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Reader Scott Visited 9 US Cities With the Southwest Companion Pass and Had a 2-Week Luxury Island-Hopping Vacation in Hawaii for Next to Nothing!

Reader Scott Visited 9 US Cities With the Southwest Companion Pass and Had a 2-Week Luxury Island-Hopping Vacation in Hawaii for Next to Nothing!

Million Mile SecretsReader Scott Visited 9 US Cities With the Southwest Companion Pass and Had a 2-Week Luxury Island-Hopping Vacation in Hawaii for Next to Nothing!Million Mile Secrets Team

We devote thousands of hours of research to help you get Big Travel with Small Money. You support us by signing-up for credit cards through partner links which earn us a commission. Here’s our full Advertising Policy.

Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers.

Welcome to the next installment of our Reader Success Series where Million Mile Secrets Readers share how they booked a trip with miles & points to get Big Travel with Small Money!

Scott is our newest reader success story to show folks it’s possible to travel without spending a lot of money.

13 Free Nights In Hawaii Reader Success Story
The View From Waimea Canyon

What’s your name and how long have you been involved in the miles & points hobby?

My name is Scott Swinson, and I stumbled into this amazing hobby a little over 2 years ago.  I was bored at work one day and found the Million Mile Secrets website.

I was intrigued by what I was reading and learning.  In fact, initially, I was on the site every day for hours trying to learn as much as I could.  I felt like I had been missing out on all of these money saving ideas and tips on how to travel using miles & points instead of cash.

I realized there were other sites that offered similar information, but kept coming back to your site every time.  I really enjoyed how the website was structured and how easy it was to navigate.

What was the goal of your trip?

When deciding on where to travel nowadays, my wife and I try to go places using miles & points instead of cash as much as possible.  For instance, because we have the Southwest Companion Pass, we visit places where Southwest flies, and plan awesome trips around that.

Once we’ve established where we want to go and have booked our flights, I start looking at different hotel chains to see where we would like to stay.  And, of course, how many points it costs to stay there.  Since having the Southwest Companion Pass, we have visited Atlanta, Pittsburgh, Salt Lake City, New Orleans, San Juan, Puerto Rico, San Francisco, New York City, Las Vegas, and Buffalo.

13 Free Nights In Hawaii Reader Success Story
Here We Are at the Jurassic Park Waterfall. We Didn’t See Any Dinosaurs

How long did you collect miles and points for your trip?

For our trip to Hawaii, we began saving points ~1 year in advance.  Because my wife’s company was paying for our flights to anywhere in the US (including Alaska and Hawaii), we decided to plan a trip to Hawaii because neither one of us had ever been there.  And, well, it’s Hawaii (need I say more?).

Which points did you save to take your trip?

We knew we wanted to make the most of this trip.  We decided to spend 2 weeks on the islands of Maui, Kauai, and the Big Island for a total of 13 nights.  Our goal was to try and stay at the most amazing hotels on each island.  And I feel like we accomplished that by staying 2 nights at the Hilton Waikoloa Village (the Big Island), 5 nights at the Grand Hyatt Kauai Resort & Spa, and last but not least, 6 nights at the Hilton Grand Wailea, which is a Waldorf Astoria resort.

13 Free Nights In Hawaii Reader Success Story
We Loved Our Stay at the Grand Hyatt Kauai

Because we knew it was going to take a lot of Hilton points, we both signed up for the AMEX Hilton Surpass Card (now the Hilton Honors Ascend Card from American Express), as well as the Hilton Honors Card from American Express, which got us pretty close to where we needed to be.  Besides that, my wife signed up for the Chase Hyatt card, which got us 2 free nights at any Hyatt (this deal is longer available), and we transferred the rest of the points we needed from our Chase Ultimate Rewards account.

How did you search and find the award flights?

Our flights there and back were covered by my wife’s generous employer, because it was her 10-year anniversary with the company!  I did however sign-up for the Barclaycard Hawaiian Airlines Card, which covered our inter-island flights, and saved us from having to pay for those out of pocket.

How did you find your hotel accommodations?

By searching far in advance, we were able to book 6 nights at the Grand Wailea for only 59,000 Hilton points per night, which was a crazy good deal.  Especially for a hotel that runs $500+ per night!

13 Free Nights In Hawaii Reader Success Story
The Grand Hyatt Kauai Has a Parrot!

What was the most challenging part about planning  your trip? How did you solve it?

We based the dates around when we could get the best rates on the room at the Grand Wailea, which was in early May.  Then we just arranged everything else around that.  We started out on the Big Island, then went to Kauai, and finally ended in Maui, which we thought was going to be our favorite island.  But it turned out, we liked Kauai better because it was less busy and a bit more secluded.

Give us a few recommendations or tips for what to do at your destination.  Parks, restaurants, hidden gems, etc.

If you’re planning on going to Maui, the Road to Hana is a must-see road trip that is all about the journey and not so much about the destination.  If your goal is to go to Kauai, then you really must see the Na Pali Coast as well as Waimea Canyon, and don’t forget to bring your camera.

We also went on a helicopter tour of Kauai.  It was amazing, because you get to see the landscape from an aerial prospective.

13 Free Nights In Hawaii Reader Success Story
Hawaii Is Full of Amazing Sunsets. Here Is One From the Big Island

What did you learn about yourself on the trip?

For us, Hawaii was the trip of a lifetime.  We had an amazing time, and really enjoyed ourselves and can say that we’ve been there now.

What would you say to folks looking to plan a similar trip?  Or to those who haven’t taken a miles & points trip yet!

Open up cards that are beneficial for the trips you are planning, unless there’s an amazing deal that’s too good to pass up.  One of the deals we’ve taken advantage of was when the Starwood Preferred Guest® Credit Card from American Express was offering a 35,000 Starwood point bonus (offer no longer available) instead of the usual bonus of 25,000 Starwood points.

We both applied for the Premier Rewards Gold Card from American Express when it had an increased 50,000 AMEX Membership Rewards point bonus (it currently comes with 25,000 AMEX Membership Rewards points).  And of course we opened the Barclaycard Hawaiian Airlines card with a 50,000 Hawaiian Airlines miles welcome bonus.

13 Free Nights In Hawaii Reader Success Story
This Luau in Maui Was Complete With Hula Dancers

Most of all, we would really like to thank Million Mile Secrets for all of the research and information that is shared on their website.  And the best part is, it’s entirely free!

Want to Share Your Story?

If you’d like to be considered for our reader success story series, please send me a note!  Emily and I would love to hear about how you travel with miles and points!

If you liked this post, why don’t you join the 25,000+ readers who have signed-up to receive free blog posts via email (only 1 email per day!) or in an RSS reader …because then you’ll never miss another update!

Hilton Honors American Express Ascend Card

Hilton Honors American Express Ascend Card

  • Earn 100,000 Hilton Honors Bonus Points with the Hilton Honors American Express Ascend Card after you use your new Card to make $2,000 in eligible purchases within the first 3 months of Card Membership.
  • Earn a Weekend Night Reward from Hilton Honors after you spend $15,000 on purchases on your Card in a calendar year.
  • Earn 12X Hilton Honors Bonus Points for each dollar of eligible purchases charged on your Card directly with a hotel or resort within the Hilton Portfolio.
  • Earn 6X Hilton Honors Bonus Points for each dollar of eligible purchases on your Card at U.S. restaurants, U.S. supermarkets, and U.S. gas stations.
  • Earn 3X Hilton Honors Bonus Points for all other eligible purchases on your Card.
  • Spend $40,000 on eligible purchases on your Card in a calendar year and you can earn Hilton Honors Diamond status through the end of the next calendar year.
  • $95 annual fee.
  • Terms Apply.
  • See Rates & Fees
Terms Apply | Rates & Fees

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Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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I’ve been to Hawaii but not Kauai and want to stay at the Grand Hyatt. I also have the companion pass and try to work my trips around SW routes and been to many places, what a deal! I agree MMS is the best user friendly website out there!