Howdy Reader!

Join us in manifesting an awesome 2026. I know travel isn't everything, but hopefully our monthly newsletter is your little slice of inspiration. This month we're starting off with a BIG idea. It's ambitious but if you can pull it off, it's the stuff of dreams.

✈️ In this issue:

• 🏖️ Maldives on points

If you haven't yet, make sure to check out the latest on our social channels: Instagram, TikTok, Facebook, Pinterest, and YouTube.

Maldives For Free-Ish

Back in 2014, we had the dream of going to the the chain of tropical islands in the Indian Ocean and the southwest of India and Sri Lanka.

It seemed like an outlandish and very expensive idea but thanks to the years of being a consultant and hoarding points, I realized that it was actually possible.

Being a Hilton Honors member, we were able to pull off one of our most ambitious trips to date.

The key for free stays with Hilton Honors

Cutting through all the BS out there on travel hacking, here's essentially how it works.

• Building up a stash of points - If you're not traveling for business, the best way to do this is by getting a credit card. This is where the Hilton Honors American Express Aspire card comes into play. As a Canadian, I was able to use an American address and Amex's Global Transfer program since I already had Canadian Amex cards. With 175,000, you're well on your way.
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• Diamond status is key - While Gold status would be good enough for free breakfast at the Conrad Maldives, Diamond is what unlocks afternoon tea and cocktail hour.
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• Every 5 nights free - As part of the program, whenever you redeem 5 nights, 1 night is free.
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• Free night with the credit card - The beauty of the Hilton Honors Amex Aspire is that you also get...
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• Resort credit - Yup, that same credit card comes with $400 in resort credits that needs to be split up into two halves of the year so at a minimum, you're getting $200 off at the resort which should cover a few meals or part of the seaplane costs.
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• Saving money on meals - This helps with keeping the trip free-ish. Late buffet breakfasts covers two meals and if you have a big enough afternoon tea and cocktail hour, you minimize dinner costs as well.
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• Transfer Amex Rewards points - Other cards such as Amex Gold and Amex Platinum has their own Membership Rewards program where you can transfer the points 1:1.
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• Buy points - This is worst-case scenario but every year, you can buy a maximum of 249,000 points but they often will have 100% bonuses so that means 480,000 points. That comes out to $2,400.00 which might actually be worth it to push you over the top.

How much many points does it take to stay in the Maldives?

Using the Conrad Maldives as the example since this is where we stayed, it costs 160,000 points per night or around $7,100 USD for 7 nights, depending on the time of year.

Applying some travel math:

• For 7 nights (1 being free and 2 nights from the credit card), you're paying 4 nights so you'll need 640,000 points.
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• Let's say two of you individually each sign up for the Hilton Honors Amex Aspire for 1 year. You'll get 350,000 points.
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• You also sign up for Amex Platinum which gets you 80,000 points (make sure you can spend $10,000 in 3 months).
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• Let's say you keep the Hilton Amex of the cards for 3 years and spend $500/month at the base 3x multiplier. That's 54,000 points.
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• You need 156, 000 points at this point and even if you don't earn any on credit card spend, you can buy Hilton Honors points the remaining points for $780 USD.

What are other costs you should consider?

When you're at the resort, you might be spending additional money on these things:

• Dinner
• Spa
• Water sports including scuba diving
• Seaplane - This is the big one. To get to the island, it requires a seaplane and this costs $700 USD per person.
• Tipping

Okay, so yes, it's not a completely free trip but with some commitment to the strategy, the trip isn't as expensive as you think it is.

Would you do it?? If not the Maldives, where are the aspirational properties that you'd want to go after?

💸 Travel Deals

It's no longer the holidays but still lots of deals coming through this month.

• Europcar: Enjoy exclusive winter deals (Up to 15% + 5% on APP). This is good for rentals between 07/01/2026 and 30/06/2026. Deal runs from 07/01/2026 and 21/01/2026.
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• WANDRD Mystery Box Sale: This limited-time drop gives customers 50% off on mystery boxes featuring some of WANDRD’s best-selling gear. Shop before they sell out!
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• MEC: Get an exclusive 15% off! For a limited time, MEC Rewards members save on one full-price item from top brands with code: 15JANB.
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• Airalo Codes in 2026: Use code NEWTOAIRALO15 for new users to get 15% off. If you’re an existing customer, use AIRALOESIM10 to save 10%. Deal expires Jan 1, 2027.
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• Radisson: Use promo code JANSL26 to save up to 35% on bed & breakfast stays throughout 2026 (Mar 1 – Dec 31, 2026) and get 3,000 bonus points per stay. Deal expires Jan 30, 2026.
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• Klook: Save up to 50% on locations around the world including Japan, Italy, France, Switzerland, UK, and US. The offers are valid for redemption from December 12, 2025, to February 1, 2026

To get notified of all travel deals we discover, go to our deals group on Facebook.
​It's free to join!

✏️What's New on the Site

In case you're not subscribed to our "let us know whenever you publish something new" list, here are our new posts. We aim to publish posts twice a week so if you subscribe you are always kept in the loop!

☝️ What's Next at Going Awesome Places

We mentioned this in our last newsletter and yes, we're headed back to the Conrad Maldives!

This is the first time we'll be going back to stay at a fancy hotel property on points. We're exited to be headed back and can't wait to share with you that experience. Look out for an updated property walkthrough video!

In addition to the Maldives, we're book-ending the trip with stops in Singapore and Bangkok in Thailand. We can't wait!

🍪 Travel Tidbits

Here's the latest from the industry with a few articles that we think you'll enjoy and make your 2026 travel even more exciting:
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• ​Take a tour of Warsaw’s top vegan restaurants: ‘We were as stuffed as the dumplings’
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• ​What are the most powerful passports for 2026: Europe once again dominates passport power ranking, with 30 countries in the top 10
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• ​A Finnish ironwoman's guide to Finland's best outdoor icy plunges: Elina Mäkinen was the first Finnish woman to complete the Ice Mile and shares her top ice bathing experiences, from plunges under the Northern Lights to paying homage to Arctic gods.
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• ​A guide to Whistler, Canada, from the godfather of freeskiing: Canadian freeski champ Mike Douglas stands at the vanguard of his hometown's ski culture. Here are his local favourites.
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• ​World’s top 100 cities revealed: Los Angeles and Orlando climb the rankings
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• ​Like a little wine with your takeoff?: This is the only airline in North America to serve free alcohol in economy on all flights:
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• ​‘Wild Wellness’ at Las Torres Patagonia Inspires a Year of Restorative Travel: Discover the kind of restoration found through wind, wilderness and authentic natural encounters.

Anyone else feeling the inevitable never-ending January?

We love hearing from you, so if there is anything you would like to share, simply reply to this e-mail and let us know!

Cheers,

Will

Your Chief of Awesome

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