Italy Travel Planner

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Boomers love traveling to Italy, especially when they use our Italy Travel Planner

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.

This article may contain referral links. Read our Disclosure.

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. Or subscribe to the My Itchy Travel Feet Weekly Broadcast to be the first to know!

Online Italy Travel Resources

Cobblestone street in Subiaco.

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.

Should you travel to Italy by air or by ship?

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.

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.

Independent travelers should book tours, too!

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 Italy independently, booking tours ahead is a time saver, especially skip-the line tours:


Where to stay in Italy? Think unique!

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.

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.

When in doubt, consult our favorite Italian travel experts

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.

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.

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.

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.

Be prepared for anything on a trip to Italy

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.

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.

Italian Trip Books, Guides and Videos

Based on first-hand travel inspections, Rick Steves Italy 2019 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. Read it before your next boomer vacation in Italy. #food #vacation #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, an excellent travel resource for visiting Italy. #travel #tip #Italy

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

Gear for an Italian Trip

Travelon Anti-theft Cross Body Bag will keep your valuables safe on a boomer vacation in Italy. #travel #gear #Italy

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 helps you travel light on a boomer vacation in Italy. #luggage #Italy #vacation

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 helps you pack efficiently for a boomer trip to Italy. #packing #tip #Italy

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.

Bookmark this page as I update the Italy travel resources that we use. Better yet, subscribe to the My Itchy Travel Feet weekly broadcast so that you don’t miss a thing. You’ll also enjoy our latest articles, timely trip inspiration and travel deals. Subscribe by clicking here.

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Italy travel planner for boomer travelers