Grab the Southwest Companion Pass Before the Door Closes ✈️

 

Southwest just made its best perk a lot harder to earn. Starting January 1, 2027, credit card welcome bonuses will no longer count toward the Companion Pass. If you’ve been on the fence, the next few weeks are your last window to use the credit card shortcut.

Why the Companion Pass Is Worth Chasing

The Southwest Companion Pass is basically buy-one-get-one airfare. Your companion flies with you for just taxes and fees, on as many flights as you want.

• Unlimited companion flights while the pass is valid
• Change your companion up to three times per calendar year

I just put this to work. My husband flew across the country as my companion. When I got home, I switched my companion to a friend and added her to my upcoming flights to New Orleans. 🎉The past 10 years, I've used the pass to take family members on college trips, family events and just plain fun vacations to places like Cuba. 

What’s Changing in 2027

Here’s what the new rules look like:

• Welcome bonuses won’t count. Credit card sign-up bonuses, referral bonuses, anniversary points, and bonus-category points will no longer count toward the pass.
• What still counts: flights and everyday spending on Southwest credit cards, which will earn 1 Tier Qualifying Point (TQP) per dollar.
• The full pass will require Platinum status: 100 qualifying flights or 140,000 TQPs. That’s roughly $140,000 in credit card spending. Yikes. 😬
• A smaller option: 75 flights or 95,000 TQPs gets you three Companion Pass trips, not unlimited. That’s still a big ask for most families.

Bottom line: if you want the Companion Pass, now is the time.

My Game Plan for Earning It Now

1. Apply for the Southwest Premier Business Credit Card FIRST,

• Bonus: 80,000 points after $3,000 in spending within 3 months
• Annual fee: $149
• Offer ends November 2. Don’t wait until the last day. Chase is known for pulling offers early.
• Your business income: side income like freelance work, consulting, or a small online shop can qualify you for a business card. You can include your salary too.

2. Then, before December 2, apply for a personal Southwest credit card.

• Any personal Southwest card works, so the $99 Plus card is an easy pick
• Minimum spend: $1,000

Hit the December 2 deadline. You must be approved on or before December 2, 2026 for the welcome bonuses to count. The good news is that they still count if you finish the minimum spend in early 2027.

Let’s Do the Math 🧮

• Bonuses: 80,000 + 50,000 = 130,000 points
• Minimum spend: about 4,000 points
• Total: about 134,000 points

You need 135,000 qualifying points to earn the pass. That means you’ll need to charge roughly another $1,000 to either card to get over the line.

Once you earn it, your Companion Pass is valid through December 31, 2027. That’s a full year of BOGO flights.

Talk to Me Before You Apply

Please reach out before you hit “apply.” We need to confirm two things:

• You qualify under Chase’s 5/24 rule and the 3/24 rule
• Your timing works, because the deadlines here are tight and there’s no do-over

Want more personal help using points and miles for almost FREE travel? Talk to me about your next trip and I'll figure out the best way to use your points and miles, Book a 1:1 consulting call, download my ebook, custom tracker or Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process.

Right now, you can use the promo code "LETSGO" to get $50 off the coaching program. I would love to help you make priceless family memories affordable. 

*For every new client, we will donate 10% of the proceeds to one of our favorite charities. 

80,000-Point Offer on the Southwest Premier Business Card — But Should You Wait? ✈️

Chase just increased the welcome bonus on the Southwest Rapid Rewards Premier Business card to 80,000 points. The Performance Business card already offers 80,000 points as its standard bonus, but this new Premier Business offer keeps the $3,000 minimum spend and the $149 annual fee — a much easier bar to clear for the same point total. 👏

It's a good offer. Not the biggest we've ever seen, but good.

However — if you have your eye on the Southwest Companion Pass for 2027–2028, hold off. 🛑

The timing that matters

This offer ends October 26, 2026, and you'll have 3 months from approval to hit the minimum spend and earn the points.

Here's the catch: to earn the Companion Pass for 2027 AND 2028, your points need to post in 2027, not 2026.

So the play is this: if you can apply after October 15th, you'll have until roughly mid-January to meet the minimum spend, which gives your bonus a good chance of posting in early 2027 instead of 2026.

⚠️ Don't cut the timing too close. It's easy to accidentally post your points in 2026 and lose an entire year of Companion Pass eligibility.

A cautionary tale

Three years ago, a friend did exactly that. Luckily, she was well under 5/24 and was able to apply for another Southwest Business card to try again. These days, though, that safety net is shrinkier: there are widespread reports of Chase enforcing a stricter 3/24 for sole proprietor business applications, so it's much harder to simply apply again if your timing slips.

Bottom line: don't take chances with this one — watch your timing carefully. If you decide to apply, please use my referral link. 🔗

I am launching a Fall 2026 cohort to help you, it's FREE to join, but limited to just 10 people. I recommend that you purchase my points and miles course, but you do not need to. You can sign up here. 

Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process. Right now, you can use the promo code "LETSGO" to get $50 off the program. 

Or you can pay a travel planning fee and we will find all the best points and miles deals for your trip! 

Or you can book a consulting call with us for just $100. I would love to help you make priceless family memories affordable. 

***In honor of every new paid client, we will make a donation of 10% to one of our favorite charities.

You Hit 100,000 Chase Points — Now What? 🎉

Two clients in the last two days have told me they either earned their 100,000-point bonus on the Chase Sapphire Preferred, or they're super close. But the very next question is always the same: now what?

And if you missed the 100,000 bonus offer from this card, you have a new option, the Capital One Venture credit card which is offering 75,000 bonus points and a $300 travel credit. 

So let's talk next steps. What can you actually do with 100,000 Chase Ultimate Rewards points? Here are your options. 👇

1. Book travel directly in the Chase Travel Portal ✈️

This one's easy — it works just like any third-party booking platform. It's a solid option for booking Alaska Airlines and American Airlines flights. I don't recommend booking Southwest this way, though — you'll usually find better value if you transfer your points to Southwest directly instead (more on that below). You can also book hotels this way. It's a great option for booking independent hotels. 

Hot tip: 🚀 Look for the little rocket icon that signifies a Points Boost — it means your Ultimate Rewards points are worth more than 1:1 for that booking.

2. Transfer your points to an airline partner and book directly

Chase currently partners with 10 airlines, and several of those airlines belong to larger alliances with other carriers, so your options open up even more from there.

One of my favorite transfer partners is Flying Blue, the loyalty program for KLM and Air France. Sometimes you can snag economy seats from the West Coast to Europe for as little as 18,750 points.

Another favorite is Iberia. I just booked a flight from San Francisco to Madrid for 20,000 points and $154. 💸

Hot tip: 🔍 Check both the Chase portal and the airline's own website before you transfer any points. Transfers are one-way — once your points move, you can't get them back.

3. Transfer your points to a hotel partner 🏨

You can also transfer your Ultimate Rewards points to four hotel chains, including Hyatt. All of them transfer at 1:1 — except Hyatt, which is shifting to a 4:3 ratio on October 1st. So if you're eyeing a Hyatt reservation, now's the time to make the move.

👀Just a reminder, this card comes with a $100 hotel credit good in the Chase Travel Portal. You can read here about how to spend it. 

Hot Tip: 💕There are usually bonus points offers every month where you get a percentage more value when you transfer your points. 

4. Book rental cars, cruises, tours, and activities 🚗

You can book all of these directly through the Chase Travel Portal too. Just always weigh the value of your points against paying cash — sometimes cash is the smarter call.

Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process. Right now, you can use the promo code "LETSGO" to get $50 off the program. 

Or you can pay a travel planning fee and we will find all the best points and miles deals for your trip! 

Or you can book a consulting call with us for just $100. I would love to help you make priceless family memories affordable. 

***In honor of every new paid client, we will make a donation of 10% to one of our favorite charities.

100,000-Point Bonus Just Posted — Here's What That's Actually Worth 🎉

100,000-Point Bonus Just Posted — Here's What That's Actually Worth 🎉

Look what showed up in my Chase account today: a 100,000-point bonus from the Chase Sapphire Preferred! This offer won't be around much longer, so if you've been thinking about applying, now's the time.

Here's the deal: you'll earn 100,000 points for a $95 annual fee (offset by a $100 hotel credit), after spending $5,000 within the first few months. It's one of the strongest offers out there right now. You can read more here about why I'm such a fan of this card and Chase Ultimate Rewards points in general.

So, what can you actually do with 100,000 points? A lot, it turns out. 👇

• Transfer to Flying Blue (KLM's loyalty program) and fly Los Angeles to Amsterdam nonstop — up to four times over
• Transfer to one of a dozen+ airline and hotel partners, including Hyatt
• Book straight through the Chase Travel Portal — think 4 nights in Hawaii covered by points alone 🌺

That's the beauty of Chase Ultimate Rewards points — they flex to fit however you want to travel. If you've been on the fence about this card, or aren't sure if you're eligible, let's talk it through.

Want a strategy session like this one? I offer 30-minute credit card audits for just $100. Book your session here.

Want more personal help using points and miles for almost FREE travel? Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process. Right now, you can use the promo code "FREETRAVEL" to get $50 off the program. 

Or you can pay a travel planning fee and we will find all the best points and miles deals for your trip! 

***In honor of every new paid client, we will make a donation of 10% to one of our favorite charities.

A 30-Minute Credit Card Audit That Changed Everything

A 30-Minute Credit Card Audit That Changed Everything

A friend sat down with me last week feeling overwhelmed — too many credit cards, no clear strategy, and a nagging sense that he was leaving points on the table. Thirty minutes later, we had a streamlined plan. Here's exactly what we did, so you can run the same audit on your own wallet.

The Starting Lineup 💳

My friend's current cards:

1. Discover
2. Marriott Bonvoy
3. United Airlines
4. American Express Gold
5. Citi Costco Visa

How He Was Actually Using Them

• His United card was doing all the heavy lifting as his everyday card — which made sense on the surface since he frequently flies United out of his home airport and gets a free checked bag and lounge access. But his travel patterns told a different story: every other year, the family heads to Mexico or another destination entirely, which means United miles aren't always the most useful currency.
• His Marriott Bonvoy card comes with a free annual night certificate (worth up to 25,000 points) for just $95 a year — which sounds great. The problem? The certificate kept expiring unused. That's $95 out the door for nothing.
• His Citi Costco card generates around $1,700 in annual cash back 💰, which he loves — and honestly, that's hard to argue with. I did flag that the Amex Gold might outperform it on certain spending categories, but cash back in hand is a real thing and I respect it.
• His Amex Gold card? Sitting in a drawer, completely unused. That's where we saw the biggest opportunity.

The New Strategy 🎯

Switch the primary card to the Amex Gold. This is the biggest move. The Amex Gold earns 4x points at restaurants and U.S. supermarkets — two of the highest everyday spending categories for most people. More importantly, those are Amex Membership Rewards points: flexible points that transfer to dozens of airlines like Delta, British Airways, Air France, and more. Though United is not a transfer partner, he could book United through the American Express Travel portal. The earning potential on the Amex Gold far outpaces a co-branded United card for non-flight spending.

Cancel the Marriott Bonvoy card. If the free night certificate expires most years and Marriott points have continued to lose value, this card is costing $95 annually for essentially nothing. Time to let it go ✂️

Keep the Discover card. This is his oldest account, and the age of that credit line matters for his credit score. It stays.

Apply for the Chase Sapphire Preferred — now. 🌟 The current 100,000-point welcome bonus for a $95 annual fee (offset by a $100 hotel credit) is one of the strongest offers on the market right now. Chase Ultimate Rewards points are also flexible, transfer to United Airlines directly, and open up a whole world of redemption options beyond just one airline. This card becomes a natural complement to the Amex Gold.

The Result

With two simple changes — activating the Amex Gold as the everyday card and adding the Chase Sapphire Preferred — my friend goes from a single-airline points collector to someone building flexible points across two of the most powerful currencies in travel. Same spending, dramatically better earning power.

---

💬 Want a strategy session like this one? I offer 30-minute credit card audits for just $100. Book your session here.

Want more personal help using points and miles for almost FREE travel? Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process. Right now, you can use the promo code "FREETRAVEL" to get $50 off the program. 

Or you can pay a travel planning fee and we will find all the best points and miles deals for your trip! 

***In honor of every new paid client, we will make a donation of 10% to one of our favorite charities.

I Already Have the Chase Sapphire Reserve — So Why Did I Just Apply for the Preferred

A 100,000-point Chase Ultimate Rewards bonus is hard to walk away from 👀 — so I didn't. Even though I already carry the Chase Sapphire Reserve, I went ahead and applied for the Chase Sapphire Preferred. And yes, my clients immediately started asking why on earth I'd want both. Here's the full breakdown.

The Preferred Earns in Ways the Reserve Doesn't 💳

The Chase Sapphire Preferred carries a $95 annual fee, which is effectively offset by a $100 hotel credit — so the card is essentially paying for itself before you even swipe it once.

But where it really shines is the earning structure. The Preferred earns 3x points on vacation home rentals — Airbnb, VRBO, the works. I have several Airbnb stays already on the books, so this one category alone is going to add up fast 💰 It also earns 3x on dining and gas (including EV charging), and 5x points when booking through the Chase Travel Portal.

Where the Reserve Still Wins 🏆

For flights and hotels booked directly, the Reserve pulls ahead with 4x points — and if you book through the Chase Travel Portal, it jumps to an impressive 8x points. The Reserve also offers better redemption rates for World of Hyatt transfers, a points boost on redemptions, plus lounge access and a stack of travel, hotel, and dining credits.

The catch? A $795 annual fee and a fair amount of mental energy to track and use all those credits each year. You can read here about how I used the credits for a whirlwind weekend in Las Vegas. 

Now that I have the Preferred in my wallet, I'm genuinely reconsidering whether I'll renew the Reserve when the annual fee hits again.

The Good News: You Can Combine Them 🔄

One of the best features of holding both cards is that you can transfer points from the Preferred directly to the Reserve — which means you earn on the Preferred's strong bonus categories and redeem at the Reserve's better rates. Best of both worlds, at least for now.

Oh, and a few more perks worth mentioning: the Preferred comes with one free year of Apple TV+ , $120 Global Entry credit, a complimentary Dashpass membership and a $10 monthly credit for groceries and great travel protections. 

Bottom Line

If you already have the Reserve and you're eligible for the Preferred's 100,000-point welcome bonus — apply. The math makes sense and the card earns its keep on its own. If you have the Preferred and are eyeing the Reserve, take your time. The higher annual fee requires a real commitment to maximizing the credits to justify the cost.

If this all gives you a headache, and you want more personal help using points and miles for almost FREE travel? Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process. Right now, you can use the promo code "FREETRAVEL" to get $50 off the program. 

Or you can pay a travel planning fee and we will find all the best points and miles deals for your trip! 

Or you can book a consulting call with us for just $100. I would love to help you make priceless family memories affordable. 

***In honor of every new paid client, we will make a donation of 10% to one of our favorite charities.

  

💳 How to Triple Stack Points on Every Online Purchase

 

💳 How to Triple Stack Points on Every Online Purchase

Every time you shop online, there's a question worth asking: how many points or miles can I earn here?

Earning some points? Nice. Earning double points by layering two sources? Even better. Earning triple points across three sources at once? That's the triple stack — and it's one of the most satisfying moves in the points game.

Here's how it actually works, with a real purchase to show you exactly what's possible.

🌸 The Triple Stack in Action: A Flower Delivery Example

The goal: Buy birthday flowers for a friend ($66 total)

Flower delivery services are basically interchangeable, so the smarter move is choosing the one that earns you the most — not just picking the first result that pops up.

🔍 Step 1: Check for Credit Card Bonus Portals

Chase has an ongoing partnership with the digital payment platform Paze that earns 10x Ultimate Rewards points plus a $10 statement credit on purchases. The first step is checking the Paze merchant directory under flowers and gifts — and sure enough, 1-800-Flowers is listed. Read here about how to link your credit card to Paze.

✅ That locks in Layer 1.

🖥️ Step 2: Check Shopping Portals

Head to CashBackMonitor.com to see every shopping portal where 1-800-Flowers is listed. This is where you decide if a hotel or airline portal makes more sense than a cashback option.

A few things to consider at this step:

• Is any airline or hotel portal running a bonus promotion right now?
• Do you need to top off a specific loyalty account before a trip?
• Are any of your points or miles close to expiring?

In this case, the American Airlines AAdvantage shopping portal made the most sense.

✅ That locks in Layer 2.

💰 Step 3: Pay with the Right Card

Check out using Paze with your linked Chase Freedom Flex or Sapphire credit card.

✅ That locks in Layer 3.

🏆 The Triple Stack Breakdown

Here's what a $66 flower purchase earned:

Source	Reward
American Airlines shopping portal	350 AAdvantage miles
Chase Freedom base earn	66 Ultimate Rewards points
Paze 10x bonus	660 Ultimate Rewards points
Paze statement credit	$10 back

Total: 350 AA miles + 726 Chase points + $10 statement credit — on a $66 purchase you were going to make anyway.

🗺️ The Triple Stack Formula

Whenever you're about to buy something online, run through this quick checklist:

1. Check your credit card bonus offer (Chase Paze, Amex Offers, 5x bonus categories, Rakuten.com etc.)
2. Check shopping portals on CashBackMonitor.com to find the best rate
3. Choose the portal that fills a loyalty gap (expiring points, upcoming trip, bonus promo)
4. Pay with the card that earns the most in that category

The key is always checking before you check out — once the purchase is done, those layers are gone. 🎯

Want more personal help using points and miles for almost FREE travel? Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process. Right now, you can use the promo code "FREETRAVEL" to get $50 off the program. 

Or you can pay a travel planning fee and we will find all the best points and miles deals for your trip! 

Or you can book a consulting call with us for just $100. I would love to help you make priceless family memories affordable. 

***In honor of every new paid client, we will make a donation of 10% to one of our favorite charities.

Wow! Another Huge 100,000 Bonus Offer From Chase

Wow! The huge bonus offers just keep coming! Chase announced an amazing 100,000 bonus offer on its Chase Ink Business Preferred credit card. 

What are 100,000 CUR points worth? If you use them in the portal, they are worth $1,000. But we show people how to use those points to increase their value up to more than $2,000. You can read here how I used CUR points to take my family to Europe. 

Here's the offer 

• 100,000 Chase Ultimate Reward points
• $8,000 minimum spend in three months 
• $95 annual fee 
• 3x points on select business purchases such as travel, shipping, internet, cable, phone and advertising

Watch the fine print here, if you have EVER had this credit card before you may not be eligible for the bonus. 

This is also a business credit card, but many side hustles qualify as businesses. You can read here about how to determine if your business will qualify. 

If you decide to apply for the Ink Preferred credit card, please use my referral link. 

Want more personal help using points and miles for almost FREE travel? We have three different options to choose from:

• Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process. Right now, you can use the promo code "FREETRAVEL" to get $50 off the program. 
• Or you can book a consulting call with us for just $100. 
• Or you can hire us to plan your entire trip using points and miles! 

I would love to help you make priceless family memories affordable. 

***In honor of every new paid client, we will make a donation of 10% to one of our favorite charities.

I Booked a Last-Minute Caribbean Solo Cruise — Here's What Actually Happened

I Booked a Last-Minute Caribbean Cruise From New Orleans — Here's What Actually Happened

I was already heading to New Orleans for a conference when it hit me: I was closer to the Caribbean than I ever am from California. Why not tack on something bigger? I hadn't added a new country to my list yet this year, so I started poking around flights and hotels. The prices — even with points — were brutal. 😬

Then I noticed Chase Freedom was offering 5x points on Norwegian Cruise Line. A quick search later and I found a 7-day cruise departing from NOLA hitting Mexico, Belize, and Honduras. That knocked out several destinations in one shot.

I hadn't been on a cruise in 30 years, but I was open to it. Full transparency: NCL offered me a travel agent discount plus some extras. I booked a solo studio — a 99 sq ft inside cabin tucked into a secure solo-only section of the ship — upgraded my WiFi for work (150 free minutes came with the booking), and locked in snorkeling excursions at three of the four ports. ✅

Boarding: Brace Yourself

NCL sends a flood of pre-boarding emails covering luggage tags, upgrade offers, and cruise logistics. What they don't fully prepare you for is the boarding crowd. It's chaotic. 

👉Hot tip: check in online as early as possible — it determines when you can board, and earlier boarding means smaller crowds. Also worth knowing: you don't have to wait for your assigned boarding time despite what NCL tells you. Show up when you're ready. 

And you can opt to keep your carry on luggage with you. 

Once on board, rooms aren't available until later in the afternoon, but the pool, bars, and lunch are all yours. I spotted people already in the hot tub by 1pm. 🛳️

The Solo Studio Setup

The solo studio cabin itself is compact but smartly designed, and the real selling point is what surrounds it. The Studio Lounge is a secure, solo-travelers-only space stocked daily with fresh fruit, baked goods, lemonade, water, and an espresso machine. For anyone fueled by coffee ☕, that last one matters more than you'd think.

Every day, a solo traveler coordinator runs a meetup — a genuinely useful way to connect with the 60 other solo guests on board. Ages ranged from 30 to 80, first-timers alongside seasoned Platinum cruisers. Some were even doing back-to-back sailings on the same ship (no need to disembark or switch cabins, by the way — you just keep going).

After the daily meetup, the coordinator organizes group dinners at one of the sit-down restaurants, so eating alone is entirely optional. The three main dining rooms share similar menus but each has its own atmosphere. The food was genuinely good — not just "fine for a cruise." One evening my new solo crew invited me to the specialty sushi restaurant and it did not disappoint. 🍣

The buffet runs 6am–9:30pm and covers a lot of ground: salad bar, sandwiches, pasta, Indian, soup, and made-to-order eggs at breakfast. You will not go hungry. There is also a bar food type pub open 24/7.

Evenings on Board

After dinner, the ship basically becomes its own entertainment district. During the cruise, I caught four shows in the main theater, a comedy set, an NCL presentation, live music at a bar, and a dueling piano night. 🎹 So funny, all the music onboard is from the 70's, 80's and 90's. 

The Escape also has a ropes course, mini golf, bowling, waterslides, a basketball court, and an arcade. You can go hard or you can find a quiet corner — completely up to you.

The Ports 🤿

I chose snorkeling for three of the four port days, and each experience was completely different.

• Roatan, Honduras: The guide took us to a dramatic drop-off — a 400-foot depth change from reef to ocean floor. Jaw-dropping.
• Cozumel, Mexico: Strong current meant drift snorkeling the whole way. You just float and let the ocean do the work.
• Belize: Snorkeling the second-largest reef in the world after Australia's Great Barrier Reef. Worth every minute.

One practical note on booking excursions: if you go through NCL, the ship is responsible for getting you back on time — and if something delays you, they'll wait. Book independently and that responsibility shifts to the tour operator. I've spoken with independent operators who take this seriously and will cover transport if the ship leaves without you, but for my own peace of mind I booked through NCL. (I can also get clients $50 off NCL excursions, so there's no financial upside to going outside.)

The ports themselves have changed a lot over the years — think high-end shops, solid restaurants, swim-up bars, zip lines, butterfly gardens, beach clubs, and yes, fish pedicures. 🦋

The Verdict

The week moved fast. My new solo travel crew has already booked a cruise together for next year — which probably tells you everything you need to know. 🌊

Want more personal help using points and miles for almost FREE travel? Join my Travel Coaching Program and we will design your personal strategy to travel for almost FREE and guide you through the process. Right now, you can use the promo code "FREETRAVEL" to get $50 off the program. 

Or you can book a consulting call with us for just $100. I would love to help you make priceless family memories affordable. 

***In honor of every new paid client, we will make a donation of 10% to one of our favorite charities.