Planning a trip a trip to Florence, Rome, sorrento /Pompeii in 2020

Two weeks is a good length of time and you should be able to see everything on your list. Be aware that in June in can be quite warm in Italy. This coming week, for example, the day time highs will be in the 90s in Rome every day. Historically, the average high in June is 84, in July it's 90. I'm not a big fan of heat and think April and May are a better time for Italy.

There is no reason you can't do the trip on your own. Italy has an excellent train system that can take you everywhere you want to go. RS's books and the app have great walking tours of many sites. You can find plenty of half-day and full-day tours of specific sites on a site like Viator. Some just meet at a specific site and provide a guided tour and, an all important skip the line, while other transport you by bus to more remote sites.

Florence is worth the trip, regardless of how much time you like to spend in art museums.

If you want to include a tour for part of your trip, there's a 2020 RS Rome tour that starts the afternoon of June 7 and ends the morning of June 13. You could visit either Florence or Sorrento/Pompeii for a few days before the Rome tour and the other location for a few days afterwards.

Hello Roger

2 weeks is a great amount of time for a first trip to Italy.
Is that 14 nights or 14 days?

I know you didn’t list Venice but we love it and I think you can not go wrong on a first trip to Italy visiting Venice, Florence, Rome.
Side trip to Sorrento or Tuscany. Your choice.
All can be easily done by train, book in advance for savings.
Rome needs 4 days minimum, Florence 2-3, Venice 2-3, Sorrento 3-4.
You didn’t mention anywhere on Amalfi coast but that can be a day trip from Sorrento.
Think of your trip in NIGHTS. 3 nights is really 2.5 days.

You will want to check out your flight options.
Open jaw- fly into one/out of another is often the better choice. It is easier to fly into Venice than out of Venice and there are direct flights to Venice from US. Venice is a perfect place to get over jet lag.
Direct flights from Rome to US.
You will need to be in your departure city the night before your flight home.
We always book a direct flight to Europe.

I am assuming you are flying from US!

If it were my first trip to Italy I would do this:

Fly into Venice
Venice 3 nights
Train to Florence 2-3 nights-(day trip to hill towns)

Train to Naples/Sorrento 4 nights
day trips Pompeii, Amalfi coast, Capri if
(OR This could be 4-5 nights in Tuscany/Umbria, you’d want a rental car)

Train to Rome 4 nights
So much to see/do in Rome. Never enough time.
If I had an extra night I’d add to Rome.

Fly home from Rome

Look at Mondo Guide shared tours for Pompeii, etc. Excellent. RS recommended.
https://www.sharedtours.com

Walks of Italy also excellent. Highly recommend. They offer a RS discount- 10RICKSTEVES maybe? not sure? email and ask for code
https://www.walksofitaly.com

We love food tours
https://www.eatingeurope.com
Code- EATWELL10 for discount

You have lots of time to plan.

Trains
https://www.trenitalia.com/en.html

Frank made a good suggestion about booking the RS Rome tour and then doing the rest of your activities on your own, before and/or after your official tour.

Of course, you can DIY your own trip to Italy, but I often enjoy the ease of letting somebody else (like RS tours) arrange things for me. It's one less detail that I have to manage on my own!

If you don't care to drive in Italy, you can always go online and find day tours that take you from Rome to Pompeii and Sorrento. You can also take the train from Rome to Florence. I'm not sure how long you want to spend in any one location so not sure exactly what to suggest for transportation options.

Have you made a list of your must see items yet? That might help you decide how to best juggle your time between your target destinations. I do that before every major trip. That way I make sure that if seeing/doing something specific is on my must see list, then I budget the resources for that option. Then I can fit in other things, but the most important sites/experiences are already drawn into the schedule.

I don't know if you have traveled with another couple before, but from my personal experience, there is a very high chance of friction between the four of you. I would think that if you take a tour, it would eliminate a lot of the arguments that might ensure if it's just the four of you trying to figure out what you want to do and how to do it. You can blame the tour for any dissatisfaction, and come home as friends.

Also remember that just because you're traveling together doesn't mean you have to do everything together. Most people don't have exactly the same interests and tastes, so it's perfectly OK to explore different sights during the day or to go to a different restaurant some evenings. I'd suggest discussing that option during the planning stage so your friends don't misunderstand and think you're bored with them in the middle of the trip.

There is nothing wrong with your plan. Because of possible increasing tourism restrictions in Venice (due to crowding) I would consider putting off Pompeii to a future trip (as we did) and go to even more iconic Venice. I didn't get to Pompeii until I was 60, on my sixth trip to Italy. One of the issues is that Sorrento is harder to get to than Venice, and it affects your "last day" there. It depends on where you live (that is missing from your public profile), but it's surprisingly easy to fly into Rome and home from Venice. (East Coast bias, I know ... ) Note also how well Venice pairs with Florence.

You can do four cities in two weeks on a first trip to Italy, so you could add something in the north, like Bologna, Milan, or possibly the lake district (which can be expensive and hard to book in high season.) You can also fly home from Milan, although Milan is not a must-do on a first trip to Italy - unless The Last Supper is a huge priority. I personally would not go to Sorrento in June without air conditioning. Pompeii is a great place, but it is unbelievably sun-exposed and you bake on the ancient stone street pavers. You need to do that excursion first thing at opening time, in June.

I'm surprised that your wife wants to go to Florence, yet Venice is not on your list. It would be useful to know if there are specific interests among the four of you - I mean like family ethnicity, art history education, cuisine, architecture, world history, one war or another, religious faith ...

I think you will find that most of us here plan our own trips, but there is nothing at all wrong with doing a RS tour- then maybe add a few days at end on your own. I've not done any RS tours but do have friends and family that rave about them
As I said above you can not go wrong the Venice-Florence-Rome
"The Best of Venice, Florence and Rome in 10 days" is a 9 night tour. You could add a day at beginning- fly into Venice and get over your jet lag ready for tour to start. Then add a few days at end and go to Sorrento from Rome. Or add another day in Rome then go to Sorrento :) (3 night in Rome is a bit short). Plenty of info and help here on how to plan that bit. Just remember you do want to be IN your departure city the night before departure- whether that is Rome or Naples.

The nice thing about the RS tour is all the figuring out of tickets, timed entries, tours etc is done for you. That can be a bit of a headache even for more experienced travel planners!
And yes- traveling with another couple has its pros and cons- if you are just 4 in a tour group of 24 or so, so you won't need to worry quite so much about some of that!

https://www.ricksteves.com/tours/italy/venice-florence-rome-2020

Welcome to the forum, Roger, and by now you've noticed that sometimes well-intended answers go well beyond the scope of the question. I love Venice but I also love having enough time to really appreciate the places I go. If your priorities are Rome, Sorrento, Pompeii, and Florence, I'd say stick to those so you spend only four part-days relocating instead of five.

I took the RS Venice-Florence-Rome tour last year and loved it, and was glad I added days on my own before and after. I think the idea of building your trip around the RS Rome tour is a good one, and I think Marty's observation about the two-couples dynamic makes a lot of sense. I'm not sure, but I think booking an RS tour entitles you to a limited amount of free consultation with the RS office, which could help you plan your other destinations. And of course there's a ton of free advice, much of it good, on this forum.