Itinerary help, please? Especially with Venice night

If you're flying into Milan, I would not go for Venice for one night. That's a long train trip and then the following day you would have another even longer train trip from Venice to Sorrento.

Are the airline tickets already bought? If not, I would try flying into Naples instead of Milan. If the airline tickets are already bought, maybe fly from Milan to Naples. Looking at Google flights in late April dates, there are plenty of Milan to Naples tickets for less than $100.

Sorrento is a bit of an outlier for this itinerary. Perhaps you could get a flight the day you arrive from the US to minimize lost time in making a transfer. One night in Venice will frustrate you, I fear. Those of us who love Venice spend several nights and get away from the crowds. Those who stay one or two nights seem to dislike the city.

To upend your plan a bit and based on what you want (avoid crowds, food, hiking, outdoors time, efficient travel) I would suggest staying Tuscany and points north. Go to Venice by train on arrival Day one and spend at least 3 nights there, then move on. Our first trip, many years ago, my husband was a reluctant European travelers. Our second day in Venice (we spent 4 nights) he said “We have to come back” and we’ve been to Venice a dozen times now. I’d go back tomorrow.

I agree 100% with Laurel.

For Venice, my favorite thing to do is put away the phone - no maps and just wander. Take turns choosing whether you go left or right at every piggly wiggly intersection and enjoy the uniqueness of these islands. If you’re navigating with your phone, you completely miss this wonderful aspect! Eventually stop and check your location. It’s islands, so you can’t be too far away! ; )

Suso gelato is my favorite so far in Italy, and I have been to A LOT of them! ; ). The Manet flavor is my favorite!

Be sure to buy entrance tickets ahead of time to go into St. Mark’s. If possible, select them for the first time slot, and be there for less of a crowd to see much more.

I like to end the day with a beverage at The Florian at the outdoor tables. It is expensive, so I don’t eat dinner there. But, savor the time seeing the special piazza in the evening with the day trippers gone, hearing the music, and having a nice conversation with your daughter.

I like to stay near San Marco and take the vaporetto back up the Grand Canal in the morning as my last look of Venice while I’m heading to Venice’s San Lucia train station.

The two main activities my daughter & I did in Florence, besides going to the Uffizi might interest you since you’re not interested in museums.

https://community.ricksteves.com/travel-forum/trip-reports/mother-adult-daughter-italy-trip-aug-sept-2022

Venice is lovely if you don't stay in the crowded areas. We like the Cannaregio areas on the quiet back canals, which is beautiful and peaceful, yet a ten minute walk from a vaporetto stop. It's easy to go a few blocks from St Marks and Rialto area and experience a side of Venice you'll want to visit more than once.

I agree , Sorrento is too far for the time you have, and I doubt you'll find lodging at this late date. Save the AC for another trip. Use the days at your other stops.
Have a great trip!

Sit down and calculate how much time you'll have to spend getting from one place to another. You'll spend a lot of your time getting there and back. I agree with others, it makes no sense to fly into Milan and then go to Sorrento. I suggest you swap Lake Como for Sorrento. If you don't like crowds you'll find the Amalfi Coast frustrating. Shoulder seasons don't exist anymore.

If you haven't booked anything in Sorrento, you might want to check on availability and prices.

Since you know your arrival time in Milan, I'm assuming you have booked your flights. If that is the case, I'd not go straight to Sorrento from Milan. Doing so, combined with your flight over, will make for a very, very, long trip. I'd also not go to Venice for just one night. It might shorten the arrival day travel, but you can accomplish that by staying in Milan or somewhere between there and Sorrento. You also indicated you think it might be a good idea to at least see Venice. You might want to consider taking one day each from Siena, Florence, and the CT. Use them for Venice. That will give you two days in each location as your arrival day in Venice will be shot due to jet lag and getting acclimated. Don't worry about Venice being too crowded. All you have to do is go several blocks from the main attractions and there'll be very few people. And then you can really enjoy on of the most unique cities anywhere. Just food for thought. Enjoy the trip no matter what you decide.

Thanks so much for all the feedback! It's unfortunate that we're flying into Milan and not further south, but the airfare was much much cheaper at the time and have direct flights. We're not big on flying, so def has to be train to get down south there.

Oh my goodness, is it really that grueling to get down to Sorrento from Milan?? We figured it would be all day on trains (10 hrs, or so?), but are okay with that. We both love train travel and don't get to do enough of it back home. Plus, we figured we'd get all that done at the beginning of the trip and then a more relaxed pace after...Now, I'm a little nervous, though...

We have a super discounted deal booked on our accommodations in Sorrento... The Amalfi Coast has always been on my bucket list and my daughter did not get to go on her 1st trip...We know it's going to be fairly crowded, but at least we'd be outside and figured we could work around it a bit. We live in a lake region and wanted to be coastal for this trip...

I thought maybe if we went from Milan airport to Venice we'd have at least a good chunk of the day so that I could just check it out, rather than not seeing it at all...I'd rather do Venice longer with my husband, but want to see it just in case that doesn't happen - and also to gauge whether it would be a good option for him. Then, we'd also just be on the train for half a day after landing, rather than heading right down south.

Thanks for the mother daughter tip, Jean. Bike tour sounds fabulous!

You might want to consider taking one day each from Siena, Florence, and the CT. Use them for Venice. --- Oh, how I wish I could do this, but the problem is I have to be down in Sorrento prior to that and can't modify that one part of the trip to add nights in Venice.

Pepper, take a look at the trenitalia website: https://www.trenitalia.com/en.html You can play around with routes and itineraries.

Since you're locked into Milan, I would consider just biting the bullet and heading straight from there to Sorrento. Or, if you really want to see Venice, head there for one day, and take an early train the next morning to Sorrento.

Just to throw something else into the mix, have you considered flying from either Venice or Milan to Naples, then taking the train or airport bus from Naples to Sorrento? Just a thought. I'd probably take the train.

...have you considered flying from either Venice or Milan to Naples...

If you fly from Venice, you'd at least have more time to get a feel for Vencie for a later trip.

Flying down to Naples is not something that I had even factored in when planning, but I will certainly explore that option...Not sure I want to add in another flight and all that's entailed, but I'm open to exploring all possible options. Thanks so much for the feedback!

Fly from Milan to Naples the day you arrive in Milan.

Going to Venice for the night of you arrival day and then onto Sorrento the next day is unlikely to produce a pleasantly memorable visit to Venice.

My $0.02 is a) skip Venice; or b) spend 2 nights in Venice and delete one night from CT.

”Is it really that grueling to get down to Sorrento from Milan?? We figured it would be all day on trains (10 hrs, or so?), but are okay with that. We both love train travel and don't get to do enough of it back home.”

I love to ride the trains in Europe, but you couldn’t talk me into this even if it was a free ticket on a day without a flight! Look at going from Milan to Salerno, instead. It’s a direct Frecciarossa fast train all the way with no connections. It’s 5 1/2 hours, and you are at the Amalfi Coast. The next day you can take a short ferry over to the town of Amalfi.

Last May, 2023, we compared flying vs trains from Milan to Naples. With all the extra time you need for getting to the airport and security, we found it was really the same amount of time, and the train is easier, in my opinion.
Please read the posts under Italy here regarding getting from Naples to Sorrento on the gritty regional train. It's like a NYC subway- often crowded , late, and you might be standing for the whole trip, which could be two -plus hours. It makes for a very long day.
I would be careful with a really good deal on lodging in Sorrento. The area is expensive and in demand. Please double check recommendations and reviews on the property, to determine if the reviews are legitimate.
Have a great trip and I hope everything works out well for you. Safe travels!

Hoping to spend more time absorbing culture, etc. than trekking from place to place...

I'm afraid that looking at your schedule, you're doing exactly what you don't want to do. You don't have nearly as much time as you think you have.

I sounds like you're locked into a schedule in Sorrento, but I also agree you really need to look at your "super deal". If it sounds to good to be true, it usually is. If the rest of your trip is flexible, I agree with others, steal a day from Siena and a day from CT and use it at the end of the trip to visit Venice.

If you think Venice would work for your husband, do something radical the next trip. Spend at least a week in Venice alone. We spent a 10 day trip staying in one agriturismo in Tuscany. We also spent an entire week in a B&B in the small village of Loches, France. You'll be much more likely to absorb the culture and make friends with the folks that live there instead of hustling from one end of Italy to the other.