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20 Step Guide To Planning The Perfect Italian Vacation Itinerary

Planning a vacation to Italy is a dream come true for most people. The country offers stunning landscapes,  cities steeped in history, beautiful architecture and amazing food at almost every corner.  With so many sights to see and options to choose from, it can sometimes become overwhelming trying to plan the perfect trip and fit everything in to your itinerary.

Before planning a trip to Italy is important to narrow down what type of vacation you are looking for.  Do you want to spend your days exploring historical sights by foot? Would you rather relax on the beach while taking in stunning cliffs and views of the sea? Or, are you looking for the bustling city life with high end shopping and 5 star restaurants? The beauty of Italy is that you can almost have it all - with a well planned itinerary that hits all of the major cities and hot spots.  Depending on the amount of time you have, a well thought out trip to Italy should include stops in Venice, Rome and Florence, with optional day trips to explore the Tuscan regions and the stunning coast.  Take a look at a sample itinerary below for the perfect Italian vacation.

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20 Start in Venice

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Located in northern Italy, Venice is an excellent starting point for your Italian vacation.  Starting off in northern Italy will allow you to travel towards southern Italy, hitting all of the major cities on the way.  Besides its location, Venice is a beautiful city that maintains its charm despite the fact that it draws thousands of tourists each year.   Walking through the cobble stone streets and exploring the canals on water taxis or via the infamous gondolas is the typical Italian experience that you can and should check off of your bucket list. As beautiful as the city is to explore, staying for one night in the city on water is sufficient and will give you the first taste of the beauty that Italy has to offer.

19 Venice: Activities

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One of the best things to do while in Venice is to simply walk around and stroll the maze of streets that surround the wavering canals.  It is easy to get lost in this city, and that is not a bad thing. By walking through the narrow, interconnected streets, you will discover hidden gems away from the busy tourist areas and stumble upon authentic restaurants that the locals usually frequent.  To get a truly unique view of the beautiful city, head to the Campinile di San Marco and take the trek up the stairs of the large bell tower at the corner of the famous San Marco square.  The top of the bell tower affords picturesque views of Venice, perfect for your insta-stories.

18 Venice: Where to Stay

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There are plenty of accommodation options in Venice ranging from typical European style hotels, to Airbnb rentals.  It is important to first figure out whether you want to spend a little bit more on accommodations and stay in central Venice, or if you want to save and stay in areas slightly outside of Venice and commute to central Venice for daily activities. The busiest areas are closest to the Piazza San Marco, where most of the tourist action takes place.  One thing to keep in mind is that the narrow streets of Venice are sometimes hard to navigate, made even harder with suitcases and luggage.  You can avoid this by staying closer to the train station- but then will have to put up with a commute to central Venice for most of the activities.  If you are looking to splurge, check out the hotels in the island of Giudecca- home to Venice's most luxurious hotels.

17 Head to Florence

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Pack your bags after a night in Venice and take the high-speed express trains towards Florence to arrive there in just under 2 hours.  The trains are spacious and comfortable, with WiFi and electrical outlets for you to upload all of your pictures from Venice. Snack are also available for purchase at the cafe on the train.  The express trains are slightly more expensive than the regular local trains, but the amount of time you save is well worth the price. Local trains will get you to Florence in sometimes 5 hours depending on the route. The trains depart regularly from the Venezia Santa Lucia train station, which is accessible by walking, or more easily with luggage, with a water taxi.

16 Florence: Activities

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Similar to Venice, Florence is a city that can be enjoyed and explored by foot.  With stunning historical architecture on almost every corner, your days can easily be filled by walking around, eating gelato and strolling the streets. If you are looking for something less touristy to do than visit the famed Duomo, why not visit a secret garden at the Bardini Villa and Garden, a garden perched on top of a hill that is surrounded by the medieval walls of the the city.  A visit to the garden provides a truly unique view of the city, in a quiet escape from the bustling city streets below.

15 Florence: Where to Stay

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Like most cities that have a high tourist rate, accommodations range from high end luxury hotels, to budget-friendly hostels, and everything in between.  The Ad Astra Boutique hotel in the Piazza Tasso neighborhood is a charming hotel that overlooks the largest private garden in Europe.  The small hotel has 7 rooms in the main villa and 2 larger rooms  situated in the private garden with terraces overlooking the garden. The hotel is conveniently located and is within walking distance to plazas and squares and several authentic restaurants. Each room is uniquely furnished with artwork and pieces by local artists, creating a truly customized experience that is a nice change from the standard chain hotels.

14 Florence Day Trip: Explore Tuscany

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Florence is the perfect location for day trips to explore the region of Tuscany. Several tour operators offer day trips from Florence to explore the Tuscan region via guided hikes or bike tours.  For a truly unique experience, explore the Chianti regions famous wine vineyards on horseback with a guided horseback tour.  The tour will take you through the beautiful countryside of rolling hills and olive groves, while you sample some of the finest wine in the world.  Tour operators will provide transportation, and will usually travel by bus or minivan for the short 45 minute ride from central Florence.  A day trip to the vineyards is the perfect way to break up a stay in Florence or add an activity in between your stay.

13 Florence Day Trip: Cinque Terra

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If you have a friend who has gone to Italy, you have inevitably seen a photograph of them in front of  the colorful tiny homes set atop limestone cliffs overlooking the sea. Cinque Terra (which literally translates into 5 lands) is 5 small villages located in the Italian Riviera that is an absolute must-see on any trip to Italy.  Tourists can hike through all 5 villages with a guided tour, taking in breathtaking views atop cliffs, and resting at each of the islands. While you can certainly plan your own trip to explore Cinque Terra, the day trip is quite long and the train ride may take up to three hours.  For the best experience and to make the most out of the day, check with your hotel concierge who can provide options for recommended tour guides and travel options.

12 Florence Day Trip: Pisa

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If visiting all of the tourist spots in Italy is high priority for you, Florence offers the perfect opportunity to visit one of the most photographed spots in Italy.  With a short one hour train ride from Florence and with trains leaving every 15-30 minutes, you can easily hop on a train for a perfect day trip to visit the leaning tower. Unlike Cinque Terra, a visit to the leaning tower of Pisa can easily be done on your own, without the need for a tour guide.  Once you arrive at the train station in Pisa, you can either walk or take a bus to the location, and take all of the cheesy 'pushing the tower' pictures you want!

11 Depart Florence for Rome

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Next on the itinerary is a 3 hour train ride from Florence to Rome.  Steeped in history, Rome is a bustling city that tourists generally flock to for the historical sights and tourists spots such as the coliseum and the trevi fountain.  The entire city of Rome is a UNESCO World Heritage site, with more art and historical monuments throughout the city, than any other place in the world. If the architecture and history aren't enough to draw you in, Rome is famous for its cuisine, with many signature dishes arising out of the region.  Spend your days exploring the food and the sights of Rome, and leave enough time for a day trip or two as well.

10 Rome: Activities

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Walking around the eternal city and among the ruins of the 2000 year old city has its own charm.  Like almost any city in Italy, Rome in particular is oozing in history and culture and can be enjoyed by foot.  For most tourists, however, a visit to Rome is not complete without a visit to the Coliseum, the Spanish Steps and the Trevi Fountain.  Beyond these tourist attractions, Rome has a lot to offer for those looking for a slightly different stay in the historical city.  Why not take in a 2000 year old pyramid in the center of the city? The Pyramid of Cestius was built during the Roman Empire period as a way to incorporate Egyptian relics into Roman culture.  Or visit the largest surviving ruins of ancient baths at the Baths of Caracalla, and take in live theater set against the historical backdrop.

9 Rome: Where to Stay

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Rome has accommodation options for every budget. If convenience factor is high on your list, you will likely want to stay in the Centro Storico neighborhood, where all of the major tourist sites are located.  While hotels in this area are more expensive than other options, you can literally step out of your hotel and walk to the Spanish steps or Trevi Fountain, leaving you more time to explore the city. If you are more of a foodie, the Jewish Quarter is the perfect spot for you.  The charming neighborhood is close enough to the city center but far away enough to avoid the crowds.  Filled with authentic Roman cuisine and restaurants, the Jewish Quarter is perfect for those looking for an escape from the tourist packed center.

8 Rome: Day Trip to Pompeii

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Rome is a convenient location to take a short day trip to the historical city of Pompeii.  While several tour operators offer group packages from Rome, you can easily plan a trip on your own by taking the train from Rome's Termini Station to Naples, and then from Naples to Pompeii.  The entire trip might take you up to 2.5 hours, but trains run frequently and there are a number of different fare grades available to suit any budget. Pompeii is a fascinating city with a rich history.  Once one of the richest and largest cities during the Roman Empire, the city was destroyed by the eruption of the Vesuvius volcano, leaving behind beautiful historical ruins of ancient wonder.  You can easily spend more than a day in Pompeii but if you are short on time, a day trip from Rome is the perfect way to explore the city.

7 Depart Rome towards the Amalfi Coast

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There are fewer places in the world more beautiful than Italy's Amalfi Coast.  The cliff side towns overlooking the sparkling blue sea are breathtaking and are the perfect spot to end off an exhilarating Italian vacation.  One of the best ways to explore the sometimes pricey region is by making Sorrento your home base, and exploring the Amalfi Coast towns by day trips or short overnight trips.  Sorrento is easily accessible from Rome, with a train ride to Naples, and then onwards to Sorrento.  Sorrento is a quaint and beautiful town, littered with lemon and olive groves and surrounded by mountains and the Mediterranean. It is the perfect location to wander on a rest day, and return to after exploring the beautiful neighboring regions.

6 Sorrento: Activities

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The coastal town of Sorrento faces the Bay of Naples and is set atop a cliff, surrounded with views of the water. In the summer, the town is filled with tourists and the main square is the perfect place to people watch, window shop and take in the street performers who wander the streets looking to entertain guests. There are cathedrals to explore, old narrow streets with quaint shops and of course restaurants perched atop cliffs and overlooking lemon trees and the sea.  The Marina Grande is a seafood lovers dream, with small family run restaurants offering up the freshest seafood dishes, caught fresh from the sea.  Spend the day exploring the picturesque town and exploring the many beaches surrounding the town.

5 Sorrento: The Amalfi Drive

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The thrilling drive from Sorrento to the Amalfi Coast is one of winding roads on steep cliffs, with astounding views of the open sea.  The most challenging part of the drive is keeping your eyes on the curving roads ahead, instead of the stunning views below.  If you want to live on the edge, rent a car and try the ride at your own risk. If you want to enjoy the views without stress, jump on one of the several buses and tours that operate from Sorrento to the coast.  The drive alone is an activity on its own- be sure to clear your storage and leave enough room for the views by day and night, each offer a distinct beauty on its own.

4  Sorrento: Day Trip to Positano

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Positano is a village along the Amlafi Coast that is the closest to Sorrento and the most easily accessible. There are several options to reach this beach town with budget friendly options such as public buses, to more personalized transport of private car rentals, or for a truly 'Italian' experience, you can always rent a scooter.  Positano is approximately 40 minutes from Sorrento, and is known as a romantic beach town with boutique hotels, restaurants and shops for the discerning traveler.  While visiting Positano you can visit the many art galleries, eat authentic pizza, or spend the day taking in the sun at the pristine beach.  It is a photogenic town that is perfect for a day trip or to even spend a night at any one of the boutique hotels that overlook cliffs, mountains and the sea- take your pick!

3  Sorrento: Day Trip to the Island of Capri

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From Sorrento, you have many options to travel to the world-famous, and celebrity favored island of Capri.  You can continue your drive through the Amalfi coast to Capri, or hop on one of the several ferry rides that depart from Sorrento daily.  The ferry ride is around 30 minutes and is a budget friendly option that offers up close and personal views of the stunning coastline.  If you don't want to join the crowds on the ferry you can always charter your own yacht with the numerous groups that offer private yachts for travel between the villages.  However you decide to get there, be sure to schedule enough time to explore the beautiful island and all it has to offer!

2 Capri: Activities

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Like almost all the cities on this itinerary, Capri is a town to be enjoyed with a stroll.  The winding narrow streets will take you through small shops, restaurants, and beautiful churches, all withing view of the beautiful coastline and views of the sea. At Monte Solaro, a chair lift will take you up to the highest point on the island, for a panoramic view of the coast.  While it is a popular tourist spot, the views are completely worth the trip and the crowds.  Off land, the blue grotto is a popular tourist destination and is known for the electric blue water that glows inside of a cave.  Either way you cannot go wrong doing any of these activities or simply lazing around the beautiful town.

1 Head Back Towards Naples

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After touring the Amalfi coast and maximizing the storage on your phone with all of your photos of the coastline, head back towards Rome, with a stopover in Naples.  Naples is the birthplace of Pizza and undoubtedly makes some of the best pie in the country. Stop in for some lunch at almost any local restaurant and you will not be disappointing. After gaining some energy,  work off the calories with a climb of the famous Mount Vesuvius if you dare, and take a look at the only volcano in Europe to erupt within the past 100 years.  Take in the views from the top of the volcano, and return to town for a lazy day at the beach.

After touring essential spots in Italy, head back towards your starting point for the sad trip back to reality!

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