Itinerary Guidance - Italy Tour

Good morning Danny

Here is my take on your itinerary- For a first timer, you are moving trying to do too much in a short period of time. You didn’t say when in October, but you will loose light and time that month and the schedules could vary slightly (the ferry to Sorrento/Positano can also depend on the weather and also don’t run as often as summer/early fall). You are not accounting for the time of checking in, checking out, finding a parking space, the time in the great museums, churches, etc. Personally, and this is just my opinion, I wouldn’t rent a car. The first time we went to Siena, we had been to Italy 3 times, but it was the first time we drove there. We searched for a parking space for almost 2 hours and parked past the stadium outside the wall and walked. The walk was not a big deal, it was just that we wasted so much time finding a space. I would stay in a town with good public transport and take a bus tour of the area, you will appreciate it. Again, its just my opinion and if you read this forum, you will find many people (even experienced travelers) who months after their return are hit with costly fines because they went through a ZTL or speed camera. Also, you are going all the way from Florence to Sorrento for just three short days. I would add onto Florence (bus tours, great public transportation to smaller towns and lots of fabulous wine shops) and Rome (same) and take away the southern part . Don’t think this will be your only time in Italy....once you are bitten by the beauty, culture, vistas, you will return and then you can enjoy Positano and that area.

I forgot to mention...adding onto Venice, since your first day you will feel the time change (remember, you loose six hours flying east)!

Hi Marie! Thank you very much for your thoughts. It's what I was afraid of then! Very hard to not get over excited in the planning stages and add too much in. I totally see what you are saying about the southern portion of the itinerary so I would scrap the time in Positano. In your mind, would it still be possible to keep Naples in the itinerary? We have a strong interest in Pompeii/Mt. Vesuvias.

As far as the Tuscany portion, what would you recommend when trying to spend some time in wine country without a car? Do we use Florence as a base and arrange day trips?

Overall, I do like the idea of staying put in places longer, so I appreciate all your help!

Hi Danny,

You’re wise to give yourself plenty of time to plan your special trip.

The good news is that numerous towns in Italy can fulfill your art, architecture, history and food requests. I have been to Italy five times and just keep adding more favorites to our list!

Locations: you have picked the most popular cities. Being from NYC, you obviously are okay with crowds, but I would try to also select one less-touristy town to get a feel for “local Italy”. Check out local festivals because those will add to your experience! My last trip, solo trip to celebrate my retirement, I planned my dates around the Stresa Music Festival, Verona opera outside in their Roman arena, and the Jousting Festival at Arezzo - all fantastic experiences! I also participated in two cooking classes in that trip which are lots of fun, and you learn more about that region’s food & culture.

My last feedback is that you have picked many water locations - Venice, Lake Como, Cinque Terre and Positano. I would cut out at least one of those. Geographically, I would drop Positano, but if you also want to see Pompeii, then I would drop Cinque Terre.

One more thought - Venice is so magical! I’d recommend flying to Milan, take the train to Lake Como and then take the train to Venice. (Yes, add a day in Venice!). Then take the train to Florence. If you want to rent a car or use train/bus, head into the Tuscan countryside. Leave off the car at Chuisi-Chianciano train station and take the train to Salerno or Naples. Train back to Rome.

Hi Jean,
Very good thoughts! If you were fine tuning the Tuscany portion of my itinerary to include a smaller Italian town, would you have any recommendations? I've read that the Val d'Orcia and Umbria regions are both absolutely beautiful, but I am having trouble narrowing down to find a small area where we could experience the countryside and do some wine tasting (we don't necessarily need to do a bunch of day trips hopping from town to town, just want to immerse ourselves in the slower pace, food/wine for a few days). Thank you!

Good start to an overall good plan! I do agree that it is a bit too much, though, and recommend you stay to Rome and north, making Positano and points south a future trip. This will allow you to slow it down just a wee bit and gives you 5 nights to slot in elsewhere.

Add a night to Venice for the reasons cited above. You will be jet lagged and it is a great place to get used to Italy. Should be very special this year as I expect it will be much quieter then normal. I am envious!

Add two nights to the Tuscany portion. Rent you car in La Spezia and enjoy the drive. We stayed in Montalcino our first trip to Italy and found it an excellent base. Good restaurants abound, cute town, ample parking outside the walls. Our B&B paid for us to park in the large municipal lot there, a five minute walk from the piazza. A classic drive is to Montepulciano via Pienza. Stunning! Also try to visit the Abbey of Sant’Antimo. We hiked there from Montalcino and took a bus back. Be sure to check locally for directions and bus schedules. There are a couple of restaurants near the abbey where you can have a nice meal if you can time it for the bus, or just drive both ways. I highly recommend the winery Ventolaio outside of Montalcino. Some of the best wine we ever bought in Tuscany at an accessible price.

Add a night each to Florence and Rome, or possibly spend two nights in Orvieto, a charming hill town an hour’s train ride from Rome.

Hi, Danny, and another welcome to the forum!

Your plan generally looks pretty good to me; a lot of moving around but at least no one-nighters so yay for that! I do think you've maybe included one too many "water" locations, and are seriously shorting Florence if, as you say, you enjoy art, architecture and history. That one is simply drowning in all three!

Day 16: Train to Sorrento via Naples, ferry to Positano

And here's my personal 2-cents on Positano: the further into the fall the stay, the higher the risk of rain + weather, such as wind, that can affect ferry services to that one. The boats can't land there when the sea is too rough although they can in most other coastal locations. You would still have SITA bus service so it's not like you'd be completely stuck there is very little to do there on wet days and it's sort of time-consuming to get from there to places which offer inside attractions, such as Naples. For those reasons, personally, I'd stay in Sorrento and day-trip Positano as weather permits. It's a mere 30 minutes or so from Sorrento to Pompeii, and an hour to Naples, both via Circumvesuviana. You could also look at Salerno as you could take "fast" trains there all the way from Florence, skip the battered-but-serviceable Circ. entirely, and be there in just about 4 hours with just 1 change (Napoli) Centrale) or even with no change at all. Pompeii can be day-tripped from there as well, or do it en-route to Rome: the site provides bag-check services.

Anyway, you will need a Plan B if ferry service is affected. Even if they're running normally, your plan involves a transfer from "fast train" at Centrale to the local Circ. and then a transfer at the Sorrento train station down to the docks, and then ferry to Positano.

I'll also question the Val d'Orcia Region, wine-tasting, car-rental piece. As you wouldn't want a car for the wine-tasting day or for Siena (that one is easily day-tripped from Florence, BTW), you'd only really use it from the drive from Val d'Orcia > Florence. You might consider just adding to those days to Florence, do Siena from there, and look at a splurging for a private guide service for a wine-tour day. We haven't done one but "Tours by Roberto" have been frequently and highly recommended by those who've done them. There are others as well, if this one doesn't suit you.

https://www.toursbyroberto.com
https://www.toursbyroberto.com/immersiontours

PS: Laurel has offered very good ideas as well if willing to skip the Amalfi Coast piece, which I think is a fine plan if those atmospheric small towns in Tuscany are of greater interest. They certainly promise to be less tramped by the tourist numbers than the coast will be. Lots of ways to skin this cat!

Hello Danny!

You're going to get plenty of advice from this forum - which is why we are all here. First timers, huh? I'm not but I remember when my partner and I went for his first time. There were check lists and schedules and sensory overload. IMHO your itinerary is wonderful and I wouldn't change a thing except the number of trips it would take to fulfill the list. Here are a few thoughts from me to you: Train travel in Italy is fast, convenient, and economical. The RS books have a map that includes the trip duration (sorta) that can help you plan even day trips from some of the main hubs (Venice, Florence, Rome). Remember that day trips mean you don't have to pack and unpack, check out and check in to a lot of hotels (big waste of your time). Settling into a city for several days and nights gives you the opportunity to see the sites but also get a fuller sense of the local culture which is very different than the tourist culture. It's amazing how different Italian food is in the north verses the center verses the south! The wine too - I'm not a fan of wine-tasting. I like the variety of 'house wines' especially from a small, family owned restaurant.

Venice is a place like no other. In museums you walk around and look at art. In Venice you walk around (or ride the vaporetto) IN the art. Daytime and night are so very different. Use the guide book to make a list of places to see, including the other islands. The nights are for romance! In the evening enjoy a drink and light buffet along any of the canals. Have a late dinner. Go dancing on Piazza San Marco. Take a quiet and (almost) private vaporetto ride up and down the Grand Canal before returning to your hotel for what I guarantee will be a great night's sleep.

Florence has plenty to keep you busy and interested. It''s also close enough to do day trips to Pisa, Lucca and Siena (although I personally stay in Siena and daytrip to Florence). Cinque Terre can be done in a daytrip too from Florence but, honestly, I'm not a huge fan.

Sorrento is my favorite base for the Naples area. The ferry from Sorrento to Capri and around the Amalfi Coast is the way to go. It's also easy to get to Pompei from Sorrento by train. For me, Sorrento is more a place to sit and relax. The views over the Bay of Naples are entertaining at any time of the day or night. The local food and wine can't be beat. Try anything made from lemons! There's also an interesting and very good restaurant - Inn Bufalito - that serves just about anything that can be made from water buffalo. The seafood on the Marina Grande couldn't be fresher. The linen shirts in Sorrento are my weakness (ok, I admit it - I buy at least 2 every year).

Rome is a great place to end your trip party because FCO is easy to get to and the security lines are moving faster in the past few years. Again, use your guide books to make a check list. Find a hotel, or apartment, that is central to everything. Then you can walk. There's plenty to discover in Rome when you walk. I give Rome about 2 weeks every year. Like Venice, Rome is very different day and night. You two might really enjoy Trastevere for drinks and dinner. I always tire myself out in Rome. I figure I can sleep on the plane going home.

Would I suggest you do all of these areas on your first trip? Not necessarily. I would suggest you make a list of 'must do' and work from there. You might be able to do 2, maybe 3, big items a day. Minimize your hotel changes. Maximize day trips. Insist on quiet time each day and in each location. See how that fits into your schedule. Make the planning part of the fun! We're here for you so let us help along the way.

As an older traveler (67) with a limited time frame for our trips, I have done the "cover as much ground as possible because you never know what the future holds" version of travel. It goes against the majority view here, and yet I have loved every trip we have taken. We spent an hour and a half in Positano on our first trip overseas, and since we have never been back I am most grateful for our chance to walk down to the beach and sample a delicious lemon pastry. One day, after I retire, I hope to be able to do an extended stay in Italy.

For what it's worth, I definitely agree with the previous suggestion to visit Orvieto from Rome. It is one of my favorite places and easy to see in a day. We arrived very early in the morning, before most of the tourists were there yet, and wandered the streets as the locals were just starting their day. I imagine staying overnight would be a real treat as well. If you have the chance to go, make sure you go inside the Duomo.

Whatever itinerary you follow, I am sure you will have a great trip!

Since you're also going to Positano, I would drop the Cinque Terre and use that time in Florence or Venice instead. Full disclosure - I found the Cinque Terre to be one of the most over-hyped places in Europe.

Does your nightly budget cover your just your hotel or "everything"? If that is your budget for "everything", I would shorten the trip to have more money per night.

Hello Danny
You could possibly do a very long day trip to Naples from Rome (via fast train, make your train reservations in advance to save $$) and then go on the Circumvesuviana train to Pompeii. This would take a long time, because of the crowds and fabulous places to see while in Naples and Pompeii. But- From NYC could you train to DC and see 3 Smithsonian museums and then go to Arlington and see everything there? Same sort of concept. I would really concentrate on the northern area and flying into Milan (access to the lakes, CT ) and then flying out of Rome.
Florence is a great base, and personally I could (and have) spent 2 weeks there and only seen a small amount (the art, the history, the food, the day trips). Orvieto is a great base and if you do have a car for a few days, we always drop the car (we use Hertz) at the hertz location steps away from the train and then train into Rome. Montalcino is another fabulous option, if you do rent a car. You do not want to have a car in Florence or Rome, and there’s no need for one. Once the libraries open, grab all the travel books you can and decide on the towns you need to visit. You will hear of hundreds of possibilities and researching where to go is half the fun.

I would skip Sorrento, Positano and Naples for this trip. Save them for a trip focused on Southern Italy.
Add time to your Northern Italy destinations especially Tuscany. From Venice you can easily travel through the Dolomites.

Thank you all for your sound advice! After some discussion, we have decided to cut the southern portion of our itinerary including Naples and Positano and save them for a future trip. After looking at our Tuscany portion and deeply weighing the car/carless options we revisited an idea we had considered earlier in our trip planning process out of ease since this is our first trip to Italy:

Venice - 4 nights (including day trip to Murano)
Lake Como - 3 nights (Varenna base)
Cinque Terre - 3 nights (Riomaggiore base)
Florence - 6 nights ( stopover in Pisa en route to Florence + an overnight in Siena used to break up break up our two days of private tours with Tours Around Tuscany)
Rome - 4 nights

I think this will help us 'stay put' more, and not feel rushed to cram in activities while still seeing a large portion of Italian sights (for first timers!)

Danny, this last itinerary looks amazing! Also, keep in mind if you really want to see Pompeii, you can do it as a day trip.

The new plan looks great, Danny. I think it was a great idea to save the southern portion (Naples, Pompeii, Vesuvius, Positano, Sorrento, Capri, Ravello, Amalfi, etc) for a separate trip. You will need all 3.5 days you've allotted for Rome JUST for Rome - there is a LOT of ground to cover there, and you'll barely scratch the surface with that amount of time - so I'd hold Pompeii for that future trip. :O)

Venice - 4 nights (including day trip to Murano)

My 2 cents: I prefer Burano over Murano. Buy a day pass for the vaporetto and go to Murano, Torcello, and Burano

Danny and partner: Good choices! Your revised itinerary will do 2 things - introduce you to not only the country but the people and culture we all love; and, it will get you planning your next trip! There's too much to see, do, experience, eat and drink in one 3 week trip!

While in Venice may I suggest you look at www.veneziaunica.it Here you can find help, and discounts, that I always find useful. Venice is expensive and some first-timers avoid some experiences in an attempt to save money for dinner. Entrance discounts are worthwhile but most important (for me) is the vaporetto pass. It doesn't take many individual trips before you will see some savings. And it's a great way to rest your feet, get to the other islands (yes to Burano and Torcello over Murano as someone else recommended), take interesting morning and relaxing late night cruises, and just plain see the magnificent views along the canal.

Enjoy!!!!!

Hi Danny, I see you asked me a question but have tweaked your itinerary in the meantime. I will go ahead and answer, anyway, since other people get ideas from other’s posts.

Anything in the Val D’Orcia area is wonderful - especially recommend Montepulciano, Pienza and Montalcino. I still have a lot to explore in Umbria, but Orvieto and Assisi were good.

You have gotten great advice and I see you tweaked your trip. Great! My 2 cents - since you now have 6 nights in Florence, take a day trip to Lucca. A smaller medieval town, surrounded by a wall that you can walk or bike ride on. Makes for a laid back, relaxing day.

I may disagree with some, but I would not add any additional time in Venice. But I would definitely spend an extra day or two in Florence.

Also, if you have a car, some of the most beautiful towns to visit in Tuscany are:

Chianti
Monepulciano (plenty of wine to taste)
Siena
Orvieta (do the underground tour)
Lucca
San Maggiano

Yvonne
Akron,OH

I have been to Italy many times in my life and it is my favorite foreign country. It is loaded with history from the Etruscians, Greeks, Romans, Venetians, Renaissance and more.

I view your plans as involving way too much travel. You will only see the exposed part of the iceberg.

You have a bit over three weeks. You need much more time in Rome and Florence. Venice, I recommend adding one more day to that wonderful city. Rome deserves 5-6 days and Florence (with day trips to Sienna and Pisa/Lucca) 5 days.

The Naples, Sorrento, Pompeii, Capri and Amalfi Coast area deserves 5 days minimum. You have four. You need a day for Capri and the Blue Grotto, a day for Sorrento, a day for Naples and Pompeii and a day for the Amalfi Coast.

You might consider doing the Lake Como and Cinque Tierre on another trip as well as visiting Milan. You could include Switzerland as well.

geovagriffith, please see Danny's revised itinerary, about 7 posts up from yours. Note as well that the Southern portion of the previous itinerary was removed in favor of a future trip. Additional time in Rome can be easily added to that return trip. :O)

Kathy,
Thanks, I don't always read all the earlier posts.

The revised itinerary is better, but you need more days in Rome.

I suggest that you go to TripAdvisor and other sites and decide what you want to do in these places. There is very much to do in Rome.

Also, I would have passed on the northern part of your new itinerary in preference to the southern.

Enjoy Italy, it is wonderful.