Flight & Transit Advice Please: SFO/OAK>NYC>Taormina and LakeOrta >SFO/OAK

The nearest airport to Taormina is Catania, which is actually the busiest airport in Sicily. I don't know how flight frequency to Taormina will compare in Milan and Rome, but you also might be able to connect in one of the major capitals to the northwest--London, Paris, Amsterdam, etc. Be careful about these issues:

• If you buy separate tickets for the transatlantic part of your trip and the flight into Sicily (and/or the flights out of Milan and Switzerland), what you will have is an "unprotected connection". That means if something goes wrong with the eastbound transatlantic part of your flight (cancellation, significant schedule change, etc.), you are going to get no help from either airline in getting to your final destination. You'll need to buy a new ticket at the last-minute walk-up fare, which could be quite expensive. If you can manage to get the entire trip to Catania and home from Milan/Switzerland booked as a single ticket, the onus will be on the airline(s) to get you where you are supposed to be without your having to buy new tickets.

• It's even riskier to have a separate ticket for some sort of short-hop flight within Europe to whatever gateway you use to get back the US. If there's an issue with the separately-ticketed intra-European flight that causes you to miss the westbound transatlantic departure, you'll have to buy a replacement one-way ticket back arcoss the Atlantic, and those can be very expensive indeed.

• I trust you have some activities planned during your time in Taormina. It is a very pretty town in a very pretty setting, but it is very small and mobbed with tourists. I cannot imagine wanting to spend two weeks there.

• You mentioned that your trip begins in July. Sicily is extremely hot at that time of year. I imagine Portofino and Siena can also be unpleasantly warm. It's one thing to spend a few days in such a climate as part of a trip, but you will be exposed to the Italian summer for at least four weeks. (I'm not sure about what it will be like in Orta San Giulio.) It will be draining. Believe me, I know; I made the mistake of heading down to Sicily, followed by Puglia, in June 2015.

Two weeks in Taormina? And Lake Orta? Curious as why do much time in those places.

Might it make sense to fly into and out of Milan, and fly from Milan to Taormina?

I also live in the Bay Area. On my most recent trip to Sicily, I booked a direct flight to Rome and spent a couple of days visiting a friend before taking a RyanAir flight to Catania. Obviously, with 2 days in Rome, I wasn't worried about missing my connecting flight to Catania. I then did an open-jaw return from Catania. I found the open-jaw + separate RyanAir flight to be FAR cheaper (for some reason that only the airline wizards understand) than a roundtrip from the US to Catania would have been. (Probably because flights to Rome were cheap at the time.)

So yes, I would encourage you to check round-trips to Milan, Rome, Naples - whatever you can find that is priced right. Then take hops on European airlines (e.g., RyanAir, Alitalia) to get to/from Catania.

We had a car and drove from Catania to (among other places) Taormina, where there is easy (paid) public parking.

If you are planning to use Taormina as a base to travel in the region, you might consider (if you have a car) Giardini-Naxos as an alternate option, with a day trip or two to Taormina. I can offer a very nice suggestion for a villa where we stayed - with gated parking - if that arrangement interests you.

Flying to Milan Malpensa (MXP) is generally the cheapest option.
Take into consideration that Air Italy (formerly Meridiana Airlines) will start flying non stop from MXP to SFO this spring (https://www.airitaly.com/en-US/).
MXP is very close to Orta San Giulio, and the closest intercontinentalairport to Chamonix as well, therefore convenient for the return trip.

Milan Malpensa is also a major hub for Easyjet, a British low cost airline (https://www.easyjet.com/us).
Easyjet has 4 to 5 flights daily from MXP to Catania (CTA), Sicily. Prices in July are, on average, €65-€75, one way. When flying on separate tickets, it is a good idea to have a very long chunk of time of layover. Or, better yet, take the Easyjet flight to CTA the day after you arrive to Italy.

I also consider two weeks in Taormina and two weeks in Orta San Giulio a long time. I understand wanting to have a home base, a hub for day trips, without too much moving around, but neither Taormina nor Orta San Giulio are logistically very convenient hubs.

Lufthansa flies JFK to Catania, with a connection in Frankfurt. It is a United partner, so that is what comes up on the United search.
Using a “multi-city” ticket, you could probably also return from Milan to SFO, maybe non-stop, but if not, certainly with one connection either in Europe or the East Coast of the US..

Thanks a bunch for these great tips -- you folks are the best! As for "why so much time in Taormina and Orta?" . . . well, we want to spend big hunks of time doing little other than staring at water (and swimming in it), my wife has been to Taormina and wants to return there for an extended stay, and Orta seems to be the Italian Lake best suited to our desire for a laid-back, charm-without-flash place (and it has very convenient transportation to the Eiger-Monch-Jungfrau region of the Swiss Alps, over which I'm salivating).

After Orta, definitely fly out of Milan.

If you are interested in any day trips over to Lago Maggiore, there is lots to do in the area by ferry.
A short train, then bus to the Pallanza Or Intra Ferry terminals.

Here’s link blog that has our Lago Maggiore Adventures. Any questions, please ask.
Lago Maggiore Adventures

If u are interested in swimming then Giardini Naxos is a better option than Taormina, which is on top of the hill.