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How the Chase Sapphire Preferred Helped Me Travel to These Dream Destinations for (Almost) Free
If you’ve been reading FinancialBeef for a while, you know I’m obsessed with two things: making my money stretch and getting the most out of travel rewards. Lately, the Chase Sapphire Preferred has been my go-to tool in that game. In this post, I’m not just going to tell you the usual reasons why it’s a good card. I’m going to walk you through exact destinations you can reach, how I’ve used the card myself, and step-by-step strategies to do the same.
Why the Chase Sapphire Preferred Is My Ride-or-Die Card Right Now
Let’s start with what matters: value.
As of May 2025, Chase is offering 75,000 Ultimate Rewards points when you spend $4,000 in the first 3 months. I’ve personally redeemed these points (and then some) for flights, hotels, and rental cars in:
- St. Kitts
- Denver
- San Francisco
- Napa Valley
- Lake Tahoe
Chase points transfer at a 1:1 ratio to 14 different partners—like Hyatt, United, Air France/KLM (Flying Blue), British Airways, and Iberia. That’s the key. The flexibility is what makes it the most valuable point currency in the game right now, especially if you’re aiming for premium redemptions.
1. 🏝 St. Kitts: Island Luxury Using Points and Portal Hacks (While Expecting Our First Child)
This trip to St. Kitts will always hold a special place in my heart—my fiancée was deep into vet school at the time, and things were stressful for both of us. Between her demanding schedule and the pressure we were under, we really needed a break. Being able to book those flights for free with points took a huge weight off our shoulders and gave us a chance to reset in one of the most peaceful places we’ve ever stayed. We rented a place just off a golf course, surrounded by green fairways and panoramic mountain views. The stillness of the mornings and the lack of distractions gave us the space to unwind, reset, and reconnect. It was exactly what we needed during that season of pressure and nonstop hustle. Easily one of the most peaceful and restorative environments we’ve ever experienced.
We weren’t looking to ball out—we just wanted comfort, great views, and a sense of space—and thanks to the Chase Sapphire Preferred, we got all of that without stretching our bank account.
When we went to St. Kitts, the beaches and quiet luxury vibe felt like something out of a magazine spread. But I wasn’t paying luxury prices thanks to the Sapphire Preferred.
Flights:
I transferred 20,000 UR points to United MileagePlus, then booked two one-ways to St. Kitts. United runs flights from Newark and DC pretty frequently. Taxes were minimal—about $5.60 each.
Hotel:
There is a Park Hyatt in St. Kitts, and while it looks stunning, it’s typically priced at over $1,000 per night or 30,000+ Hyatt points per night. At the time, that wasn’t a justifiable use of our points given everything else going on—vet school loans, baby planning, you name it. Instead, I used the Chase Travel Portal to book a boutique hotel for ~$300/night. At 1.25 cents/point, I spent 72,000 points for three nights, all covered—and still got a great experience right by the water., so I used the Chase Travel Portal to book a boutique hotel for ~$300/night. At 1.25 cents/point, I spent 72,000 points for three nights, all covered.
Strategy:
- Use United or JetBlue (also a Chase partner) for Caribbean redemptions
- Don’t skip the Chase portal when transfer partners aren’t ideal
- Sapphire Preferred gives you 1.25¢ per point value on the portal, which adds up fast
2. 🏔 Denver: Mountain Vibes + Urban Cool — All on Points
Denver is underrated in the travel hacking world. Between the breweries, the views, and the proximity to mountains, it’s a perfect long weekend destination.
Flights:
I booked roundtrip flights using Southwest points—transferred from Chase Ultimate Rewards. The roundtrip cost was about 22,000 points plus a couple bucks in taxes.
Hotel:
Stayed at the Hyatt Centric Downtown Denver for 12,000 points per night. Three nights = 36,000 points. Walkable to everything.
Strategy:
- Pair Sapphire Preferred with a Freedom Unlimited to earn faster and transfer to Southwest
- Hyatt properties are often cheaper in points but high in value—perfect combo
- Denver is a good example of where domestic hacking can still be impressive
3. 🌉 San Francisco: Chase-Fueled City Escape
I used to think San Francisco was just expensive. Then I learned how to book smart with UR points.
Flights:
Used Chase Travel Portal to book roundtrip flights from Philly for around $350. That was 28,000 points total, and it saved me from dealing with limited transfer partner availability.
Hotel:
Booked the Hyatt Regency San Francisco on the Embarcadero using 20,000 points per night. For a city like SF, that’s a steal.
Strategy:
- Always compare portal vs. transfer partners. Sometimes the portal wins.
- Use Sapphire Preferred’s 1.25x bonus on portal redemptions
- Look for off-peak weekends to stretch your points further
4. 🍷 Napa Valley: Wine Country for Less Than the Cost of a Bottle
If you know me, you know Napa is my kind of place. Great food, better wine—and it’s not cheap. That’s why points made it possible.
Flights:
I used Southwest points (transferred from Chase) to fly into Oakland, then drove up to Napa. Flights cost around 24,000 points roundtrip.
Hotel:
Used Chase portal points to book The Meritage Resort & Spa, which usually runs about $400/night. I spent 80,000 points for two nights, all covered.
Strategy:
- Always check for luxury properties on the Chase portal
- Book weekday stays for better redemption value
- Combine a Southwest Companion Pass with UR points for even more savings
5. ❄️ Lake Tahoe: Mountain Adventure on a Budget (Kind Of)
Tahoe was one of those trips where a mix of portal and partner redemptions saved me a couple thousand bucks.
Flights:
Booked flights into Reno using Ultimate Rewards through Chase Travel, about $425 roundtrip, covered by 34,000 points.
Hotel:
Stayed at the Hyatt Regency Lake Tahoe Resort, Spa & Casino in Incline Village. Used 30,000 Hyatt points per night, but got over $700/night in value.
Strategy:
- Use Chase to book Tahoe in summer or winter—both seasons have value
- Hyatt redemptions here are incredibly valuable compared to cash rates
- Book early, as Tahoe fills up fast (especially weekends)
My Chase Sapphire Workflow (a.k.a. How I Maximize Every Point)
Here’s what I personally do to make the most of this card:
- Track all bonuses and deadlines in Notion (I even made a template—link below)
- Funnel all big purchases toward current signup bonus
- Pair it with a Freedom Unlimited for 1.5x on non-category spend
- Set calendar reminders for annual fees, downgrade options, and transfer bonuses
- Transfer only when I have a redemption ready
Want to Do the Same?
If you’re not sure where to start:
- Use my Notion Credit Card Tracker (I designed it to match these strategies)
- Check your 5/24 status—don’t apply if you’re over 5 cards opened in the past 24 months
- Set up spending automation (utilities, streaming, insurance) to hit minimum spends
- Book off-peak or shoulder season trips to stretch your points further
And if you’re traveling as a couple or family? Player Two strategy: stagger card applications with your partner to double your points potential.
Closing Thoughts
If you’ve read this far, you know I don’t just throw random advice on this blog. Everything above is something I’ve personally done or helped others plan. The Chase Sapphire Preferred is hands-down the most powerful card in my wallet right now. And it’s not just about the points—it’s about the freedom to book a trip you otherwise couldn’t afford, or wouldn’t justify.
And if you’re someone who values flexibility, simplicity, and real travel experiences over hoarding points, then this is the strategy that works.
Next Steps:
- Apply for the card if you haven’t yet
- Set a goal destination (then reverse-engineer the redemption)
- Use my templates and guides to stay on track
Let the banks pay for your next trip. You’ve earned it.
Resources:
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