If you do decide to fly Hawaiian, I'd suggest you and/or your spouse consider applying for the Hawaiian Airlines World Elite MasterCard for the bonus miles and benefits to bring down the cost of your trip. The standard signup offer is 35,000 HawaiianMiles after spending $1,000 within 90 days of opening the card, and you get one complimentary checked bag for the primary cardholder and a one-time 50% off companion fare discount. There is a $89 annual fee for the card. If you decide to keep the card after the first year, you'll also get 5,000 HawaiianMiles each anniversary if you've spent $10,000 or more on the card the previous year, and you'll get $100 off a companion ticket.
Don't settle for this signup offer! You can get a better offer of 50,000 HawaiianMiles by going through a "dummy booking" on HawaiianAir.com. Just visit Hawaiian Airlines' website -- but don't log in or create an account just yet. Pretend like you're booking a flight, any flight, continue through several more pages of entering your personal information and selecting seats until you get to the payment page. When you get to the payment page, select "Credit/Debit Card" as your payment method. Don’t worry -- you're not actually booking the flight. An ad for the Hawaiian Airlines MasterCard should appear asking if you'd like to earn 50,000 HawaiianMiles. Of course you do! Click "Apply Now" and use this application to apply for the card. If you meet the minimum spending requirement, you'll be awarded the bonus miles that you can use to book your trip to Hawaii!
You'll eventually need to set up a HawaiianMiles account to login to and search the awards page. Awards are priced by Coach SuperSaver, Coach Saver, Coach Flex, First Class Saver, and First Class Flex tiers. The awards table looks something like this:
North America To/From Hawaii (One Way)
North America-Hawaii 20,000 (Coach SuperSaver); 30,000 (Coach Saver); 40,000 (Coach Flex); 40,000 (First Class Saver); 80,000 (First Class Flex)
There are no blackout dates for using HawaiianMiles and availability is pretty good. However, I've never flown out of BOS, and I don't know if you can mix awards on Hawaiian flights with other airlines. Something to look into. Good luck!