Member Success Story: Travel Freely Members Save $7,400+ on Anniversary Trip to Hawaii!

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We love hearing about your success stories using points and miles for epic vacations. Travel Freely member Tim and his wife spent their 1st anniversary in Hawaii and they saved over $7,500 using points and miles! You can take amazing trips like this too! Tim shares their strategy and offers some advice for anyone interested in taking a similar trip to Hawaii. Psst… Have you seen our latest points & miles update? Click here to unlock your dream vacation like Tim.

Tell us about yourself. How long have you been using points and miles towards free travel?

My wife and I live in the Washington D.C. metro area. I have my own startup real estate business and I’ve been using points since 2017.

Tell us about your trip. Where did you go?

We went to Hawaii for our 1 year anniversary trip! We were there for 9 days, 8 nights – half the time on the Big Island and half the time in Kauai. The Grand Hyatt in Kauai was freakin’ awesome. There’s a restaurant on site and it’s like you’re eating dinner in bungalows over the water with koi fish swimming below. It’s super neat! Definitely a must see and very worth it. The Hilton Waikoloa was super family friendly, had a lagoon on site you could just walk out and snorkel with fish and sea turtles. That was epic!

How much money did you save by using points and miles for your trip?

We saved over $7,500 on this trip by using points and miles! We booked the hotels on points so there was no out of pocket cost. We only paid the fees for the flights (we used 3 one way flights, fees are $5.60 per person) so $33.60 total out of our own pocket!  If we had booked the hotels out of pocket, they ranged from $350-$700 per night, it would have cost at least $5,000 for the entire trip if we had paid the cash rates. The flights would have been close to $1,200 per person so that’s another $2,400 saved on flights. So to conservatively estimate, we saved at least $7,500 on hotels and flights.

What kind of points did you use for this trip?

We used a few different types of points:

• Southwest miles and the Southwest Companion Pass: We only used 24K Southwest points in total, which was an unusually epic deal! 13K points from DC to the Big Island, 3K points from Big Island to Kauai, and 8K points from Kauai back to DC. Of course with the companion pass, one of us flew for essentially free!
• Hilton points: Four nights at 60K points per night, and 5th night free, which is a perk when using points.
• Chase Ultimate Rewards transferred 1:1 to Hyatt (the Grand Hyatt was 25K points per night).

Summary of Tim’s total costs:

• Southwest miles: 24,000 miles
• Southwest fees: $33.60
• Chase Ultimate Rewards: 88,000 points
• Hilton points: 240,000 points

What advice would you give to someone interested in booking a trip like yours?

Using the companion pass to get to Hawaii is a no brainer! Also remember Hilton’s 5th night free, and transferring Chase points to Hyatt for redemptions can be an incredible value. The food and drink cost felt similar to just about any nice big city in the mainland US so that seemed fine to us. When the flights and hotels are practically free, then we are able to travel to all sorts of other places and much more frequently because of it. 👉 Inspired by Tim’s story? Start tracking your cards with Travel Freely today – it’s free, beginner-friendly, and built to make stories like this possible. Have a success story you’d like to share? We’d love to hear it! Reach out to us at or fill out our form here.

• Category: Member Success Stories
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