25th Anniversary - Draft Italian Itinerary

In keeping with the dates and the number of days you posted, you need to reduce overnights someplace on your list to add another base for either Tuscany or Umbria.

I would travel to Tuscany or Umbria from Florence. You can rent and drive out of Florence, or train to another town and pick up rental car there which can be more relaxing for some people.

I'd definitely remove 1N-Cinque Terre and reduce that to 2N stay, unless there is a reason you want 2 full days/3N there without travel.

You need 1-2 Nights more to make Tuscany/Umbria a worthwhile stay. A total of 3 Nights in 1 place can add value to your trip.
What city of the big three, VeniceFlorence-Rome, you take these nights from is up to you.

You will receive many different reviews on which one and why from fellow travelers. So think about which city deserves more of your time. Think about why you really want to be there: art, food, certain museums, certain sights. If you have visited any of the three cities before that can be a factor in your decision, too.

One way to finagle dropping an additional night in one of the cities is to take an afternoon train. This allows you the morning with your bags left at your hotel or the train station, and moving on to the next place and arriving by late afternoon/early evening. Like if you stayed 2 nights in Venice, spend 3rd morning there-take afternoon train to Florence putting you in Florence by September 27.
Now you gained a night for Tuscany/Umbria stay.

Did you check to see if there are any festivals or feast days during your itinerary dates?

Great job of planning and congratulations! I would definitely keep 3 nights in Venice because you will be getting over jet lag and it is a wonderful city to wander with plenty to entertain and inspire you. I would not rush it. Also, 4 nights in Rome is a minimum. That leaves you 6 nights which are nicely allocated between Firenze and the Cinque Terre, I think you have to either drop a location or add two or three nights to the total trip to fit in your countryside time. Can you see your way to staying October 8 & 9 and fly home on Saturday the 10th? You can add your agriturismo experience right before or after Firenze.

No travel hints, just sincere congratulations on your anniversary and your wisdom in celebrating it with a special trip.

Thanks All.

This will be our first time in Italy. Does it make sense to rent a car after our stay in Firenze? Then we can stay in the agriturismo for 3 nights and tour around. Perhaps we can drop the car off in La Spezia on the way to the Cinque Terre. We can drop a night from the Cinque Terre and add a night or two at the end to make this work.

Thanks again,
David

Congrats on 25 years together. Anyway, you presented good planning by flying multi-cities into Venice and home from Roma. You will maximize your time in-country.

IMHO, I would drop one night from Le Cinque Terre and add it to either Venice, Florence, or Roma. Personally, Le Cinque Terre is JAMMED in the summer with tourists. We were there in 1994 when they were five sleepy little towns. It's different now. I might even skip this area altogether and spend more time in the other cities.

By adding another day to either of the three mentioned cities you could: 1.) take a vaporetto to Burano or Torcello, 2.) you could take train to Pisa, or 3.) you could make a day trip to Orvieto or Ville di Este/Hadrian's Villa or Ostia Antica.

Go and have fun.

Buon viaggio,

Does it make sense to rent a car after our stay in Firenze? Then we can stay in the agriturismo for 3 nights and tour around. Perhaps we can drop the car off in La Spezia on the way to the Cinque Terre. We can drop a night from the Cinque Terre and add a night or two at the end to make this work.

Yes I think a car after Firenze to spend time int he countryside and then drive to La Spezia is a great idea. Depending on where in Tuscany you are when you head out to the CT, it can be a trip involving several train changes. Since you'll have a car anyway, it's a perfect plan. Glad you can extend your trip a couple of days!

I think 2 nights in the CT are enough. I would not worry too much about it being "jammed with tourists." My visit there was in mid-October, 6 years ago. I hiked the first two parts of the trail from Riomaggiore toward Monterosso and most of the time I was alone on the trail. Be sure to take the ferry in the late afternoon from one end of the towns to the other for the very best views of the towns with the sun behind you.

This is draft version two of our Italian itinerary based on suggestions to date. We dropped one night in the Cinque Terre and included three nights in an agriturismo (location TBD, suggestions welcomed). This plan gives us 15 nights in Italy:

Thursday, September 24 - Overnight flight to Venice
Friday, September 25 - N1 - Arrive Venice
Saturday, September 26 N2 - Venice
Sunday, September 27 N3- Venice
Monday, September 28 N1 - morning train to Florence
Tuesday, September 29 N2 - Florence
Wednesday, September 30 N3 - Florence
Thursday, October 1 N1 - pick up rented car and head to agriturismo (near Siena?? perhaps Volterra??)
Friday, October 2 N2 - touring countryside in Tuscany
Saturday, October 3 N3 - touring countryside in Tuscany
Sunday, October 4 N1 - drop car in La Spezia and train to Cinque Terre (Monterosso?)
Monday, October 5 N2 - Cinque Terre
Tuesday, October 6 N1 - morning train to Rome
Wednesday, October 7 N2 - Rome, touring
Thursday, October 8 N3 - Rome, touring
Friday, October 9 N4 - Rome
Saturday, October 10 - Flight home

The flight home leaves FCO at 8:30 AM. I am considering staying in the Trastevere neighborhood. Does this cause any transportation problems on a Saturday morning? If it matters, we fly FCO > LHR > YYT.

My wife and I are celebrating our 40th anniversary this year with a 37 day trip to Italy. We are starting in Rome and taking a Windstar cruise around the boot and up the Adriatic (Croatia, etc. side) to Venice. The rest of our itinerary takes in the same places as you are thinking about but is organized differently:
4 nights in Venice
take the morning train to Monterosso in the Cinque Terre - 4 nights there
take the morning train to Florence - 4 nights there
morning train to Cortona in southern Tuscany - near Umbria border. We are renting a car when we get there and staying at an agritourisme for 8 nights. Name is Agrisalotto - 5 rooms, wonderful people, Trip Advisor highest rated restaurant in the area.
Finally, morning train to Rome and 5 nights there.
Except for the agritourisme, we are staying in airbnb apartments in each location - marvelous locations, wonderful looking places and actually cheaper than equivalent nice hotels.
Enjoy and congratulations.

If your flight is that early, arrange for a taxi the night before to pick you up in time the next morning. That way you can spend your last celebratory night of the trip in Rome. I've reserved taxis all over Italy, they are very reliable. One tip for early departures: pack up everything possible the night before and throw the morning stuff into the bag at the last minute.