14 days in June 2020 Transportation Options

A happy anniversary in advance, David!

Oof, yours is a more aggressive itinerary than I'd want to take on - you're going to lose a lot of valuable sightseeing time dealing with transport and hotel changes - but yes, you can do it all by train except Positano: no train service to that one. You'd need to take a train to Naples or Salerno and ferry (no direct ferries from Naples unless Lucibello is still operating their limited runs during high season), bus or private transfer from there. There's also commuter train service from Naples to Sorrento, from which you'd take a bus, ferry or private transfer.

No, I wouldn't recommend a car for any of the points-to-points listed.

Regarding some of the transport times you're looking at, Varenna to Vernazza will involve taking a very early train (6:23 AM), 2 train changes and nearly 5 hours of rail time to get from one to the other before noon. There's a 10:37 option with two changes that takes just 4 hours, 38 minutes but doesn't arrive until 15:15 so, well, you're basically killing most of a day.

(Edited to add additional info)

No you don't need a car. BUT - as Kathy just told you, that's a very busy itinerary and you are going to spend almost half your days in transit (and a car would NOT make it any better). I would seriously consider dropping one of your places ( some 'slow' travelers would drop half of them, but fast paced itineraries can be enjoyable as long as they are reasonable). I would drop either Cinque Terre or Amalfi Coast. Both are wonderful but even though you have three nights in each they are going to take so much time to get to that you really only have 2 days. And while Venice does not 'require' much time, one night after arrival means you will probably not love it.

How about this: Fly into Venice and spend 2 nights, train to Lake Come 2 nights (this means really only 1 day), train to Florence 3 nights (2 days plus a little on the travel day), train to Amalfi Coast for 4 nights, then Rome for 3. I would also seriously consider staying in Sorrento instead of Positano and doing day trips. It will make the day from Florence there shorter and easier, as well as the day going back to Rome. And the bus ride from Sorrento to Positano (and Amalfi) is, as Rick says, a "three star site" itself - but not with luggage when you are tired from a long train ride. Doing it as a day trip is wonderful. The ferries run that time of year as well. I'd spend 4 nights in Sorrento and do one day trip to Positano/Amalfi by bus, another day do the trip again by boat and add in Ravello. If you like hiking you can hike down from Ravello to Atrani, then Amalfi. And the third full day you could day trip to Capri or Ischia or stay in Sorrento.

Thanks for the advice. I realize it's a packed itinerary. For some context, my wife and I are thirty somethings and both athletes/fitness professionals. We are going to Italy a little more for the outside sights, views, interesting air b&b's and relaxing coasts then the museums and waiting in lines. That's why we chose lake como cinque terre and Amalfi as must sees for us. For the cultural sights, we decided a night and half day would be enough to say we saw venice and get to lake como to decompress from our travel. Cinque terre to soak in sun, drink, and eat. Florence would be the first real museum/sights stay. Then from Florence to maybe Sorrento for more beach and sun, ending our trip in rome, we also don't fly out until 8pm on friday evening so we have a good amount of time there. For me first time planning a trip to Europe, its exciting and this forum as well as Rick's TV show has been so helpful.

Can I suggest you go online and try to map this out by train? Personally, I think trying to see three water destinations (Lake Como, Cinque Terre, and Positano) is too much. I would eliminate Positano because you are going to spend a lot of time traveling there and reallocate your days. You will have to take a train from Florence to Naples, a local train to Sorrento, and then take a bus to Positano. Right now you are not going to have any time in Venice with flying in and spending just one night. If going to Positano is a must I would suggest you fly into Milan instead of Venice and skip Venice this trip. I would add that day to Lake Como.

I just bought tickets from Verona to Milan as part of a trip to Lake Como. It will take us four hours by train and then ferry. The train from Milan to Varenna on Lake Como goes at most once an hour so you have to coordinate with it if you are coming from Venice. If you are tight on time, try to stay in Varenna as it is where the train station is and that saves you a ferry ride (we are staying across the lake). If you did that and were careful with what train you took from Venice (as to not have too long of a layover in Milan) you could probably get there in four hours. But you can see you just used up 1/2 a day and you aren't even including checking in and out of your hotel.

There is really no reason to spend one jetlagged night in Venice to say you saw it. If you're not interested in Venice, for heaven's sake don't go there. You're going to end up being just two more people who thought one night in Venice was just fine because the city was horribly crowded. At the beginning of a trip you need at least 2 nights in Venice--and 2 is enough only if you promise not to go to the most popular places like the Rialto Bridge and Piazza San Marco, where you'll be rubbing shoulders with thousands of other visitors. Enjoying Venice is all about wandering away from the crowds along the small canals.

Thanks everyone again. After taking into consideration and a little more staring at the calendar, we have decided to reduce our itinerary and travel needs greatly.

Venice - 2 nights
Vernazza - 4 nights
Florence - 4 nights (1 day trip to Sienna)
Rome - 4 nights

Looks much more doable !

This looks much better, Nice work!
I’m fairly young, in my low 40s now, and have a few suggestions for you to consider. In the Cinque Terre, my most memorable hiking day was from Levanto to Monterosso. My wife & I got up early, took the train from Manarola to Levanto and the hike takes a few hours. Once we arrived in Monterosso, we ate beachside at a cafe under the umbrellas. Then rented beach chairs and lounged & swam the remainder of the day. It was glorious.
In Rome, we did the Scooteroma tour and highly recommend it. Check them out and see what you think. If you do it, I’d recommend it on your first morning, cause the scooter drivers are really cool locals that will recommend places for you to do and see. This way, you’ll have time to possibly do that stuff.
Anyway, I’m excited for you. Good luck!