While I'm not comfortable sharing specific flight or hotel information until after our trip, I can shed some light on how we are making it work:
American Airlines Aadvantage miles for free airline tickets, and a combination of cash-back credit cards and travel reward credit cards for (hopefully almost) free hotel nights.
Our Southwest Rapid Reward miles and companion pass have served us well for travel within the continental U.S. But I wanted to start planning a bigger trip to somewhere farther away and have a goal to attain...we had talked about France, Russia, Hawaii and Alaska. We narrowed it down to France and Hawaii, and after much deliberation, decided on Hawaii.
For starters....I asked the miles and points travel experts. And I'm not one of them. My friends at Miles for Family, Mommy Points and Million Mile Secrets were all happy to answer my questions and offer suggestions.
The biggest task was to get enough miles for 5 round-trip airline tickets. And while there are many good options for getting to Hawaii on miles, we pursued American Airlines Aadvantage miles. We live near Dallas, the hub of American Airlines. And Aadvantage miles can be used to get tickets to Hawaii on partner airlines like Hawaiian Airlines, US Airways and Alaska Airlines. Tickets during the off-season require 17,500 miles each way, which is lower than Delta and United. When the tickets are booked with miles on an American Aadvantage credit card, you receive 10% of your miles back.
In 2013, I applied for a Citicard Aadvantage credit card that offered 50,000 bonus miles after spending $3000 in 3 months. A few months later, I applied for the business version of the same card (I do freelance work that qualifies me for business credit cards) and received another 50,000 bonus miles. My husband had received an offer in the mail for the same credit card but with a 60,000-miles bonus. He already had around 20,000 Aadvantage miles in his account from business travel.
We spread out these credit card applications and charged our normal monthly bills on the credit cards. (We pay them off every month to avoid interest and other charges). Soon, mostly because of the credit card bonuses, we had nearly 190,000 Aadvantage miles, which was enough to get us all to Hawaii.
Accumulating the points was the easy part; finding flights for 5 on the week we wanted to go was harder. For about a week straight, I got up in the middle of the night to see if flights were available with miles. Unlike Southwest, most airlines have very limited tickets for award travelers. My husband thought I was crazy, I thought it was hopeless. But sure enough, one day early in the morning, I saw 5 flights available on miles. For our return, we could not find tickets all the way back to Dallas, so we booked a flight that landed in a Western state. We are using Southwest miles to get us back to Dallas the next day.
Each ticket would have cost us around $1000. We only paid $50 total in taxes, so we saved $4950 by using miles.
Next, we had to think about our hotel strategy. As I was researching hotels in Hawaii, most of them did not allow 5 in a room. Now some people would argue that we should sleep one child on the floor, but many of the hotels require a wrist band for the pool area and would not permit 5 people registered to one room, so squeezing 5 people in a room would not work. Saving up enough points at any hotel chain for 2 rooms a night would not be the easiest option. And there was a certain hotel on the west side of the island that we had to visit, at least for a few nights...that doesn't accept traditional hotel points.
So a cash-back credit card or travel-reward credit card was our best option for lodging. My husband and I each applied for the Barclay Arrival Plus credit card (at different times of the year). We completed the minimum spending of $3000 on each card over a period of several months and received $400 in travel rewards as a sign-up bonus on each card ($800 total). These dollars can be used to offset any expense on the credit card that is coded as travel, like hotels and airline charges. The card earns 2% rewards for every dollar spent and gives 10% of the reward points back after redemption. The Barclay card also has an online travel community that pays travel rewards for writers to share photos and travel stories, and I have enjoyed writing about our travel adventures on that site for extra money. With the bonuses, extra points for writing and charging our normal monthly expenses, we anticipate having the majority of our hotel expenses covered before our trip.
Food and entertainment are the other two major expenses of any trip. We have free breakfast for 7 out of 8 nights of hotel, and $100 food credit (which we will purchase with points) for one hotel. We have a full kitchen in one of our hotel rooms, so we will buy some groceries for lunches and dinners. Of course, we will splurge for meals out a few times.
To save on entertainment costs, we will search for discounts and coupons before our trip. While we plan on doing a lot of free or lost-cost things like hiking and enjoying the beach/pools, we do have a few excursions in mind that will cost more money.
So that's how we are going to Hawaii with 5 people on (mostly) miles and points.