Travel To Italy September Or October Places to stay

I'd say just hold your horses until you get your book and make some choices. It is overwhelming at first with so many choices--all equally good ones--but once you have looked at pics and selected your top places (I would choose about three for two weeks), it will be easy to sort out the rest. Have each traveler choose their top three, then see where you overlap.
The train system is a snap. Flights will be determined by your ultimate itinerary, but I do recommend flying open jaw.
For accommodations, I always use Booking.com. It is convenient to me to have everything in one app.

Welcome to the forum, ovahjay!

First things first? Your questions are really broad so it will help if you can narrow the field. For instance, Italy is a long country so trying to do it top to bottom and everything in between in 2 weeks isn't realistic. So, the first thing your group should do is determine WHERE you want to go. Those wheres may also need to be culled to fit into your 14 nights or so. Oh, and you want to count your time on the ground in Italy in nights versus days, and understand that every location move you make will eat TIME.

What can you tell us about your group? Have any of you traveled abroad before? If so, where? Approx. ages? Any of you have mobility challenges? What are your collective interests? What sorts of things do you want to see and do?

Starting at the top, the most common cities to fly into will be Milan Malpensa (abt an hour out of the city) and Venice. I would probably choose Venice unless you have no desire to visit that city. Flying home, I'll say Rome but explore ticketing prices from where you are.

Getting around in Italy: trains are the most common method, and usually the most efficient. With 4 of you to split costs, there may be opportunities to use private drivers, depending on where you're going. A useful primer for train travel:

https://www.seat61.com/train-travel-in-italy.htm

Hotels: I use booking.com, as do quite a number of other forum posters. You can filter per price, location, desired amenities, ratings, etc. You can also browse the RS forum history for recommendations using the search box at the very top of every page. IMHO, there's no such thing as 'best rates', just best choices for location, amenities and ratings within your price range. Be sure and browse the reviews.

https://www.booking.com

You might want to consider apartments, although newbies abroad often feel a greater sense of security with the 24/7 desk staff many hotelsprovide. Apartments almost always involve cleaning fees so are not great choices for short stays, and what they call a 'bed' can be a fold out in the living room. That may not bother you but... Your group of 4 may want a little individual privacy now and again as well so think about if you want to be ALL together, ALL the time? Some of you may be early risers, some of you may be night owls.... you get the idea. Different strokes are also a consideration when it comes to moving around: you're only going to do that as quickly as your slowest dawdler.

As well, you probably want to divide and conquer! For all sorts of reasons, one person shouldn't take on this entire task! Duties split amongst you can be researching train tickets, attraction lists and advance ticketing, accommodations, meals, etc. Also, agree IN ADVANCE how you're going manage the costs amongst you. This is really important as there will be a point in time when the stake has to be firmly in the ground as far anyone backing out. This can include everything from non-refundable attraction tickets, accommodation reservations and train tickets.

You should all make sure you have health insurance with good coverage abroad as well. You may need to purchase a travel policy in addition to what you have.

Just a start! So start drilling down to where you want to go and give us those thoughts, and tell us more about your gang? You'll find oodles of help here!

Easy answer first: take the train. It find it relieves my stress but there are trade-offs.
First define your interests and those of your travelling companions. Personally, I recommend a minimum of 2 nights in each stop which will give you 1 full day and probably half a day when you arrive at your stop. On my recent trip, I basically stayed 3 nights.
There are a number of posts on RS Forum with some suggestions that should be quite useful in defining your trip.
I use booking.com for my accommodation. It shows options with prices on a map. Read the descriptions carefully. As we age, I’ve moved a little upscale: must have ensuite bathroom; should be ground floor or have an elevator (no more 100+ stairs to a cheap apartment in downtown Florence); doesn’t need a kitchen but coffee maker is nice as we don’t cook dinners. Look for free cancellation as you plan your trip and before your get approval of all travellers. We don’t need a spa, pool, room service, included breakfast etc.
Planning can be fun and I plan and prepare a budget and itinerary and get my wife’s acceptance. Budget has increased over the years. Sort out cost sharing and how you will deal with cancellation by 1 of your party.

This has been on my bucket list for years so I want it to be amazing.

You've gotten good advice so far. You need to make this a group project with your traveling companions. Make it fun, have meetings where you cook Italian food and if so inclined, drink Italian wine. Make a list and then look for YouTube videos. Consider your interests. Is it art? History? Religion and churches? Shopping? Cities? Villages? Factor your interests into your trip.

Where are you on the West Coast? California? Imagine trying to cover all of California in two weeks. Trying to "start at the top and go down the country" would be just as daunting.

A common trap is to try to do too much. In an effort to see everything, you end up seeing nothing. In two weeks, you can either do Venice south to Rome or Naples north to Rome. Even then choices will have to be made. You also will need to choose between two types of trips: the fast-paced whirlwind "hit as many high spots as possible" or the slow-paced deeper dive but seeing far fewer sights. Our favorite trip to Italy was when we spent all 10 days at one agriturismo in Chianti, with one day trip to Florence. We spent the rest of the time exploring small villages and hill towns.

Finally, make sure to plan in a down day halfway through trip where there's nothing planned. Have fun working on your itinerary. Be sure to share your work in progress and we can give you more specific, practical advice.

It will be tempting to want to see everything you've ever heard of so you're going to need to restrain yourselves. Remember that two nights in one location just gives you one full day there. You'll need more than that in the big cities so plan at least 3 nights if not 4 or 5. You'll leave the West Coast on Day 1 and Arrive on Day 2 and that day may be kind of shot due to jet lag and travel tiredness so you'll not want to plan much except walking around outside and getting your bearings. You'll depart on Day 14 (or whatever) and that day will be consumed with getting to the airport so you'll not plan any activities for that day.

You can get some ideas by looking at Rick's tours of Italy BUT his tours move very quickly and they are experts at getting you to the center of a city quickly, and moving efficiently. You'll not have that advantage and you'll be newbies so expect travel between places to take at least half a day if not 3/4 of a day including checking out of your hotel, getting to the station, the actual train ride, reversing it at the end.

Your most efficient way to travel is probably to fly in someplace in the North (Milan or Venice??) and fly out of Rome. This is called an open jaw itinerary and you'll book it on the airline website of your choice under multi-city or multi-destination. You'll do better to book directly with the airline.

Be cautious in booking air and hotels, you'll want to read the cancellation policy. If the pandemic taught us nothing else, it was to make sure you can cancel expensive plans!

What fun!! You'll love Italy! Even if you wind up going alone, it's a wonderful place to travel for a solo female.

In addition to Steves' guidebook, review his many DVDs for Italy. Your local library should have his DVDs so check them out. I think the Italian guidebook has a detachable map. Get it out and put some pins in it. Personally I find straight line travel generally works best. The train system in Italy is extensive and cheap. Use it. You cannot cover all of Italy in two months so two weeks is barely a start. Look at three, four nights as a more relaxing approach instead of one or two nights, For example -- you could fly into Venice and home from Rome. We generally find open jaw or multi-city tickets to be the same price or cheaper than RT to a single city. Best rates for hotels is what they are offering. I don't spend a lot of time looking for cheap hotels. I look for location even if I have to buy a premium. Convenience (time savings) outweigh cost savings. Most of the hotels in Steves' guidebook are good value.

I agree with the above posters. Figure out what you (collectively) must and want to see and do. Let those things drive your agenda. Is it sites - leaning tower of Pisa, Pompeii, touring St Peter's in Rome or seeing David, The Last Supper, eating in a specific restaurant or whatever it is you're interested in. Watch Rick's videos on Italy, dig into other videos about Italian cities and travel and think about what it is you don't want to miss and agree collectively.

Be realistic about how many places you can go and things to see in the time you have. Any big city you're visiting needs at least a couple of days and allow time in your schedule to relax and breathe since a lot of enjoying Italy has to do with experiencing everyday life as much as famous sites. Rick has "what to see if you have X number of days" guides on the website and in his books so balance that against what you're interested in seeing and try out some sample schedules.

If you're flying from the west coast you'll need to fly through somewhere - either east coast of the US or London - to fly into Italy itself. Your agenda will probably dictate your flight destination. Want to go to Venice? Fly into Venice and then work your way south and fly back from Rome - if Rome is on your list. Do fly into one city and out of another - called open jaw or multi-city - to prevent losing a day travelling back just to fly out.

Get Rick's book and once you have a plan check his hotel recommendations in each town. Determine your price per comfort level, decide on your people per room situation and contact them for reservations. Not everywhere is going to have rooms for four and each getting your own room will drive your costs up so figure out how that is going to work out. Your are booking early so you'll probably have your pick of places, but it all depends on your agenda. Also many famous sites and museums should/must be booked in advance but all that is covered in Rick's books.

September will be warmer and probably slightly more crowded than October so choose accordingly.

Have a great trip,
=Tod

Most people here recommend flying into Venice and out of Rome, vs the other way 'round, since international flights from Venice tend to leave very early in the morning. We did it the other way, though, and it's still doable, because of the timing of our connecting flight home.

I recommend the train for easy movement through the country, with a few exceptions, depending on what you want to do and see. We used "My Day Trip" one time, so we could access some smaller locations on the way to our destination.

I'll post a link to my trip report here, in case you might find it helpful. It was our first trip to Italy, too, and we didn't try to see it all. For instance, because it was November, we skipped Cinque Terre.

https://community.ricksteves.com/travel-forum/trip-reports/amsterdam-and-italy-finally-in-november-2021

I research places to stay by: looking at Rick's recommendations; searching past posts here; reading reviews at TripAdvisor and other sites like Booking.com Usually I book directly with the accommodation after doing my research, but occasionally I will book through Expedia or Booking.com.

Our hotels in Italy were as follows:

Rome: Incentrum (We had an apartment between the Piazza di Popolo and the Spanish Steps. We liked the apartment and the location.)
Orvieto: Hotel Duomo Orvieto (Right around the corner from the Duomo. Good breakfast.)
Florence: Palazzo Alfieri Residenza d’epoca (Wow! Wow! Wow! Would normally be out of our budget, but it was shoulder season.)
Verona: Hotel Milano and Spa (Small room but modern. Steps from the Arena.)
Venice: Residenza de l’Osmarin (REALLY great location, quiet, charming, and nice owner.) For our last night, before our early morning flight: The Best Western Titian Inn (great breakfast served very early, shuttle to airport (for a small fee)).

Hope that helps! Happy planning!

I use booking.com to research hotels, but then book directly with the hotel, which usually results in a discount. Some of the smaller hotels don't book directly , I've found, but many will communicate nicely in English with you. Make sure you get the cancelation policy in writing. Also, for Aug and Sept, you'll likely need air conditioning, as the windows don't have screens, and there are bugs. Can your group do steps? Many hotels don't have elevators. Check for this feature.
Also, when using trains, travel lightly, as you must be able to jump on and off trains quickly.
Have a great time planning this adventure.

Great advice so far. Less is more. I'd recommend no less than 3 nights in each location. Otherwise, you are spending a lot of time regrouping and traveling to the next stop.

Unless you fly out of LA, you will almost certainly need to change planes somewhere. It is generally considered best to fly direct to a European hub, then go on to Italy. The reason being that in the event of a delay that causes you to miss your connection, there are way more flights to Italy from FRA, CDG, etc. than from any U.S. airport. Also regarding flights, book directly through the airline. Resist the temptation to purchase through 3rd parties, as well as that of doing a cheap connecting flight. All travel should be on one ticket. If you book direct, the airlines are required to get you to your destination. If not, you would be on your own to deal with problems like a missed connection. This forum has many tales of woe from travelers who used even the more reputable 3rd parties, like Expedia. Use a site like skyscanner, kayak, or googleflights to scope out the possibilities, but book direct.
With just two weeks, it would be well to limit yourselves to three locations. The “big three” , i.e., Rome, Florence, and Venice, are obvious choices. Each also offers the possibility of attractive day trips. If art is not a big interest for any of you, you might consider a stay in the Tuscan countryside, with a day trip or two into Florence. There are many attractive towns and villages to consider. Just be sure that the one you choose has good transit possibilities.
It is amazing to me what you learn about your friends when you travel with them. Reduce the possibilities of friction by deciding some stuff in advance, like how to manage money, a BIG one. One way that has worked for us is to take turns picking up tabs. Keep receipts and do a reconciliation at the end.
Don’t feel you need to be joined at the hip. If interests diverge, you can go off in twos, or even solo, for a day.

RS’s guides are very good for first timers; especially, because they contain useful “ nuts and bolts” information. However, I find some of his enthusiasms peculiar, like his touting of Civita da Bagnoreggio, as his favorite hill town. Also, some of his hotel recommendations are poor. I use booking.com, a lot. Only people who actually stayed at a place can post reviews. Prices are close to, or sometimes a little better than on hotels’ own sites. What I said about air tickets doesn’t apply, because booking will deal with problems.
Buon viaggio. You’ll love Italy.

Passionate bunch, aren't we. 😉

Locations: as has wisely been counseled above, less can be more when it comes to moving locations. Consider that day trips are easily done from some cities - Florence is especially good for day-out adventures - which allows you to spread your wings a bit without all the packing up, checking out, checking in, unpacking, etc. that moving hotels involves. Just grab your day bag and go.

I'll second the wise advice to locate yourselves IN the historic centers versus try to save $ by booking further out. It's great to be able to sightsee at pleasurable walking distances from your doorstep, and for individuals in your group to come and go at will, should they wish to. Rambles after dark are especially nice - and SAFE - in many cities/towns so you'll want to be able to easily pop in and out for some of those. Forget something back at your room? You can go fetch it without much ado.

For a two week trip, I would stick with the big three, Venice, Florence and Rome. You could squeeze in a trip to Sorrento/Capri/Pompeii, but it would cut down on time in the big three.
suggest minimum of 3 days in Venice, 4 in Florence and 6 in Rome.
Fly into Venice (open jaw) then take the high speed train to Florence, then to Rome and fly out of Rome.

If you go just with carry ons, you might need to do laundry on the trip.

For hotels and local tours, TripAdvisor is great. It has a map feature that you can use to book close to city center (hotels are indicated with prices).

You can use booking.com, which is good, but Kayak.com INCLUDES booking as well as most other sites, so you may beat booking's prices. Much of the three cities can be done on your own without taking a local tour, but if you prefer a tour (especially in Rome), then TripAdvisor can assist as well.

"Passionate bunch, aren't we."

Hahaha...yes...poor gal. We've hit her with a firehose haven't we?

There is a lot to digest here! I'd have your friends start reading the forum as well!

We've been to Italy 4 times in different locations; Rome twice, both on cruises; twice by car. We spent 4 weeks by flying in Milan; we spent time in Lake Como, Venice, Cinque terre ; two weeks in a Tuscan Villa visiting small walled towns, Positano then Rome which we flew out of.
We rented a 2bed 2bath condo in Venice & in old Rome for about $170 CAD per person per night; they had all the amenities, i.e. Washer, dryer, dishwasher, etc. We had breakfast in the Condo they toured had lunch then came back to condo to change for dinner or we ate in, depending on how tired we were. They were closed to sites & eateries.
We been in early May but prefer October; capri weather. September can be too hot to tour.
Agree don't fly out of Venice, early flights and airport is not close.
Jean

We want to start at the top maybe and go down the country for 2 weeks.

Does that mean 14 nights in Italy, or are you using 2 of those days for travel to/from Italy?

This might give you a framework to build on ( look at the "Itinerary")
https://www.ricksteves.com/tours/italy/venice-florence-rome

Since you wouldn't have the door to door bus service the tour has, adding one more day to each location offsets the extra travel time and pretty much would fill your '2 weeks'

I know it is impolite to ask a woman her age ( so I won't) , but what others may suggest, could be more/less aggressive depending if you are in your 30s vs 70s

Happy travels

You have gotten a lot of good advice so far. I have been to Italy four times for three weeks each time and still have places I want to explore. In fact, we are planning another trip for Fall 2023, and it is still overwhelming: so much to see and so little time. We always use trains and sometimes a driver and stay at each location for at least three nights. Also, if you do a small group wine or food tour you can see the countryside without worrying about driving yourself. We travel light and do laundry once or twice on the trip. It becomes part of the experience. I agree that concentrating on Venice, Florence, and Rome is the best idea depending on your interests. However, I would add one visit to a hill town that is easy to get to, such as Assisi or Orvieto. We find that even though we love the museums and art some of our best memories are just exploring the narrow streets of a hill town or enjoying a glass of wine in the main piazza of the town. Whatever you and your friends decide it will be a wonderful trip.

We just returned from a three-week trip in Italy with four women. In retrospect, we had too many stops but had to plan for those who had been to Italy and who had not. We flew into Milan and out of Venice bc we were flying from JFK.

I agree Rome, Florence and Venice are the big three. We took the train from Florence to Venice and it was a beautiful and relaxing trip.

If you can squeeze it in, a side trip to Cinque Terra is incredible! We stayed at the La Pasquale, in Monterosso, a delightful hotel with balcony views of the ocean. We visited all five villages in one day on the easy on and off train. We were there mid-October so it wasn’t packed.

We hired private drivers for some excursions bc it eliminated hassles with public transportation and it was split four ways. Enjoy!

How exciting!!!!
Some basic rules we follow:

• A Fast-Slow method. So Big City then Small city or fast/Slow. This allows use to go go go then just chill.
• We also only plan ONE thing a day then let serendipity take us where it may for the rest of the day. The usual desire is to plan multiple things and see it all, which you just can't joyfully accomplish, you may land up not remembering anything
• Start watching You Tube Vlogs on "My trip to Italy" to see how others have done it, where they went then start jotting down places that you find interesting. This is how I have found so many places and experiences I would have never thought of. Once you zero in on where you want to go start watching You Tube video's on those places.
• With 2 Weeks I would do City (Rome), Country (Florence/Tuscany) and the Beach (The Amalfi Coast-Positano, Sorrento (See Pompeii))
• Travel 100% by Train. I Have never taken a train in my life before Italy and I found it very easy. Use the Website "Rome To Rio" where you just plug in you from/to destination and he will offer different solutions. Use the website Trenitalia and Learn the different train station names so you book correctly (for instance the main train station in Florence is "Firenze S.M Novella")
• You can consider AirBNB for stays longer than 3 days (my personal rule) and just use Hotels if your just going to be someplace for a couple of days. This may make it more budget friendly.

This group is so kind and generous with their time and expertise, search the forums for any questions as I am sure someone else has had the same one. I start here when I plan all my trips, I have excel spreadsheets for countries/places I have yet to visit with their wonderful suggestions.

Be very careful when using the Rome2Rio website. It's usually accurate about the existence (or lack) of trains and where you might need to switch to a bus, but as for the nitty-gritty details--fares, travel times and frequencies--it can lead you badly astray. You need to get that kind of information from the websites of the train and bus companies. If you keep drilling down on Rome2Rio, you'll find the company names you need and usually also a link to their websites.

Trenitalia: https://www.trenitalia.com/en.html

Italo: https://www.italotreno.it/en

Italo only goes to the major cities; Trenitalia also serves many smaller places. As already mentioned, Trenitalia insists that you use the Italian, rather than English, station names.