Travel Resources

Let’s be completely honest for a second. Planning a vacation with kids can feel like a part-time job. Between hunting down the best family vacation spots, figuring out logistics, and packing enough snacks to prevent a mid-flight meltdown, it’s exhausting.

Over the years—first traveling as a trio with our son, Ollie, and now exploring as a family of four with our baby girl—we’ve developed a streamlined travel system.

We don’t do staged photos or theoretical advice around here. Every platform, booking engine, and piece of gear on this page is something we actually use to make family travel smoother, more budget-friendly, and way less stressful.

(Full disclosure: Some of the links below are affiliate links, which means we earn a small commission if you book through them at absolutely zero extra cost to you. Thank you for supporting the crew!)

Booking Flights & Logistics

Google Flights

Our absolute holy grail for tracking flight prices. We use the map matrix features to find affordable routes to the best family vacation spots without blowing our budget.

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Skyscanner

Excellent for those moments when we just want to look at a month-long view to see which days are cheapest to fly with kids.

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TripIt

Because trying to find confirmation numbers in your email while holding a diaper bag and a toddler at airport security is a special kind of nightmare. This app keeps our entire itinerary in one single, clean layout.

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Family-Friendly Accommodation

boston public garden boston walking tour

Booking.com

Our go-to for hotel stays. The filter settings let us easily toggle for “cribs available,” “free breakfast,” and “swimming pools” (because a pool is mandatory if you want Ollie to burn off energy).

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VRBO

When we travel with a baby and a child, sometimes a standard hotel room just doesn’t cut it. We use this to secure rental homes with full kitchens and separate bedrooms so we don’t have to sit in a dark bathroom while the kids sleep.

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Road Trips & Transit

Enterprise

Reliable, clean layout, and great customer service when plans change unexpectedly.

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Delta Cars and Stays

Finding rental cars that actually fit strollers and massive suitcases can be tricky. This platform compares local rates seamlessly so we don’t get hit with last-minute hidden fees at the counter.

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Budgeting & Credit Card Rewards

Chase Sapphire Preferred

The exact starter card we recommend to families who want to get into the points-and-miles game. We utilize these signup bonuses to cover flights and hotels that would otherwise be way out of budget.

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Delta Amex

If Delta is a major carrier at your home airport—or if you find yourself booking them for your big family vacation spots—the Delta Gold Amex is a massive sanity-saver. It carries an introductory $0 annual fee for the first year, and if you play your cards right, you’ll save way more than that on your family trip.

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The Simply Sid Gear Guide (Our Amazon Storefront)

The physical gear that survives real-life family travel.

If a piece of gear doesn’t survive airport baggage handlers, a bumpy road trip, or a blowout diaper change on an ancient ruin, it doesn’t make our list. Period.

As an Amazon Influencer, I keep our absolute favorite, trench-tested items continuously updated in our dedicated store.

Explore our Simply Sid Travels Amazon Storefront

What you’ll find inside our curated lists:

Baby & Toddler Travel Essentials

The lightweight strollers, portable white noise machines, and travel cribs we swear by.

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Packing Hacks for Real Parents

The compression packing cubes and diaper bag organizers that keep us sane.

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boy eating snacks on airplane during a long flight with kids

In-Transit Entertainment

Kid-friendly headphones, road trip activities, and mess-free toys that actually hold their attention.

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This is not a sponsored post. These are the websites and companies I use and recommend for my travels. Some of these links are affiliate links and, at no cost to you, I may earn a small commission that helps run this website — keeping it free for all to use!

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