25th Wedding Anniversary - Italy 2019

This might break the bank but we did it on my wife's 60th birthday. We rented a boat (yacht or something more than a row boat) and went to Capri. We stopped a swam in the Med for a brief period. Very memorable and lots of fun.

Yay! Congratulations! Italy is a great place for an anniversary trip!

My advice is to get a Rick Steves Italy book and read it. He loves Italy and has some great ideas. I used it to plan our trip last year (Rome, Cinque Terre and Florence w/ a day in Pompeii). We loved all 3 places. Rome is magical, especially at night.

I think you'll find that get better suggestions from people here if you have a few more details-when you are going, what you like to do (museums, art, music, outdoors, hiking, water, beaches, food, wine etc)

While in Venice, do a rowing lesson with Row Venice. You will learn to row a gondola and will actually row on the Grand Canal (after prior practice 😉). If you choose the late afternoon lesson you will also row to a few canalside bars and enjoy wine and snacks. My husband and I did it for our 43rd anniversary and it’s one of my favorite memories.

Congratulations Mike! 25 years is quite a milestone. I agree with others, tell us more about what time of year you will be going and what interests you (museums, churches, food, wine, etc.).

Here's some general suggestions. Fly open jaw so you don't have to backtrack to fly out. Be sure to factor in travel time. For instance, high speed train from Florence to Rome is ~2 hours. Rome to Sorrento is ~3 hours. Therefore, you are losing half a day with each move. You might consider traveling in the evening.

Does your four nights each include a day on either side for arrival/departure? Be aware 4 nights in Florence (not counting arrival day) is only three days in Florence. If you leave for Rome after night 4 in Florence, you get just 2 1/2 days in Rome. If you feel the need to take other adventures, plan on only one for Florence and Rome and maybe two for Sorrento. For an "off the beaten track" from Florence, consider a visit to a winery in Chianti for a food and wine pairing lunch.

Don't over plan. RS talks about this a lot. We all tend to try to cram too much scheduled time in a day. Give yourself at least an entire morning or afternoon in each location of totally unscheduled time. You could just wander and soak in the sights or this gives you a chance to add something to your itinerary that wasn't included in your plans.

Since this is your first time to Italy, think of it as a scouting trip. You'll want to go back. Make notes of what you want to visit the next time you're there. This trip will only scratch the surface.

Thank you all for the responses so far!

As for time of year...it will be June. Wife works for a school district, so we'll have to go after school is over.

Interests - really love architecture, museums, FOOD, and my wife would hate if I didn't add in some shopping...as long as there is a bench where I can people watch!

You could fly into Naples and head straight to Sorrento for 4 nights. Then train to Rome for 4 nights. I think you will find you will need all of your 3.5 days for Rome. Train to Florence for the last 4 nights. A day trip to somewhere in the country side and if it interests you, a half day to Pisa. Fly home from Florence. This way you're not backtracking.

Congratulations!
Since you want to visit Rome, Florence, and Sorrento, it might be cheaper if you book round trip from Rome. You could fly out from Florence, but flights are limited. Or you could fly from Naples.
A nice side trip would be Orvieto, a nice smaller hill town, about an hour from Rome.

As far as restaurants, there are many threads here that list favorites. Just don't go to "tourist menu" ones or any that have someone outside trying to beckon you in.