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Feathers and Stripes

Boston mom blogger | motherhood, baby + kids, family travel, + home

The Ultimate Guide to Family Travel with Multiple Kids

Family travel can feel really daunting at first. I remember when we packed up and took our then-6 month old on her first cross country flight: I felt SO relieved when we were back at home and had accomplished such a big trip as parents. Now we’ve taken our kids to many different cities and countries, and I’m here to share my knowledge so that you can take on travel confidently with your kids in tow. My travel philosophy is this: You can go anywhere with the right gear and the right plan, and have a successful trip.

Table of Contents

If you want to jump directly to specific content below:

  • Planning Trips for Newborns to Big Kids
  • Travel Gear that Makes Travel Easier
  • Destination Guides: MA & Cape Cod
  • Destination Guides: USA
  • Destination Guides: International Travel
  • Destination Guides: Disney

Planning Trips for Newborns to Big Kids

|our travel diaper bag backpack for long flights and adventures with our family|||packing list for weekend with toddler|flying with a baby from Boston to San Francisco: how to survive a cross-country flight with a baby|flying cross-country with a 6 month old baby from mom and travel blogger Alyssa from feathersandstripes.com
Planning + Packing

My Best Tips for Flying with a Baby

|activity bag for traveling with a toddler - perfect for flying with a toddler! feathersandstripes.com|tips on flying with a toddler - what to pack, tips and tricks, and the big mistake we made - feathersandstripes.com
Planning + Packing

Flying with A Toddler: Tips, Tricks, + the Mistake We Made

resort-pass
Planning + Packing

ResortPass Review: Is ResortPass Worth It for Families and Long Travel Days?

travel with 3 kids
Planning + Packing

Traveling with 3 Little Kids: Less Stress, Packing and Flights

what to bring on a beach trip with kids
Planning + Packing

What to Pack for A Family Beach Vacation with Kids

tips and tricks for traveling with kids||tips and tricks for traveling with kids|what to bring traveling with a baby||
Planning + Packing

Mom Hacks for Traveling with A Baby in 2026

Traveling with a Car Seat: Tips & Tricks
Planning + Packing

Traveling with a Car Seat: Tips & Tricks

airplane flying
Planning + Packing

What to Pack for a Long Flight with Kids

Travel must haves with toddler
Planning + Packing

The Ultimate Weekend Trip Packing List (With Toddler Essentials Included)

activity bag for traveling with a toddler - perfect for flying with a toddler! feathersandstripes.com
Planning + Packing

The Best Travel Toys for Toddlers That Keep Them Entertained (Plane + Road Trip Tested)

|
Planning + Packing

The Best Packable Travel High Chairs- Tested!

Travel Gear that Makes Travel Easier

If you’re looking for more gear reviews, check out the Baby + Kids Gear Reviews hub page!

best compact travel stroller
Gear Reviews

The best travel stroller (and comparisons)

Cosco Scenera Next Review
Gear Reviews

Cosco Scenera Next Review

best packable high chairs
Gear Reviews

The best packable high chairs – tested!

miamily ride on suitcase review
Gear Reviews

Miamily ride on suitcase review

ergobaby metro stroller review
Gear Reviews

Ergobaby Metro+ travel stroller review

bob renegade wagon review
Gear Reviews

BOB Renegade Stroller Wagon Review

slumberpod honest review
Gear Reviews

Is the SlumberPod Worth Buying? My Honest Thoughts (You Might Be Surprised)

quince luggage carry on review
Gear Reviews

Quince Luggage Review (Lightweight Carry On Luggage)

Monogrammed Travel Bags
Travel Gear

Monogrammed Travel Bags

Destination Guides: MA and Cape Cod

Boston with kids Boston Children's Museum
MA & Cape Cod

Boston with Little Kids: What to Do/Skip in 2026

What to do on Cape Cod in the Rain
MA & Cape Cod

What to do on Cape Cod in the Rain

Chatham MA with kids
MA & Cape Cod

What to do at Cape Cod with Kids in Chatham 2026

Boston City Guide: What to do, where to eat, and where to stay from a local
MA & Cape Cod

Boston City Guide: My Favorite Spots

Cape Cod packing list featured by top Boston travel blog, Feathers and Stripes
MA & Cape Cod

A Complete Cape Cod Packing List

Cape Cod sailboat charter
MA & Cape Cod

On a Cape Cod Sailboat (So fun!)

Cape Cod July 4th
MA & Cape Cod

Our Cape Cod July 4th: A Favorite Tradition

what I wore last week - real outfits for mom and baby
MA & Cape Cod

A Week on Cape Cod: Real Outfits

Cape Cod trip recap feathersandstripes.com
MA & Cape Cod

Cape Cod Recap – 8 Days in Chatham

76 Main Nantucket boutique hotel, fall getaway to Nantucket
MA & Cape Cod

76 Main Hotel Review (Nantucket Hotels)

renting bikes on Nantucket is a great way to get around the island when you don't have a car on Nantucket!
MA & Cape Cod

Nantucket in the Fall: the Ultimate Travel Guide

Our Harvard Square Staycation
MA & Cape Cod

Our Harvard Square Staycation

2 Days in Boston with Kids
MA & Cape Cod

2 Days in Boston with Kids: What to Do + Where to Go

woman skiing
MA & Cape Cod

Best Places to Ski Near Boston (Day Trips)

Destination Guides: USA

4 Days in NYC with Kids
USA Travel

4 Days in NYC with Kids

Our One Week San Diego Trip (Itinerary, Where We Stayed, + What I'd Change Next Time)
USA Travel

Our One Week San Diego Trip (Itinerary, Where We Stayed, + What I’d Change Next Time)

Honest Resort Review: Hilton Hawaiian Village Waikiki
USA Travel

Honest Resort Review: Hilton Hawaiian Village Waikiki

Resort Review: Fairmont Kea Lani Maui (+ Why We Loved It)
USA Travel

Resort Review: Fairmont Kea Lani Maui (+ Why We Loved It)

What to wear on vacation in Hawaii
USA Travel

What to wear on vacation in Hawaii

Kennebunkport in the Fall
USA Travel

Kennebunkport in the Fall

Clearwater Beach Family Vacation: What You Need to Know
USA Travel

Clearwater Beach Family Vacation: What You Need to Know

Resort Review: Marriott Sand Key in Clearwater Beach, FL
USA Travel

Resort Review: Marriott Sand Key in Clearwater Beach, FL

Weekend in Fort Lauderdale
USA Travel

Weekend in Fort Lauderdale

Desert Pearl Inn Review: Zion and Bryce
USA Travel

Desert Pearl Inn Review: Zion and Bryce

2 Days in Zion National Park
USA Travel

2 Days in Zion National Park

Hiking Bryce Canyon
USA Travel

Hiking Bryce Canyon

Where to Stay in Las Vegas: Wynn vs. Aria vs. Mandarin Oriental
USA Travel

Where to Stay in Las Vegas: Wynn vs. Aria vs. Mandarin Oriental

Pet Friendly Day Trip to Maine
USA Travel

Pet Friendly Day Trip to Maine

The W Hotel Fort Lauderdale Review
USA Travel

The W Hotel Fort Lauderdale Review

Our Weekend + Hotel Review: Providence Biltmore Hotel
USA Travel

Our Weekend + Hotel Review: Providence Biltmore Hotel

City Guide: 3 Days in Orange County
USA Travel

City Guide: 3 Days in Orange County

Weekend in Portsmouth
USA Travel

Weekend in Portsmouth

Carmel & Monterey Travel Diary
USA Travel

Carmel & Monterey Travel Diary

Pacific Coast Highway Road Trip
USA Travel

Pacific Coast Highway Road Trip

Weekend in NYC
USA Travel

Weekend in NYC

Day Trip to Legoland Florida
USA Travel

Day Trip to Legoland Florida

Our Favorite Sedona Hiking Trails with Kids
USA Travel

Our Favorite Sedona Hiking Trails with Kids

Where to Stay in Sedona Arizona with Kids
USA Travel

Where to Stay in Sedona Arizona with Kids

Chicago with a Toddler
USA Travel

Chicago with a Toddler

Maine Family Vacation
USA Travel

Maine Family Vacation

Destination Guides: International Travel

London travel with kids||||
International Travel

2 Days in London with Kids (What We Loved and Would Skip Next Time)

The Perfect 1 Day Bruges Itinerary with Kids
International Travel

The Perfect 1 Day Bruges Itinerary with Kids

Thailand packing list - what to pack for 2 weeks in Thailand // feathersandstripes.com | The Ultimate Packing List for Thailand featured by top Boston travel blog, Feathers and Stripes
International Travel

The Ultimate Packing List for Thailand

Island Life: Our Stay on Koh Lipe Thailand
International Travel

Island Life: Our Stay on Koh Lipe Thailand

3 days in Bangkok, Thailand: where to stay, what to do
International Travel

City Guide: What to do with 3 days in Bangkok Thailand

Where to stay in Koh Lipe, Thailand (Thai islands)
International Travel

Where to Stay on Koh Lipe Island (Thailand)

10 days in Tuscany - where to go and what to do, including 3 day trips you HAVE to take! | 10 Day Tuscany Itinerary featured by top Boston travel blog, Feathers and Stripes|10 days in Tuscany: Where to go and what to do|10 Days in Tuscany - the ultimate itinerary||traveling Florence, Italy|non-maternity t-shirt and a bike ride in Lucca, Italy|||||||Pisa day trip
International Travel

A Complete 10 Day Tuscany Itinerary

Cinque Terre in one day|Cinque Terre day trip|Cinque Terre day trip|Cinque Terre day trip|Cinque Terre day trip|Cinque Terre day trip|Cinque Terre day trip|Cinque Terre day trip|Cinque Terre day trip|Cinque Terre day trip
International Travel

Cinque Terre Day Trip

Destination Guides: Disney

Disneyland Paris|||||
Disney

Disneyland Paris with Kids: Highlights, What to Do + What to Skip

travel with 3 kids
Disney

Where We Stayed for Disneyland Paris: Hotel L’Elysees Val d’Europe Review

Disney After Hours Hollywood Studios at Walt Disney World: What is it and is it worth it?
Disney

Disney Packing List + 5 Days in Orlando Itinerary

|||matching swimsuits for mom and daughter||||cool mom shirt|Character breakfast at Ravello Four Seasons Orlando with Mickey, Minnie, and Goofy|Character breakfast at Ravello Four Seasons Orlando with Mickey, Minnie, and Goofy||||||||||||||||night time view from park view suite at Four Seasons Orlando|Suite at Four Seasons Orlando (photography provided by Four Seasons Orlando)|Lazy River at Four Seasons Orlando (photography provided by Four Seasons Orlando)|||
Disney

Resort Review: Four Seasons Orlando (THE BEST)

Disney After Hours Hollywood Studios at Walt Disney World: What is it and is it worth it?|Disney After Hours Hollywood Studios at Walt Disney World: What is it and is it worth it?|Disney After Hours Hollywood Studios and Toy Story Land at Walt Disney World: What is it and is it worth it?|Disney After Hours Hollywood Studios and Toy Story Land at Walt Disney World: What is it and is it worth it?|Disney After Hours Hollywood Studios at Walt Disney World: What is it and is it worth it?|Disney After Hours Hollywood Studios at Walt Disney World: What is it and is it worth it?|Disney After Hours Hollywood Studios at Walt Disney World: What is it and is it worth it?
Disney

Our Night at Disney After Hours

Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)|Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)
Disney

How to Do Disney World with a Toddler

|https://feathersandstripes.com/wp-content/uploads/2024/03/disney-outfit.jpg|https://feathersandstripes.com/wp-content/uploads/2024/03/disney-park-outfit-moms.jpg|https://feathersandstripes.com/wp-content/uploads/2024/03/disney-park-outfit-scaled.jpg|https://feathersandstripes.com/wp-content/uploads/2024/03/disney-magic-kingdom-outfit-scaled.jpg|https://feathersandstripes.com/wp-content/uploads/2024/03/disney-magic-kingdom-outfit-1-scaled.jpg|https://feathersandstripes.com/wp-content/uploads/2024/03/disney-park-outfit-1-scaled.jpg|https://feathersandstripes.com/wp-content/uploads/2024/04/disney-capsule-wardrobe.png|||||||
Disney

What to Wear at Disney: My Real Outfits + Tips

|||
Disney

Omni Orlando Hotel Review: Our Stay for Disney World

Visiting Disney World with a Toddler: Tips, Tricks, and Our Mantra for the trip from mom- and travel-blogger Alyssa (feathersandstripes.com)||
Disney

Disney World Tips + Is Lightning Lane Worth It? From a Mom of 3

About Alyssa


Hi, I’m Alyssa. Mom of three, wife, dog mom, blogger. I write tips and tricks on motherhood, focusing on baby gear reviews, the best toys for kids, family travel, and home organization.

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