pizza restaurant where you can get the largest pizza you might ever see and several small shops. Note that the shops and restaurants close very early.

San Grimignano

San Grimignano

A very popular medieval hill town known for its fourteen watch towers, San Gimignano is a great place to walk around and experience a busy Tuscan town. Recognized as a UNESCO World Heritage Site, it gets very crowded in the main areas but if you walk away from the main squares you can find quiet streets and views of the surrounding countryside.



Walk around this quiet and romantic Tuscan town with beautiful views. Tip: Near parking number 1 pedestrian entrance there is an incredible view of the town and the surrounding vineyards (as seen in the above picture).

Where to Stay

Chianti is a good option for the first night in Tuscany as it is closer to Cinque Terre. In Chianti there are many Airbnbs where you can stay directly on a vineyard.

Day 4: Tour a Winery and Walk Around Tuscan Towns in Val D'Orcia

Tour Ricasoli, Castello Di Brolio

Albola Castle New Part

Ricasoli is a winery in Chianti known for creating the Chianti Classico wine recipe (by Baron Bettino Ricasoli). There are several tour options which you should book ahead of time because they do sell out. The classic tour is a great option if you are interested in the history of the castle from the 11th century and Chianti Classico Wine. The classic tour is about 2 hours and allows you to tour Brolio castle as well as the wine facilities. This tour finishes with a tasting of three great wines in a private room.

Tip: There is parking right next to the castle but it is very limited. Get to the castle at least 15 minutes before the tour starts to make sure that you get parking and don’t have to hike up



A quiet Tuscan town in Val D’Orcia known for its Brunello wine. This is the perfect town to relax, drink wine, and have lunch (just remember to eat lunch early because almost everything closes at 3!)



A small town in the middle of Val D’Orcia, Pienza is worth a quick stop for a glass of wine and cheese with views of the rolling hills. You don’t need more than 30 minutes to see the entire old town, but you can always spend more time relaxing and enjoying the views.


Montepulciano View

A dreamy Tuscan town perched on a hill, Montepulciano will steal your heart. This town is known for the delicious Vino Nobile di Montepulciano and Rosso Di Montepulciano which you can enjoy at any restaurant or winery. With narrow streets, lots of local restaurants, small shops, and incredible views, Montepulciano is a must-visit. Walk to Piazza Grande, Montepulciano’s center, where you will find the Cathedral and the clock bell tower. A visit to Montepulciano is not complete without climbing the clock tower to get a view of the town and the Tuscan Countryside, with Val D’Orcia and Val Di Chiana on either side. If you want to spend a night in a Tuscan town this is the one that I would recommend. 

Where to Stay

Stay in Montepulciano so you can experience the town at night when the streets are quiet and early morning as the town is waking up. It is a beautiful town and a great option if you want the opportunity to stay in a Tuscan town.

Day 5: Visit Pompeii and End the Day in Amalfi Coast

Leave Tuscany late morning and make the four hour drive to Pompeii. In 79 AD an eruption buried this large ancient city, preserving the roman ruins.


Tips for Visiting Pompeii

Arrive in the late afternoon after most of the big tour groups have finished. It is less crowded and also starts getting cooler at this time. When you purchase your tickets, rent a phone guide in order to better understand the stories behind the ruins.

Where to Stay

Book an Airbnb or guesthouse using in Bomerano for the next 2 nights. Benefits of staying in Bomerano is that there are much cheaper options, many accommodations include parking, and the food prices are good. Bomerano is where the Path of the Gods hike starts which will make it easy the next morning to begin the hike.

Day 6: Hike and Visit Positano

Hike the Path of the Gods

Path of the Gods

Your one week Italy road trip is not complete without hiking the Path of the Gods. Potentially the most beautiful hike you will ever experience, the Path of the Gods takes you along the cliffs from Bomerano to Nocelle (continue to Positano). Make sure you hike from Bomerano to Nocelle and not the other way around, or you and your legs will suffer. The views are incredible along the entire way: First you see cliffside vineyards, followed by Praiano from above, huge cliffs, and finally Positano from many perspectives.
Follow the Path of the Gods guide to see the best way to do this hike and details on where the trailhead is located.

Explore Positano

Positano View

You just hiked a long way to get here, so spend the rest of the day enjoying Positano. Note that all of the restaurants here are pricier, so go for the cheapest entree to save money. Positano get very crowded, especially at the beach and the boutiques near the beach.

Tip: If you want to get away from the crowds, climb up the stairs to the opposite side of the town from where you hiked to (towards Sorrento). Here you will get a different perspective of Positano than most of the photos you have seen and take a relaxing walk with views of lemon trees, the beach, and the colorful houses.

Note: There is no direct bus back from Positano to Bomerano. You will need to take a bus to Amalfi and then another bus from Amalfi to Bomerano.

Day 7: Amalfi Coast

Wake Up Early and Drive to Amalfi

Amalfi View

The benefit of a road trip through Italy is having flexibility and getting ahead of the crowds. If you want to see several of the towns in two days, you have to get up early. The Amalfi Coast doesn’t get busy until around 10:00 AM, which gives you plenty of time bright and early to explore before the crowds arrive. Get lost in Amalfi going up and down stairs and through narrow streets. Find different viewpoints by climbing up stairs as high up as as you can.

Parking in Amalfi: Luna Rossa is a good parking option. Located between Atrani and Amalfi, it has a tunnel that you can walk through to get to Amalfi. They require all passengers to wait for the driver to park, so don’t be surprised when they ask everyone but the driver to get out of the car before entering the parking.

By Bus: There is a direct SITA bus from Bomerano to Amalfi

Relax in the Cute Town of Atrani

Atrani View

Atrani is a short 10 minutes walk from Amalfi. This town is very similar to Amalfi but a lot smaller, and you can quickly get lost through the little streets, find your way back to your car, and drive off to the next town!

Enjoy the Views in Ravello

Villa Ruflo View

Ravello is a town higher up in the mountains with spectacular views. The atmosphere here is a lot more relaxing and less crowded than most of the towns down along the coast. Explore Villa Rufolo which offers some of the most beautiful views in Ravello.

Admire Ceramics in Vietri Su Mare

Vietri Su Mare

Known for its ceramics, Vietri Su Mare is a beautiful town to explore with ceramic walls and lots of little ceramic shops.

Cruise the Amalfi Coast

Amalfi Coast Cliffs

If you can allow yourself to spend a little more money, a cruise on the Amalfi Coast is an incredible experience! Don’t rent a boat in Positano- that would cost you hundreds of dollars. Instead, there are experiences on Airbnb that offer cruises along the coast.

Disclosure: Please note that some of the links above are affiliate links for products and services I recommend. At no additional cost to you, I earn a commission if you make a purchase and the income goes towards maintaining this site. As an Amazon Associate I earn from qualifying purchases.

Reut and Zack Elopement-5

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