Traveling to Italy: How To Plan The Ultimate Trip

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Taking a trip to Italy is an entirely exhilarating experience. You’re taking yourself out of your usual routine, out of your usual location, and putting yourself down in one of the oldest civilizations on the planet — a place filled with both natural and man-made beauty, home to art and excellent cuisine, and a people who are warm and welcoming by nature. Any trip to Italy is a wonderful one, but we should make the most of the time we have, shouldn’t we? With that in mind, we have a few reminders for you to keep in mind when planning your Italian vacation.

Planning The Most Memorable Holiday Ever

  1. Decide on Locations, Timing, and Your Budget

Before anything else can be planned, you must know where you would like to go, when you would like to go, and how much money you have to spend on getting there and enjoying these locations. 

Summer (June to August) is very warm and the peak tourist season. We advise against booking your holiday over this period.

Fall (September to November) begins to cool by October but remains relatively busy in all the tourist centers. Rain begins to fall in October, but Italy is incredibly enjoyable nonetheless.

Winter (December to February) is very cool on the coast and often snowy inland and in mountainous regions. Christmas in Italy is quite magical, but some places, like Venice, can become very costly.

Spring (March to May) is like a movie in Italy, with flowers blooming and tiny animals being born on the farms and in the woods. Visiting the countryside in spring is incredible, but note that many Europeans travel to Italy over Easter.

We advise choosing the “in-between” months for the mildest weather and minimum tourist population. Travel and accommodation costs are far lower during these times, and you’ll find booking and enjoying experiences far easier. Your budget, which should be researched according to prices in Italy and set with a reasonable financial buffer, will go far further during these times. You may even be able to indulge in extravagances; perhaps you could book a private jet to get close to remote locations like Pilato Lake in Marche for a unique experience.

  1. Do Your Research

Once you’ve decided when, where, and how much, you can research places to stay, ways to get around, and experiences you can have at your chosen destinations. Taking this portion of the planning phase seriously will give you as many wonderful experiences as time allows and ensure that you have contingency plans.

  • Take a look at blogs and Instagram feeds that feature travel tips: those who travel a lot will have lots of advice to give you that you may never even have thought of. Check out online guidebooks and sites like Conde Nast Traveller Viator, Get Your Guide, or Lonely Planet for exciting things to do and places to see.
  • Learn a few phrases in Italian, especially if you plan to travel to remote locations where people may not speak English. Things like “How are you?”, “Where is x location?”, “Where can I buy x thing,” and “Thank you very much” might be helpful. It is also polite to try to speak the language of the country you are visiting.
  • Find out which areas are unsafe or which attractions are unseasonal — you don’t want to put yourself in a dangerous location or waste time and money on an experience you can’t enjoy.
  • Save train and bus schedules, car service numbers, maps, directions, etc., in a folder in your cloud for easy reference. Remember to note areas where you may not have Wi-Fi or a phone signal, and ensure that you have physical copies of all this information on hand when you visit these locations.
  1. Expect the Unexpected

Planning is essential when you travel. Having a backup plan might mean knowing what time the second train of the day is in case you miss the first one. Or have a physical copy of your passport on hand should your passport be misplaced. What you can’t plan for, however, is the unexpected. It may rain on a day when all weather reports predict sunshine, and you may miss the last train even when you planned to be at the station two hours ago. You need to know that things like this will happen, so remain calm when they do. It’s important to have a backup for your backups, especially when traveling alone, so that you’re always safe and able to move around. In case your plans for the day come undone due to weather or something like that, it’s a good idea to have alternate plans lined up or just enjoy the unexpected time to rest.

  1. Have Everything You Need

Consider the seasons when you pack. Autumn, winter, and spring travel will need both hot and cold weather options, while summer packing is a little easier. Remember to pack the following essential items:

  • Your travel documents. Have physical copies and copies saved to your cloud service.
  • Comfortable and supportive walking shoes.
  • Your camera and charger or film and batteries. 
  • An adapter for your plugs.
  • A spare phone charger.

All That’s Left Is To Enjoy Yourself

The best way to plan and prepare for a sensational trip to Italy is to remember to relax and have a good time! You’ve done the work of prepping, researching, and ensuring you have backups in place — now you get to enjoy the fruits of that labor.

Traveling to Italy: How To Plan The Ultimate Trip

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