Please help with 3 week Italy itinerary

Jul 7th, 2019, 06:32 PM
Original Poster
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Please help with 3 week Italy itinerary


I am planning a 3 week trip with 21 nights not including flights. I will be going from Toronto and since I am using Aeroplan points , I will be passing through Lisbon. My flight will be: Toronto to Lisbon, Lisbon to Venice (open jaw) and Rome to Toronto through Lisbon again. Since I am going through Lisbon and it looks beautiful, I am thinking of spending 3 nights there. Thoughts on this? Is it worth it or should I just spend all 21 nights in Italy?

I am a seasoned traveler having been to Europe many times but this will be my first time spending 3 weeks or most of it in one country. While I have an idea of my itinerary, I keep getting greedy and wanting to do other things as it looks like there are endless options. This will be my second trip to Italy. My first one was through Florence (4 nights) including a day trip to Pisa and Venice (2 nights). I am revisiting Venice again because 2 nights was not enough (1 day was rainy) and I simply loved it. Most magical city I have been to. I am skipping Florence as I got my fill on the first trip. I also want to keep the trip rather compact and so not going south of Rome which I will leave for another trip.

My plan so far is:
Lisbon - 3 nights
Venice - 3 nights
Cinque Terre - 3 nights
Tuscany - 7 nights
Rome - 5 nights

I am good with the cities and I don't plan on doing any day trips but still a lot of questions about Cinque Terre and Tuscany.
Is 7 nights in Tuscany too much? We will be renting a car to travel.
Is Cinque Terre worth it? especially given my route from Venice and into Tuscany?
Would some of the other Riviera towns (Portofino, Santa Margherita, Genoa) or even the Como area be better?
Anything else to look for?

I would appreciate any help you can provide with my plan. I love food and beautiful places. My wife loves culture and villages (hence Tuscany and Cinque Terr).

Thank you!
Travel_To_Eat is offline  
Jul 7th, 2019, 06:46 PM
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What time of year? There are times when the Cinque Terre would not be "worth it" to me because of the crowds.

Whether 7 days in Tuscany is "too much" or even too little depends on your plans. Tuscany encompasses nearly 9000 miles, so you need to do some research on what you want to see/do.
Jean is offline  
Jul 7th, 2019, 07:18 PM
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bookmarking, thanks
lauramsgarden is offline  
Jul 7th, 2019, 07:32 PM
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We will be going last 2 weeks of May and first week of June next year. For Tuscany, it is all about seeing villages and seeing wineries. We are thinking of staying in a central village or central farm house/B&B. What would you recommend? So far thinking about dividing up the time between Val d'Orcia and Chianti as base but not sure about best places to visit. The choices are so many it is overwhelming.

For Cinque Terre, it is more about the sights, and atmosphere than the beach. We don't really care much for the beach as that is what our winter vacation to the Caribbean is for.

Thank you.
Travel_To_Eat is offline  
Jul 8th, 2019, 09:49 AM
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So your time in the Cinque Terre would be in the last week of May... I think you may be OK in terms of crowds, but there are no guarantees on the weather.

I know planning for Tuscany can feel overwhelming, but you (not us) need to decide what the "best places to visit" are. For example, not everyone thinks Lucca is "magical" or that Pienza is the best of the Val d'Orcia, but those are two towns that are recommended here over and over and over. I think Chianti is underrated, but it's mentioned less often. The area around Lago di Trasimeno is only promoted by me and one other Fodorite (hello, StCirq!), but we find it very interesting and scenic. Do some research and try to narrow your focus to few towns that will give you some variety in atmosphere, scenery, history, etc. Try to travel on the more interesting secondary roads as opposed to always being on the boring autostrada or main roads. Check travel times and add 10% to estimates which are generally optimistic. Also add a few minutes to account for parking and walking into/out of the city centers.

When you've narrowed your focus, come back for more help.
Jean is offline  
Jul 8th, 2019, 10:04 AM
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I'd almost replace Cinque Terre with Lucca or Florence. Either would be a sweet place to which to return after any day trips (including CT!). No help with Lisbon but the rest sounds great to me.
TDudette is offline  
Jul 8th, 2019, 10:07 AM
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That time of year is perfect. Days are long and warm enough to wear short sleeves or only a light long sleeve, and not yet too hot.

We recently spent 2 weeks in a small Tuscan hill town liked the western Chianti area. We'd been to Italy numerous times before and had no interest in staying in a big city. From that base it was ~15min drive to San Gimi, ~30min drive to Siena (easy in / easy out) or Volterra, a little longer drive to Florence (did a few day trips), or a bus/train to Florence, or a drive to the beach. Many parts of the area don't have bus/train service so if that matters to you then stay somewhere that does.

There are pros and cons of staying in a town vs in the countryside. The pros of staying in a town are the ability to walk to shops & restaurants (& home afterwards). The con's are less open space and having to walk up/down hills everytime / anywhere... that is if you stay in a hill town. On previous trips I've stayed at a farm house (podere) in the Tuscan countryside and that was perfect for July when it was >100F, since there was less heat retained vs a city and the place had a pool steps from our apartment door.
J62 is offline  
Jul 8th, 2019, 11:21 AM
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I mostly like your plan. For me I'd add 2 more days to Venice, skip CT, and try to rent a house for a week in Tuscany (with a pool). That to me would be a perfect balance of city stuff and country fresh air and relaxation.
suze is offline  
Jul 8th, 2019, 12:54 PM
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I wouldn't count on a pool being heated at that time, esp. if the weather is still changeable.
Jean is offline  
Jul 8th, 2019, 01:48 PM
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Regarding your question about whether to spend a few nights in Lisbon, my answer would be a resounding “Yes!” since you will already be passing through. We spent two weeks there in March of this year and never tired of it. We took a few day trips to nearby cities, but stayed in Lisbon the majority of the time. We rented an apartment in the Alfama neighborhood and found it to be both lovely and lively. My only words of caution would be during June, which is the festival in celebration of St. Anthony. There are nightly parties all month and I’ve been told they continue well into the early morning hours in some areas. Some people might find it noisy and disruptive while others might find it to be an unforgettably fun experience.

Lisbon is full of hills, which could be a problem for people not capable of walking the steep inclines and steps. We walked everywhere, miles each day. Our legs were quite sore initially, but it was great exercise and we acclimated after a few days.

The food and wine was fresh, excellent and inexpensive. We usually ordered from the list of daily specials, which sometimes included wine, cafè and dessert. We tend to seek out small, casual family-run restaurants, often deciding where to go by paying attention to places that are crowded with municipal workers at lunchtime. We’ve found those places usually provide good food and good value, and they were plentiful outside the more touristy or commercial areas.
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