Sassafrass

Rome, Florence (Pisa as a morning or afternoon from Florence) and Venice would be a piece of cake in 14 days. You could see a lot with little travel time. There is a direct train line between them and Pisa is an easy, short day trip from Florence. You could even include a couple of other places.

This is actually easier than visiting Williamsburg and going over to Jamestown or Yorktown, easier even than going to Newport News or Virginia Beach because you do not have to drive or park, won’t have traffic. There is just a hundred times more things to see and explore in Venice and Florence.
We lived in Newport News and I worked in Williamsburg, thus the comparison)

Best would be to fly into Venice (several reasons, can amplify later).

Something like this, but there are so many options depending on your personal interests.
Venice, 3 nights (I would do 4 because I love Venice and would also see the islands, Burano, etc.) You need arrival day to chill, walk, rest, get acclimated, then two+ days for sightseeing.
4th day, Morning train to Florence,
Florence, 3 nights or 4 or more if you love Renaissance Art and want to visit Pisa and Siena. I highly recommend a day trip (easy by local bus to beautiful Siena. There are other Tuscan towns you could visit. You could do a local tour of Tuscan countryside with a private driver. For one morning in Florence, I recommend a local guide for walking tour.
7th or 8th day?, Train to Rome
Rome, As many days as you want, perhaps Day trips to Orvieto, Ostia Antica, Tivoli.
Depart from Rome.

If you can add a day or two and could fly out of Naples, you could see Pompeii and the Amalfi Coast, but might be too much for first independent trip.

Venice to Florence is a bit over 2 hours to just under 3 hours, depends on train.
Florence to Rome is about 1 & 1/2 hours.

janisj

As others have said -- Italy would be a lot easier logistically in 14-ish days than Greece/Greek Islands. Say you have 11 full days 'on the ground' (not counting the 1.5 days to get to Europe and a full day getting home) something like 4 days (5 nights) in Venice, Florence 3 full days (4 nights) with a day or half day trip to Pisa, and finishing up with 4 days (5 nights) in Rome . . . all by train. Fly in to Venice and home from Rome -- a perfect introduction to Italy.

SusanP

I agree, in Italy the train connections are easy, all direct with no changes.
Do your 14 days include travel time? If so, your first day is an overnight flight to get there and the last day is your flight home, so the last night is just leading to the trip home. This leaves you 12 nights actually in Italy, so similar to the suggestions you already have:
Fly into Venice, 3 nights (4 would be better, but you don't have the days)
Train to Florence, 4 nights with a day trip to Pisa
Train to Rome, 5 nights Rome
Fly home from Rome

When searching for flights, select multi-city flights to go into Venice and out of Rome.
This would be a wonderful trip!

janisj

I'd definitely add another night to Venice (assuming that's the arrival city) because the first day/night is pretty much a lost cause what with formalities/transit/checking in and jet lag. For that reason I always try to build in an extra night at the first stop. Plus Venice is just about the most photogenic/romantic city anywhere. So 5/3/5 nights would be my personal preference -- but either version is doable.

SusanP

Of course, you make a good point, janis, but they have 12 nights (unless the 14 days doesn't include travel time, but I didn't get that impression). I divided it the way I did to give time for Pisa. Actually, I would do 4 Venice, 3 Florence and forget about Pisa, and 5 Rome.

mjs

I agree that Italy with 14? days is a nice first trip to Europe. I love Venice but would give it 3 nights for 2 full days, 4 nights for Florence with some trips outside the city such as Pisa, Siena etc, 5 nights Rome.

Cjar

I think Italy would be a winner. Our first trip to Europe was Italy. In the cities previously mentioned ,we found that almost everyone has at least some grasp of English so language isn’t really a problem. You could split your time based on what city holds the most interest for you. For us, we loved Florence and Venice. Rome was great too just not our favorite. We also used Hill and Roads for transport between Siena and Florence.They arranged a lovely meal and we had the pleasure of really getting to look at Tuscany since it’s a bit slower pace. Train between Florence and Rome is easy as well as Venice to Florence. It is terribly romantic to arrive in Venice first and splurge on a water taxi especially if your hotel has an entrance from the water. As mentioned above no train changes.

Spain would also make a lovely anniversary trip with similar ease of travel and language. madrid is such a cosmopolitan city so much great food, museums, parks. Seville feels to me like an exotic blend of old and new and Granada with the Alhambra and its gardens are one of my favorite places I’ve ever visited. It is magical.
I’ve never been to Greece so can’t comment on that. For a wonderful experience, slow travel is more enjoyable and everyone on this website is so very helpful.
If you truly prefer to have things arranged for you, I did find this website offering a 15 day Italy Greece. The itinerary feels more rushed than doing it yourself, but you could see parts both countries with perhaps less worry for you.

https://www.pilgrimtours.com/greece-...-italy-15.html

If budget is no problem, it looks like Kensington tours does some bespoke tours.

https://kensingtontours.com

I hope you have a happy anniversary trip.