First trip to Italy and out of the country

You have enough already considering the trip is 7days.
If your plane ticket is roundtrip to and from Milan, you might cut out Rome on this trip and just concentrate on Venice Florence and Pisa, since Rome further south. And you should consult a guide book on Italy. That way you get idea about else you want to do based on your own interests.

Where are you flying out of? Rome I hope.
When are you going (you don't say)? If it is within 2 months you need to buy your train tickets for Venice - Florence and Florence - Rome. Do not buy Milan - Venice in advance as you cannot predict when you will emerge from Milan airport.
Read here for more info: https://www.seat61.com/Italy-trains.htm

Sounds like you’ll be busy with the itinerary you have planned. It’s always nice to have a slow day or two to just wander around and see the architecture and atmosphere of a place. Venice, Florence and Rome can easily fill 7 days each.

Unless your budget is unlimited you don’t want to show up in Venice without a room pre-booked. Even if you have unlimited money, not a good idea. For such limited time stick to Venice-Florence-Rome. Also flying into Milan when you want to start in Venice is not ideal. You should definitely get a guide book as soon as possible and start with fundamental research.

My first suggestion is that you re-think arriving in Milan, unless you already bought your tickets? It's the least interesting of the places you've listed. Depending on where you are flying from in the US, you could fly directly to Florence, Venice, Pisa or Rome. You could also fly into one city and out of another, so your route could be a straight line rather than a circle. Getting from one place to another takes time. So you don't really have 7 days to see Italy if you are traveling on 4 days... If it's too late to change your flight, then (as someone said above), cut out Rome on this trip and stay in the northern/middle part of Italy (Florence-Venice).

If this is your first trip to Italy, it's tempting to want to see everything, but you could spend the entire week in Rome and never run out of wonderful, amazing, beautiful things to do and see (and eat!). Same goes for Florence or Venice. (Not so much Pisa...) If it was me, I'd cut out Pisa and Milan and the vineyards this trip, at the very least. If you can bear to go just one place, make it Rome. If you have to do 2, go to Florence and Venice, and save Rome for the next trip.

Also, if your trip is between now and the end of September, get your train tickets and B&B reservations NOW. 30 years ago, it was possible to just show up and find a great place to stay anywhere in Italy (unless the Pope was in town). Not any longer. Several million tourists will be arriving in Italy this summer. Get a copy of Rick Steves' book on Italy and start emailing places to stay right away.

Once you've nailed down the cities you are going to visit, post again and ask us for advice on what to see. I'm going to Belgium this summer, and I've gotten some amazing suggestions on hidden gems (and major sights that are worth the crowds) from people on this Forum.

Have fun!

These cities are packed with famous art, architecture, parks - and you don't know what to do? Also, all of them offer short travel day trips to other places of interest. I recommend a guide book, Instagram, Pinterest, or some mode of research to see your options and decide from there. Not everyone has the same interests, and just because someone says to 'go there', doesn't mean you will enjoy it so a bit more independent research is required.
Hopefully you are flying into Milan, and our from Rome. As mentioned, book all but your first train ticket ahead of time to save $. If you aren't aware of the website yet, seat61 dot com is fantastic for helping with train travel information.
(for what it is worth, I am looking at flying into Milan and going straight to Venice as well. Because of my personal complicated travel routing, I can save a whole lot of money arriving in Milan instead of Venice itself. It can sometimes be the best budget solution even if not most efficient).

You need to be aware that every time you change hotel cities, you will lose 1/2 day-changing locations is time-consuming. I don't understand why you haven't gotten Rick Steves Italy guidebook. It would be very helpful and increase your confidence in what you are doing.

Hi Jae,

lol, You might have 'jet sneakers.' Your plans are very ambitious and your visit will be like a drive-by experience, if that.

traveling to Italy. We will be there for 7 1\2 days... flying into Milan then taking a train straight to Venice...we want to go to Florence to visit Pisa and a few vineyards...we will be traveling to Rome where we will be there for 2 days and visiting the Sistine chapel...don't know what else to do.

Are the 7-1/2 days including your travel days? Also, 7 days is not a lot of time to see what you want in all those places. You'll be spending time going to and from, packing and unpacking, probably tired.

As you stated, you have not reserved a place to stay in Venice - which can be very expensive to begin with.

With one week, I personally would stay in one place. But, if your reasons are such, then perhaps you can somehow choose only two places?

I don't know if you think this will be your only visit to Italy. But, I'm not sure you'll really enjoy it all - it will seem like a "quick flash of a bulb cam."

There is a ton of things to do in Rome - some things free and some need a booked entry ticket. Rome is a walking museum in itself.

Some of "the" major attractions for travelers...

Beautiful -

Piazza Navona (a beauty of a place with four fountains steeped in history),
Piazza Della Rotonda (home to The Pantheon - an active Church),
Campo de' Fiori (an open market with little side streets of shops and eateries),
Piazza di Spagna, More history. Climb the stairs to reach the gorgeous Church.
Colosseo, (Timed tickets are needed to enter.) But, you can just walk around the outside Amphitheater.
Vaticano (Sistine Chapel), (security check - no big bags allowed - around 14 inches should be okay.)
Piazza San Pietro (St. Peters), (security check - no big bags allowed - around 14 inches should be okay.)
Castel Sant'Angelo (Bridge of Angels - a short walk from The Vatican area)
Fontana di Trevi (Trevi Fountain with its rich Roman history and majestic sculptures and mesmerizing beauty.)
Borghese Gallery (no bags allowed - must be checked) - Need timed tickets which can be hard to get at late date.

** Keep in mind - When entering a Church in Rome, it is required that shoulders and knees be covered. No exceptions. Be prepared with a scarf similar to a Pashmina (if wearing shorts or sleevless tops.) No revealing shirts - guards will not let you in.

There are many, many, many niches in and around Rome. Beautiful churches around every corner, awesome architecture, ornate sculpted buildings, lively neighborhoods, hustle bustle of a city, and the list goes on and on.

Rome is a very walkable city and can be relatively inexpensive to eat and stay. You just have to do some research.

Jae,

Here is another consideration:

Say you stay in Rome for a few days, you can train it (from Termini) to Orvieto. The schedules meet most travelers' plans.

It is about one hour from Rome. You can take the funicular uptown. In the Piazza, you'll come face to face with the gorgeous, active Duomo - https://en.wikipedia.org/wiki/Orvieto_Cathedral

Orvieto is a quaint, "hill town" of sorts. It is in the Umbria region. Very walkable, traveler friendly, inexpensive, beautiful scenery. You may not be able to visit vineyards as stated in your OP, but, here is an alternative:

https://www.orvietoviva.com/en/orvieto-wineries/ Orvieto is well known for its "Classico" wines.

Florence is a two-hour (fast train ride) from Roma Termini. Get off at Santa Maria Novella (SMN.) Important to know the names and stops. The train may "read" a different end point, but as long as SMN is part of your ticket, you're okay.

It is always a very good idea to read each attraction's, site's, Church's policies - Italy is very strict with some things.

If you are fortunate to secure "timed entry tickets" for an attraction, make sure you are there 15 minutes ahead. If you happen to be just a few minutes late, they may not, more on the "not," won't allow you in. There have been reports from some who were unfortunate to lose track of time for whatever reason and were not allowed in.

Read up on how to get Euro, how to secure your extra Euro and cards. Don't put anything of great value in a pocket or bag pocket where it can be easily accessed from someone behind you. That includes your phone. Don't lay your phone on a table, don't hang your bag on the back of a chair.

Rome is relatively safe. But don't give peeps temptation. Don't make yourself a target or vulnerable. Think "big city awareness." Inside Termini Station is where you should be aware of your surroundings. There are police there, but they can't catch everyone.

All in all, Rome is terrific! A lot of friendly, helpful people < use caution if someone random comes up to help you with your ATM (Bancomat) withdrawal or buying a ticket from a kiosk at the train station. Either go to the window clerk or look for the official ticket associates.

If you happen to take a bus in Rome, (you probably won't, lol unless you take Express #40 to The Vatican), make sure you validate your ticket right away in the machine located in the bus. Transit Inspectors randomly stop buses in the city, board, inspect passengers tickets. If you don't have one to show, you could or would be fined a lot of Euro.

love,

A bit more information would be helpful. For example, where are you flying from and does your 7.5 day time frame include flight days. Also, when is this trip taking place? What prompted this desire to visit Italy (ie: what type of sights are you interested in seeing?).

To begin with, if you plan on starting in Venice it makes absolutely no sense to fly into Milan. By the time you get out of the airport, to Milano Centrale and then to Venice you will have wasted about 4-6 hours. That will be a grueling trip after after a long international flight, especially as you won't be familiar with the country. I'd suggest flying into Venice or skip Venice this time. With such a VERY short trip, you're not going to have a lot of time to fit in other destinations or sights.

As this is your first trip to Europe and first trip to Italy, I would highly recommend reading Europe Through The Back Door prior to your trip and use the RS Italy 2019 guidebook to plan sightseeing, hotels, transportation, etc. You should be able to find copies of those at your local library if you don't want to buy them. Most of the RS guidebooks are also available as E-books in various formats.

There are some potentially expensive "caveats" to be aware of when using trains and other public transit in Italy. Be sure that you're aware of those. If you need more information, post another note here. There's also the possibility of pickpockets and scammers, so a Money Belt would be a good idea. You'll also have to give some thought to Plug Adaptors, money issues, etc.

Good luck with your planning!