Italy Travel Planner

This article may contain referral links. Read our DISCLOSURE

Planning a trip to Italy is both exciting and frustrating. With so many incredible things to see and to do, narrowing your trip down can be a bit overwhelming.

To help you with the planning, and hopefully add a bit of inspiration to the process, we’ve compiled our tried and true Italy travel tips along with a list of recommended Italy travel planning resources for your next boomer travel adventure.

small street in an Italian village

Use our Italy Travel Planner to make the most of your active boomer trip. And come back often as we continue to update and verify our recommended online resources and products for you.

What you'll learn in our Italy Travel Planner

  • tips on getting started
  • which is better: arriving in Italy by air or ship
  • how to find the best places to stay in Italy
  • tips for booking a private tour
  • why you should consider guided city tours and how to find them
  • where to find the best online Italy travel resources
  • which Italy travel guides and books to read
  • gear for an Italian trip
  • the most iconic Italy destinations
  • off-the-beaten-path Italian travel ideas

Boomer Travel Tip

Subscribe to the My Itchy Travel Feet Weekly Broadcast to be the first to know when we post new Italy travel articles! Subscribe here.

Tips for getting started with Italy travel planning

Blue, red and gold fresco ceiling

Of course you want the trip to go perfectly. Don’t we all? But when it doesn’t, you’ll be reassured by the plans and strategies you made ahead of time.

Will you need a Visa? What are the passport regulations? Since our readers are mostly from the U.S., your best bet is to check the travel section at the U.S. Department of State.

Beginning in 2021, U.S. citizens traveling to Europe (and Italy), will need to apply online for a ETIAS visa waiver. Here are the details.

We think purchasing a travel insurance policy is essential for any international trip. Insure My Trip is an excellent resource for comparing travel insurance policy rates. Remember to check your medical insurance provider to see if they cover international travel. Medicare does not provide international medical coverage, however some supplemental Medicare policies do.

And don’t forget to purchase a medical evacuation membership with MedjetAssist. Before starting on a trip, we make sure that our MedjetAssist evacuation membership is up-to-date. Peace of mind with short-term travel protection starting at $99.

Should you travel to Italy by air or by ship?

Island with historic buildings in the middle of a lake in Italy

Obviously, if you want to maximize your time in Italy, flying is the way to go. Before booking flights to Italy, we search the best rates in flights with Skyscanner. Be sure to download their app for researching while you’re on the road: Skyscanner iOS App Download or Skyscanner Android App Download.

One of our favorite methods of traveling to Italy is arriving or departing by cruise ship, as part of a transatlantic cruise. In our opinion, the very best combination is to fly to Italy for a 10-day private driving tour (cruise luggage stays with you), then board the ship in Civitavecchia for the ride home.

We’ve also cruised from Ft. Lauderdale to Rome and then flown home. This approach has two downsides. First, there are a lot of 23 hour days as the ship cruises toward Europe. And, second, touring at the end of a cruise doesn’t fit our travel style as we’re usually anxious to go home.

How to find the best places to stay in Italy

We’re fans of Italian lodging that exudes character, which usually means staying at inns, boutique hotels or bed and breakfasts. Our research begins at Hotels Combined to see what’s available and compare prices. Then we click over to TripAdvisor to compare reviews.

Be aware that when it comes to inns or bed and breakfasts,  4-star in Italy is not the same quality as 4-star in the U.S, so be careful when booking. One thing we always look for—a private, ensuite bath.

Our favorite places to stay

If you like boutique hotels or unique accommodations in slightly off-the-beaten-path Italian destinations, be sure to read about our favorite places to stay in Italy. We’ve been there to check them out for you. Here are a few of our favorites.

Il Lavatoio offers charming lodging in Castel di Sangro.

Quaint Il Lavatoio: Staying in an Italian Wash House in Castel di Sangro

If you enjoy traveling Italy as much as Alan and I do, part of the reason is probably those quaint accommodations that ooze with charm. We certainly found that to be true on a stay in Castel di Sangro in the province of L’Aquilla. Read our Il Lavatoio review to find out why we quickly […]

Read More >
Boomer travel - Italy - stay at La Tavola Rotonda on your boomer vacation in Italy.

La Tavola Rotonda: My Italian Castle

When you think of places to stay in Italy, does a castle come to mind? It does if you’re staying at La Tavola Rotonda.  My idea of castle lodging is a fairytale building perched in the Bavarian hills of Germany, perhaps with snow-capped mountains in the background. I never expected to be sleeping in an […]

Read More >

Romantic Relaxation in Tuscany

The end of a long-anticipated trip should leave travelers wanting more, don’t you agree? That’s what Alan and I appreciated so much at the end of our trip to Italy…the ending. When Alan and I stepped through the nondescript entry to Sovana Hotel and Resort in southern Tuscany, we discovered a lobby that felt as […]

Read More >

Tips for booking a private tour

Booking a private tour to Italy is a smart choice that offers true value. A La Carte Italy Tours has planned our two road trips in Italy. We shared our travel ideas with owner, Claudio Fontana, who then created an itinerary for us. The all-inclusive price consisted of a driver/guide, all accommodations, meals, wine and entrance to most activities and museums.

This is a luxury experience that’s well worth the price. Please note that we are not an affiliate nor do we receive any referral fees from A La Carte Italy Tours. We’re simply sharing one of our favorite travel resources. Read more about our trips with Claudio at road trip to Northern Italy and Southern Italy road trip adventure.

Why you should consider guided city tours

Yes, I know, you’ve read up on the destination and know all there is to learn about it. Right? Wrong.

A day tour offers valuable insight into a destination. We think it’s beneficial to add a couple of Italian day tours to your itinerary. If you’re traveling independently, booking tours ahead is a time saver, especially skip-the line tours:

The best online Italy travel resources

Large white limestone building with a dome

Whether you’re planning a land adventure in Italy or researching Italian ports for Mediterranean cruise excursions, online travel resources equal instant information at your fingertips. But we’ve found that too much information complicates research rather than speeding it up.

That’s why we’ve included only the best online resources in our Italy Trip Planner. Bookmark our favorites for your Italian travel itinerary. We’ve also included our favorite apps.

Reading from a variety of sources is the best way to plan a trip. And it’s always important to find travel information that best fits your style of travel. Here are a few of our favorite resources for travel in Italy:

Rick Steves Italy Travel Guide provides travel advice from the king of traveling independently in Europe. You’ll learn a lot from Steve. Budget travelers, this is for you. Luxury travelers? Take note of the unique experiences knowing you will up the quality of lodging and transportation.

Official Italian Tourism Website is a good place to start your planning process. Although it might not be the best resource for off-the-beaten path destinations, the website offers a lot of helpful information and a great calendar of local events throughout the country.

You’ll find many article on travel in Italy here at My Itchy Travel Feet. Based upon the personal travel experiences of either Alan and me, or guest writers, these articles share the best of where to go in Italy.

Via Michelin allows you to design an itinerary based on things you want to avoid—like toll roads. The site also calculates the amount and cost of the fuel that you’ll use, plus there’s a hotel database for finding lodging along your route. We could get lost for hours designing trips on Via Michelin.

We’ve become experts when it comes to curating and vetting travel apps. And if you’re a travel app user, check out our favorite apps for Italy travel.

The best travel guides and books for traveling to Italy

Based on first-hand travel inspections, Rick Steves Italy 2020 takes boomer travelers from the Alps to the Mediterranean. You’ll learn all of Rick’s tips and tricks for authentic travel in Italy.

Di Palo’s Guide to the Essential Foods of Italy is the perfect guide for those who like to travel by taste. Not only does the guide offer some must-have plates from various regions throughout the country, but the authors also describe the history behind each traditional plate.

Lonely Planet Italy’s Best Trips is for those of you trying to decide between Italy’s many diverse regions.

Gear for an Italian Trip

Travelon Luggage Anti-Theft Cross-Body Bag is a good idea for anyone hitting Italy’s bigger cities, especially Rome. Pick pockets and bag snatchers are everywhere so you can never be too safe! We like the chic look—a plus for traveling in travel-conscious Italy.

Eagle Creek Luggage Load Warrior Wheeled Duffel 22 bag will fit into the trunk of those small Italian rental cars. I traveled for 21 days in China with this bag.

Eagle Creek Travel Gear Pack-It Specter Starter Set is the secret to packing light. Shh!

Ceptics Small Size Worldwide International Travel Plug Adapter Kit is a great tool to have for every trip thanks to its compact size and weight.

The most iconic Italy travel destinations

While we’ve published many articles about where to go in Italy, there are certain must-see cities that boomer travelers should experience at least once in their lifetime and that includes Rome, Florence and Venice.

Sunset glow over ancient Rome

Baby Boomer Adventures in Rome

If you’re looking for tips on baby boomer adventures in Rome, Italy, you’ve come to the right place. Read on to add this trip to your bucket list. After covering Italy quite extensively over the years, including writing our Italy Travel Planner, it’s clear that we love to get off the beaten path in this […]

Read More >
man steering a gondola with passengers inside

Travel Tips for Venice from a First-time Visitor

Is this your first time in Venice? The Floating City has been a top Italian destination for well, forever. Recently, the Venice has made headlines for its efforts to crack down on rampant tourism that has overrun the iconic city for decades. However, that doesn’t mean you can’t enjoy a responsible trip to Venice these […]

Read More >
View from Bell Tower

Exploring Florence: Art and Culture in Italy

They say that you haven’t really seen Italy until you’ve seen Florence. This gorgeous town is where the Renaissance period began and today, Florence is very much a work of art in itself. Sure, it’s an incredibly popular tourist area, but its full-on Italian splendor and sophistication will leave you breathless nonetheless. Today’s guest contributor, […]

Read More >

Off-the-beaten-path in Italy

After exploring Rome, Florence and Venice, it’s time to visit off-the-beaten-path Italian destinations. It’s our favorite way to experience the country. Here are a few ideas to get you started. You’ll find more on the where to go in Italy page.

Alan and Donna Hull in Trani, Italy

Walking With History in Trani

On a Southern Italy road trip, Trani turned out to be one of our favorite destinations—one that Alan and I have talked about visiting again on our own. Along with Claudio Fontana of A La Carte Italy Tours, our guide for the trip, and Stephanie, a local expert, we spent the better part of two days […]

Read More >
Boats in the harbor at San Domino in Italy's Tremiti Islands

Tremiti Islands: An Off-the-Beaten-Path Adventure in Italy

Want to go off-the-beaten-path in Italy? Visit the Tremiti Islands off Italy’s Gargano Peninsula. Okay, I’m sure that most Italians and Western Europeans know about these tiny islands near the Adriatic coast. But how many Americans visit? Alan and I are raising our hands, here, and giving you reasons to add them to your next […]

Read More >
Charming Orta San Giulio, Italy

Orta San Giulio: Northern Italy At Its Best

Cobblestone streets, a 1580’s era town hall with a frescoed facade, outdoor cafes on a plaza bordering a mountain lake, a fairy tale looking island in the middle of that lake—atmosphere, atmosphere, atmosphere. This is exactly what Alan and I hoped to find on our road trip in Northern Italy. When we told Claudio Fontana […]

Read More >

Don’t forget to sign up for the Weekly Broadcast!