How I Saved $10,000+ on Luxury Hotels

All the Hacks: Money, Points & Life

Chris Hutchins

Business, Education, Investing, Society & Culture, Places & Travel, Self-improvement

4.7 • 1.4K Ratings

🗓️ 3 September 2025

⏱️ 63 minutes

🔗️ Recording | iTunes | RSS

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Summary

#244: I'll explain how I saved over $10k on luxury hotels in Costa Rica and Carmel Valley using points, free nights, and elite perks. I’ll walk you through every step, from how to book with points, when to buy them on sale, how to stack hotel credits, which hotel programs give you upgrades and free breakfast, and more! Link to Full Show Notes: https://chrishutchins.com/maximize-savings-costa-rica-carmel-valley Partner Deals Daffy: Free $25 to give to the charity of your choice NetSuite: Free KPI checklist to upgrade your business performance Vuori: 20% off the most comfortable performance apparel I've ever worn Thrive Market: 30% off your first order of organic groceries + a free $60 gift LMNT: Free sample pack of my favorite electrolyte drink mix For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned Credit Cards Hilton Honors American Express Aspire Card Hilton Honors American Express Surpass® Card The Business Platinum Card® from American Express Blog Posts How to maximize your Hilton cards How to use Hyatt's Guest of Honor Globalist benefit How to earn up to 6 free nights with Hyatt Brand Explorer Award Search Tools Rooms.Aero AwardTool ($20 off annual plans with code ALLTHEHACKS) Points Path Chrome Extension PointsYeah Hotels Awayz ($10 for ATH listeners and 50% off for ATH members) Gondola MaxMyPoint StayWithPoints Costa Rica Waldorf Astoria Costa Rica Punta Cacique Adobe Rent a Car Playa Hermosa, Guanacaste Sensoria Diamante Eco Adventure Park La Finca Carmel Valley Ranch: Little Ranchers | River Ranch Earthbound Farm Lucia Restaurant & Bar The Great Tide Pool Revival Ice Cream Snack Shack at Lovers Point Lucy's On Lighthouse Monterey Bay Aquarium Alila Ventana Big Sur Hotel Buy World Of Hyatt Points For 20% Off Elemental Movie ATH Podcast Video Episode with Photos/Videos⁠ Luxury Hotel Upgrade Program Ep #157: Costa Rica: A Top Travel Destination for Adventure, Rainforests and Relaxation with Javier Echecopar Ep #167: Best Tools for Booking Hotels with Points & Miles with Greg the Frequent Miler Ep #182: Shortcuts to Elite Travel Status with Greg the Frequent Miler Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: [email protected] Full Show Notes (00:00) Introduction (00:47) How Chris Got Six Free Hilton Night Certificates (01:53) How Hilton Free Night Certificates Work (02:59) Earning Free Nights with Hilton Credit Cards (04:13) Planning the Trip to Costa Rica (06:23) Buying Hilton Points (and the Caveats) (09:40) Ways to Earn Hilton Status (13:48) Stacking Amex and Hilton Credits (16:14) Booking Flights with Points & Leveraging Alerts (19:35) Renting Cars in Costa Rica (20:55) The Flight Experience (22:16) Adobe Car Rental Review (23:03) Waldorf Astoria Costa Rica Overview (25:20) How We Handled an Issue at the Hotel (30:09) Resort Layout, Pools & Amenities (33:16) Our Sensoria Rainforest Excursion (35:46) Diamante Eco Adventure Park & Zip Lining (37:06) The Dining, Drinks & Staff Experience (40:33) Sharing Feedback & Tipping the Hotel Staff (41:59) Overall Costa Rica Takeaways & Total Costs (45:33) How to Maximize Travel Perks without Points (48:50) Booking Carmel Valley Ranch with Hyatt Points (51:29) Hyatt Globalist Perks & Guest of Honor Certificates (54:08) Hyatt Brand Explorer Program (54:37) The Experience at Carmel Valley Ranch (58:21) Off-Property Activities & Local Recommendations (01:00:06) Trip Recap & Key Takeaways Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Today, I want to walk through how I saved over $10,000 at two luxury hotels across a few
0:05.7	recent trips, including how I booked a $2,000 a night Ocean View Suite at the brand new
0:11.7	Waldorf Astoria in Costa Rica for effectively under $300 a night.
0:16.1	But this isn't just a trip review.
0:17.7	I'm going to break down the exact strategies I used to make it all happen.
0:21.8	And the best part, these tactics don't just work with points. They can unlock huge savings
0:26.7	on cash bookings as well. So whether you're planning a big international trip or just a local
0:31.4	getaway, I'm going to show you how to maximize your savings, cards, credits, elite status,
0:36.4	points, and your booking strategy to get amazing
0:39.3	stays for way less. I'm Chris Hutchins. If you enjoy this episode and you want to keep upgrading
0:44.3	your life, money, and travel, click follow or subscribe. So let's start with a trip we just took to
0:49.9	Costa Rica. And the whole trip was inspired by six Hilton Free Night Certificates we had.
0:55.1	But when I walk through this whole process, I'm going to show you how you could get a very
0:58.8	similar, if not the same deal, which is effectively 65% off a five-star hotel with Hilton
1:05.4	points, with Amex points, or even just paying all in cash. So let's first talk about how we ended up with all of these
1:13.6	Hilton free night certificates. So it all started when we opened our first Hilton Aspire card.
1:18.3	It's a card from American Express. The card comes with diamond status, which is Hilton's top tier of
1:23.0	status. It comes with $200 in statement credits every six months for Hilton Resorts.
1:29.1	And then the big one is it comes with a free night reward.
1:32.0	And I'll talk in a second about how those free night rewards work.
1:34.9	But the card also comes with a clear credit each year.
1:37.9	And it comes with a $50 every quarter credit for different flight purchases that you make on the card.
	...

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