Episode #17: How to Plan a Family Trip Step-by-Step: Stress-Free Travel for Parents

Today, we are diving into one of the MOST requested topics I get from parents:

“How do I plan a family trip without feeling overwhelmed?”

Planning a vacation with kids is not the same as planning one before having kids — we all know that.
There are nap schedules, budgets, logistics, car seats, airport meltdowns, food needs, and a million moving pieces.

But here’s the good news:
Family travel doesn’t need to be chaotic. It can be organized, doable, and even fun to plan — when you have the right system.

Today I’m going to walk you through my exact step-by-step planning process, including how to choose the right destination, when to go, what to book first, and how to build an itinerary that isn’t overloaded.

And throughout this episode, I’ll be referencing my guide, Family Travel Made Easy, which is your travel-agent-in-your-pocket, with destination ideas, itinerary templates, packing lists, cost-saving tips, and timed checklists to keep you on track.
You can grab it in the show notes!

Let’s jump in.

💡 STEP 1: Decide WHEN You Want to Travel

Before you choose where, you need to decide when. This helps narrow down weather, pricing, flight options, and crowds.

Ask yourself:

• How many days can we take off?

• Do we want to travel during school breaks or avoid them?

• Are we okay with shoulder season or do we need peak weather?

• What’s our budget for this season?

General tips:

• School breaks cost more (Thanksgiving, Christmas, spring break)

• Shoulder season can save you hundreds

• Weather varies wildly depending on the month (Hawaii vs Florida vs Europe)

🌎 STEP 2: Choose the Right Destination (Without Getting Overwhelmed)

This is where most parents get stuck. There are SO many options, and they all look amazing.

But here’s how to simplify:

Consider your kids’ ages

• Babies/toddlers → low-key destinations

• Preschoolers → beach, parks, slower pace

• Older kids → cities, national parks, adventure trips

• Teens → big cities, hiking, international exploration

Consider how far you want to travel

• 1-hour flight

• 4-hour flight

• Road trip

• International long-haul

Consider the type of trip you want

• Beach

• Disney

• Cities

• Outdoors / national parks

• All-inclusive

• Relaxation vs adventure

Great beginner family destinations:

• Disneyland (California) or Disney World (Florida)

• Beach trips: California, Florida, Hawaii, Texas (rented house in galvaston for extended family trip)

• Cities: San Diego, Chicago, New York, Los Angeles

• Outdoors: National parks, state parks, camping, cabins (zions national park, yocemite)

👉 My Family Travel Made Easy guide includes destination ideas broken down into beach, cities and nature to get your vacation planning wheels turning.

✈️ STEP 3: Look at Flights or Road Trip Routes

Once you have the rough “where,” check the “how”:

If flying:

• Start with Google Flights

• Compare airports

• Check flexible dates

• Look for mid-week departures

• Use “explore” mode if destination is flexible

• If you feel nervous flying with your kids for the first time or maybe the last time didn’t go so great, listen to episode 3 all about how to survive a flight with kids.

If driving:

• Map the route

• Identify kid-friendly stops

• Break the drive into smaller chunks

• Choose hotels along the way

👉 Inside Family Travel Made Easy, I have flight search tips, budgeting, and a whole section on how to find the best deal — step-by-step.

🏨 STEP 4: Choose Your Accommodations

Where you stay can make or break a family trip.

Airbnb / VRBO is great for:

• Large families

• Needing a kitchen

• Needing multiple sleeping areas

• Longer stays

Hotels are great for:

• Amenities (pools, breakfast, housekeeping)

• Reward points

• Convenience

• Safety

• Shorter trips

What to consider:

• Sleeping arrangements

• Walkability

• Proximity to activities

• Kitchen vs no kitchen

• Pool

• Parking

• Family-friendly reviews

👉 My guide helps you decide which option fits your family best AND includes a digital planning doc to organize all your booking details in one place.

🗓️ STEP 5: Build Your Itinerary (Without Overpacking It!)

This is the mistake almost every parent makes:
Doing too much. Trying to squeeze everything in. Overplanning.

Kids need:

• Downtime

• Wiggle room

• Flexibility

• Time to play

• Space to reset

The golden rule:

Plan 1–2 things per day. MAX.

Examples:

• Morning activity + afternoon rest

• Beach day + evening walk

• Museum + lunch + playground

• Hike + pool time

Don’t forget:

• Buffer time

• Jet lag days

• Weather backups

• Free play time

👉 In Family Travel Made Easy, I include printable itinerary templates, daily planners, and sample schedules so you can build a trip that flows smoothly.

🧳 STEP 6: Think Through Weather, Packing & Food

Weather:

• Research temps

• Rainy seasons

• Humidity

• What activities are seasonal

Packing:

• Layering

• Swimsuits

• Rain gear

• Comfortable walking shoes

• Snacks

• Travel medicine kit

• Beach gear

Food:

• Are you eating out every meal?

• Do you need a kitchen?

• Is breakfast included?

• Are there nearby groceries?

• Do your kids have allergies or restrictions?

👉 My guide includes complete packing checklists for:

• Babies

• Toddlers

• Big kids

• Parents

• Specialty lists (beach, road trips, international)

🎟️ STEP 7: Choose Activities (But Keep It Simple)

Look for:

• Local playgrounds

• Beaches

• Kid museums

• Walkable neighborhoods

• Cultural experiences

• Easy tours

• Free activities

• Family-friendly restaurants

Tip:
Book your big activities ahead but keep several time blocks open.

Kids love:

• Pools

• Beaches

• Hotels

• Walking around

• Snacks

• Playgrounds

• Finding animals

• Choosing souvenirs

You don’t need to fill the day — kids fill it themselves.

👉 My guide teaches you how to find the BEST activities at the BEST price (and avoid tourist traps).

💵 STEP 8: Set a Budget (and Stick to It)

Consider:

• Flights

• Hotels

• Food

• Transportation

• Activities

• Souvenirs

• Travel gear

Ways to save:

• Travel off-peak

• Use points & miles

• Book Airbnbs with kitchens

• Choose free activities

• Pack snacks

• Plan around cheaper destinations

• Use flight tools + Google Flights alerts

💼 STEP 9: Put It All Together (This is Where the Magic Happens!)

Take all your info and drop it into one organized place:

• Flights

• Confirmation numbers

• Hotel details

• Daily plans

• Packing lists

• Budgets

• Addresses

• Transportation notes

👉 My digital planning dashboard inside Family Travel Made Easy keeps EVERYTHING in one place — no more tabs, screenshots, or chaos.
Truly a sanity saver.

💛 STEP 10: Final Tips for Stress-Free Travel

• Don’t compare your trip to someone else’s

• Let go of perfect

• Embrace spontaneity

• Focus on connection

• Build in “slow days”

• Remember that kids will remember the moments, not the itinerary

• You’re doing an amazing job

Family travel doesn’t need to be fancy — it just needs to be fun, intentional, and doable.