First time in Italy. Suggestions for a 14 day itinerary.

Since it may still be a little cool in the north in April, I would start south and head north. A simple route would be

Sorrento, Pompeii, Amalfi Coast - 3 days
Rome - 4 days
Florence, Tuscany - 4 days
Venice - 3 days

You could also do the trip in reverse. Fly into Naples and out of Venice. Be sure to consider the number of nights you have and the actual number of days on the ground in Italy. if day 1 is arrival day, jet lag may be an issue for you. You can take high speed trains between locations.

Think in terms of nights and where you will lay your head. No less than 3 nights in each location so you have two FULL days minimum in each stop. So with Stephen’s nice itinerary:

3 nights Venice

4 nights Florence with day trip(s) into rural Tuscany

3 nights Sorrento to visit Pompeii and the Amalfi Coast

4 nights Rome (a bare minimum of time IMO)

Fly into Venice and out of Rome. You will experience a lot of you don’t move around too much.

Meant to add, April is lovely in Venice!

If your 14 days includes your travel days, you really have only 12 days in Italy, and the arrival day may be pretty useless due to jetlag and severe sleep-deprivation. I never plan anything for my arrival day except either a bus or train to my first stop or walking around outside, trying to stay awake.

If you don't have at least 14 nights on the ground in Italy, I'd reduce the number of stops to three, postponing either Venice or the Amalfi Coast/Sorrento/Pompeii until your next trip. You would still have plenty of great sights to occupy your time in the remaining three areas. The Amalfi Coast in particular takes time to get to and to travel around.

Thank you, we are planning 14 full days in Italy and two travel days.

Any suggestions where we should stay overnight and day trips?

You really should pick up the RS Italy Guide 2019 on this website. He lays it out for you and helps you plan your trip.

I agree with staying 3-4 nights at each location. Any more, you are just packing and moving too much. I like to visit at least ONE big city and then smaller villages for the rest of my trip. That is just my preference. I find the smaller villages more charming and conducive to what I consider a vacation.....not hectic, quiet, slower pace, etc.

Venice or Amalfi coast ??

Venice or Amalfi coast ??

Venice

For a first trip to Italy- and just 14 nights- you cannot go wrong with Venice-Florence-Rome- or vice versa.
Venice is an easier place to arrive than depart- also a great place to get over jet lag.

3 or 4 nights stays are always better than less. A 3 night stay means you have 2.5 days or less- once you figure in time to get to/from, check-in, get your bearings etc. Count your trip in NIGHTs not DAYs

Rome needs a minimum of 4 nights, Venice 3, Florence 2 or 3- depending on your interests.

Tuscany is very easy to add in with Florence. Amalfi/Sorrento takes a bit of effort to get to and get around.
Since you've got time - keep an eye on flights to determine what's the best route. You would want to fly into (or out of) Naples if you decide to keep Sorrento.

If you have not already- do get the RS Italy book. Determine what you actually want to see and do in each location.
Don't book flights til you have a pretty firm itinerary- and "open jaw" flights usually work best (multi-city).
Ex: Fly into Venice- out of Rome

Have you been to Europe before? If you have done a similar trip - several stops over 10-15 days, you'll have an idea of what your "travel style" is. Some folks like to zip through, spending a day or two (which usually equals 2-3 nights) in each place and they are very efficient at moving (pack quickly, don't get lost, plan out their sightseeing). Most of us like a slower pace, taking time to explore, to relax and soak up the atmosphere. If you haven't, then a slower pace is best, especially since you'll be learning the ropes as you go. You might want to take the RS 10-day Venice/Florence/Rome tour, then head for the Amalfi Coast for the remainder and fly out of Naples. With a tour, you'll be moving very efficiently and see more than you probably would on your own.

Change in plans, thinking Venice, Bologna,Florence and Rome.
Maybe a day trip to Cinque Terre?
Suggestions?
Going May 2020

All four cities you are considering are worthy of, minimum, 3-4 nights each--and that means spending all of your time in the city. Since you mentioned day trips, you will want to seriously consider reducing your locations to three so you have enough time to explore the base city and, possibly, take one day trip from each. Before choosing your cities, spend a little time comparing itineraries and perusing your personal interests in different guide books (Rick Steves, Lonely Planet, DK, Fodor's, etc.) from your local public library. When looking at those itineraries, think about how quickly you want to move--some travel writers move pretty quickly:).

When you begin planning, three to four days sounds like quite a bit of time in each location. I assure you, that time flies by--and you want to be sure to enjoy what you are experiencing so that it's not just a blur when you return home. Once you've defined your interests, come back to this Forum with more questions--there are so many experienced travelers here who generously help others in planning enjoyable trips.

We doing pretty much what you are aiming for (minus Venice). Flying into Rome, getting right on a train for Florence. We will spend 3 nights there. One afternoon we are doing an organized trip to a farm in Tuscany to make pizza and gelato. Then on to Rome for 3 days. Then train to Salerno, followed by ferry to Positano. Staying in Positano for a 7 days we will relax, and do some short trip to other plces including Capri. Then we will go to Pompeii for. Day and sleep in Naples for 1 night and catch a flight home from there the next day. Staying in VRBO’s in each location. Happy to share any details. If you are interested.

Thank you
That would be great.