Planning a Trip to Italy or Europe from the US

Planning a trip can mean hours of research, comparing destinations, hotels, transport, itineraries and things to do.

At Canvas Travel Club, I provide personalized travel advice to help you make confident decisions and create a trip that fits your time, interests and travel style.

If you’re planning a trip to Italy or Europe from the US, you may already have a long list of places you want to see.

Rome. Florence. Venice. The Amalfi Coast. Paris. Barcelona. Maybe Switzerland too.

Seeing lots of places on a map is one thing. Putting them together into a trip that actually works is something completely different.

I’ve worked in travel for many years, and one thing I’ve learned is that the best itinerary isn’t necessarily the one that fits in the most destinations. It’s the one that fits you.

Start with your time, not your destinations

How much time do you have?

If you have 10 days in Europe, for example, I wouldn’t automatically suggest four or five cities just because they look relatively close together.

Imagine flying from New York to Rome and having only 10 days. You could technically visit Rome, Florence, Venice, Milan and Lake Como.

But every time you change cities, you lose part of a day packing, checking out, travelling and checking in again.

Instead, I might suggest Rome, Florence and Venice, depending on your interests. That gives you enough time to actually experience each place rather than constantly feeling like you’re on your way somewhere else.

And if you particularly want to see the Amalfi Coast, I might rethink the itinerary rather than simply adding it on.

Don’t underestimate distances in Europe

Europe may look small compared with the US, but that doesn’t mean travelling between places is always quick or simple.

A journey that looks easy on a map can involve a train, a connection, a transfer and another journey once you arrive.

This is particularly true in Italy. If you want to visit the Amalfi Coast, for example, your journey may involve several different types of transport depending on where you are coming from and where you are staying.

I always look at the whole journey, not just the travel time shown for a flight or train.

Think about what you actually want from the trip

Two people can visit Italy for the same number of days and need completely different itineraries.

If you love art, history and food, I might plan something very different from a trip for someone who wants beaches, scenery and long lunches.

For example, if you tell me:

“We have 12 days, we love food and wine, we don’t want to rush, and we’d rather have a few memorable experiences than see everything.”

That immediately tells me something about how I would plan your trip.

I wouldn’t fill every morning and afternoon with sightseeing. I’d leave room for a long lunch, a walk with no particular destination or a small wine tasting.

Those are often the moments you remember.

How many days do you need in each place?

I prefer to ask what you want to do there rather than simply counting attractions.

Rome, for example, can easily fill several days. If it’s your first visit and you want to see the Colosseum, Vatican Museums and historic centre, I wouldn’t try to squeeze it into one or two nights.

On the other hand, you don’t necessarily need five nights everywhere.

A good itinerary has a rhythm. Some places deserve more time, while others work well as a shorter stop.

What should you book first?

I generally like to establish the overall route first, then look at flights, accommodation and the key experiences or transport that could affect the itinerary.

There’s no point finding a beautiful hotel in one town before deciding whether that town actually makes sense for the route.

Some things are worth booking well ahead because they are particularly popular. Others can be left flexible.

If you’re not sure where to start, you may also find my guide on how far in advance to book a holiday useful.

Your first trip to Europe doesn’t have to include all of Europe

I understand the temptation. If you’re flying from the US, you may feel that you need to make the most of the trip.

But you don’t need to see five countries just because you’ve crossed the Atlantic.

A slower trip through Italy can be much more enjoyable than trying to combine Italy, France, Switzerland and Spain in two weeks.

Maybe your first European holiday is Italy. Next time, you could explore Portugal or Greece.

You don’t have to turn one holiday into a European grand tour.

A few practical things to remember

If you’re travelling from the US, your holiday starts with a long-haul flight, so it’s worth being realistic about how much you can comfortably do once you arrive. I’ve also shared some practical tips for making a long-haul flight easier.

Before travelling, remember the less exciting but important details too: check your passport requirements, think about travel insurance and phone data, look at luggage restrictions for internal flights and consider how you’ll get from the airport or train station to your accommodation.

After a long flight, having your airport transfer arranged in advance can make arriving in a new city much easier, especially if you’re travelling with luggage or arriving late. Welcome Pickups is one option for arranging a private transfer.

If you’re travelling around Europe, an eSIM can be a convenient way to stay connected without having to find a local SIM card when you arrive.

I usually compare a couple of eSIM providers before choosing one. Airalo is a good starting point if you want a straightforward eSim option, while Yesim is worth considering if you're looking for more flexible or unlimited data plans.

And don’t forget that travelling around Europe can be different from travelling around the US.

You may walk much more than you’re used to. You may encounter cobblestone streets and stairs, and some older buildings don’t have lifts.

A centrally located hotel can sometimes be worth paying a little more for simply because you can walk out of the door and start exploring.

So, where should you start?

If you’re sitting in the US with a vague idea that you want to “do Italy” or “see Europe” but you’re not sure how to turn that idea into an actual trip, start with three questions:

How many days do I have? What do I really want to experience? How much travelling between places am I comfortable with?

Once you know those three things, the rest becomes much easier.

And if you still don’t know where to start, that’s exactly where professional travel planning can help.

At Canvas Travel Club, I don’t believe in creating the same European itinerary for everyone. I look at your time, interests, travel style and priorities and help you work out what makes sense for your trip.

Because planning a European holiday shouldn’t be about seeing how much you can fit in.

It should be about making the time you have count.

How I Can Help

Destination Planning

Choose destinations that fit your interests, available time and travel style.

Itinerary Planning

Create a realistic route without trying to squeeze too much into your trip.

Accommodation Recommendations

Get recommendations based on location, style and what matters most to you.

Transportation Advice

Understand the best ways to move between destinations, including trains, car travel and other options.

Activities and Experiences

Find experiences that fit your interests rather than simply following the usual tourist checklist.

Travel Plan Review

Already planned your trip? I can review your itinerary and help you identify gaps, unnecessary travel or opportunities to improve it.