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Traveling Alone in Italy: It’s All Good, It Just Depends Where and in Many Instances Joining a Small Group May Be Your Best Bet!

Jesse Andrews by Jesse Andrews
January 8, 2026
in Luxury & Private Italy Travel, Tourism in Italy
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Home Luxury & Private Italy Travel

Venice

Over 16 years of arranging travel experiences in Italy we have learned a thing or two about how to organize tours. Having worked with thousands of people and organized thousands of tours one of the questions we often get is: Can we do it on our own? 

The fact of the matter is that the answer depends.  Sometimes you can, sometimes you should and sometimes you definitely should not.

In fact, now for groups of 8+ traveling outside of the major tourist areas, we often recommend to employ the services of a tour escort and some non-Italian tour leaders have learned the hard way that the right tour escort can really make a world of difference.

Here’s why:

Language 

In many of the more touristic places in Italy, some people speak English, but many do not.  Ferry operators, even taxi drivers and many waiters do not speak English and in some of the most beautiful areas in Italy outside of the major city centers, most people do not speak English and so you definitely do want an escort for larger groups or an English speaking driver guide who can help make your experience much better.

Knowledge

Local knowledge and insight about the places you are visiting are really second to none and can make a huge difference during your trip.

Peace of Mind 

Traveling with a group can be stressful especially when you don’t know anything about the place, the people, the local customs and the time it takes to get from one place to another!  An escort or guide can give you the possibility to actually ENJOY YOUR vacation and provides an incredible amount of Peace of Mind! Enough said!

Ease and Efficiency 

Knowing where the ticket office is at the Vatican, getting there in the first place or figuring out how to get to the most beautiful gardens in Ravello on the Amalfi Coast is not as simple as it might seem and if you don’t know it can sometimes take hours to figure it out.  Having somebody who knows the area, speaks the language and knows their way around can help you enormously!

Ordering at Restaurants 

You want to enjoy the best restaurants in Italy in a variety of regions outside of the tourist traps, GREAT! If it weren’t for the fact that so many of the best restaurants don’t really cater to tourists and often don’t have menus in English.  Not only this, but Italians have a totally different way of eating than the rest of the world. They have multiple courses and side dishes are all served separately.

Having someone just to translate the menu in and of itself is a HUGE asset!

Dealing with Locals & Local Temperaments 

Italy’s largest industry is the tourism industry and this said you would think people everywhere would be extremely friendly to tourists…. however unfortunately this is not the reality in so many places.  Dealing with language issues and stressful situations is not easy and an escort or guide can truly help in making things go much more smoothly.

There are many components that go into making a tour run smoothly from start to finish, perhaps more than you realize, so for groups of 8+ we really do recommend having a local Italian escort help facilitate your journey in Italy.  It really does make a huge difference!

And for people who are not traveling with a group of friends or family, some couples and single travelers can really benefit by taking an escorted tour rather than doing Italy on their own.

Having the possibility to move around easily and not have to worry about some of the very real and very annoying aspects of travel in Italy will allow you to actually have a vacation rather having to worry about logistics. Not only this, but taking escorted tours can often be MUCH LESS expensive than you can do it on your own.

We have some great guaranteed departure tours with fine tour escorts that run all over Italy.

Take a look at some of these here:

https://www.italyvacationspecialists.com/signature-small-group-tours-italy.html

For more information about planning a great trip in Italy get in touch with the experts: team@italyvacationspecialists.com

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Jesse Andrews

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