LAIN provided great advice to go with the CIP. If a branch isn’t close you can apply online.
The CIP will give you 80,000 UR points after you spend 5k in three months.
You can transfer Ultimate Rewards points to 9 airline programs (
British Airways,
Flying Blue,
Korean Air,
Singapore Airlines,
Southwest,
United,
Virgin Atlantic and Aer
Lingus and Iberia) and four hotel programs (
Hyatt,
IHG,
Marriott and
Ritz-Carlton). All transfer ratios are 1:1. You can also book flights and hotels on the chase travel portal. I’d start looking at some hotels that you would want to stay at.
The next step after the CIP (wait at least 30 days) is to double dip with the CSP/CSR. The CSR has a high annual fee of $450 dollars but you get Global entry or TSA precheck fees reimbursed and a $300 travel reimbursement every year. If you can spend 8k in three months you have to apply for both on the same day. Chase instituted a rule with only one sapphire card every 24 months, but the way around the rule is to apply for both on the same day. Preferably, a business day incase you get the 30 day message. If you can’t spend 8k I’d pick which one you think is a better value. Some people think the CSR with the $450 annual fee is worth it others would rather the CSP where the annual fee is waived the first year. They are both definitely worth it in the first year if you can get both bonuses. After your first year one of those cards you should downgrade. You may even want to downgrade both to a no fee version.
Do you have someone else in your family that is willing to play the game too? If so you can refer them for the CIP and CSR and CSP. That would be 400+ URs but is 26k in spend so that should keep you busy for awhile. Lol
You can also look into Amex Delta Business and the Amex Starwood Business. Delta maybe helpful for your flights I don’t know if your airport has delta though. And Starwood can be used for Starwood and Marriott properties. They can also be transferred to some airlines.
For Rome I really like the Boscolo. It my plan to stay there. It is 180k Marriott points for five nights, but you can book it using UR through the Chase portal often for less points. I’m flying to Rome on Delta since Delta is at my home airport.
I don’t have any specific hotels that I am looking at for Hawaii but for flights Southwest maybe a good option. I’m hoping it’s cheap. Hopefully, they release dates soon.