Lake Como, a place to visit if you are wondering how to plan a trip around Italy
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How to Plan a Trip Around Italy: 10 Places You'll Love

By Catarina Santos9 min read

If you're wondering about how to plan a trip around Italy that perfectly blends history, art, food, and stunning landscapes, look no further. This simple guide will walk you through how to plan a trip around Italy and introduce you to 10 incredible places you'll fall in love with. And, if it's not too much trouble, take me with you once you decide to go. Please and thank you!

10 must-see places in Italy

1. Rome

No guide on "How to Plan a Trip Around Italy" would be complete without the nation's beautiful capital. This bustling city is an essential stop on any Italian travel itinerary. Overflowing with historical sites like the Colosseum and Vatican City, Rome is a feast for the history buffs.

The capital city of Italy is home to the Colosseum, the Roman Forum, and Vatican City, where you can witness the grandeur of St. Peter's Basilica and the Sistine Chapel. While planning a trip around Italy, make sure to sample the local Roman delicacies at eateries like Da Francesco and Roscioli. Don't miss a chance to toss a coin into the Trevi Fountain, a tradition believed to ensure your return to Rome.

How to plan a trip around Italy - where to stay in Rome:

  • High-end: Hotel Eden - Set in the heart of Rome with stunning views of the city, this hotel offers luxury rooms and a rooftop restaurant.
  • Budget-friendly: The Beehive - An eco-conscious guest house located near the Termini train station, offering private and shared rooms.

2. Venice

Venice, a place to visit if you are wondering how to plan a trip around Italy Known for its romantic gondola rides and intricate architecture, Venice is one of the best cities to visit in Italy. As you glide down the Grand Canal, you'll be enveloped by the city's charm and beauty.

Venice boasts iconic landmarks such as St. Mark's Square and Doge's Palace. A gondola ride through the city's canals is an absolute must-do but don't forget to have some of the best things in life, good food. For a taste of Venetian cuisine, visit local gems like Trattoria Antiche Carampane and Osteria alle Testiere. Be sure to visit the colourful island of Burano and the glassmaking island of Murano.

How to plan a trip around Italy - where to stay in Venice:

  • High-end: The Gritti Palace - A luxurious hotel set in a former noble residence on Venice's Grand Canal, with views of St. Mark's Basilica.
  • Budget-friendly: Combo Venezia - A stylish hostel set in a former convent, offering a range of accommodation options.

3. Florence

Florence is a must-visit for art lovers. From Michelangelo's David to the grandeur of the Duomo, this city brims with masterpieces.

The Tuscan city offers the Uffizi Gallery and the Accademia Gallery, housing world-renowned artworks. A climb up to Piazzale Michelangelo at sunset is a must for breathtaking views of the city. For Tuscan flavors, head to Trattoria Sostanza and Mercato Centrale.

How to plan a trip around Italy - where to stay in Florence:

  • High-end: Four Seasons Hotel Firenze - Offering spacious rooms and suites, this hotel boasts a large park, an outdoor pool and a spa.
  • Budget-friendly: Ostello Bello - A budget-friendly option with a lively atmosphere, located close to the Florence Cathedral.

4. Milan

Milan, a place to visit if you are wondering how to plan a trip around Italy Milan is Italy's fashion capital and an integral part of your Italian vacation planning. Shop at high-end boutiques, admire The Last Supper, and don't forget to take in the modern city vibe. The fashion and design capital also houses the iconic Duomo di Milano, so make sure to stop by and admire its greatness. Dining at Cracco and Luini Panzerotti is a must for any food enthusiast. Also, don't forget to see a performance at La Scala Opera House.

How to plan a trip around Italy - where to stay in Milan:

  • High-end: Armani Hotel Milano - Situated in the fashionable Quadrilatero della Moda district, this hotel exudes style and sophistication.
  • Budget-friendly: Ostello Bello Grande - Located close to the central train station, this hostel offers free dinners and cultural activities.

5. Bologna

Any foodies out there? One essential touring Italy tip is to not overlook smaller cities like Bologna. Known for its rich food culture, Bologna is the perfect stop for those who want to dive deep into Italian cuisine.

The city offers food markets like Mercato delle Erbe for those wanting to taste local produce. Visit Piazza Maggiore and the iconic Two Towers. For authentic Bolognese cuisine, Osteria dell'Orsa and Trattoria Da Me are great choices.

How to plan a trip around Italy - where to stay in Bologna:

  • High-end: Grand Hotel Majestic "Gia Baglioni" - Housed in a lavish 18th-century palazzo, this hotel offers luxury in the heart of Bologna.
  • Budget-friendly: Dopa Hostel - A modern hostel located centrally, offering a shared kitchen and cosy rooms.

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6. Naples

Naples, a place to visit if you are wondering how to plan a trip around Italy Naples is your gateway to the stunning Amalfi Coast and the historical site of Pompeii. This vibrant city is also the birthplace of pizza, making it an important stop on your Italian travel guide. Experience the authentic Margherita pizza at Pizzeria Starita. Don't forget to visit the National Archaeological Museum and explore the stunning **Amalfi Coast **nearby. Cities such as Positano, Sorrento, Ravello and Atrani are essential entries in the how to plan a trip around Italy list.

How to plan a trip around Italy - where to stay in Naples:

  • High-end: Romeo Hotel - A design hotel offering rooftop dining, a pool, and a wellness centre with views over the Bay of Naples.
  • Budget-friendly: Hostel of the Sun - A friendly, well-located hostel offering private and shared rooms.

7. Verona

For those seeking romantic travel routes around Italy, Verona is a must. Visit the famed Juliet's Balcony and the well-preserved Roman amphitheatre, making sure to get lost in the city's medieval streets. Ristorante Il Desco and Trattoria al Pompiere are perfect spots for an Italian meal.

How to plan a trip around Italy - where to stay in Verona:

  • High-end: Due Torri Hotel - Located in the historic centre of Verona, this hotel offers luxury rooms and an impressive lounge area.
  • Budget-friendly: Hostel Verona - Centrally located, offering comfortable dorms and private rooms with a modern touch.

8. Cinque Terre

Cinque Terre, a place to visit if you are wondering how to plan a trip around Italy Exploring Italian destinations isn't complete without the colourful villages of Cinque Terre. It's a must in our list of how to plan a trip around Italy. Hiking between these cliff-side towns offers breathtaking views of the Ligurian Sea. Visit the beautiful beaches in Monterosso and eat fresh seafood at Trattoria dal Billy. A boat trip to see all five villages from the water is also a must-do.

How to plan a trip around Italy - where to stay in Cinque Terre:

  • High-end: Hotel Porto Roca - Located in Monterosso al Mare, this hotel offers rooms with sea views and a cliff-side pool.
  • Budget-friendly: Ostello Tramonti - Located a short bus ride from the main towns, this hostel is a cheaper alternative in this popular area.

9. Sicily

When planning an Italian vacation, don't forget the beautiful island of Sicily. Visit the Valley of the Temples, Mount Etna, and indulge in unique Sicilian dishes. Sicily offers other diverse attractions, from the Greek temples of Agrigento to the bustling markets of Palermo. Sample Sicilian pastries at Maria Grammatico Pasticceria in Erice and relish seafood at Bye Bye Blues in Mondello.

How to plan a trip around Italy - where to stay in Sicily:

  • High-end: Belmond Grand Hotel Timeo - Located in Taormina, this hotel offers stunning views of Mount Etna and the coast.
  • Budget-friendly: Cappuccini Flats - Located in Palermo, offering budget-friendly apartments in a historic convent.

10. Lake Como

Lake Como, a place to visit if you are wondering how to plan a trip around Italy What about finishing your trip with some relaxation by the stunning Lake Como? It's one of those must-see places in Italy with its mountainous backdrop and picturesque lakeside towns. This idyllic lake offers villas like Villa Carlotta and Villa del Balbianello. Take a boat ride on the lake for stunning views of the surrounding mountains. For a taste of Lombardy, visit Locanda dell'Isola Comacina and Il Gatto Nero.

How to plan a trip around Italy - where to stay in Lake Como:

  • High-end: Grand Hotel Tremezzo - Offers stunning lake views, a floating pool, and a spa in a luxurious setting.
  • Budget-friendly: Lake Como Beach Hostel - Located in Domaso, this hostel offers a relaxed atmosphere and lakefront access.

This is also important if you're wondering how to plan a trip around Italy

Now that you've got a list of cities, how to plan a trip around Italy will largely depend on the time you have. A well-rounded two-week itinerary could include Rome, Florence, Venice, Milan, and a choice between Lake Como or Cinque Terre.

Take note that travel within Italy is relatively easy, with an efficient network of trains connecting most cities. Depending on your preference, you can also opt for renting a car, especially when exploring more rural areas.

When figuring out how to plan a trip around Italy, consider spending at least two to three days in larger cities like Rome, Venice, or Florence, and one to two days in smaller ones like Bologna or Verona. However, remember that each city offers a unique experience and it's important not to rush through them.

Knowing how to plan a trip around Italy comes down to identifying what you want from your Italian adventure. From soaking in history and culture to enjoying delectable cuisine, Italy has something for every traveller. So get started with your Italian vacation planning and prepare for an unforgettable journey!

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