You are looking at this backwards. Ideally, you want a card that accumulates enough points through spending to get a free round trip ticket to Italy, or at least jax to Phili. What you need to tell us is how much card charge on your card (yearly), what categories you spend the most in and what airlines you fly. For example, if you spend 20k a year on your card, mostly at restaurants and fly mostly on star alliance carriers, I would vote chase sapphire preferred. If you fly Alitalia and stay in hotels a lot, Starwood Amex makes more sense, or one of the delta cards. Just knowing miles doesn'tfive us much to go on.