Family Travel, Points & Insurance

Family Travel, Points & Insurance

ByEvan Parker

Traveling with family isn’t just about herding everyone through airport security (though, let’s be honest, that’s a sport in itself). It’s about making memories, not losing your sanity, and—if you play your cards right—saving a decent chunk of change using travel points and smart insurance. I’ve dragged my own crew through Europe and South America, so here’s a straight-shooting guide on what actually works, built from red-eye flights, nap-time meltdowns, and those “wait, where’s the stroller?” moments.

Why Family Travel Feels Like Leveling Up

If you’ve ever traveled solo, you know how fast you can pivot. With kids? Every step is a negotiation, and logistics matter more than ever. Spain, Portugal, and South America are fantastic for families—if you plan for naps, snacks, and the occasional “I just want to go home” breakdown.

Pro tip: The right itinerary means fewer meltdowns (for kids and adults alike).

Case Study: 10 Days in Spain with a Toddler (and a Carry-On)

Last spring, my family (two adults, one three-year-old) did a 10-day loop: Madrid – Seville – Granada – Barcelona. We survived with only carry-ons, a collapsible stroller, and sanity mostly intact.

  • Flights: Used 90,000 Chase Ultimate Rewards points, transferred to Iberia for nonstop flights (saved ~$1,200 vs cash fares).
  • Accommodation: Booked apartments with kitchens—essential for early breakfasts and post-nap downtime.
  • Transit: High-speed trains booked in advance; kids under 4 ride free on Renfe if you get a child ticket.
  • Insurance: Used a credit card with included travel insurance, but topped up with World Nomads for extra medical coverage (cost: $84 for the whole trip).

Kid-Tested Itineraries: Spain, Portugal, South America

Spain: Focus on cities with walkable old towns (Seville, Granada, Barcelona). Schedule outings between 10am and 2pm, then plan downtime or stroller naps.

Portugal: Lisbon’s trams are a hit with little ones. The Algarve beaches are stroller-friendly (just avoid steep, cobbled towns if you value your back).

South America: Buenos Aires offers playgrounds every few blocks and family-friendly parks. In Peru, Lima’s Miraflores district is easy to navigate; skip Machu Picchu with toddlers—Cusco’s altitude isn’t fun for little lungs.

Printable Carry-On Packing Checklist

  • 2-3 days’ worth of clothes per person (laundry is easy in apartments)
  • Collapsible stroller (e.g., Babyzen YOYO, fits overhead bins)
  • Favorite comfort toy or blanket
  • Lightweight baby carrier (for stairs/cobblestones)
  • Snacks, refillable water bottles
  • Basic first aid kit
  • Plug adapters (universal or country-specific)
  • Travel insurance documents (digital and paper)
  • Download offline Google Maps, Netflix, and translation apps

Stroller & Nap Logistics: What Actually Works

Here’s the deal: not every city is stroller-friendly. In Spain and Portugal, historic streets mean cobblestones and stairs. I recommend:

  • Bring a stroller only if it’s genuinely compact and lightweight.
  • Plan for at least one nap in the stroller (sling a light blanket for shade).
  • Scout playgrounds in advance—Google Maps reviews are weirdly reliable.
  • Restaurants in Spain/Portugal are cool with kids, but dinner is late. Plan early meals or pack a snack attack kit.

Travel Insurance: Spoken Like a Human, Not a Lawyer

Why you need it: Medical care is solid in Europe and South America, but out-of-pocket costs can sting. If you’re carrying a stroller, a backpack, and a sleep-deprived child, accidents happen. Travel insurance covers medical emergencies, cancellations, and, if you’re lucky, the cost of replacing a lost pacifier (okay, maybe not the pacifier).

Here’s what I look for:

  • Medical coverage: At least $100,000 (higher if you’re going somewhere remote).
  • Trip interruption/cancellation: Enough to cover your prepaid costs.
  • Children included for free or low cost (World Nomads and Allianz are good bets).
  • Simple claims process (check reviews, not just the policy details).

Don’t just rely on credit card insurance—it rarely covers family members fully. Read the fine print, or at least the bolded sections.

Beginner Points Strategies: Real Math, No Magic

Points can make a huge difference, but only if you play by the rules. Here’s what worked for us:

  1. Chase Sapphire Preferred: 60,000-point signup bonus after $4,000 spend = $750 in travel when booked through the portal. Points transfer 1:1 to partners like Iberia, United, Hyatt.
  2. American Express Gold: 60,000-point bonus, great for foodies (4x at supermarkets and restaurants). Transfers to Air France/KLM, Iberia, and more.
  3. Family booking tip: Always add kids as frequent flyer members if the program allows. On Iberia, kids under 2 fly on a lap ticket for 10% of the adult fare (pay with points or cash).

Safe Use Rules:

  • Don’t buy points unless you know exactly how you’ll use them.
  • Avoid “dynamic pricing” airlines (e.g., Delta, sometimes United) for long-haul family trips unless you see a deal.
  • Always search for award space before transferring points.
  • Keep a spreadsheet of your balances, expiry dates, and program logins—a boring task, but it beats losing 80,000 points to inactivity.

Sample Budget Table: 10 Days in Spain for Family of 3

Category Points Cash
Flights (Iberia, RT, 3) 90,000 $240 (taxes/fees)
Accommodations (10 nights) 0 $1,000 (apartments)
Trains/Transit 0 $350
Food 0 $500 (groceries + eating out)
Insurance 0 $84
Activities 0 $200
Total 90,000 $2,374

Printable Pre-Trip Checklist (Download & Go)

  • Book flights (points or cash, add frequent flyer numbers for everyone)
  • Reserve accommodation (check for kitchen, laundry, crib availability)
  • Buy travel insurance (double-check coverage for kids)
  • Apply for necessary visas (for South America, check reciprocity fees)
  • Set up international phone plan or eSIMs
  • Download offline maps, entertainment, and translation apps
  • Notify banks/credit cards of travel dates
  • Sort meds, first aid, prescription copies
  • Packing: See carry-on checklist above

Tools & Links to Make Life Easier

Final Thoughts from the Trenches

Every family trip is a mix of chaos and magic. The trick is to accept the chaos, prep for the worst, and remember that a well-timed snack or nap solves 90% of problems. Don’t stress about “doing it perfectly”—just do it with a plan, a backup plan, and maybe a third backup snack.

Some links in this post may be affiliate links. You get the same price, and I may earn a small commission—helps keep the site running (and my coffee cup full).

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