Help Me Decide Where to Go Next Month

This is why I absolutely love points and miles. My wife and I have two weeks blocked off for vacation in September, and as of today have no flights or hotel reservations booked. The old me would most certainly have non-refundable air reservations purchased already, or would be completely freaking out if I hadn’t booked anything yet with just 1 month to go.

But nowadays, this type of situation actually gets me excited. I pretty much have enough airline miles to fly my wife and I anywhere in the world, and maybe that’s actually a bad thing to have that much choice since it has been hard to narrow our focus. We’ve been noodling on a few different itineraries, in particular Seychelles and Bhutan, but generally we are open to any type of trip anywhere in the world.

The problem that I’m running into is that I’m in no-man’s land in terms of award availability, having missed the really early booking window (~330 days out) and the just early enough window (~3-6 months out), but am too early for the last-minute window (~14 days out). So it’s been challenging to find any award availability that will allow us start the booking process and begin building a trip.

My Account Balances

That’s where I could use some help from y’all! What are some of the top destinations that we should be considering for our 2-week trip in September? Here is a summary of my current points and mile balances:

• Alaska Airlines: 155,000
• American Airlines: 154,000 (account 1), 75,000 (account 2)
• Lifemiles: 52,000 (only 40% of miles are required for bookings, so this is effectively 130,000 by purchasing the difference at ~1.5 cpm)
• Korean Air: 30,000
• Singapore Air: 21,000
• Chase UR: 86,000
• Amex MR: 52,000 (account 1), 53,000 (account 2)
• Hilton: 100,000 (account 1), 50,000 (account 2)

• SFO-DXB-SEZ or SEZ-DXB-SFO on Emirates Biz Class using Alaska miles, free stopover in DXB
• SFO-DXB-CMB on Emirates Biz Class using Alaska miles, free stopover in DXB. ex-CMB fare back to SFO
• LAX-AUH-SEZ or SEZ-AUH-LAX on Etihad Biz Class using AA miles
• SFO-Asia on Cathay Pacific First Class using AA miles or Alaska miles
• SFO-Asia on ANA or Asiana Business Class using Lifemiles
• SFO-Europe on Lufthansa or Austrian Business Class using Lifemiles; KLM or Air France using Alaska miles
• Transfer Chase UR and Amex MR to Singapore Airlines, use to book 2 seats in Suite Class (likely available routes will be Singapore to Europe (CDG, FRA, ZRH) or Australia (SYD, MEL))
• If need be, can use ex-DXB paid Business Class fare on Cathay Pacific for $1,900 one-way to get home (will be big help for Alaska MVP Gold re-qualification)