Bookings and flights troubleshooting

Unless something has drastically changed in the last three years we have never had problems obtaining hotels around the six to three month mark. We always establish the transportation first and then fill in where to stay. We tend use open jaw tickets (multi-city) for almost all of our travel. Obviously, I would stay away from Paris this summer but the rest should be fine.

Planning a trip to Italy should be fun - it is also a bit stressful. Many places just don't have their calendars ready for 2025, that includes the airlines. You have an added issue for 2025 - it's a Holy Year. That means Rome can, and probably will, be more crowded than usual. And I'm sure people will travel beyond Rome, making Italy more crowded than usual maybe.

Affordable flights (from where to where, when to when, class of service) can be monitored (to a certain extent) by looking at individual airlines and also search engines (skyscanner.com and google.com/flights are two I use a lot). Flying into Florence may not be the most economical route. Look at Milan (and check train schedules to your first destination) and Rome (easy and economical fast train to Florence). Compare different days of the week - midweek seems to have the lower fares.

If you see an apartment or hotel that you are very interested in, make a direct contact and give your intended dates. Many will reply with an idea of when their reservation desk will begin for 2025. Keep checking and pounce. They may not have their rates published yet.

I have one hotel/apartment booking left to do for my 2024 trip. I've been working on it for 10 months. Luckily my plane ticket allowed a change (difference in fare only - and there was none). I was able to add a week! Hey, I deserve it . . . and so do you!!!

It’s a year away. Why stress now?

Define affordable.

Reserve your accommodations first. Loads of options in Florence; hotels, BnB’s.

Then check your flight options. Can you fly direct?

Can always use trains in Italy.

ksmomma

I do not think that you can book flights yet or hotels yet. It is too early.

You can book a cruise for 2025 but you have not expressed any interest in a cruise. There are cruises that leave from ports close to Florence. You can fly into and out of Florence.

You can relax because you are way too early to book anything now. You probably will not be able to book a hotel for summer 2025 until maybe September 2024 and same with planes.

You can go to booking.com and then book a hotel or whatever dates you might want in Florence but be certain to book with free cancellation. Then you can change dates or cancel altogether if you find something that you like better.

You might also seek a well recommended T.A. ands have him / her help you. I think that Rick Steves has travel consultants who can help you plan a trip but it is fee based.

Have you gone back recently to check some of those hotels for 2024? I'm working on a trip to New Zealand Nov 2024. When I initially started looking in October it appeared (on booking.com) that places were completely sold out for Nov. I was suspicious so played with dates and discovered that many smaller hotels were releasing rooms at 11 or 12 months out. The problem is they don't tell you that they haven't been released yet, they just look sold out. If you were looking at Aug 15-20 2024 on Aug 5 2023 could that be the case? Go back now and look again?

Peace of mind has its own price tag. If you’re concerned about it all coming together, then the premium you’re paying by hypothetically passing on a future “deal” is completely worth it. As I’ve gotten older, finding a cheap deal is less important than finding the right plan. I think too, that in the current environment it’s going to be harder and harder to really score a sweet deal. Everyone, everywhere is using the same tools.

If you’re traveling in summer, high season, then you should absolutely feel justified in getting well ahead of things. I booked an early July trip to Croatia last year back early December, and frankly would have had a better flight plan booking just a few weeks earlier. I was able to stay in the exact accommodations I wanted, and it made a massive impact on how well the trip went. To your point, in Dubrovnik my host told me at the time, that he was already booking into the following summer. This was not something he was used to, and certainly shows where things are.

I think 9 months out is about the latest I’d want to book all my first choice airfare and accommodations for high season. I would also recommend checking for airfare directly with the carrier. I found flights through the airline website that seemingly didn’t exist when I searched the big travel sites. You might find the travel protection to be a little better with the airline as well. In short, find a trip that makes you happy, book it and don’t second guess it.

I agree with the above, especially booking lodging around 9 months out.
Start now reading the posts on this site every few days. You'll find you will quickly develop a feel for the on-the- ground conditions . Many of us check the Forum each morning before we look at the news. Posters take the time to answer questions in great detail, and the Trip Reports are very helpful. I have learned so much from fellow travelers, and hopefully, I have helped a few.
There are several discussions here on airline rates and working to get an acceptable price for flights, for instance. Just do a Search.
Have fun planning and enjoy the process.
Safe travels.

Thank you for all of the kind replies. The poster who mentioned about bookings showing as full when not released yet, the does indeed appear to be the case on some platforms, but not always. As other posters mentioned high season you need to really plan ahead, that is my situation. I've already booked an agriturismo that was recommended to us for the first week of July 2025 and glad I did as this really are getting booked way ahead of what you might expect. My main concern is what if the flights I'm able to get don't match up with our stay dates, but by the time I'm able to get flights all the hotels are booked up and we have no place to stay if we get in a day or two early?

Also, one of you mentioned that 2025 is a holy year - do you mean the entire year? What does that mean exactly, and would it affect us much in Tuscany/Umbria, or just mainly Rome? We plan to go late June and return mid-July.

Your worries about your flights are causing you distress for no good reason. Unless you are planning on using frequent flyer miles for those flights, there should be no issues with capacity. You will be able to get flights. I see no issue with making hotel reservations if that is important to you. You may have more choices if you wait a bit.

The holy year that was mentioned is the 2025 Jubilee Year. It seems to be mostly centered in Rome. Here’s one link to an article about the Jubilee activities that has links to a calendar of events: https://www.catholicnewsagency.com/news/254346/rome-prepares-for-35-million-pilgrims-during-2025-jubilee-year
I’m sure there will be more info online about the Jubilee in the coming year. I have to think that Rome is going to be super-crowded most of the year 2025.

As things these days seem to book up so quickly, we're already starting to plan for summer of 2025 trip.

Hotels do not establish their rates a year and a half in advance. That's 18 months away. Airlines do not have their Summer 2025 schedules published yet - at best they sell tickets a year in advance.

Calm down

There are travelers for whom lodgings with charm/personality are a major part of the experience. Those folks are well advised to do their research in advance, put together a list of top choices at each planned destination and reserve as early as they can (but with cancellable reservations unless they purchase full-coverage travel insurance immediately that will cover the cost).

Then there are people like me for whom lodgings are just a means to an end. Unless you're traveling to a seasonal destination with inadequate infrastructure for peak demand (Norwegian fjords, Scottish highlands, coastal Cornwall, etc.), you are unlikely to encounter booking difficulties unless your stay coincides with a high-impact local event. The latter don't necessarily turn up without in-depth Googling, and I've been burned by those a few times, because I make most of my hotel reservations just 1 to 7 days in advance. Travelers who operate on a more typical planning schedule (months rather than days ahead) will have plenty of advance warning it there's a problematic event at the time of their visit and will have the option of tweaking their itineraries.

Booking last-minute, as I do, will fairly often cost extra money. Occasionally it produces a real bargain in a nice, modern hotel in a city depending partly on business traffic that lowers its rates when occupancy is lagging.

Flights will not be an issue, but it would be smart to look at the pattern of airfares for your approximate travel dates this year to see whether departing on specific days of the week may yield lower airfares. I'm retired, so I don't have to get my employer's clearance for vacations. I usually head out on a Tuesday, Wednesday or Thursday, but what works for me from Washington-Dulles might not be the best choice from all origins.

I really think you should relax.

No place I know of will offer reservations more than a year in advance. And the small, charming hotels and inns often do not start taking reservations for summer until January of the same year. The exception would be in popular mountain resort areas like the Dolomites, where some small family-run hotels are booked up by the same guests year to year—-they made their reservation for 2025 when they were there in 2024. These places may not open up reservations to new guests until all their “regulars” have their preferred dates.

We have made 3 post-covid trips to Italy, in September 2022, March 2023, and September 2023. I am currently working on September 2024. The only things I book a year or so ahead are flights (we fly with miles so I book the award seats the day they are released), and small-group guided hiking tours if we are doing one of those. For example, our 2022 trip included 10 days of hiking in the Dolomites with a small Portland company that only takes 12 people. We and our travel companions were taking 4 of those spots, so we booked early.

Then, since my start and end dates are set, I start planning a route and looking at lodging. I may start booking lodging 8 months in advance, but not before that.

I will note that September and March are different from earlier in the summer (July or August), and our travels have never included Florence ( which I believe is, along with Venice, the most crazy-crowded city). But we have stopped in Rome and Venice, as well as Bologna, Lecce, and Milan, and I never had difficulty finding just the right place to stay in those popular cities.

So start now to get ideas and build an itinerary, but please do not stress about early booking. Plan on starting that later, this summer. Watch flight prices and book when you see one you like. Then you will have your dates set and can book lodging accordingly. I think we are already seeing summer 2024 prices start to climb, and I have seen some people complain that they missed the lower prices.

And think hard about when you really want to travel: do you really near to go in summer high season for some reason? You are teachers, or have kids in school? Or can you move trip to May or September?

Thank you for all the replies, feel a bit better now. We do have a few very specific things in mind, and this had been a dream of ours for many years, so I want to do it right. My daughter will be on her summer break from college and a couple of other factors were involved in our decision to go during late June/July. I didn't know about the holy year - hopefully it won't affect us much as we're steering clear of Rome, but will keep that in mind. Florence accommodation is my biggest concern in the event plans need to change later on due to flights, but as someone mentioned Milan being a better option to fly into, and another state that it's also easier to find accommodations there anyway, perhaps that will be the way to go. Thanks again.

The problem with flying into Florence is there are not as many flight options, and no direct flights from the US. So you could be looking at a 2-stop flight, depending on your starting point in the US. That would also be true of other airports nearby, such as Pisa and Bologna. But there are direct flights into Milan (and Rome) from a number of US cities.