5 of the Best Itineraries for an Amazing 2 weeks in Southern Italy

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While it is well known that the northern half of Italy has plenty to offer and most of the well-known sites that tourists flock to are located to the north of Rome. While there is plenty to do there, you can experience a whole new side of the country when you venture to the south. There are pockets of the region that attract fewer tourists but still have the unparalleled beauty that Italy is known for. If you want to explore Southern Italy but aren’t sure where to start, here are five of the best itineraries perfect for 2 weeks in Southern Italy.

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Itinerary One: 2-Week Southern Italy by Train

If you’re traveling to Italy from another country, it’s very likely that you will not have easy access to a car when you’re visiting. You can rent a car of course, but you don’t have to. You can opt to explore the southern region of Italy by train for a charming experience.

Start your 2 weeks in Southern Italy train journey in Gagliano del Capo. This small town is perched on a series of cliffs and overlooks the ocean on the southernmost tip of Italy. This small town has plenty of restaurants, cafes, marketplaces, and places to relax and immerse yourself in Southern Italian culture. If you’re interested in swimming, you’ll have the chance to swim in some deep and remarkably clear water.

Next, catch a train to Taranto. There are plenty of historic sites to explore such as the waterside Castello Aragonese. This castle and fortress were built circa 900! The Museo Nazionale Archeologico has a collection of historical artifacts you can browse to learn more about the history of the region. The ruins of the Tempio di Poseidon are a fantastic sight to behold as well.

From Taranto, you’ll be able to catch a train to Crotone. This historic city was established in 710 BC and was notable for its success in the original Olympic games. The buildings built into the cliffside overlook the ocean and provide a beautiful view. Spend time exploring the waters by boat or the surrounding landscape on foot. The region is known for exceptional wines and Crotone also has several Michelin-starred restaurants that you can treat yourself to when you visit.

Finally, catch a train to Reggio Calabria to finish your trip. Spend time wandering the picturesque beachside promenade known as the Lungomare Falcomata. You can also relax on the Reggio Calabria Beach where you can lay out on the warm golden sand or take a tip in the turquoise waters. If you’re looking to explore the natural beauty of Southern Italy, hike up the Rocca di Pentedattilo and soak in the views.

You’ll be able to have an incredible Southern Italian vacation without renting a car!

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Itinerary Two: 2-Week Island Time in Sicily

As a historical center of activity for trading on the Mediterranean, Sicily supports rich history and culture. Take all of this in with a tour of the port cities along the coast.

You can start your tour in Palermo when you land at the international airport associated with the city. You can spend days admiring the primarily Norman architecture although with a city as large and historic as Palermo you will see dozen of well preserved architectural styles. There are also several UNESCO World Heritage Sites throughout the city as well as exciting highlights such as the Norman Palace and Teatro Massimo. A guided trip into the Capuchin Catacombs may not be for everyone but you can get a unique perspective on the history of the city in a unique way, surrounded by thousands of mummies. After sightseeing makes sure to get some Sicilian-style pizza and arancini to refuel.

A two and a half hour drive away is Catania, another historic port city with incredible architecture. Built at the base of Mount Etna the city sprawls along the coastline with plazas, churches, and gardens dotting the landscape. A trip up to the top of Mt. Etna provides the best views you can get out of the city while wandering the streets lets you appreciate the ornate details of the Baroque architecture in the city. A trip through the fish market will surely be an adventure as it constantly buzzes at most any time of day. The location, as well as the market, means fresh local seafood is hard to beat.

About an hour away by train or car puts you in Syracuse, the final of the three port cities you will visit as part of this itinerary. Syracuse has well-preserved ruins in and around the city which can take a couple of days to take in. The Piazza Archimede is a great way to spend an afternoon and take in the sights and sounds of the city with the beautiful fountain as a backdrop.

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Itinerary Three: A Food Tour of Southern Italy


The entire country of Italy is synonymous with incredible food. Not only is the cuisine of the region unforgettable but many dishes you’ll be able to try in the southern part of the country are part of Italy’s illustrious culinary heritage.

Start your trip by sampling some authentic mozzarella in Campania. This traditional type of cheese is made from buffalo milk and is typically served fresh. You can always sample a bite by itself but one of the best ways to enjoy fresh mozzarella is over a fresh Caprese salad.

Next, head towards Italy’s west coast to the town of Naples, the city famous for pizza! It is said that the dish was invented here and you can even eat a slice at Antica Pizzeria Port’Alba, which is widely believed to be the world’s first pizzeria.

What food tour to southern Italy would be complete without limoncello? Head to Sorrento, further down the coast. While there are several areas of the Amalfi Coast that produce fine lemons, Sorrento is said to produce the best lemons that will therefore produce the best limoncello.

To head to your final stop on your southern Italian food tour you will next drive about eight hours south to Sicily. Along the way, you can explore countless wineries and small restaurants, but save room because Sicily is famous for several different types of delicious food. One of the most famous dishes that were created here is the cannoli! This tube-shaped pastry is filled with ricotta and occasionally topped with fruit or chocolate.

Itinerary Four: Step Back in Time as You Explore Southern Italy


Before heading down to Southern Italy, consider starting your adventure through Italy’s history in the capital city of Rome. The city was founded in the 8th century BC and served as the major hub for the Roman Empire. This ancient civilization consisted of a population of anywhere from 50 to 90 million, which means that the Roman Empire included nearly 20% of the earth’s population at the time. As you can imagine, there are countless historic sites to see here. You should plan for at least five days to explore Rome although you could easily spend several more. Some of the best places to go include the Colosseum, the Roman Steps, St Peter’s Basilica, and the Trevi Fountain.

An easy three-hour drive south will take you to the Flavian Amphitheater in Pozzuoli. It’s considered to be the third-largest of its kind. Construction dates back to the first century AD and you can learn a lot about the history of gladiators and animal fights that were popular in ancient Rome.

Less than a half hour further south is Pompeii. This is a can’t-miss for those who are passionate about history. Pompeii is one of the most well-known and well-visited archaeological sites in the world. The ancient Roman city was destroyed by Mount Vesuvius’ eruption in 79 AD, and was buried under four to six meters of volcanic ash. Because of this the site has been incredibly well-preserved and provided archaeologists and historians the unique opportunity to see what a day in an ancient Roman city might have looked like. Only a small portion of the site is open to the public as they prioritize preservation, but there is still plenty to see.

Itinerary Five: The Amalfi Coast


No trip to the south of Italy is complete without a stop by the Amalfi Coast. This enchanting stretch of coastline is known for lemons, warm weather, and a warm and hospitable culture.

Start your Amalfi Coast adventure in the beautiful town of Positano. This is one of the most popular spots on the coast and there are many who come to visit. The town is defined by its warm neutral tone buildings and the vibrant shades of greens and blues that surround it. This is a great start to your trip as you can spend time here either exploring the narrow alleyways and seeing everything there is to see, or you can simply relax on the beach and acclimate to a new time zone.

Next, head a half hour east to find Amalfi. The town that shares its name with the coastal region is beautiful and charming. It’s a prime spot for soaking in southern Italy’s sunshine as well as heading slightly inland to hike or explore some local wineries.

Finally, head to the small island of Capri via Naples. You’ll get to enjoy a scenic three-hour drive from Amalfi to Naples, where you can catch a ferry to Capri. One of the most magnificent stops you can make when you’re in Capri is a trip to the Grotta Azzurra or the Blue Grotto. This cave is accessible by boat and when you go inside you’ll be stunned. The waters inside take on a vivid blue color that you’ll have to see in person to believe. To visit you must book a tour on a small rowboat that only carries four passengers. It’s smart to book this in advance if you are traveling during the peak season as it’s an understandably popular stop.

Video Guide: 5 Amazing 2-Week Southern Italy Itinerary Ideas

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Additional Travel resources for planning a trip to Southern Italy

To make planning your 2 weeks in Southern Italy trip easier, we included some of our recommended travel resources below. You can search and find the best flights, transportation options, hotels to stay in, tours/activities, and things you can do in each destination during your 2 weeks in Southern Italy and other European cities.

Flights: 

Agoda: Search thousands of destinations around the world & quickly compare prices to find amazing deals on the best flights.

CheapOAir: You can find airline tickets, hotel rooms, rental cars, and vacation packages all on one site!

Kiwi.com: What we like about Kiwi is the fact that they are able to create combinations of flight, train, and bus tickets and offer them in a single itinerary. Also, Kiwi has what they called “Nomad” which helps you find the best way of visiting multiple destinations, saving you time and money.

JetRadar: You can search and compare airfares from 726 airlines and dozens of travel agencies and systems.

Hotels

Agoda: Agoda is one of the world’s largest online travel accommodation platforms with a network of over 2,000,000 vacation rentals and hotels worldwide.

Hotellook: They have more than 250,000 hotels in 205 countries, working with data from more than 10 online booking systems, such as Booking.com, Agoda.com, Hotels.com, Expedia, and others.

Transportations: 

Airport TransfersKiwiTaxiViator

TrainEuRailTrainline or RailEurope 

BusFlixbus: Very affordable (as low as $6) and convenient way to transfer between cities in Europe.

Car RentalsAutoEuropeEconomyBookings, or  GetTransfer (transfers & car rentals with a personal driver)

300x250 AutoEurope

Bike RentalBikesBooking (Bikes & scooter rentals) 

Transportation ComparisonOmio (search, compare, and book tickets for buses, trains, and flights all in one site)

Tours & Activities:

TakeWalks (WalkofItaly): This is our favorite site for walking tours & day trips.

Tiqets: Great site for entrance tickets. It offers directly bookable, instantly available, and completely mobile tickets for museums, shows, and attractions all over the world.

Musement: They have good activities and tours in Italy and Spain, also many great day trips you can choose from.

GetYourGuide: A large number of tours, excursions, and other travel activities

Viator: The largest one. It has everything from tours, attractions, shore excursions, and private guides in over 2,700 destinations worldwide. It also has many transportations and transfers options and some unique experiences we didn’t find anywhere else.

Want to spend 2 Weeks in Southern Italy and need help planning?

Want to spend 2 weeks in Southern Italy but don’t know where to begin? If you find this type of trip planning to be too complicated to plan on your own, we’re here to help!

At MultiCityTrips, multi-destination travel and complicated itineraries such as a multi-city trip to Southern Italy are our specialties. Contact us today to learn more about how one of our experienced travel experts/destination specialists can personalize your multi-city vacations at the best price.

Don’t want to start from scratch and need some trip inspiration? Check out our marketplace for customizable pre-designed packages available right now for many amazing destinations.

To learn more about how our process of trip planning works in detail, please see our “How It Works” page or check out our video on “How to Plan a Multi-City Trip to Europe in  5 Easy Steps”  here.

Have questions for us? Schedule a FREE Call with us here or contact one of the travel experts/destination specialists at [email protected], call/text us at (888)223-2316 today.

Private Travel Coaching & Consulting Call

Want to plan and book your upcoming trip yourself? If this is your first time traveling to any of the European destinations or you are new to multi-city, multi-country travel but prefer to manage every part of your trip on your own, this option is for you! 

For just $150 per hour, our destination expert can answer any questions you might have as you plan and book your dream trip. From assisting with route planning, and destination selection, recommending the best areas or places to stay, the best transportation options, things to do and see, saving tips and so much more! 

Ready to plan your trip with our help? Book your private coaching session with our destination expert now and we’ll confirm your appointment within 24 hours!

Travel Resources for Planning Your Own Trip

To make planning your European trip on your own easier, in addition to what already mentioned in our travel guide, we included some of our recommended travel resources below. You can search and find the best flights, transportation options, hotels to stay in, tours/activities, and things you can do in any destination using these travel resources:

European River Cruises:

Uniworld River Cruises: The world’s best and most awarded luxury river cruise line—offers itineraries in spectacular destinations throughout Europe, Russia, Egypt, Asia, and Peru. The company’s European fleet features luxurious ships with an average capacity of 120 guests, the highest staff-to-guest ratio in the river cruise industry, enticing shore excursions, world-class gourmet cuisine, impeccable hospitality, and numerous other all-inclusive benefits.

Pre- and Post-cruise/Tour Extensions: Uniworld curated pre-and post-cruise/tour extensions make it easy to add a few days to the front or back end of your trip while leaving the planning to them

The packages include a variety of hotel options, transfers, and a dedicated destination expert to escort you along the way.

Flights: 

Agoda: Search thousands of destinations around the world & quickly compare prices to find amazing deals on the best flights.

CheapOAir: You can find airline tickets, hotel rooms, rental cars, and vacation packages all on one site!

Kiwi.com: What we like about Kiwi is the fact that they are able to create combinations of flight, train, and bus tickets and offer them in a single itinerary. Also, Kiwi has what they called “Nomad” which helps you find the best way of visiting multiple destinations, saving you time and money.

JetRadar: You can search and compare airfares from 726 airlines and dozens of travel agencies and systems.

Hotels

Agoda: Agoda is one of the world’s largest online travel accommodation platforms with a network of over 2,000,000 vacation rentals and hotels worldwide.

Hotellook: They have more than 250,000 hotels in 205 countries, working with data from more than 10 online booking systems, such as Booking.com, Agoda.com, Hotels.com, Expedia, and others.

Airport Transfers & Transportations: 

Airport Transfers: GetTransfer offers both airport transfers & car rentals with a personal driver. Other airport transfer options are KiwiTaxi and Viator.

TrainEuroRailTrainline, or RailEurope are all great sites for train tickets as well as Rail Passes if you would like to add more flexibility to your trip. They are good for most trains throughout Europe. For trains in Italy, we like and recommend ItaliaRail. As for Portugal, you will need to go to the official website for Comboios de Portugal (the Portuguese train company) to book your train tickets when traveling in Portugal.

BusFlixbus: Very affordable (as low as $6) and convenient way to transfer between cities in Europe.

CarRentalsAutoEuropeEconomyBookings, or  GetTransfer (transfers & car rentals with a personal driver)

Bike RentalBikesBooking is a great site for bikes & scooter rentals

Transportation ComparisonOmio (search, compare, and book tickets for buses, trains, and flights all in one site)

Tours & Activities:

TakeWalks (WalkofItaly): This is our favorite site for walking tours & day trips.

Tiqets: Great site for entrance tickets. It offers directly bookable, instantly available, and completely mobile tickets for museums, shows, and attractions all over the world.

Musement: They have good activities and tours in Italy and Spain, also many great day trips you can choose from.

GetYourGuide: A large number of tours, excursions, and other travel activities

Viator: The largest one. It has everything from tours, attractions, shore excursions, and private guides in over 2,700 destinations worldwide. It also has many transportations and transfers options and some unique experiences we didn’t find anywhere else.

Travel Insurance:

Travel Guard:  Their comprehensive travel insurance programs, starting at $30, include per-trip & annual plans, coverage for trip cancellation, trip interruption, trip delay, medical expenses, baggage loss & more! Travel Guard provides 24/7-customer service with a personal touch through its World Service Center.

DISCLAIMER: Links included in this description might be affiliate links. If you purchase a product or service with the links, MultiCityTrips may receive a small commission at no additional charge to you.

Trip by Travel Experts

Need help planning a trip and find the best vacation package for your multi-city trip to Europe? If you find this type of trip planning to be too complicated to plan on your own, we’re here to help!

At MultiCityTrips, multi-city, multi-country European vacations, and complicated itineraries are our specialties. Contact us today to learn more about how one of our experienced travel experts/destination specialists can personalize an amazing multi-city trip to your dream destinations in Europe.

Ready for a trip? Check out our planning options and get in touch with us today!

Featured Pre-Designed Packages

These air-inclusive, pre-designed multi-city European vacation packages can be personalized to suit your needs!

Private Travel Coaching & Consulting Call

Want to plan and book your upcoming trip yourself? If this is your first time traveling to any of the European destinations or you are new to multi-city, multi-country travel but prefer to manage every part of your trip on your own, this option is for you! 

For just $150 per hour, our destination expert can answer any questions you might have as you plan and book your dream trip. From assisting with route planning, and destination selection, recommending the best areas or places to stay, the best transportation options, things to do and see, saving tips and so much more! 

Ready to plan your trip with our help? Book your private coaching session with our destination expert now and we’ll confirm your appointment within 24 hours!

Schedule a FREE Consultation

Not sure or can’t decide which planning option is right for you? Schedule a free 30-minute call with one of our travel experts to discuss your travel needs today!