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Travel Planning Italy: Organizing Your Dream Italian Getaway Step by Step

Updated: Mar 6


travel planning for   Cinque Terre italy

Embarking on a journey to Italy can be both exhilarating and overwhelming. With iconic destinations like Florence, Venice, and Rome frequently in the spotlight and social media platforms enticing us with drone photographs of  Positano and the Cinque Terre, it's easy to feel lost amidst the abundance of choices. So, where does your travel planning for Italy begin?

Define Your Italian Travel Experience

Don’t choose your location until you envision the Italy you wish to experience. What scenes unfold in your mind's eye when you think of Italy? Italy is a small country, yet each region has a different landscape and cuisine. You’ll find world-class hiking and skiing in the Dolomites along the Austrian border. Sicily puts you in the heart of the Mediterranean world, with a culture and cuisine that share more in common with Morocco than Rome.

That’s why reflecting on your desired experience will guide your trip-planning process and help you choose the best cities and regions.


Travel planning for rome
Caravaggio's paintings in San Luigi dei Francesi in the heart of Rome Photo credit: Danielle Oteri

Consider the following questions to define your ideal experience of Italy:

  • What emotions do you hope to evoke during your Italian getaway? Do you see relaxation and quiet locations? Do you want to be on the go and surrounded by the hustle of a city? Do you want to feel awe and wonder as you explore ancient ruins or hike sea-facing cliffs.

  • What activities would you choose if you were planning a weekend getaway closer to home? Would you have reservations at a Michelin-starred restaurant, or would you want to try all the best local taco trucks? Would you be in a city or nature? Would you have everything planned, or would you prefer to go with the flow and see what happens?

  • Are you drawn to bustling cityscapes, tranquil countryside retreats, or coastal paradises?

  • How do you feel about crowds? Be honest about this question, because the crowds for the Colosseum in Rome or Michelangelo’s David in Florence are truly massive. And if it is at holiday travel time, are you prepared for the stress of those crowds?

Understanding the essence of your desired experience will streamline your itinerary planning, remove the feeling of being overwhelmed and allow you to prioritize activities and destinations that resonate with your vision.

Italy Travel Budget Considerations


budgeting for travel in Italy
Every Italy trip has many ingredients

Your overall budget plays a pivotal role in shaping your Italian adventure. Rather than fixating on nightly accommodation costs, view your budget as a puzzle waiting to be assembled. Allocate funds based on your priorities, ensuring you can indulge in the experiences most matter to you.

For instance, if a once-in-a-lifetime tour like the Key Master’s Tour – a  6am private tour of the Sistine Chapel beckons, adjust your budget accordingly to accommodate this unforgettable experience. Remember, it's not about adhering to a strict daily spending limit but making conscious choices that align with your overarching travel goals.

It’s also important to remember that prices throughout Italy vary greatly. Venice, Lake Como, and the Amalfi Coast are the most expensive destinations. In general, Northern Italy is the most expensive, with a daily cost of living similar to what you’ll find in the northeastern United States. Southern Italy which is far less industrialized is much more affordable, especially as it comes to the cost of food. 

If you have a tight budget, take Lake Como and the Amalfi Coast off your list. It may be tempting to book a cheap Airbnb that says it’s very close to Positano, but what that listing is probably not telling you is about all the steps you’ll need to climb to reach the apartment high above the resorts and beach-accessible hotels that pay all those influencers and their drones to market the Amalfi Coast. Luxury destinations done on a budget will cheat you of the best of Italy which may be just a few miles from those artificially famous places. 

Seasonal Factors Travel Planning Italy

When planning your Italian escapade, consider the seasonal nuances that can enhance or detract from your experience. Summer months may beckon beachgoers to Italy's coastal havens, while early spring offers ideal conditions for exploring cities like Florence, Venice, and Rome sans the summer crowds. Also know that most residents flee the cities during August and go to the mountains or the coast for their own vacations.


October presents an opportune time to venture into the Italian countryside where when the weather is temperate and olives and grapes are being harvested. Meanwhile, the enchanting Christmas markets offer a magical ambiance despite the chill in the air.  

Navigating Destination Selection for Italy


italy food experiences
Neapolitan pastries at Poppella in Rione Sanità. Photo credit: Danielle Oteri

As you narrow down your options, consider the unique offerings of each region in Italy:

  • Culinary Delights: If food is your biggest interest, skip Rome in favor of Naples, or choose Modena instead of Florence. The best food in Italy is not found in the most famous places, which must cater largely to budget-conscious tourists but in less well-known regions like Irpinia, Puglia, or Abruzzo, where ancient food and wine traditions are still practiced and industrialized food is rejected. 

  • Natural Wonders: Seek solace amidst Southern Cilento's pristine beaches, the rugged landscapes of the Dolomites, the geothermal parks in Ischia, or the most classic views of Tuscany, which are found in the Val d’Orcia.

  • Cultural Treasures: Immerse yourself in the artistic legacies of Florence and Venice with visits not just to museums but to the artisan shops of Florence’s Oltrarno or the Carrara marble quarries, where sculptors since Michelangelo go to see the best material for stone carving.

By aligning your destination choices with your desired experiences and budget parameters, you can curate a personalized itinerary that reflects your travel aspirations.


Travel Planning Practical Considerations


As you delve deeper into your travel planning, address practical considerations such as transportation and airport logistics:

  • Determine whether you prefer the flexibility of driving or the convenience of train travel.

  • Select an airport that best serves your itinerary, considering major hubs like Rome and Milan first, then secondary airports like Naples, Venice, or Palermo.


Common Mistakes and Personalized Experiences for Italy


strenuous hiking in italy

Navigating the plethora of online information can be overwhelming, leading travelers to make common mistakes that hinder their Italian experience. Here are some pitfalls to avoid:

  • Misjudging the Amalfi Coast: While it may seem like a budget-friendly destination, its infrastructure struggles to accommodate the influx of visitors. Opt for a resort or hotel to fully enjoy the experience, or explore the more budget-friendly Cilento Coast for a similar vibe.

  • Cinque Terre Hiking Expectations: Don't visit the Cinque Terre expecting strolls; hiking is the main attraction here. Consider alternative destinations like Procida or Burano for picturesque views without the strenuous hikes.

  • Underestimating Venice: Venice deserves more than a day trip. Avoid the crowds in San Marco Square and explore the city's northern lagoon for a magical experience. Additionally, prioritize lesser-known attractions like the Accademia for a quieter museum experience.

  • Winging it in High Season: Spontaneous travel is challenging in popular Italian destinations due to high demand. To avoid disappointment, make reservations in advance for attractions like the Colosseum and top restaurants.

  • The "Under the Tuscan Sun" Fantasy: Tuscany's countryside villa rentals offer idyllic retreats but come with logistical challenges like grocery shopping and transportation. If you're using Airbnb vs a villa management company, be prepared to ask lots of questions ahead of time about the amenities included and what the villa is stocked with by the owner vs what is the renter's responsibility.

Personalized Experiences

To truly immerse yourself in Italy's rich culture, prioritize experiences that resonate with your interests and budget. Here are a few more ideas you won’t find on the mass travel market but ones that Feast Travel can help you realize:

Irpinia vinyeard
Strolling through the vines in Irpinia. Photo credit: Jessica Scranton
  • A visit to the San Ambrogio market in Florence with a chef, then a cooking class in her kitchen in the Chianti hills, overlooking the city.

  • Snorkeling through the ruins of Baia, the Miami Beach of ancient Rome, which is now partially underwater close to Naples

  • Tasting wine with a family of winemakers, hearing the stories of multiple generations while you have a home-cooked lunch with them surrounded by the vines.

  • A catamaran tour through Venice’s northern lagoon at sunset, led by a local expert who will show you the lesser-known islands like Torcello and even bring you to a monastery where a community of monks makes their own honey.

Embrace the essence of Italy by curating a personalized itinerary that aligns with your passions and budget. This will allow you to create unforgettable memories that capture the true spirit of La Dolce Vita.


At Feast Travel, our specialty is designing unforgettable memories for our discerning travelers. Our Trip Consultation and Planning services are tailored to help you explore Italy’s secret beauties, ensuring a journey that is as unique as you are. Whether you're dreaming of wandering through the cobblestone streets of a small medieval town or relaxing on a secluded beach, Feast Travel can make your Italian adventure a reality. Contact us today to plan your unforgettable journey to Italy's lesser-known spots.


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