Looking to go to Italy next year with the inclusion of a holiday to save a day of pay that my wife will have to miss over the 2 weeks we're taking (was thinking using Memorial Day weekend in May), and would like to do the following in First Class if possible using my UA miles, but would consider AA miles if it made more sense: Outbound: MCO - VCE (a stopover would be cool for a night somewhere in a connecting city, doesn't really matter where unless it's not worth visiting) with visits in Venice, Florence, Rome and a final night or 3 on the Amalfi Coast. Likely just taking the train in between cities. The biggest problem I'm noticing is that my best option is LH (direct MCO-FRA), but they don't open award space to UA until 2 weeks out from DOD, so it sounds like I might need to position, but don't know the best way to maximize. If I booked something with UA miles and then award space came up on LH, would it be worth the cancel fee? What's a good strategy there? Return: NAP-MCO Suggestions on good hotels in each city would be preferred as well. I've got IHG (Plat status), Hilton (Gold) and Club Carlson (Gold) points to use, as well as 2 IHG free night certs, and 2 free weekend certs from the HHonors Reserve card as well as maybe some SPG points. Relevant Balances: UA: 198k UR: 45k AA: 126k US: 40k Hilton: 232k (with another 150k waiting in the wings in my HA account if necessary) & 2 wknd certs IHG: 135k & 2 anytime certs CC: 86k SPG: 37k I'm crazy excited to show my wife the payoff of all the mile hunting I've been doing over the last year. Hopefully, that'll help her get into the game as well a bit more.