Two Weeks in Northern Italy....Add Switzerland?
 

My wife and I are doing two weeks in Northern Italy in September. We are in our early 40's and like both a mix of adventure and relaxation in our trips.

I just found out it's actually just as cheap (if not a little cheaper) to fly into Zurich or Munich than Milan. Wondering if we should add Switzerland (the Bernese Oberland area) or if that would be too much in too short a time and we should just stay focused on Northern Italy instead.

Our current Itinerary (note that we land on Day 2).

Day 1: Flight to Milan
Day 2: Land in Milan, explore
Day 3: Drive to Dolomites (Ortisei)
Day 4: Dolomites (Ortisei)
Day 5: Dolomites (Ortisei)
Day 6: Dolomites (Ortisei)
Day 7: Drive to Cortina
Day 8: Dolomites (Cortina)
Day 9: Dolomites (Cortina)
Day 10: Travel to Lake Como (Varenna)
Day 11: Varenna
Day 12: Varenna
Day 13: Varenna
Day 14: Train to Milan
Day 15: Flight Home

If we did Switzerland as well we'd do something like this.

Day 1: Flight to Zurich
Day 2: Land in Zurich, travel to Lauterbrunnen area
Day 3: Lauterbrunnen area
Day 4: Lauterbrunnen area
Day 5: Travel to Lake Como (Varenna)
Day 6: Varenna
Day 7: Varenna
Day 8: Varenna
Day 9: Drive to Dolomites (Ortisei)
Day 10: Dolomites (Ortisei)
Day 11: Dolomites (Ortisei)
Day 12: Drive to Cortina
Day 13: Dolomites (Cortina)
Day 14: Trains to Zurich
Day 15: Flight home

I'm just wondering if that second plan with Switzerland added would be too much and if we'd be better off just better exploring the Dolomites on this trip. If we do pass on Switzerland I'm sure we'd get there some day, but likely not any time soon.

There is too much travel.
Lauterbrunnen and Varenna look close to each other on a map, but as there are 2 mountain chains inbetween, the journey will take almost a full day.
Varenna - Ortisei or Cortna is a rather long ride too (unless you take the boring motorways)..

May be you land at Milan, go by public transport to Varenna, rent there (resp. at Lecco or Como) a car and drive then to Treviso - Cortina - Pordoj Pass - Sella Pass - Ortisei and via Bolzano/Bozen - Lake Garda back to Milan airport.
Venice airport is closer to Cortina than Milan airport.

If you want to do the whole thing by public transport (perfectly possible) that gives:
Milan airport - train - Varenna.
Varenna - train - Tirano - Bernina Express (Switzerland) - Pontresina - Zernez - bus - Malles - train - Merano - Bolzano - bus - Ortisei (better done in 2 days as there are tons of nice places along the itinerary)
Ortisei - bus - Alta Badia - Bruneck - Toblach - Cortina d'Ampezzo.
Bus Cortina d'Ampezzo - Venezia Mestre - train - Stresa or Milan (Milan airport is between these 2 places).

I'd stick with your first plan. Plenty to keep you busy. Leave Switzerland for another time.

Which weeks in September?

I personally don't like the Malpensa, Milan, Varenna, Dolomites, Milan, Malpensa circle. I wouldn't pick up a car IN Milan because of the city's multiple ZTLs, and you don't need a car at Lake Como for only a 3-day stay. However, after your time at Lake Como, there's no car rental office in Varenna, so you'd need to travel somewhere to rent the car... perhaps train to Desenzano del Garda or Verona or even Bolzano.

If you could fly into one city and out of another, you could eliminate the backtracking. Fly into Venice or Munich and train to Bolzano to rent the car. After the Dolomites, return the car in Bolzano and train to Varenna. Train to Milan the morning of the last day and take the Malpensa Express train to the airport the next morning. While you're briefly in Bolzano, you could visit the Ice Man exhibit at the South Tyrol Archeology Museum.

Alternatively, if you land in Venice, you could train to Verona for one night. Then pick up and return the car in Verona, train to Varenna, etc. Starting the car rental in Verona (or Desenzano del Garda) would give you the opportunity to see a bit of Lake Garda on your way to the Dolomites.

Re the option via Zurich, you don't say how you'd do all of the transfers... train or car? You should definitely rent and return the car in the same country, and as I mentioned there is no car rental office in Varenna. If you're thinking of picking up the car in one city and returning it in another, make sure you know how much the one-way surcharge will add to the overall rental. The train ride back to Zurich from where you drop the car (most probably Bolzano) is long. There is no train service to/from Cortina.

Don't just compare air fares to different cities. Add up ALL of the transportation costs before you decide which itinerary is cheaper.

First two weeks of September.

Unfortunately because we're coming from the USA via long-haul flights this isn't really an option, as one-way flights are actually more expensive for each individual leg than an entire round trip flight in/out of the same city.

Thanks, this is a good thought and I hadn't dug too much into the logistics of it yet. We would likely either just rent the car in Zurich and park it at the hotel while in Varenna and Lauterbrunnen area (it looks like there are hotels where we can park it), or rent a car in somewhere like Bolzano like you said and return it there. I do understand the train ride back to Zurich would be long but we'd have a whole day for that, and being from the US trains are still a bit of a novelty to us :p

We're West Coast U.S., so I'm well aware of long-haul flights to Europe.

Don't look at one-way flight fares. Search "multi-city" (aka open jaw) flights. Consider also the cost (money + time) of returning to the fly-in city. Even if one direction involves a connection, it can be cheaper and time-saving compared to a circle itinerary.

I don't understand "rent the car in Zurich and park it at the hotel while in Varenna and Lauterbrunnen area"... for a week? And then what?

A train ride from Brixen (Ortisei) to Zurich will take 6 hrs indeed.

Pickup car at Zurich Airport
Drive Zurich to Lauterbrunnen area, park at hotel
Drive Lauterbrunnen area to Dolomites
Explore Dolomites w/ car
Drive Dolomites to Varenna, park at hotel
Drive Varenna to Zurich

I just meant that during our time in Lauterbrunnen and Varenna, we most likely wouldn't be actively using the car since those areas are mostly explored by train/ferry/foot, and would just leave the car parked at the hotel (I realize not all hotels have parking in these areas, so we would have to choose one that does).

Thanks, I was really screwing that one up by looking at it as two one-way flights. I guess you can tell I haven't traveled overseas in the last 10 years :p

That definitely opens up a different world of possibilities and seems to be a much better option.

Unless there is a problem renting a car in Lauterbrunnen, it seems that it would make more sense to take the train there from Zurich and just pick up the car when you're going to start driving rather than paying for a car when you're not using it and possibly paying for parking as well.

A direct journey from Lauterbrunnen to Ortisei, bypassing the most scenic and and interesting places of Eastern Switzerland and Western Tyrol is just a nonsense. It takes a whole day, either by car or by public transport.