Travel Party of 5 | Points & Miles for Family Travel

We share how our family trip through Milan and Rome goes sideways and somehow still turns into one of our most memorable travel weeks. We break down what we do when plans fall apart, how we use points and miles to reduce the damage, and what we learn about city travel with three kids.
• extending Switzerland because Italy prices surge
• booking a multi train route to Milan with the SBB app
• why first class seating helps on long train days
• what to do after missing a train connection
• first impressions of Milan plus a very small room
• Duomo crowds rush hour metro and dead phone stress
• the Stussy shirt mix-up and making the train
• a standout pizza night with surprise drinks
• high speed train booking timing to unlock family discounts
• how we handle the Thompson Rome cancellation and get rebooked
• Rome activities that work well for kids plus what feels overrated
• our pasta and tiramisu cooking class highlights
• airport lounge reality checks in Rome and Paris
• using Air France Flying Blue points and Marriott free night certificates
• reflections on outdoor trips versus big cities for our current season
If you have any questions, feel free to message me on Instagram at travelpartyof5

We move our family of five from Wengen to Grindelwald and turn a simple transfer day into a Lauterbrunnen biking adventure. Along the way, we share what surprised us most about costs, crowds, and how points and miles actually play out when you’re traveling with kids.
• choosing between Wengen and Grindelwald as a home base
• storing luggage in Lauterbrunnen and timing the transition day
• renting bikes for five and navigating busy streets with a young rider
• seasonal trade-offs like chilly weather and low waterfalls
• Switzerland sticker shock like paid condiments and restaurant water
• walking to Bergwelt Grindelwald and the hidden hill and stairs
• booking an SLH Hilton hotel on points plus paying an upgrade fee
• what we get right and wrong about room setup for a family of five
• free breakfast value and the spa rules including towel-only saunas
• comparing Grindelwald First crowds with Pfingstegg fun factor
• why the alpine coaster is worth repeating
• laundry realities, a too-cold pool, and mini golf with a view
• dinner lessons on reservations plus a surprise win at Hotel Bodmi
We Will Catch You Next Week All About Milan And Rome.

We take our family of five to Wengen, a car-free village in Switzerland’s Jungfrau region, and share what worked, what cost the most, and what we would change next time. We also walk through our points flights to Zurich, the Swiss transit pass decision that saved us money, and our favorite kid-friendly mountain days.
• pivoting from an Italy-first plan to more time in Switzerland
• booking five business-class seats to Zurich with points and managing a tight Frankfurt connection
• deciding between the Swiss Travel Pass and the Swiss Half Fare Card using real trip math
• using the SBB app, adding kids correctly, and handling frequent ticket checks
• choosing Wengen as a peaceful, walkable home base and booking a spacious apartment with laundry
• planning day trips with live webcams and staying flexible on timing
• riding to Murren and Allmendhubel for a mountaintop playground lunch day
• doing Wengen marble runs and using the Co-op grocery store to reduce meal costs
• splurging on Jungfraujoch Top of Europe, plus tubing, zip line, ice palace, and cold-weather packing
• visiting Mannlichen for the giant cow playground and hiking the Lieselotte trail downhill
• noticing how hills and walking can limit accessibility and affect taxi decisions
If you want to see like where we stayed or pictures or videos or anything, go check out the highlights.
And if you have any questions, find me on Instagram. Let me know.

We turn a Boston positioning flight into a mini trip and share what worked for our family of five, from points bookings to kid-friendly sightseeing. We also give our unfiltered take on the Hyatt Regency Boston, the Boston Tea Party Museum hype, and the airport logistics we’d handle differently next time.
• why positioning flights can feel stressful or feel like a bonus trip
• booking a nonstop Phoenix to Boston flight with American Airlines points and Main Cabin Extra seats
• the Chase lounge wait and the $90 backup meal lesson
• using Amex Platinum Uber credits for rideshare
• Hyatt Regency Boston on free night certificates, upgrade request and junior suite realities
• breakfast highlights, late starts and planning activities around the time change
• Freedom Trail tour pros, pacing and what keeps kids engaged
• Boston Tea Party Museum expectations and what the experience is really like
• dinner at Legal Sea Foods and a lobster roll worth ordering
• using Blacklane for airport transfers and navigating terminal construction
• a reminder to stay kind when airline disruptions overwhelm staff
If you'd like to see the photos, there's one on my Instagram story on the on the Boston highlight, so you can go take a look. Um, and then let me know your thoughts. What do you think? Explosive diarrhea or murder toilet? You you let me know.

American Airlines status can look pointless for family travel until you break down how loyalty points are earned and what perks actually reduce stress on travel days. We share our honest take on whether chasing AAdvantage elite status is a money move, a comfort buy, or a little of both.

• AAdvantage status tiers and loyalty point thresholds
• Miles vs loyalty points and why the difference matters
• Four main ways we earn loyalty points: flights, card spend, hotels, shopping portal
• Why basic economy pricing drives family decisions and what it costs you on status
• What each status level really unlocks: boarding groups, bags, seats, upgrades
• How status benefits apply to everyone on a booking and where upgrades break down
• Why living in an American Airlines hub changes the value
• The psychological payoff: less gate stress, overhead bin confidence, better service recovery odds
• A real travel story that shows the downside of having no status perks
• Upgrade expectations at Gold, Platinum Pro, and Executive Platinum
• Shopping portal strategy and watching for elevated offers

If you have any questions about anything that I talked about today, feel free to send me a DM on Instagram.

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As always, thank you for using our links when possible ❤️

In this episode I walk through what’s changing in our points and miles strategy right now, including the credit cards we’re opening, the programs we’re leaning on, and the mistakes we’d avoid if we could rewind. We also share real-time trip planning updates, from a last-minute Rome hotel problem to the challenge of finding five business class award seats for Europe and Asia.
• tracking Duane's 5/24 status and why we pace personal cards
• why we applied for the Qatar card and why we regret it after the rule change
• targeting Bank of America cards for Alaska miles and Flying Blue benefits
• building a path to a Chase business card by forming an LLC and getting an EIN
• reacting to the Aeroplan card refresh and what it changes for grocery spend
• watching elevated Hilton offers to stockpile free night certificates
• using Bilt points and accelerators plus paying the mortgage with Bilt
• dealing with Switzerland and Italy planning plus Rome hotel uncertainty with Hyatt
• mapping spring break with Orlando and Turks and Caicos to avoid red-eye flights
• searching for five business class seats to Norway and Copenhagen
• explaining phantom award availability after a Flying Blue transfer
• planning a return to Japan with a Guam add-on and airlines we’re considering
• transfer bonuses on our radar including Avios and Hilton
If you're thinking about getting a built card, I would absolutely love it if you would use our referral link. I will link it in the show notes.
If you found this episode useful please follow the show so you don't miss the next one and I will catch you next time on the podcast or on Instagram.

We compare a brand-new Park Hyatt Los Cabos stay with a Waldorf Astoria Los Cabos Pedregal stay, down to the rooms, pools, food, and spa experience. We also break down the exact points and certificates we used, what Cabo costs surprised us most, and which resort we would pick next time depending on whether we’re traveling with kids or not.
• choosing Cabo for a short kid-free getaway and why low season changes the vibe
• booking the Park Hyatt Cabo with Hyatt points and a suite upgrade award
• what the Park Hyatt plunge pool suite is like and the privacy trade-offs
• Cabo resort pricing reality and why a grocery stop can save your trip budget
• Park Hyatt food impressions and the spa discount misunderstanding
• getting to Waldorf Astoria Pedregal and what feels different on arrival
• concierge planning, birthday surprises, and romantic turndown details
• Waldorf dining strategy: when to skip the restaurant and order poolside
• Hilton Diamond breakfast rules and how to avoid being charged
• Waldorf spa facilities vs massage upsells
• our “best of” picks across Park Hyatt, Waldorf, and the Cape
• the full redemption math: miles, points, free night certs, and cents per point
go check out my Instagram stories for the next few days, and you'll see all of the um both rooms that we stayed in and all that fun stuff.

We finish our Scotland trip with our Edinburgh stretch: the drive in, our Outlander stop at Midhope Castle, where we stayed on points, and the places that were actually worth the effort with kids. We also break down our Air France business class flights home booked with points, including the fees, lounges, and what we’d do differently next time.
• motion sickness on Scotland roads and why Dramamine matters
• Midhope Castle as Lallybroch for Outlander fans and what to expect on-site
• using Hilton points at the DoubleTree Edinburgh and setting realistic hotel expectations
• returning the rental car, cracked windshield costs, and Chase Sapphire Reserve primary coverage claim
• Dishoom Edinburgh, ordering shareable plates, and low-pressure ways to help kids try new food
• Edinburgh Castle tour pros and cons and why audio equipment makes or breaks it
• Flightographer family photos, timing trade-offs, and getting more variety from group shots
• fishing attempt lessons, Albys sandwiches, and easy wins when plans flop
• riding the alpine coaster, buying tickets early, and taking Edinburgh buses with tap-to-pay
• late-night dining challenges with kids in Edinburgh and planning around closing times
• Mary’s Milk Bar on the Grassmarket and a fun Somebody Feed Phil tie-in
• Air France business class from Paris, lounge access, and the reality of award taxes and fees
If you have questions, as always, message me on Instagram
Let me know if you have questions about Scotland or the United Kingdom, and I'll do my best to answer them

Sheepdog Experience in Uig

The Wolfie Lodge in Carbost (Easily in the top 3 AirBnB's we've EVER stayed in!)

Airbnb in Onich (near Ft William)

The Isle of Skye completely wins us over with misty roads, unreal scenery, and a base in tiny Carbost that feels like a movie set. We share our exact itinerary, our biggest planning mistakes, and the specific stops that make a Scotland family road trip feel doable and memorable.

• flying London to Inverness early to save money
• renting a car for left-side driving and using primary rental insurance coverage
• choosing Carbost as a home base and why we want more nights next time
• finding food in small towns and what to buy as backups
• Staffin Bay dinosaur footprints and why low tide timing matters
• the sheepdog herding experience in Uig and why it becomes a trip highlight
• Portree stops for photos, shops, and a reliable dinner plan
• Fairy Pools hike lessons learned and how to avoid turning back too soon
• Three Chimneys lunch and pairing it with Talisker nearby
• Talisker Distillery tour plus how water changes peaty Scotch
• leaving Skye for Fort William with a stop at Eilean Donan Castle
• Glenfinnan viewpoint for the Jacobite steam train and what the crowds are like
• Glencoe visitor center, history notes, and quick food options
• The Geographer in Fort William and our first haggis taste test

Find me on Instagram if you have questions
If Scotland has been on your bucket list and you're waiting for a sign, this is your sign

We’re back from a break and sharing how our family of five tackles three sweaty days in London while using points and miles to make business class happen. We break down what worked, what flopped, and the small decisions that mattered most when traveling with kids in a heat wave.

• taking a needed podcast hiatus and what it’s like recording at home with kids
• the washer saga and why appliance research became a full-time hobby
• booking six business class seats to London with points, plus the mistake that nearly derailed it
• positioning flights to Dallas and using airport lounges to survive a long travel day
• arriving in London and checking into Hyatt Regency London Churchill on points
• dealing with the London heat wave and inconsistent hotel air conditioning
• London highlights including Westminster Abbey, Borough Market, and Mercado Mayfair
• why we would not repeat the Mad Hatter afternoon tea experience
• Tower of London strategy, Beefeater tour tips, and prioritizing the Crown Jewels line
• the wild coincidence of running into our kid’s teacher at the Tower of London
• the Heathrow Express saved us after a confusing early-morning transit mess

We share a quick life update and explain why we are taking a four to six week break so we can reset and come back stronger. Then we dig into the latest Chase and Hyatt changes, run our midyear points and cash back totals, and share how we finally locked in business class seats for our upcoming London and Scotland trip.

• announcing a short podcast hiatus and the reasons behind it
• plans to set up a guest scheduling system for future episodes
• reacting to the Chase Sapphire Preferred Hyatt transfer cut to 4:3
• what the change means for Hyatt fans and award booking value
• why Chase is pushing elevated offers after recent nerfs
• midyear recap of cards opened and total points earned so far
• cash back strategy including bank account bonuses and tracking
• frustrations with US Bank central billing and bonus timing
• warning story about Chime and why we are waiting on a resolution
• booking last-minute business class to London using American Airlines miles
• focusing more on family travel stories alongside points and miles

If by chance no one in your family has a Chase Ink business card and you would like to get one, please use our links above.

We just pulled off a travel move that still makes us laugh: a luxury stay at Waldorf Astoria Monarch Beach that was booked on Hilton points, covered by stacked Hilton resort credits, and somehow ended with us up $38 thanks to a perfectly timed Amex offer. If you’ve ever wondered whether points and miles are actually worth the effort, we walk through the real math, the real cards, and the real checkout moment where Raya hands over a stack of credit cards and asks the front desk to split the bill across all of them.

Along the way, we rewind to our annual Oceanside getaway, the trip we protect on our calendar because it has almost no itinerary. Beach, pool, good food, and a reset. This year includes a surprise birthday dinner for Dwayne with friends he hasn’t seen in more than 20 years, plus little details that made it feel special, like a custom menu and a table that just kept growing as more people arrived.

We also get practical about family travel logistics: when a “standard room” starts feeling too small for five people, how we think about suites, and why an ocean view matters when one of us is working during the trip. We share our experience at The Seabird, how we handled a disappointing initial room assignment, and the polite ask that got us into a true oceanfront suite. Expect plenty of California details too, from the Monarch Beach club shuttle to June gloom weather timing, plus our favorite eats and one meal that went off the rails.

If you want more strategies like this for affordable luxury travel, subscribe, share this with a points-obsessed friend, and leave us a quick review so more families can find the show. What’s the next hotel you’d love to book entirely on points?

Rakuten Referral Link: www.rakuten.com/r/RAYAPI6?eeid=28187

Chase Sapphire Reserve 150K REFERRAL LINK!

Capital One Shopping Referral Link(turns out I do have one!!!!)

We share the exact tools we use to plan trips faster, keep packing under control, and squeeze more value out of everyday spending. We also break down a 10x Chase Ultimate Rewards play using Paze, including where it works, how to stack it, and what to troubleshoot if your accounts get messy.
• noting the elevated Chase Sapphire Reserve offer and why we still use it heavily
• using Rakuten to earn cash back or points on regular online shopping
• testing Capital One Shopping for strong cash back offers
• building trip idea lists and reusable packing checklists in Google Keep
• planning itineraries with Trava linked to TripIt for confirmation email imports
• earning 10x Chase Ultimate Rewards with Paze on eligible retailers
• maximizing the promo with Newegg gift cards including Airbnb
• stacking card category multipliers on top of the 10x where it applies
• fixing Paze issues by separating emails and phone numbers across accounts
If you have questions, find me on Instagram and we will catch you on the next episode.

We share how we’re reshaping our points and miles strategy after Hyatt devaluations, including new card moves and the reality of planning family travel when award space disappears. We also walk through our Italy and Switzerland pivot, plus a credit score rebound that lets us apply for new cards with confidence.
• choosing the Bilt Palladium for the signup bonus and transfer partners
• why we skip mortgage payments through Bilt for now
• using Bilt cash to activate the 3x accelerator on planned spend
• targeting Japan Airlines miles and watching hard expiration rules
• adding Capital One Savor for uncapped 3x groceries
• pending Wells Fargo Autograph Journey verification and what we’re sending
• navigating Chase 5/24 and our plan to earn more Chase points via a business card
• booking Hyatt stays before devaluation while keeping options open
• dropping Lake Como due to missing standard award space for two rooms
• deciding between Florence costs and a Switzerland-heavy itinerary
• planning Rome with hotel openings still uncertain and building a backup
• timing credit card applications after utilization drops and scores rebound above 800
If you listened to last week's episode where I had our very first guest on, I would love feedback if you haven't already sent it. Find me on Instagram at travel party5, and we will catch you on the next episode.

Istanbul Bosphorus Cruise

Istanbul Full Day Guided Tour

Reliable Travel (booked everything in Cappadocia for them)

Balloon Turca (booked by/through Reliable Travel)

Ariana Sustainable Luxury Lodge (an SLH property!)

We trade our usual family travel format for a couple’s Turkey anniversary recap that is packed with points and miles tactics you can steal for your own peak season trips. Melissa walks us through how she booked business class flights, stacked hotel perks, and built a Cappadocia hot air balloon day that actually runs smoothly.

• How Melissa plans travel around a strict school schedule
• Booking KLM business class with Flying Blue miles and Amex transfers
• What KLM business class is like including Delft houses and the Amsterdam lounge
• Repositioning to Mexico City to find Turkish Airlines business class saver seats
• Istanbul hotel strategy with Hyatt Globalist benefits at the Grand Hyatt
• Istanbul sightseeing with a guided walking tour, Galata Tower and a Bosphorus cruise
• Cappadocia logistics, why local drivers and guides help, and when cash beats points
• Using Chase The Edit and points to book a boutique Cappadocia lodge with credits and upgrades
• Hot air balloon ride details: weather rules, pickup timing, what to wear and what it feels like
• Returning to Istanbul with an Amex Fine Hotels and Resorts stay at the Park Hyatt and a hamam plan
• Turkish award booking tips, credit card requirements and why travel insurance matters
• School break booking rules: calendar open, flexibility on destination and smart repositioning

Let me know your feedback if you think that this would have better been split into two episodes or if you like the kind of longer format. If you have any questions, feel free to send me a message and I will ask her for you.

Chase Sapphire Reserve 150K Offer!!! (thank you for using our link!)

Marriott Homes & Villas Promotion- register and book by 5/14/26!

Spirit Airlines disappears, Hyatt pricing shifts again, and we map out how we keep our family travel plans steady when loyalty programs and flight options change. We also share updates on three international trips and the exact points and miles moves we’re making right now.

• Mother’s Day recap and the economics of buffet pricing versus hotel status value
• Orlando work trip at the Disney partner Swan and Dolphin and how Marriott free night certificates can help
• Why losing Spirit Airlines hurts competition and what it can mean for fares
• How points create flexibility when low cost airlines reroute or disrupt trips
• London and Scotland itinerary pivot after award availability changes, plus a Paris overnight to make business class work
• Switzerland and Italy planning, including Wengen lodging sticker shock and backup hotel strategy for Rome
• Marriott Homes and Villas promo basics and using points to offset cash costs
• Capital One Shopping versus Capital One Offers and how targeted cashback emails can show up
• Hyatt devaluation deadline, booking 13 months out, and dealing with missing standard room availability
• Chase Sapphire Reserve 150K offer, new eligibility rules, and how we think about credits versus the annual fee

Any questions, as always, DM me on Instagram at travelpartyof5

We break down a simple way to think about travel insurance so we stop guessing and start choosing coverage that matches the trip. We also share what happened on our Thailand trip and how our annual policy reimbursed a missing-bag wardrobe and an unexpected ER visit.
• thinking in four layers: health insurance, credit card coverage, standalone policy, evacuation membership
• deciding when travel insurance matters more for international trips than domestic
• credit card travel protections and the need to pay with the right card to activate coverage
• what Chase Sapphire Reserve, Amex Platinum, Venture X and Bilt coverage can look like at a high level
• why we use an Allianz annual family plan and what it covers
• when cancel for any reason can be worth the upgrade
• evacuation options like Medjet and what they do differently
• Thailand claim walkthrough, what we submitted, and what we would document next time
please send me a DM on Instagram.

We share why points and miles meetups can unlock the next level of award travel learning when free online info stops being enough. Raya recaps her Phoenix Award Travel 201 meetup, the best nuggets she picked up from real conversations, and a few credit card strategy updates tied to American Airlines status goals.

• quick family update after Flu B runs through the house
• what the Award Travel 201 meetup format looks like in real life
• CardPointers and SaveWise for auto-adding card offers and tracking value
• American Airlines awards talk that sparks a push toward Executive Platinum
• the most useful insights coming from casual networking, not the stage
• unscrewed.ai as a fast way to check likely trip protection coverage
• why meetups help you find “expert earners” and “expert redeemers”
• upcoming in-person events to watch including Chicago Seminars
• new card moves, approval rules, and the realities of credit utilization swings
• waiting on an Allianz travel insurance claim decision

If as always, if you have questions or if you’re planning to attend any of the meetups that I talked about, send me a DM on Instagram.