First time traveler. Packing/overall advice??

I would skip duty free. Unless it's a very unusual olive oil that you feel you must have, you can get quite a few Italian brands here in the U.S.
In my travels to Italy what have I brought back? A silk scarf, a necklace from Murano (with murano glass) a bracelet, an unframed watercolor painting, a leather jacket from Florence (wore it on the plane coming home).
The only thing I shipped were two handmade copper pots - and they were well worth the shipping fee as they bring me joy every time I use them and they are gorgeous!!
The best "souvenirs" from all my trips have been my photos!
Gifts for family and friends included earrings for the ladies, dried herb blends I found at a lovely street market that were unusual and unique, small leather wallets for the men and a small leather crossbody bag for a dear friend.

Flying to Florence and Venice as well ? And will your first landing in the U.S. be your home airport or will you have a connecting flight ? Asking because intra-Europe carriers may have more stringent requirements for carry-on sizes and weights than your transatlantic carrier. And while you can bring sealed Duty Free shop items onto a transatlantic flight you may have to check them for a domestic connecting flight if they do not meet TSA rules for carry-on (for example liquids over 3 ounces.)
Many things you might want to bring back from Europe can be bought here (on Amazon ? Cost Plus ?) for about the same price without worrying about carrying weight and breakage in transit.

If you are taking trains instead of planes while in Italy, you could buy an inexpensive tote bag/ suitcase in Rome to carry your extra souvenirs on the trains and just pay the $60 to check the bag on your flight home.

fmarvette, we travel with checked bags (not huge ones) but even so don't bring back wine, olive oil and other considerable amounts of heavy liquid. We also don't have them shipped as that's very expensive to do, and you can get a lot of quality food products right here in the U.S. without the additional expense. Those products you might pick up at the airport? You likely won't be able to sample them for quality or personal taste.

The stuff we bring home is usually confined to museum books (some weight there!) a Christmas ornament or two, some lighter-weight "dry" edibles (chocolate, cookies, etc), and maybe a shirt or other fabric item. If determined to stay with a carryon-only plan, I'd dispense with the heavy liquids and go with smaller, lighter-weight keepsakes such as jewelry, scarves or other wearables.

I know you want to leave your choices wide open, but I can assure you that you can find many lovely gifts that won't require a bag check. Of course that means no heavy bottles of olive oil or wine which is so easy to get in the US anyway (there are many online marketplaces even for very high quality Italian products that would be cheaper to ship). I would argue it's better to focus on bringing back truly unique items (preferably small and easy to pack). The one upside of traveling light is that it helps you make smarter choices on what to carry back because you are somewhat constrained by how much room you have in your luggage.

Best of luck to you on your first (very exciting) trip!

Thanks for the advice ladies. Nancy, the experience and photos will surely be what I value most also. Laura, I'll be traveling by train from city to city, and I love shopping at World Market(Cost Plus). Kathy, lighter weight items will definitely be easier to travel with, and less of a concern when it comes to weight limits.

Thanks Agnes. I'm very excited!!!

Weigh it up--22 pound max.
Measure the height--21" max for European budget carriers. 22" for Legacy carriers.
Pack it up. Remove 1/4th of what you're taking. Zip the bag up.

Another light weight, non-breakable gift suggestion: fine paper products. For instance, there’s a store in Venice, close to the Peggy Guggenheim Museum, called ‘Il Pavone Stamperia’, where they do all their own block printing. I have a little handmade book from there.

You have done your planning and research. Well done. You will have a great time.
Relax now and enjoy,

If your Milan to US flight does not require any changes anywhere, duty free liquids are not an issue. If you have to change planes in the US to your final destination the 3 oz rule could be a problem.

Checking a bag for $60 may be the cheaper way if you buy that much bulky items. The cost of shipping plus duty for shipped items makes beating the $60 bag fee hard to do. Goods you carry with you can be included in your personal duty allowance. Items you ship do not enjoy that exemption

If you 'shop big' I would pay the airline bag fee rather than shipping.

My $0.02

There is almost nothing you might bring home that anyone needs or cannot get online. Kitsch is universal and has been totally globalized. The energy you would spend trying to find the perfect knick knack could be used for many more interesting things. You may stumble across unique handmade items. You will know.

Just bring yourself home.

I've traveled many times to Europe and just bring a carry-on wheeled suitcase and carry a small daypack on my back when going between cities. A nice souvenir from Italy that I love is a ceramic pitcher. When I purchased it, I carried it in the daypack to keep it from breaking. It's good to wrap some clothing items around it, and can also fill it with small clothing items.

I've never checked a bag to or from Europe, so can't give any advice there.

For your train tickets, they are much cheaper if you purchase them a couple of months before your trip on-line. You can buy them at www.trenitalia.com. For flying out of Milan, I stayed overnight at the MOXY hotel at the airport. It's very handy! Nice modern room; slept well.

For Venice, be sure to walk away from the Rialto bridge-to-San Marco route, so you aren't just walking in a path of tourists. The Dorsoduro neighborhood and others are fun to explore. Wonderful, unique city!

Have a great time!

Just pay the $60. I bought six bottles of beer (packed in bubble wrap paper and dirty clothes) back from Belgium in a bag I carried on and checked when leaving after a 2 week trip; it was legendary stuff that you absolutely can not get or ridiculously marked up onlinr. That was a lot fun cracked that open with other beer nerds friends that could not believe

We really try to avoid buying souvenirs that will sit on a shelf and just collect dust and try to get souvenirs that have a practical use. We also like things that are easy to transport. On a recent trip we purchased a number of decorative dish towels; some will make lovely and useful Christmas gifts and when we use them they make drying the dishes a more pleasant experience. Drying a large pan is so much more pleasant when thinking of Venice. The best souvenir from our recent trip to Italy is a pillow case with the Allegory of Good Government from a museum in Siena. The colors go perfect in our family room and it is a lovely reminder of Siena.

Have a great trip and try to focus on the experience and not what to buy to bring home.

Bring some small pieces of bubble wrap to protect any small, fragile items you find. Lightweight. Take nearly no space. Sometimes you can stash them inside the zippered lining of your suitcase.

Get a lightweight foldable duffle bag with a trolley sleeve. Pack it in your personal bag on the way over. Buy what you love and what will bring you joy. On the way home, pack your clothes in the duffle and pay the $60 to check it. Pack your souvenirs in your carry on. Shipping is often VERY expensive from Europe. You can fit a lot of souvenirs in a carryon, as long as they aren’t liquids.

My favorite souvenirs include jewelry, Christmas ornaments, dish towels, magnets, scarves, figurines that line my windowsill at work and unframed artwork. Find things that will bring happy memories each time you use them/wear them/see them.

Checking a bag for $60 is much cheaper than shipping things home, just FYI.

We have a lovely collection of Christmas tree ornaments and dish towels. They both make me smile and bring back so many wonderful memories every time we use them. For the grandchildren I can usually find something unique and small at a street market or a tee shirt. They are thrilled!! The only items I have ever shipped back were handprinted ceramic bowls and a platter from the Amalfi Coast. Sometimes you just need to pay the shipping, or the cost of the checked bag, and in a couple of years you will have forgotten the extra cost but still enjoying the items....if they are used and not collecting dust on the shelf!!

It has been decades since I mailed purchases home from Europe. The cost is so high now that for me it doesn't make sense unless the object itself is rather expensive and/or unique (handcrafted). I wouldn't pay 5 times the purchase to ship something home just because it would be a purchased-in-Italy souvenir; instead, I'd find something tiny/lightweight that I could carry with me. So much is imported these days that there's a major risk you'll find your food purchase at World Market or even your local supermarket when you return home. A quick check of what's available on Amazon.com is good idea if you're contemplating an allegedly-special olive oil or something like that.

Dish towels are a good idea. For myself I often pick up one or two inexpensive necklaces at a market stall or craft show--things I can wear on the current trip, usually pendants that weigh very little. I'm often able to buy them straight from the craftsperson.

Thank you all so much for your reponses, helps with my decision making, and thanks for the well wishes. Looking forward to joining your ranks as an international traveler.

For David;

Weigh it up--22 pound max.
Measure the height--21" max for European budget carriers. 22" for Legacy carriers.

I checked AA carry-on policy and it says 40# limit. Where is the 22# reference?

I use an expandable suitcase just for this very reason. Carry on and traveling around it is closed, on the way home I expand and fill it with all my goodies and check in. I have a hard shell 21". We always shop duty free because there are liquors that we can't buy in the US. The store places our liquid items in a special bag that seals on top, I usually buy a canvass bag at the store (nice souvenir and functional) and place the items in there. We carry the bag on. At Customs the bag is opened and the contents weighed.

A souvenir suggestion for Florence are leather bookmarks. They usually have a really beautiful design on front and are inexpensive. I purchased 10 on my first trip as gifts (and i kept a few) for my book club ladies and they all loved them. In the shops were they sell the bookmarks you will find lots of small gifts unique to Florence, plus it's just fun to poke around all the nooks and crannies in these stores.

I like the suggestion to bite the bullet and check in for the $60.

Some airlines (Ryanair, WOW) have a 10kg / 22lb weight limit for carry-on luggage. Every airline is different, as you've seen with AA's policy. Fare classes within a single airline can also differ, with economy type classes having stricter limits.

So you have to check with each carrier that you (may) fly, and your specific ticket class.

Lufthansa has an 8 kg (17.6 lbs) carry-on weight limit in addition to maximum size limits.

One option is to bring a lightweight travel duffle bag in you carry-on outbound and check it full on your return. e.g. https://www.rei.com/product/137647/rei-co-op-stuff-travel-print-duffel-50l

Carry the duffel by its nylon luggage handle or included detachable
shoulder strap

Duffel stows in its own zippered pocket so you can stash it in your
luggage or use it to carry home souvenirs and extra gear

Dimensions 22 x 10.5 x 10.5 inches (50 liters)

Weight 9 ounces

Since this is your first visit to Europe, you will definitely want to buy souvenirs. Why worry about $60 when it's your memories your are bringing home, It's such a small percentage of the trip cost. For my first trip to Italy (had gone to Europe twice previously years ago) and my sister-in-law's first trip out of the US, we each used a RS Rolling Carry-on and a tote with a trolley sleeve. We also took packable backpacks. Outbound we did carry on only. But coming home we expanded the suitcases and checked them. Then we stuffed the totes and backpacks full to carry on. She had a few small souvenir-size bottles of limoncello packed in her suitcase. My SIL shipped Christmas ornaments home from Rome, our first stop on our trip. It cost her $35 and they arrived in two weeks. We both carried more Christmas ornaments home -- overkill but good memories.
You will love Italy. Buon viaggio!!

Have you read "Rick's Packing List" that is listed on the lower right hand corner of the Travel Forum? Good advice.

Also, if you really don't want to check a bag going home, look at what you are going to pack now and see what will not be in your suitcase on the way back ---- I find that disposable stuff and stuff that gets used up will leave a space about the size of a loaf of bread. Enough for some small Italian treats, some pottery, etc.

Remember that you can wear sweaters, scarves, etc. just to get onto the airplane. And it's often cold on the transatlantic flight anyway.

The only things I have had shipped home are beautiful pottery from Tuscany and Deruta, blown glass from Venice and olive oil from Puglia( they had a 29.95 flat rate to ship) one time I bought cheap luggage in grocery store in Greece (9..95 € for five PCs, used one)

I am not the typical Rick Steves traveller, I don’t travel carry on only to Europe. But, I’d have strong reservations about being back wine or olive oil. This day and age, you can pretty much get anything online. I’m not sure I’d take the risk of ruining an entire suitcase of clothes with a broken bottle of wine or olive oil.

For myself, I’m an art lover and when I see a bulky art book in a museum gift shop, I’ll often go online and order it to be shipped to my apartment back home from the gift shop online. That way, I’m not lugging around a heavy art book the rest of the trip.

Pack light and you can fit some things to bring back home.

We went to France this summer with no intention to purchase anything to bring back home. We ended up buying 6 bottles of wine. Since we had packed so light, with each of us having 3 bottles in our suitcases, we were still under 30 pounds each to come back home! We found some wineskins in a store and some cardboard to pack our wine.

I didn't buy any olive oil or other heavy items.

This was the first time I had ever purchased anything to bring back home other than snow globes.

$60 to check a bag is cheaper than shipping.

I always pack a Sea To Summit travel duffel just in case. It's expensive, but it weighs less than three ounces and is very durable.

https://www.amazon.com/Sea-Summit-Ultra-Sil-Duffle-40-Liter/dp/B004YAU3JK/ref=sr_1_6?dchild=1&keywords=sea+to+summit+duffel+bag&psc=1&qid=1572615969&sr=8-6

As others have mentioned, a lot of the olive oil, vinegar and other items that you find in Italy are available on Amazon. I recall carefully nursing a bottle of fig vinegar back from Apulia only to find out when I got home that I could order it on Amazon. Many wines, however, are not available in the US. If you visit a winery and fall in love with a particular wine, it might make sense to have a case shipped back.

Scarves, along with other textiles, paper or the occasional piece of jewelry, are my most common souvenirs. They are easy to pack.

We purchased a hand turned flat spatula made of olive wood in Cortona for 6 euros. I use it almost every day and it reminds me of beautiful Tuscany. It fits easily in carry on luggage. In a previous trip I bought a small handmade book in Florence and earrings. The only time I use duty free is if I have a few extra euros I forgot about.

Thanks all for taking the time to reply, it's been very helpful in my decision making process. If I see something that I fall in love with I'll get, if I have to check a bag, oh well, worth it for joy and memories. Italy in 2 days!!!!

Take a carryon bag going, thus saving that fee; but check it coming home if you do some shopping there.
I always buy calendars in Italy, to look at every month of the year, reminding me of my trip.
They weigh nothing.
Also: bookmarks, scarves, small Murano glass earrings, soap,some spices such as pepperoncino.
Just lightweight things.
I went carryon for the first time this Fall, and still didn't wear everything I brought with me!

I have a packable duffel that I take if I want the option (Eagle Creek). If I do find things, I pack my clothes in the duffel and check it carrying on the breakables. If I don't need it the duffel folds very small and it is extremely light so it can just stay packed in a corner.

I don't do liquids anymore - even duty free purchases have to be checked when you touch your luggage at your first domestic connection if they don't fall under the 3-1-1 rule (and as I don't live at an international hub I always have to connect domestically). Found that out the hard way as I lost a purchase at security