Italy with husband for 25th anniversary and 18 year old daughter for the first time

The Florida coast and the Amalfi Coast (note spelling of Amalfi) are very different things. I wouldn’t worry about duplicating experiences.

Instead of the Amalfi Coast add time in Santa Margherita Ligure or Camogli. They are waterfront towns near each other in Liguria and SML would offer the shopping. But maybe you get enough waterfront in Florida?
Or Bellagio on Lake Como. The mansions around the lake were built by the Silk merchants in Milan. We have returned there four times for up to two weeks.
And not to miss on your trip is Milan for fashion!!! We had fun in the fashion district . Pricey leather and shoes galore! And get reservations way in advance to view da Vinci’s “The Last Supper.”
Or consider Bologna, a wonderful university town with a focus on food would be fun too.
We have been to Tuscany many times. Our favorite area is of the Chianti villages between Siena and Florence such as Radda, Castellina, Oanzano and Greve.
We did not venture south of Rome until our seventh or eighth trip to Italy and we have never mixed trips with northern or southern Italy, just one region at a time as they are so different.. Do not spread yourselves too thin!

Maybe stay in Salerno for your Amalfi coast portion. One can ferry to Positano and Capri. Train to Pompeii for the day and then train to Rome to continue on your journey.

If you do stay in Salerno, as suggested above, you could do a day trip to Paestum by train. It’s best known for its really well-preserved Greek temples. Also, the ferry company for the Amalfi coast is Travelmar - you can check out their website (Travelmar.it).

Welcome to the forum! You are lucky to have that amount of time.

Investigate doing an open jaw flight, arriving in Milan and flying out of Rome. I agree with others, Milan is a hub of fashion and shoud be on the list. Perhaps your daughter can check into a visit to a similar school there or a fashion house.

A lot of our suggestions will be determined on how you plan to get around. Will you be using public transport? Are you considering renting a car for at least part of the trip?

Venice, Florence and Rome are the default tourist destinations and certainly worth visiting. However, there's lots more to Italy other than the big three. If nothing else, when in Florence take a day tour of Tuscany.

Sit down as a family and watch some YouTube videos and study guide books to come up with a list of must sees. That's the easy part. The hard part will be to pare down that list into a reasonable itinerary. That means you'll have to sacrifice some items. Also, especially with a trip that long, be sure to schedule in some down days where you have no schedule. You can use these days to amble and explore.

Happy travels!

You are lucky- there's been a wealth of info posted here on the Forum in the past 12 months. Just check under the Italy section, and read the last year's posts. Many of your questions have already been answered.
Have a great trip!

Milan is known for fashion. Lake Como is a little over an hour by train from there. You might consider Lake Como instead of Amalfi coast. We live in Florida too but thoroughly enjoyed Lake Como. On an earlier trip we went to Amalfi coast and enjoyed that too but Lake Como is more accessible and better to do as part of a longer trip. The beaches on both are rocky and not as good as Florida's but one thing we especially enjoyed on Lake Como was the water with mountains in the background.

For a first trip, you definitely want to see Venice, Florence & Rome, and you have plenty of time to enjoy some of the quaint less touristy locations which I absolutely love. I’ve stayed in 25 Italian towns and the only one that was “so-so” for us was Bologna. There’s wonderful museums in many cities, architecture, etc. so no bad choices. Would you like to attend a local festival? I think your teenage daughter would love it! Arezzo has their jousting festival - June 17 in 2023, as one example. (Search on “festival Italy” and each month to see more ideas.). Montepulciano could be your next stop after Arezzo, and Montepulciano is about the opposite of the flat landscape in Florida!

Since your daughter likes fashion, I would either fly into or out of Malpensa, so she could see some of the shops in Milan.

Please use the search box here top left blue menu to read about the Amalfi Coast and Capri. There are a lot of complex decisions to be made (like where to sleep the night before your flight home), and how crowded those two places are by mid-May. You need a lot of information, more than you can get in one discussion thread. It is no substitute for the actual "rag trade", but note that Positano and Capri are both famous for (my own opinion) endless international high-priced fashion boutiques that WE never enter. (That is not a reason to not go there, I'm just mentioning.)

Just for example, you can't just ask about "Amalfi". Many people don't know that Sorrento is not physically on the Amalfi Coast, but also, we don't know when you write "Amalfi" whether you mean "The Amalfi Coast" or "Amalfi the town", or even, possibly "Sorrento." Another aspect: The Mediterranean is not as warm as Florida; and the Positano beaches are small, pebbles, and you have to pay for a chair or umbrella. They tend to be crowded. Some Positano residences can require a stair climb of hundreds of steps. Start your detailed research. Sorrento only has one, tiny, public beach, which is literally located between the two big marinas.

I should add that we stayed five nights in Sorrento, in a luxury hotel, and were very happy for our travel plans and objectives. (You did not, for example, use the word "Pompeii." This is not a slam of the area!

Our first trip to Italy we toured Tuscany (started in Florence) & Umbria. Our next trip (Culinary Tour) we started in Rome>Southern Italy/Sicily. It wasn’t until 4 years later that we stayed in Venice x 1 week prior to an Adriatic tour. It was amazing. Still have more to see in Italy!

You mentioned interest in Positano. We enjoyed our 2 nights there. It is the perfect walking city wandering the winding roads of the village. I went shopping with a gal from our tour. Her luggage never made it to Italy. We went to a local boutique- Brunella (not an international high priced fashion boutique). She was able to find an affordable 3 piece outfit that she could sink wash. She also picked up some other tops, etc. along the way. Our lovely hotel in Positano was Hotel Savoia. Well appointed, view, and great food. Enjoy your planning!

Edited to add: I will add that we spent 2 nights in Sorrento as a base for Capri, Greek Temples of Pasteum, & Mozzarella tasting at a Buffalo Farm. Our next 2 night stop was Maratea, an impressive village high above the sea on the southern Tyrrhenian coast. We ended our tour in Sicily…

You have some great possibilities! If you decide to go to the Amalfi Coast area, Sorrento makes a good base. You can take a boat from Sorrento to Capri for a day. If you stay at a Sorrento Hotel on the cliffside by the water you will see amazing sunsets over the Bay of Naples. There is a lovely Centro Storico area in Sorrento with quaint shops and restaurants as well. We stayed 3 nights in Sorrento and 3 nights in Positano. From Positano we took a boat to the town of Amalfi, The views from the ferry along the Amalfi Coast are spectacular. In Amalfi town we took the City Sightseeing bus up to the town of Ravello which we enjoyed also. It is challenging to get to the Amalfi Coast with winding mountainous roads, so if you decide to go to that area stay awhile.

Consider this itinerary. I’ve included 2 additional stops to your original wish list. With suggested minimum nights for each location. Add or subtract nights as you see fit. Just don’t go under the minimum #.

Day 1 Travel to Venice.

Day 2 Arrive Venice. 3-4 N.

https://quickvenice.com/transportation/index-transportation.htm
https://www.venetoinside.com/attraction-tickets-in-veneto/#VENICEMUSEUMSANDMONUMENTS
https://venicefreewalkingtour.com/

Day 3 Venice.

Day 4 Venice.

Day 5 Venice.

Day 6 Train. 1Hr28m Venezia Santa Lucia to Peschiera del Garda. 3-4 N. Beautiful lake some very nice beaches. New stop.

https://lakegardatravel.net/lake-garda-italy/

https://www.visitgarda.com/en/lake-gara-ferries/#&l=en

Day 7 Peschiera/ Desenzano to Limone sul Garda by ferry.
One of the best beaches. If time permits, ferry to Desenzano.

Day 8. Peschiera/Desenzano to Bardolino by ferry. Afternoon to Lazie by ferry.

Day 9 Train Peschiera/Desenzano to Milano Central. 57min.
3 -4 N Milano. 2 designer shopping streets Via Monte Napoleone & Via Della Spiga.

https://www.getyourguide.com/milan-l139/itinerary-48-hours-in-milan/?cq_src=google_ads&cq_cmp=6654624646&cq_con=131954736684&cq_term=milan%20itinerary%203%20days&cq_med=&cq_plac=&cq_net=g&cq_pos=&cq_plt=gp&campaign_id=6654624646&adgroup_id=131954736684&target_id=aud-905885568202%3Akwd-651989142424&loc_physical_ms=9022129&match_type=e&ad_id=565259003690&keyword=milan%20itinerary%203%20days&ad_position=&feed_item_id=&placement=&device=m&partner_id=CD951&gbraid=0AAAAADmzJCPOaF8x1TbHlL3W8ee9Skgey&gclid=EAIaIQobChMIhdeE9MSv-wIVO_TjBx2ZvQWyEAAYASAAEgJkXvD_BwE

Day 10 Milano. Duomo, Castel.

Day 11. Milano. Day trip. Varenna on lake Como or Bergamo, see the old city Alta.

)Just to the right of the medieval stone staircase, you’ll find the Bergamo Alta Funicular. This is a fantastic and surprisingly cheap way (under €2 euros per ticket!) to get up into Bergamo Alta.)

Day 12. Train Milano Centrale to Firenze SM Novella. 1Hr54m. 4-6 N Florence. Minimum 3 Days in the city with 3 day trips to Tuscan towns/villages.

Museum tickets. https://www.b-ticket.com/b-ticket/uffizi/default_eng.aspx.html

Day 13. Florence.

Day 14. Florence.

Day 15. Florence. Day trip. Train Pistoia &/or Monticattini Alto

Day 16. Florence. Day trip. Train Lucca & Pisa. Visit Pisa last.

Day 17. Florence. Day tour. Montalcino, Pienza & Montepulciano.

https://www.getyourguide.com/florence-l32/val-d-orcia-cheese-and-wine-tasting-tour-t62160/

Or San Gimignano & Siena by bus. # 130&131. Change in Poggiobonsi train back from Siena to Florence.

Day 18. Train. Firenze SMN to Napoli Central. 3 Hours.
Taxi to Port. Ferry to Ischia. 1H. 4 N.
Much mor relaxing area than Amalfi coast. Great beaches, lots to do. New

https://www.ischiareview.com/things-to-do-in-ischia.html

https://www.ischiareview.com/getting-around-in-ischia.html

https://www.ischiareview.com/towns-of-ischia.html

Day 18-21. Ischia.

Day 22. Ischia to Naples 1H Napoli Centrale to Roma Termini 1H17m. 5 N Roma.

Day 22-27 Rome.

Day 28 travel home.

For trains, Trenitalia.it. Use Italian names as listed above.

That is a fantastic itinerary gerri!

I'd add Last Supper in Milan. Not to be missed. Book tix as soon as available.

We were in Italy in May and June. We live less than an hour from the northern Gulf Coast with sugar white sands and beautiful aquamarine waters. The Italian coast is simply different—a lot of cliffs and “peebly” but the architecture and views are astounding. I suggest that each family member write a list of three things/places they want to see/do and let that be your starting point and see where it guides you. Frankly, the “must sees” are different for everyone and do not feel pressured to do what everyone tells you have to see or do while there…unless of course it is gelato…

Maybe as a starting point, each of you need to think about and discuss your individual ideas about how to spend your 3-4 weeks in Italy.

Some people would emphasize sight-seeing in historic sites and museums, while others might prefer scenery with hiking or lounging by the water. Is there a "foodie" in the family who would emphasize trying out regional dishes while someone else wants to shop 'til they drop?

Discuss ahead of time how "busy" you want your schedule to be. Is the attitude that this is your one opportunity to see Italy so nothing should be missed, or is your approach going to be that you're there to relax. What mix of big cities, smaller towns, and pretty scenery works for you?

Discuss spending and expenses ahead of time, too. Where do you plan to sleep: hotels, b&b's, short term apartment rentals? For a trip as long you are planning, you might consider at least one apartment with a washing machine in the middle of the trip. Are you driving or using public transit? Talk about what you plan to pack. My "rule" is that each adult needs to pack and be able to move his/her own belongings. If you're using public transit, avoid huge suitcases.

Discuss whether you're spending every minute together, or will you sometimes split up. With three people, be certain that no one is left out.

After you've discussed each person's perceptions of what this trip should be, then you can figure out an itinerary.

The Amalfi coast is breathtaking(in more ways than one-I would want a very trustworthy and experienced driver on that road) and with the amount of time you have, I think Pompeii is a must-see.

I have been to both Gulf Coast and East Coast beaches in Florida and this will be very different.

Here are the best shopping areas in Florence.
https://www.butterfield.com/get-inspired/best-shops-in-florence

Rome.
https://renatoprosciutto.com/via-condotti-rome/

Make sure your daughter takes photos of the designer windows, some are truly inspirational.