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.

MFNYC

I agree with many of the comments above suggesting focusing on 1 country. I'm in mid 60s, husband in mid 70s. I love to plan my own trips, so many great resources around (like this forum) to do that. I do book individual tours for many of the locations, mostly walking tours (especially of the bigger cities or major sites), but some with driving depending on where we want to go. I mostly go with small group tours (not a fan of the big bus tours), and on most occasions there may be 1 other couple, or even just us!

I know people who have gone on Tauck, OAT and Roads Scholar tours and all were pleased.

michaelpianko

I went to Italy in July 2017, Greece in October 2018, and Spain in March 2022. Each trip was solo, 14 nights total, 13 on the ground, one night on the plane on the way there. You should pick just one of those countries if you only have 14 nights. In Italy I skipped Venice because i wanted to see Roman ruins. I spent 6 nights in Florence (which was probably a night too many but included a day trip to Pisa); 3 nights in Naples including a day trip to the ruins of Pompeii, 4 nights in Rome (I should have deleted a night from Florence and added a night to Rome.

In Greece my only time on an Island was 2 nights and most of 3 days, on Crete, but I should have saved Crete for when I could have given myself at least 6 nights on Crete. The mainland has too many ruins and sights to justify going to islands on your first trip to Greece. The Florida Keys, Mackinaw island in Michigan, and Hawaii are Islands if you just want islands for the sake of islands. I spent 3 nights in Nafplio on the cost of the mainland, including a day trip to Epidauros and Mycenae, then Crete, Delphi, and Athens. If I was going to pick other islands I would probably go to where there are good ruins and towns, probably Santorini and Rhodes.

My trip to Spain was flights to Madrid, train to Seville, first 4 nights in Seville, bus to Granada, 2 nights there, Alhambra on the day after my first night; 2 nights in Cordoba but I took a day trip by bus to the castle of Almodovar; and 5 nights in Madrid but that included a day trip to Toledo. The army museum in Toledo needs 3 hours to see properly.

In Greece it might be 10% "harder" to travel between cities without a car because there only long distance buses and the bus schedules are hard to find online. I rented a car only 3 times, twice in Florida, once in southern California. There might be a train between Athens and Thesalonika in Northern Greece.

travelerjan

All of the above experienced travelers have given you wonderful arguments for focussing on just one country (and I agree Italy would be it, altho I am a passionate Grecophile) -- and also explaining the advantages of independent travel vs. tours. However, I sense your discomfort with having to make all the arrangements yourself. I want to point out that you can have a knowledgeable country-based travel agency make all your arrangemwents, for an Indivdual Tour instead. And when I say all, that includes • hotels, • trains or car services, • transport from airport or train station to hotel, • booking of small-group half-day or full-day tours in a city or out into country • choice of private or small-group 3-hour tours of special interests, such as foods or art. This is the BEST Of both worlds -- avoiding the mass-movement tour group thing, but having everything managed. I stress that you should find a well-rev iewed and recoommended ITALY-based agency, because they know the local scene & opportunities best. Also, if there's a glitch, just a quick phone call to them, and you get problems solved. I often recommend Athens-based agencies with great re views for serving US first-timers; I am sure the Fodor "Italy vets" can give you some super names based in Italy. One thing to be sure... you email the agency FULL Details so they can serv e you best -- estimated time of travel (Fall is wonderful), desired length of trip, wish lilst of destinations, special interests, any physical considerations, any no-nos... and theyll work it out & send you a plan, with budget.

janisj

The OP hasn't posted since March - not sure why the conversation has resumed??

travelerjan

OOPS ... my bad. wasted effort probably.

janisj

Nah it was topped before you posted . . .