5 Tips to Plan the Best Trip to Italy Stress-Free
When it comes to planning a trip, no matter where you go, it is easy to quickly become overwhelmed. Especially traveling to a country like Italy, where the beautiful places to see are endless, the culture to experience is so rich, and the google search results are inundating.
If you work full time, chances are you only have 10 days to two weeks to cram it all in; you may be on a budget, and those two reasons alone are usually enough to turn something fun into a time-consuming nightmare.
If you have been dreaming about the perfect trip to Italy, here are 5 tips that will make your planning easy and worry-free:
TIP #1 - Choose off-peak season months
Off the beaten bath on Mt. Etna, Europe’s most active volcano.
If you are looking for a more authentic, less crowded experience, you will want to avoid the peak summer months of July and August. The weather is too hot, and prices are higher. Beginning of June is beautiful as the temperatures are warming up, but it is still considered high season with higher costs and bigger crowds. If you are not looking to do water activities, enjoy the cooler weather, and don’t mind some occasional rain showers, April and May are good months to go. Prices are lower, although you should keep in mind that in some beach destinations, especially in southern Italy, many hotels and restaurants will be closed until the beginning of May.
Our favorite time a year for almost any type of trip, especially adventure, is the fall. From boat charters to snorkeling, hiking and biking, September and October are the best months to visit most places in Italy. The water in September is still warm from the hot summer months but lower temperatures (in the mid to high 70s during the day and 60s in the morning and evenings) will make everything much more enjoyable and less sweaty. And if you are into wine, you may just catch the sacred wine harvest.
If fact, we plan a yearly trip to a stunning wine resort on Mt. Etna to participate in wine making activities. If you are looking for a fall trip full of adventure, relaxation, and of course outstanding wine, join us for our next.
Wine & Wellness Sicily Trip
We will hike Europe’s most active volcano, snorkel in pristine waters, enjoy fresh seasonal food and partake in one of Italy’s most ancient traditions: the grape harvest.
Space is limited to 8 people and this trip is sure to sell out fast!
TIP #2 - Choose to see less and experience more
We understand that when traveling to Italy, especially all the way from the U.S., we want to make the most out of our time. However, more is not always better. Trying to see everything and running from place to place just to take the Instagram-worthy shot, will leave you drained and unhappy. Sure, you will have some cool pictures to share but, in the end, you won’t have experienced the culture, the food nor the lifestyle… probably some of the reasons why you chose to come to Italy in the first place.
Unfortunately, we know so many people that even after our advice, decided to go to five locations in a week. Others who hopped on a three-hour train ride (each way) for a daily trip to Pisa to simply take the photo. The consensus after it was all said and done? “It was way too much, we were tired all the time, it was hot, and we don’t even remember half of the places we saw, nonetheless the people we met. We want to come back, but this time we are going to do it differently and enjoy fewer locations in a more leisure, deeper way.”
Differently from the Canary Islands, where there is somewhat of a sense of urgency to visit, Italy isn’t going anywhere anytime soon. You may need to split all the places you want to see between two or three trips. Heck, I’m from Italy and even though I’ve been living in the U.S. for about 10 years now, I go back at least twice a year and still haven’t seen everything I want to.
I’m sure you’ve heard of the term La Dolce Vita, the Sweet Life, or Il Dolce Far Niente, the sweetness of doing nothing.
Italy is a country to be savored… slowly!
I remember as a teenager, spending countless hours at the local bar (coffee shop) with friends and literally do nothing, other than observe the passerby and enjoy each other’s company. And of course, growing up, our meals, especially on weekends were at least three hours long. If you have had the pleasure to go on a food-focused trip, I’m sure you have experienced the long evenings at the dinner table and I’m even surer that during that time, you’ve made some of the best memories and meaningful relationships.
Our recommendation is that you choose quality over quantity and truly experience the lifestyle and the culture that our amazing country is so envied for.
TIP #3 - Talk to a local (expert or not)
There is nothing more valuable than conversing with a local or someone who has lived in Italy for a significant amount of time. Sometimes, I spend hours doing online research, only to become drained and even more confused by the information overload. Now, I’ve learned that picking up the phone and talking to a real person is far better than the web. I’m not saying the online information is bad or shouldn’t be used; but unless you have the time to understand each location, distances, weather, tourist waves etc., without your brain getting fried like mine, talking to someone is far more valuable and efficient. And even though they may not know everything about each place on your bucket list, they may have the right resources to point you in the right direction.
People connections are the best connections.
I wasn’t an expert back then and I’m certainly not an expert now on every single region, but I sure knew all the local spots my family and I enjoyed, the typical dishes that every visitor should try and the unknown gems where my friends and I would go hide away from the tourists. Disclaimer, I grew up in Rome and you’d be surprised of how many restaurants you can find in the city center where you can count more Italians than foreigners. You just have to know where to go. More articles to come on that later. When someone asks me about a place I don’t know much about, I have the network of friends, local guides, drivers and business owners who can help me.
You may be thinking, "Karen, you’ve made your point. But what if I don’t know any Italians?" Fair enough, I’ll give that to you. Then, you can talk to me! Life Beyond the Room was born out of talking. I was teaching Italian to students who obviously wanted to visit Italy and we would spend a lot of time, even the entire lesson, talking (in Italian) about the country, our customs, traditions, food, you name it! Eventually, one student was so enthusiastic that asked me to create an itinerary for him, focused of course on the local and authentic.
Our business was born out of the love and passion for our country, and we give everyone a chance to talk to us during a complimentary consultation so that you can ask us any questions and see if there is a way we can help you create the trip of a lifetime 100% stress free.
Would you talk to me even if I don’t want to use your services?
We hope you will change your mind after our conversation; however, we respect the decision of wanting to plan your own trip or simply having budget limitations. But the answer is sì! We love every opportunity to share our knowledge and we are confident that you will spread the word even though this may not be the right time for you. Does that sound like a good deal?
TIP #4 - Plan a year ahead
With the post-pandemic travel rush, everyone is eager to travel. Often in times the best boutique, family-run accommodations are the first to book up. Even though you may not be able to reserve many places online that far ahead, we personally know most of the owners or managers of our selection of boutique accommodations and can secure the booking prior to online availability. Some people may think that we place a mark-up on the cost of the accommodations and therefore assume that booking through us will cost more. However, that is incorrect and in fact, quite the opposite happens. As an IATA-accredited travel agency, we receive commission from hotels all over the world and are often able to split that commission with you, which means you pay a lower rate, and we get a cut. Plus, you know exactly what you’re getting because we’ve been there!
This principle doesn’t apply just to accommodations; reserving the best guides, boats, drivers etc. is often about timing. They are the best at their job and won’t be available last minute! I can’t tell you how many times I was able to puzzle in different clients, all traveling within the same week, with the same guide simply because we planned ahead. If you want to go to authentic restaurants instead of ending up in the tourist traps right outside the Vatican or the Colosseum because you are hangry, put a reservation in a few days early and plan your itinerary accordingly.
Don’t get me wrong, we have worked with travelers who have contacted us less than two months before their trip and while we still do our best to make it happen, we have to be very honest about the limited availability and higher pricing of last-minute bookings.
TIP #5 - It’s all about fun!
Ever felt like you’re good at something but you really don’t enjoy it? I have… many times. And eventually, I stopped trying to make myself like it! If you know you’re good at planning but are the type of person who easily gets stressed out, then don’t do it! Hire an agency, your husband or let your friends help you. The point is that if it ain’t fun, it ain’t worth it! See how well I learned English?!
Life and especially traveling is all about fun! A trip without laughter is a waste of time, energy, and money. But a trip of laughter, love and enthusiasm enriches life forever.
From our Tuscan Culinary Retreat a few years ago
I hope this article has shed some light on some best practices to follow when planning your trip to Italy. This year, whether for Christmas, birthdays, or anniversaries,
CHOOSE THE GIFT OF TRAVEL
It’s the only thing you buy that makes you richer.
Gift cards for travel credit are now available for purchase through our website. They never expire and are transferable to any person.
Explore Gift Cards
As theologian and philosopher Agostino d’Ippona put it,
“Il mondo è un libro, e quelli che non viaggiano ne leggono solo una pagina.”
The world is a book and those who don’t travel only read one page of it.