All three major alliances have Rome on sale in the $640s from January to May 10. There are a few secondary airports in the mid-to-upper $600s for destinations like Bari.
Star Alliance also has Palermo, Sicily for $651. I come across few discount airfare deals for Sicily and Sardinia.
Rome FCO
United/Star Alliance $641 – $683
Air Canada San Francisco SFO – Montreal YUL – Rome FCO – Montreal YUL – SFO
$640.95 round trip Thursday March 9 – Friday March 17
Lufthansa Airlines San Francisco SFO – Zurich ZRH – Palermo, Sicily PMO – Munich MUC – San Francisco SFO
$654.78 round trip Sat May 6 – Sun May 14
Swiss Airlines San Francisco SFO – Zurich ZRH – Olbia, Sardinia OLB – Zurich (20 hr overnight transit layover) – SFO
$669.90 USD round trip Thu May 4 – Sun May 14
Sardinia, Italy is the playground of the rich and famous in peak July-August summer yachting season. Hotels, like Costa Smerelda Resort, an SPG category 7 property, is available and a whole lot less pricey in May compared to July.
Cervo Hotel Costa Smerelda Resort, Port Cervo, Sardinia, Italy SPG Category 7
EUR 142/night with breakfast May 8-12 or 30,000 points/reward night.
Cervo Hotel Costa Smerelda Resort, Port Cervo, Sardinia, Italy SPG Category 7
EUR 360/night with breakfast July 10-14 or 35,000 points/reward night.
Loyalty Traveler curated Airfare Deals and Google Flights and Kayak Explore tutorials.