In this episode of the BoldlyGo Podcast, DeAndre and Taryn pull back the curtain on exactly what their points and miles strategy has looked like so far this year. They share the credit cards they've opened, the massive welcome bonuses they've earned, and the transfer opportunities they jumped on before valuable promotions disappeared. From Bilt's 100% transfer bonus to Japan Airlines and Citi's Preferred Hotels transfer ratio before devaluation, to Hilton free night certificate strategies and American Airlines loyalty planning, they explain the thought process behind every decision instead of simply listing card recommendations.

The episode also shifts from earning points to putting them into action with a long weekend in Charleston, South Carolina. DeAndre and Taryn review their first experience flying Breeze Airways, break down their Hilton hotel redemption, and share why Charleston quickly became one of their favorite food destinations in the United States. Along the way, they discuss buying points when the math works, balancing multiple hotel loyalty programs, and how thoughtful planning continues to create luxury travel experiences for a fraction of the retail cost. Rather than focusing on one perfect strategy, this episode offers a real time snapshot of how experienced travelers continuously adapt, diversify, and maximize every opportunity throughout the year.

Timestamps:

(00:00) Why This Is Our Biggest Mid Year Strategy Update

(03:51) Every Credit Card We Opened This Year

(05:49) Bilt Rewards and the Japan Airlines Transfer Bonus

(09:26) Amex Business Platinum and Hilton Strategy

(14:04) Citi Transfer Bonuses Before the Devaluation

(17:59) When Buying Points Actually Makes Sense

(22:21) Flying Breeze Airways to Charleston

(31:13) Our Hilton Hotel Stay Using Points

(36:30) The Best Food We Ate in Charleston

(43:23) Final Lessons From Our Mid Year Points & Miles Strategy

Key Highlights:

• Bilt Strategy: DeAndre shares why the Bilt Mastercard has become one of his favorite cards thanks to strong transfer partners and a 100% Japan Airlines transfer bonus.
• Credit Card Openings: Learn why the couple added cards like the Bilt Mastercard, American Airlines Globe, Amex Business Platinum, and multiple Hilton cards this year.
• Transfer Opportunities: Hear how they locked in valuable transfers before Citi reduced its Preferred Hotels and Choice transfer ratios.
• Buying Points: Discover why buying hotel points can sometimes deliver incredible value when redemption costs outweigh purchase prices.
• Hilton Diversification: Find out why they're intentionally expanding beyond Hyatt and building balances with Hilton and IHG.
• Charleston Getaway: Get a complete review of their first Breeze Airways flight, Hilton redemption, and favorite experiences around Charleston.
• Luxury Food Scene: Charleston impressed with outstanding restaurants, oysters, caviar, Southern cuisine, and memorable dining experiences.
• Mid Year Strategy Review: See how experienced points collectors constantly adjust their approach as welcome bonuses, transfer bonuses, and loyalty programs evolve.

Resources:

• BoldlyGo LIVE! Miami 5-7 Registration
• Check out our Podcast Library
• Become a BoldlyGo Blog contributor
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• Sign up for our newsletter!
• BoldlyGo Travel With Points & Miles Facebook Group

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Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

• Get Autopilot: Never Overpay for a Flight or Hotel Again
• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course:
• Use coupon code "BOLDYGO" for a 50% discount!

Connect with DeAndre & Taryn:

• Instagram: BoldlyGo.world
• TikTok: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld
• YouTube: BoldlyGo.Travels

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