Anyone care to help me start my planning?
 

My husband just surprised me with funds for planning my dream trip to Italy (belated 50th birthday gift) with our 2 teens and a 20 year old. I was there in 2000 with my husband but it was with his youth orchestra so I always dreamed of returning without 30 high school students with us:)
I am just starting with trying to set out an outline of the places we will visit.
What I think are must haves: Venice, Florence, Siena, Pisa, Rome
What I really want to add: the Amalfi coast (me for the beauty, my daughter for the beach)
My 17 year old asked for Milan but if shopping is good elsewhere, isn't required. She's my fashionista - no one else cares about that stuff.
Our budget would be about 20-25K for the 5 of us.
Is anyone able to help me figure out the order of where we should go? Are there stops you would leave off? Do we need to save more money to make this doable?
Since we are from South Jersey, we would fly over from either Newark, JFK or Philly depending on prices. I will take any and all input anyone is willing to offer. Thanks a ton.

For how long and what time of the year - that will make a huge difference to your budget. Are 2 rooms enough?

It would likely be during the summer (possibly spring break if everyone's break lines up). And 2 rooms would be fine.

What month is spring break in? And how long would you be away for?

All the places you've mentioned seems like a 6 week trip to me!!. But I'm guessing that you have much less time than that. Please specify how many weeks you have for this trip!!!

See attached

Stu Dudley

Fly into either Venice or Rome. Fly out of the other. That's fairly easy.

Take the train to Florence for your second base. Stay there for day trips to Pisa and Siena.

Take the train to your final departure city.

I'd really try and find some videos of the beach in Amalfi to see if that's what you want. It might not be.

If you leave off Amalfi it's all fairly easy and depending on your interest level two weeks. Obviously longer would be useful but it's doable.

There is the Lido in Venice. There are beaches on the outskirts of Rome. If all you're looking for is a bit of sand and sun. The Rome beaches aren't tropical but you get the sea.

The question to ask yourself is how much time do you have? How important is Amalfi to you?

Many people will be giving you lots of great advice, but it is always fun to get quick responses, so here are some of my thoughts. Others will have different ideas, you can have fun thinking about them.

The number of days is really important to get the best itinerary advice. The more, the better, IMHO. If you would have more in Summer than on Spring break, do that. It will be hotter, of course, and likely cost more, plus more tourists, but I would still want as much time as possible and I enjoy hot weather. Plus, if you want to swim at all, it is not warm enough during Spring Breaks. Also, in Summer, being out on the water on boats along the AC is wonderful!!! Evenings are wonderful! People out and about and you can sit outside to eat.
Spring can be pretty, but iffy, cool and rainy. OTOH, if you hate heat, you might prefer Spring.

Traveling takes time and costs more, so the more places you try to see, the more time you eat up in travel and the less time you have for actual sightseeing. Milan is out of the way from your other choices and there is great shopping all over: Florence, Rome, Naples (amazing custom wedding gown shops there), etc. There is so much to see around Naples and the Amalfi Coast (Pompeii, Herculaneum, Capri, Positano, Amalfi, etc.) and it is stunningly beautiful. It takes a bit of extra time to get there, so don’t shortchange it. Where to stay there depends on what you wish to do.
BTW, there are a few Sandy beaches, but many are pebbles and rocks, nothing like the Caribbean, the Southern US East Coast or the Florida Gulf. People do swim and sunbath anyway, and many boats make stops for people to swim in the open sea.

Best to get multi-city (not two, one-way) tickets, not RT, so into one city and out of another. It may seem to be more costly, but saves usually a costly day of wasted vacation time backtracking and the cost of travel to backtrack. If it comes down to it and you absolutely must do RT, do not stay in the same city twice. It adds to cost and time of two check ins. On arrival, go directly to your first destination. A good plan might be, arrive in Venice, depart from Naples, or the reverse.

I'm too old to remember when spring break is - but many years ago we were in Tuscany for Easter, and it snowed. We drove to Rome for the flight home, and trees were just starting to bud. Doubtful an Amalfi trip/sun would be a good choice before May.

Stu Dudley

Stu, We were in Pompeii once in very early Spring when there was a rare snow on Vesuvius. I should try and find the pictures. It was actually very pretty, but we were all wearing coats. Sure not swimming weather!

Another quick comment about beaches at the Amalfi coast - the Amalfi cost is beautiful but it's beaches (in my opinion) are not.

Your budget of 20-25K - is that euro? If not, you really need to start thinking in euro. That's what you'll pay in Italy and many on this forum would have to look up to see what a USD is worth in euro (including me). As a super rough guide, we almost never spend more than 100euro/night/room - we expect a great location but not luxury (Venice would be one place where we might pay more).

Witthout knowing your timeframes, my first rough suggestion for a first time visit to Italy which had to encompass Venice, Florence, Siena, Pisa, Rome and Amalfi coast would be Venice (4nights), Florence (3), Siena (3), Pisa (3), Rome (4), Amalfi coast (6) but you could shorten this by visiitng Siena and Pisa as day trips from Florence if time is limited (and adding time to Florence of course). Of course, you will find many, many different opinions on how long to spend in each place. If time permitted, it would be wonderful to double most of those durations. And definitely agree it's best to fly into one port and home from your last destination (this rarely costs more nowadays).

There is fashion available in every large town or city in Italy, no need to visit Milan. My fashionista daughter would be seeking out the second hand and vintage stores/markets.

Final point - travel as light as you can possibly get away with - large or heavy luggage is just a giant pain.

There's heaps of experienced people on this forum who can offer great advice. But overall time available is crucial.

Ok, avoid late July and August. 1) it is very hot and 2) up until the 15th Aug everyone is on holiday

If you want to go to the beach (and in italy this means a very organised thing) then April would be too cold not only for the weather but also because most of the facilities are still not up and running. Where to go for a good beach is a question with many answers as there are lots of sanding coves so plan that in last.

Are you town people or country people. if you are town people you would do better with trains for getting about as the centre of many towns have ZTLs and a rented car becomes a bit of a problem. If you prefer to stay in countryside hotels/B&B/AirBnB/agriturismi then the car will work out fine. Milan shop visiting is well worth the experience if you are a disciple. However, the people of Milan are true religionists so unless your daughter is rake thin, dressed in the most expensive styles etc she may not be allowed into many of the shops. So take of what you wish for.

Venice, Milan Florence, Siena, Pisa, Rome
Amalfi coast

Do take the water taxi from the Airport into Venice, with your budget that is an easy decision and even for the jet lagged well worth the experience. The least of Venice needs 4 nights. I assume you are not going to Padova, Verona etc but if you are then you need to add extra days for these. Milan is certainly another 4 nights unless you want to add football, Florence again 3 to 4 nights, Pisa is a pass-by full day and easy by train from Florence. Siena could be a bus trip from Florence (train possible but difficult) or better I might get a driver to take you as you can see the countryside and possible add in St Gimignano (note that the whole area around Siena is worth at least 10 days). Rome would take me at least 5 nights unless I was religious in which case goodness knows. Amalfi coast, well it depends on how many antiquities you want to visit.

One more question to understand your budget: will this include? What class do you want to fly? What type of hotel do you want to stay in? How long will you be there? Prices can be pretty steep especially in high season. $20-25,000 sounds like a lot but you do need to figure out your priorities for travel.

A thought - in doing a search on booking.com, I found nice-looking apartments in decent locations at roughly $200+/night in Florence and Venice which would accommodate your group very well. I input “5 adults” and tried dates in June as a test. Of course it will vary from city to city, and other places might be a bit costlier, but an option instead of 2 hotel rooms.

I do agree that July and especially August would be good to avoid, if possible. June would be better - still high season, but not as busy or quite as hot. Of course, all of this I could be impacted by how things evolve with the you-know-what and what restrictions might still be in place.

A lot of the planning requires knowing "How many days?" Practical calculations must account for the loss of one day for each of the following: Arrival/jetlag day, departure day, and each intercity travel day. What remains are the days for actually doing things. You might have a couple of hours "free" at the beginning or end of a travel day, but the overhead of checking out and checking in and grabbing meals means those scrap hours can't be counted on.

Oh, yes, also depreciate days when things are closed, although traveling on closure days eliminates that consideration.

The rule of thumb: Too many places means too much traveling and too little doing. At least your budget is more reasonable than when you asked for the same trip a few years ago.

So: How many days?

Sorry for not being very clear. We would go in the summer given the time we would need (2 of my children will be in college by the time we take the trip) and my husband is a teacher and professor so our ability to travel in off season isn't possible. I would like to keep it under 2 weeks. Given the recommendations already made I would shoot for June (this doesn't have to be in 2022)

We don't ever fly first class and wouldn't on this trip. I would actually prefer accommodations described above....an apartment like setting given the size of our group. I like the idea of a home base with day trips then moving after several days to a new home base. We don't want to overdo it with museums and churches but do want to see things like David, the Sistine Chapel, etc. We do want to enjoy the cuisine, the beautiful countryside, historical sites the kids have learned about but never imagined seeing in person.

For 2 weeks I'd focus on doing less to enjoy it more. If you have to have Venice and Milan then lets just drop Amalfi and I might consider dropping a lot of Rome and just focus on the North. Venice 4 nights, Milan 2 nights, Florence (and Pisa) 4 nights and Siena with local towns 2 nights, Rome the rest plus preflight town.

"Under 2 weeks" . . . How much under?? To give an idea for a starting point -- let's use 12 days. 1.5 days for travel to Italy, 1 day flying home. Leaves 9.5 days free for seeing/doing. Then as AJPeabody mentioned, each 'moving day' will eat up another .5 to .75 of a day, sometimes a full day depending on logistics. So with just say 3 destinations (Venice/Florence/Rome? ) you would have less than 3 full days per city.

That's the bad news. The good news is with a short trip like that your money doesn't have to go as far. Again, just for discussion, say your airfares are $1000 each. That leaves $15k to $20k for on-the-ground things. So between $1500-$2000 per day which is very generous. Could you possibly add more time? With 3 weeks you'd have time for Venice/Florence/Rome plus the AC, plus maybe even an agriturismo in Tuscany for a few days. and not need to up the budget.

Do all 5 of you have to follow the same vacation duration and schedule? If only 1 0r 2 need the shortish trip, let them fly home. The others could stay longer at the third destination (Rome, for instance) or even go on for a 3 or 4 day stay in the Amalfi area.

My logistics sense says fly into Venice, train to Florence for the city and day trips, then on to Rome for the last destination. There are fast and, if purchased in advance, cheap trains for the two hops.

Just me, but I wouldn't make it all big cities. Even Siena isn't small anymore.

Under 2 weeks with a group of five? I'd slash the list to 3 bases at most with perhaps 2-3 day trips. Someone mentioned the high temps in summer... they will make you slow down for sure. So does a group of 5, no matter how agreeable and in sync you all are. Again, just me, I'd enjoy a couple of days without the younger ones and their priorities/desires.

Given your available time and wish list, my suggestion would be:
Venice (3nights)
Florence (4nights with day trips to Siena and Pisa)
Amalfi or Sorrento (3nights with day trip to Positano)
Rome (3nights)
plus travel to/from home.

Very busy but a great sampler of Italy. Personally, I might be tempted to drop Pisa and stay in Siena instead of Florence but if a visit to Pisa is on your must-see list, then definitely easier to visit from Florence. However, keep in mind that the journey to Amalfi or Sorrento would be longer from Siena than from Florence.

What a brilliant opportunity - enjoy!