Asking for Advice about Itinerary

There will always be opinion whether one city needs a day more or a day less. You'll have to figure that out. But I would ask whether you would consider refundable bookings, or taking the chance of only booking hotels a few days before - at least in the middle parts. This means you aren't as locked into 5 nights somewhere. I understand the desire to pre plan, but I am learning to re-evaluate the need to prebook every minute. Many of your train routes are short enough to not make a lot of price difference whether you book 3 months or 2 days ahead. And your dates are not high season requiring locked in commitment 6 months ahead. Of course, you also don't want to be left out of pocket or with a hand full of vouchers (not refunds), if plans go awry due to pandemic.

I have had travel with foot issues, even over a year after injury. Stretches, ensure hubby does lots of stretches. And good shoes. So consider any extra days as days for him to rest his foot and both of you take a breather.
If all goes well, and you find the pace is slow, if you can shift plans, there is an entire area around Bologna that could take many days. Instead of visiting Bologna as a day trip, use it (or better yet, Ferrara) as a home base for a few days for day trips to Verona, Vicenza, Padua, and famous Byzantine mosaics in Ravenna.
Otherwise, you have given yourself a pretty balanced schedule with longer sojourns every few moves.
You also want to plot what are the exact dates for specific places and travel. April has Independence Day and then May 1 can make a mess of any public transport plans.

will the early morning (often very early) flight from Venice work well for you? Often goven advice is to fly into Venice and home from Rome as the flights work out better and it saves you leaving your Venice hotel in the middle of the night.

Have you looked at what flights from Venice will work for you?

It sounds like Burano is really the main reason for going most of the way across the top of Italy?

Do you know where you want to stay on Lake Como? I love Varenna, others prefer some other places. The town of Como would be quite far down my list. Varenna is well served by trains from Milan. Have you considered Lake Magiorre instead? Stresa has the magnificent Borrommean Islands and their associated gardens, particularly beautiful when we visited most recently April 2019.

If you want waterfalls on the way to Siena have you considered a trip from Rome to the water gardens of Villa d'Este in Tivoli? I'd suggest Hadrian's Villa just nearby while you are out there but you said you don't like museums so maybe it is too museumish for you.

We have spent a lot of time in the beautiful Chianti region and Siena but do not recall any waterfalls. Maybe we missed them? When I remember waterfalls we have visited, they were in Switzerland. However, Siena and the nearby villages in the Chianti region are beautiful, charming.
Flying out of Venice is not a good travel memory! Tides affected our ultra early water taxi in the very very early morning. Fly into Venice, out of Rome for easier travels.
After doing day trips into the Veneto from Venice, , we planned a dedicated trip just to the Veneto, something to consider as there are many wonderful towns and cities to explore.

Looks like a wonderful trip. I would make only a couple of observations. First, it is much easier to go to Florence from Siena by bus rather than by train. The "Rapido"- the direct bus, leaves from the station right in the center, runs daily and takes only 1 hour 15 minutes to Florence. Five days in Sorrento may be a bit long but you can squeeze in a trip to Naples for a day in addition to Pompeii and Capri. You may want to consider going directly to Largo di Como from Cinque Terre (avoiding a one night stay in Milan) and then, unless you really want to go to Venice, I would skip it entirely and spend that time in Milan. Check out flights from Milan to return home. Another alternative to to put Florence at the end and return home from there.
In general I avoid one night stays anywhere. By the time you travel to the location and get located in a hotel, you have only a small number of hours to actually see the city.

We too are planning to go to Italy next Spring. We will keep our fingers crossed.

We all have our favorite spots in Italy, but I wouldn't find the pace too slow at all. In fact, it's the short stops I question. Otherwise, your itinerary looks like one of mine, though I never rent a car. I wouldn't stop in Milan for just one night. One-night stops are the antithesis of relaxing, and there's currently a train departure that will get you all the way from Monterosso to Varenna in just under 4-1/2 hours. If you don't want to spend even that much time on a train, I recommend adding a night in Milan and going to Bergamo if your husband can cope with a hill town.

As already mentioned I wouldn't go all the way over to Venice for such a brief visit. If you're heading there anyway, I'd encourage you to add some time in that area (since you can) and see Padua (just minutes away) and Vicenza.

Since you plan to do a lot of day-tripping by car around Siena, I wonder whether Siena itself is the best base. Will parking be challenging and/or expensive? Will navigating around ZTLs be a major pain? Maybe this would be a nice opportunity to try out an agriturismo in the area?

Given the timing, I'd take a look at some historic weather statistics for Venice before reversing the trip; I think it might be cool and wet in April (but I've never been anywhere in Europe in April except Andalucia). Timeanddate.com has about ten years' worth of actual, historical, day-by-day weather data. I suggest checking out at least the last three years. During shoulder seasons, monthly averages hide extremes.

I was in Venice in late April, and it rained the whole time. Being taller, I was dodging umbrella spoke ends to the eyes all the time. We also had to deal with aqua alta, but nothing too high.
I would think most of the waterfalls would be in the Dolomites, or the mountainous region east of Spoleto, but here is a quick list for consideration. There is a hot springs near Saturnia in Tuscany for your Siena time. https://www.thecrazytourist.com/15-amazing-waterfalls-in-italy/

You may want to consider making a slight detour to Rasiglia on your way from Orvieto to Assisi. It's a hillside village with waterways used to create small reservoirs and waterfalls. It's very pretty.

Wow--I am so appreciative for all the very helpful comments.

Follow up:
Maria F: We will not book anything that is not refundable. If we are able to go, we will book Award tickets on AA so that we can either change dates or have our miles redeposited. If AA cancels either of our open jaw flights, there is no redeposit fee. If AA makes a schedule change, we can accept the change or have miles redeposited with no fee. If we cancel more than 60 days before travel, there is no redeposit fee. If we cancel arbitrarily less than 60 days prior to travel, the redeposit fee is a total of $175 for both of us. We can take that risk.
As far as lodging, we will book with hotel points or Chase points and only make reservations that are refundable (although the timeframe varies a little).
Thanks for the heads up about Italian holidays. We did run into that on May 1 on a Mediterranean cruise but it's a good reminder to consider it.

Nigel: We currently have a flight on hold that leaves Venice @ 11 AM. I saw many 6 AM flights but avoided them. Do you think an 11 AM departure is acceptable? There are 2 problems with flying into Venice and out of Rome. AA Business Mile Saver awards are often hard to find and already I see no availability into Venice. Also that would put us into Venice around April 20 and as a another person mentioned, it might be cool that early.

Our original plan was to fly into Rome, work our way up through Italy and then going from Lake Como into Switzerland (Lucerne and Bernese Oberland), then to Heidelberg, and flying home from Frankfurt. I think that may make the trip a little too complicated to suit my husband and would add another 7-10 days to our trip. Flying home from Milan is doable but a little iffy since many flights involve an airport switch in NY City and therefore not ideal. So if we opted to stay in Italy for the entire vacation, rather than retrace back to Rome, Venice seemed like a better option. We did not have time to go to Burano when there before so just thought that might be fun. Obviously none of this is set in stone and I am constantly rethinking things based on what I read as well as input from this group.
We could look into flying in to Milan and back from Rome but again that would mean being in Lake Como in the earlier part of our trip. I thought that starting in Rome and Sorrento might be better weather wise.
Have not booked anything around Lake Como but thought perhaps Varenna or Bellagio.
I will definitely look into the water gardens of Tivoli! I think I would love that but need to see how that would work as a day trip. The only thing that we really have on our to-do list other than walk around and reminisce is going back to St. Peter's Basillica. We are Christian but not Catholic but loved the Vatican and would like to book a tour of the underground crypts.

Suki: This is what I was referring to as waterfalls from Siena: https://www.visittuscany.com/en/attractions/cascate-del-mulino-hot-springs-in-saturnia/

*charylm : Thanks for the tip about getting from Florence from siena. That is great advice! I will definitely consider some of the other suggestions you make. Re: Naples--what would you suggest doing there? Frankly, its reputation intimidates me but maybe I just don't know enough about it. I will give flights home from Milan or Florence another look.

acraven: I completely understand your concerns about 1 night in Milan. Truthfully I have gone back and forth on that one.
I chose Siena as a base b/c we can stay there with Marriott points (and the 5th night is free). I think there is free parking at the hotel. I know that avoiding the ZTL's requires careful attention but like the idea of having a car to come and go as we please to the small towns.
You reiterate my hesitation to flip the order.

Ah, so points puts a whole other perspective on travel planning :-)
It means backtracking, but can you go to Venice from Cinque Terre, then Lake Como and then leave from Milan? Or if you have have flights that leave around noon instead of 6:30 am, then stick with Venice at the end.
My flights to Ottawa depart between 11:30 - 12:15, so easy to get the airport bus after the sun comes up.

3 nights in Rome is almost silly, unless you have been to Rome before, you need more. Need at least 5-6 days. Five nights in Siena seems a bit much.
Bologna is OK, but not in the same class as the other places on your list. My old green Michelin guide gives it two stars and the other places generally three stars.

Someone has already mentioned getting to Venice.

I suggest spending more time in Rome and save the Milan and Lake Como for another trip. Also, spend more time in Venice.

geovagriffith--We spent over a week in Rome on our first trip and then another day as a cruise stop (not really worth it IMHO). We only want to stay in Rome to a) get our bearings after the flight b) stroll around and reminisce about previous experiences c) do a tour of the underground crypt area of St. Peter's Basillica d) possibly go to Tivoli Gardens as someone else suggested. So for us, 3 nights in Rome isn't silly. It would not be difficult for us to stretch it to 4 if we opt for that. I appreciate your input.

Mary,
That's a solid plan and you've gotten some good responses.

I'd like to offer an opinion regarding Siena. There is a charm that would make me stay within the town, but if you are going to spend most of the time doing day trips, I suggest you consider staying at a nearby agriturismo as your day trip base. Getting in and out of town is time consuming and parking can be problematic, especially if you stay within the walled city. Look into 3 nights in an agriturismo, then spend 2 nights in Siena before catching the train to Lucca.

I hope the trip works out for you. We were supposed to return to London this Spring for a combined work/pleasure trip. We were very disappointed we had to cancel.

Regarding flights ...I have flown into Rome out of Venice multiple times. I always found it a good route for me (live in the Pacific NW). One time had to leave early on an emergency return home and reserved a water taxi at 3am-ish. Not a problem. I often fly into one city and out of another for the convenience of not needing to back track, too. Certainly depends on your final itinerary and preferences. Sounds like an amazing trip - enjoy!

DougMac I appreciate the tips about Siena. We will most likely stay at the Four Points by Sheraton with points. Website says: "minutes from Siena's walls and historic city center" and parking is free. Would that be a decent compromise? Maybe not to difficult to get into the city but also for driving to other areas?

Melinda Thanks for your encouraging comments! I really think at this point that going into Rome and home from Venice is our best option.

It depends on how you define "minutes" and what mode of transportation you plan to use. I think they're fudging. You will be almost 3 miles from the Duomo and 1 mile from the train station. That would be "minutes" by most people's definition only if you were driving, but driving into the historic center would not be practical.

The train station is outside the walls and inconvenient enough for visiting the city that it is typically recommended that people day-tripping from Florence take the bus to Siena rather than the train, so staying well beyond the train station does not put you in a convenient location.

However, I assume there is decent city-bus service from the train station up to the historic center, and Google Maps suggests there's a bus stop quite close to your hotel. If not, you could always take a taxi. If you want to take buses back and forth, ask locally about bus tickets. It's very common in Italy to need to buy a ticket (often at a tobacco shop) before you board the bus.

acraven. ** Our plan was to rent a car in Orvieto, drive to Assisi, drive to Siena, and keep until we leave Siena so we could use it for day trips. Thought we would need to park outside walls of Siena when going into Siena (either leave at hotel & take other transportation or park near city walls). We would also need to get from rental car drop off to train station when heading to Florence for our next stay. Since Tuscany is all new to us, this may painfully naive and not feasible. Asking for input from those more familiar with the area!

We will most likely stay at the Four Points by Sheraton with points. Website says: "minutes from Siena's walls and historic city center" and parking is free. Would that be a decent compromise?

The only time we stay in a chain in Europe is at the Hilton Rome airport the night we'll be flying home. I travel extensively for work and spend far too many nights in bland, cookie cutter motels and hotels. I looked at the photos of the Sheraton and while it looks OK, it is certainly uninspiring. If that's the type of accommodation you like, then it would be serviceable.

Some of the most memorable experiences we've had is at B&Bs we've stayed at in Europe. We stayed up one night with our guests on the Isle of Mull, helping them boil fresh caught crabs on their AGA stove to make out of this world crab salad. We stayed in an extra room in a dairy farm farmhouse and got to visit the 17 newborn calves in their barn. We stayed with a doctor and her architect husband in his grandfather's home in Paris. We slept on the top floor, which was his grandfather's studio. His grandfather constructed camouflage for in WWI. We joined tour bus drivers for their Christmas Holiday dinner at our B&B in Tuscany. Wine and hugs abounded.

Though some time ago, we daytripped to Sienna. There is a large parking lot at the base of the hill. We walked up but it was 25 minutes or more. Slower going back due to friend's bad knee. There was a bus stop right across the way. We could have caught a bus up, but it was some statutory holiday so only running on holiday schedule. It also meant most things were closed except we did see the Duomo and enjoy the afternoon in the lovely Campo with the locals eating gelato, watching the kids play, enjoying the sun. I think RS guide discusses logistics in the guide book. These old guardian cities built on the tops of hills for defense makes some things more complicated than North Americans have experience with.

Mary you asked why I suggested Naples. So here goes....
It is true that Naples can be a bit intimidating (like any big city worldwide) but it is also fascinating. Walking through the Spaccanapoli neighborhood from Via Girabaldi to Via Toledo is a real experience. (and it is not far from the train station.) People and motor scooters crowd the streets, laundry hangs from the high windows, neighbors yell their greeting to one another.....the place is full of life. Places to visit: the city fish market (early in the day), the Church of Santa Chiara to see the beautiful cloister filled with majolica tile, the Pio Monte Misericordia Church to see their famous Caravaggio, or the Archeological Museum where the art of Pompeii, Herculaneum and other ancient sites is displayed. You can eat some of the best pizza you will ever have and finish off with great gelato!
Rick Steve's Guide Book will give you lots of information and he filmed one of his shows in Naples so you can probably find that.
Hope you visit.

Buon viaggio!!

hey hey mary
i agree with charylm about naples.
people either love it or hate it because of intimidation and just passing by on a train/bus, never stepping foot in the city.
some years ago my first visit to rome, i wanted to ride the fast train. our day trip to naples was a great adventure.
one of the oldest cities with it's vibrant, gritty, alive, and unique atmosphere. lots of history and art, motorscooters, narrow streets, shops, souvenirs, bars, pizza, pastries, hole in the wall restaurants, yummy food, plazas (piazzas), churches, kind people, famous alleyways (san gregorio armeno spaccanapoli), clothes hanging out to dry, saw a woman drop a basket down to grocer and yelling what she needs for the day, he fills it and up it goes, browsing thru markets looking at interesting things to bring home like sauces, shaped pasta, the bay of naples, ceramics (my friend always likes to pick up a ceramic piece and a small photo in frame of city we are in, limoncello tasting since this area and south are known for their lemons and cooking with them, ride the funicular to the hilltop for great views down below.
streaty.com and culinarybackstreets.com (food/city tours with locals to learn about the area and history)
theculturetrip.com/delicious italian desserts
trattoriadanennella.it a friend went for lunch and really liked it.
napolike.com/tourism
spend the night to see what it offers before sorrento, keep your guard up like any other city you are visiting, wear comfy shoes, give it a chance. we really enjoyed our long day there, so much to see and do, keep you occupied. stop in a piazza, people watch, "free" entertainment, have a drink and appetizer like in other places you'll be staying. i have other info and ideas i'll share with you at another time. i will send it in a private message, it becomes a novel LOL
aloha

DougMac & MariaF--I appreciate your helpful comments about Siena and have no doubt that you are much more familiar with the area than I could possibly be but my thoughts:
--we all travel a little differently. We have done well on previous trips to Europe & Australia by creating our own "hybrid" approach to lodging. In larger cities (London, Amsterdam, Budapest, Sydney, etc.), we often book 5 night stays at hotels such as Marriott & Hilton properties with points (getting the 5th night free). This works for us as we have a chance to settle in a bit and do day trips via public transportation. We get free breakfast (and often executive lounge access) b/c of our status with these chains and save a substantial amount of money. In less urban areas, we book smaller boutique properties (often with Chase Ultimate Rewards) and/or AirBnb's. We have done this in the Rhine Valley of Germany, along the Great Ocean Road, along the Sunshine Coast, and in Tasmania in Australia,. For this trip, I have refundable reservations with Chase UR in Sorrento, Orvieto (wine resort), Assisi, CT, & Lake Como. In Rome, Florence, Venice, I have refundable point stays reserved.
--Four Points Sheraton--I do not expect this hotel to have the amenities of other places we hope to stay such as Hotel Splendid Royal in Rome,, Sina Villa Medici, Autograph Collection in Florence, & Hilton Molino Stucky in Venice. However, reviews of the Four Points make me consider it as an acceptable option--not luxurious, not a lot of character, but ok for our needs:
”free parking, which makes it ideal if you drive to experience Tuscany"

"Great location for driving trips throughout Tuscany! "
"The hotel is a bit away from the old town and we took the bus but it was no hassle.The bus stop is right next to the hotel - we purchased tickets for the bus at the lobby."

I do think the points you raise are valid but am just trying to figure out our own compromises.

charylm & princess pupule--Wow--so much wonderful insight into sights in Naples. You have definitely piqued my interest and am eager to read more. I have previously only heard negative comments about Naples so you have certainly educated me!

Question: We will be coming to Naples by train and planned to then go directly to Sorrento with only a transfer in Naples. Obviously we will have our carry on luggage with us. Is there a place to store luggage safely and then explore Naples for a few hours? We could get a feel for it and decide whether to come back as a day trip from Sorrento (or make another stop on our way from Sorrento to Orvieto? Even with 5 weeks, we will not have time to do everything everywhere so have to be creative when possible.

Thank you for being so helpful!

I don't know whether there is luggage storage inside the Naples train station, but here are three commercial services you might use, the first of which claims to be just a few minutes from the station:

https://www.stowyourbags.com/en/shop/naples/luggage-storage-naples-central-station/

https://stasher.com/luggage-storage/naples

https://radicalstorage.com/

As of about six years ago there was reported to be a staffed left-luggage counter at the train station. I wouldn't expect an operation like that to close in the middle of the day in a large city like Naples, but any time you use a staffed counter rather than a locker, it's critical to verify that you'll have access throughout the day. They do take their lunch breaks seriously in Europe.

I would suggest checking the date of Easter in 2021- many things close Easter Sunday & Monday. On the other hand, Masses in the Cathedrals are spectacles of the choir, orchestra, and church art. So - either plan to avoid it or include it, but be aware of it.
Safe- and healthy- travels!

acraven--Good tips about the luggage storage option. Would not have thought to confirm hours of operation and the way Italian lunch habits could have an impact. Thank you.

Pat--At your suggestion, I did check the dates for Easter and it is early in 2021 (April 4, I believe) so several weeks before our planned trip.

The other "event" that I am aware of is that our travel will most likely put us in Assisi the week of their festival Calendimaggio. The actual festival dates are May5-8 in 2021 but from what I have read, the whole week builds up to that. I think that we will be there May 4-6. Part of me feels like this is wonderful and part of me wonders if it will be overwhelming for someone unfamiliar with the culture and even more so with the changes in the way most of us think in the context of Covid 19. This probably is not the best place to ask so if no one replies, I will repost in a later post but just in case...

It looks like a great plan and I only have two comments.

Milan: one night is worth it just to see the Duomo.

Venice: Burano is totally worth using a whole day for a visit IMO. Much more than Murano is. Use a day pass, so you can visit Torcello on the way.