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Travel Tips

Top Travel Stories & Tips of 2020: Our Year in Review

Posted December 31, 2020

Jennifer's hat sits on a table with swimwear next to the poolside of a Holiday Inn Club Vacation Resort.Jennifer's hat sits on a table with swimwear next to the poolside of a Holiday Inn Club Vacation Resort.
Close-up of Jennifer Harmon in front of a colorful wall.

Jennifer C. Harmon

Jenn was the founding Editor-in-Chief of the Checking In travel blog and is now President of the creative agency, Content Unicorn. She’s a storyteller and proud maltipoo dog mom to Bode McNugget, and she loves coffee, wine, writing, cycling and traveling. Jenn and her husband, Anthony, have mastered the art of the long weekend couples’ getaway (sans kids). And while it’s too hard to pick just one type of “favorite vacation,” her three-way tie would be a snowboarding trip, going to Hawaii or sailing with Disney Cruise Line.

Wow, what a year! Even though 2020 was full of challenges, surprises, hardships and lots of mentions of “new normal” and “unprecedented”-ness, it was also a big year for us here at Checking In.

We launched our new travel blog! And getting to share travel stories and advice from Club members, bloggers, real families and our own team of travel experts has definitely been our “silver lining” to this crazy past 365 days. Even though we haven’t hit our one-year Blogaversary just yet, a lot happened around here, and that’s why we’re taking a walk down memory lane and sharing our “Year in Review” nonetheless!

Family sitting near the pool at Orange Lake Resort in Orlando, FL
Mia and family of @greyslittlecloset

I sincerely hope you’ve found some bright spots and silver linings to your year as well. Thank you for reading and as always, we’re wishing you Safe Travels and a bright fresh new year in 2021.

Throwing it Way Back to Virtual Vacations

Orange Breeze Resort Zoom Wallpaper background containing the HICV logo and palm trees with hammocks.
A dreamy Orange Lake Resort Zoom Background

Earlier this year, while we were all sheltering in place and anxiously awaiting the full (and safe) reopening of our resorts, Checking In editor Tori Ferrante and team shared some ways to take a virtual vacation from home and bring some travel-inspired smiles your way:

  • We made sure your background image needs were covered for all your Zoom calls with our Picture Yourself at Our Resorts with These Dreamy Backgrounds post
  • Even if the only places we were going at the time were the grocery store and home, we gathered up 5 Spotify Playlists to Keep You Dreaming of Your Next Vacation in this post.
  • Even Cinco de Mayo was still celebrated—from afar—with our Tried-and-Texan-True Hill Country Resort Recipes post.

Reminiscing Over Favorite Vacation Memories

Jennifer and Anthony Harmon stand in front of the Ne-Pali in Hawaii

We also boosted our spirits by looking back at some favorite vacation memories of days past—they’re priceless after all—while we were (stuck), (working from), (virtual schooling), (baking sourdough bread), (forever wearing pajamas) at home:

  • Our resident Smoky Mountain area expert, Becca Clark, shared her wisdom in this Top 5 Day Trips from Gatlinburg story.
  • Looking for beachside romance? For some inspiration, take a look at this Marco Island Couples’ Getaway: 5 Ways to Enjoy Your Trip story by our fearless leader and Chief Brand and Innovation Officer, Denise Godreau.
  • The only thing our Editor-in-Chief, Jennifer C. Harmon, loves more than a good hike on vacation is eating and drinking lots of delicious local flavors after all that trekking. She shared some favorite trails and watering holes in this Hikes & Bites: 6 Favorite Vacation Treks & Post-Hike Places to Eat story.

Learning How to Take an RV Adventure

Josh (left) and their daughters (right) seated in their RV rental ready for departure.

Family RV travel became THE new way to travel as stir-craziness and wanderlust set in. We gathered up some stories written by RV-savvy moms to share their tried-and-true tips for how to safely hit the road in an RV as a family:

  • Jessica of Bring the Kids brought her big rig expertise to the table with this RV Trips with Kids: 10 Tips for Success story.
  • When COVID-19 canceled the Johnston family’s spring break plans to visit some (closed) Florida national parks, they bailed and nailed a pretty amazing plan B: How to Do 5 Utah National Parks in an RV story by Chris Johnson, local award-winning Kindergarten teacher and mama of two.
  • Driving, homeschooling and vacationing—oh my! Angelica from Toddlin’ Across America covered it all in this Helpful RV Travel Tips: Branson Road Trip Edition story.

THE Year of the Road Trip

Mindy McKnight (right) and daughter (left) sit outdoors on the hood of a white SUV.
Mindy of @mindymcknight and @hairitagebymindy

Even without RVs, this was THE year of the road trip and we were here. for. it.

  • Ever considered a cross-country road trip with your significant other, but been just a touch nervous about … killing each other? Definitely check out our 5 Tips for Surviving a Couple’s Road Trip with Your Spouse (and Dog) story by New York Times best-selling author Lauren Layne and her husband Anthony LeDonne.
  • Taking five kids on a road trip to the beach is no small feat. Read all about the journey and the destination in Our Family’s First (Road) Trip to Myrtle Beach story by Brenda of @she_plusfive.
  • Our Travel-Perfect Hairstyle Tutorial story by one of our all-time favorite partners, Mindy McKnight, shared how to do a road trip-proof Double Dutch Braid style for your next family adventure.
  • We hit the road, pumpkin spice latte in hand, for our Top 10 Fall Getaways to See the Leaves Change Colors story by Checking In team members Jessica Salina and Tori Ferrante.

Wide Open Spaces Full of Fresh Air

Angelica hiking with her kids.
Angelica and family of Toddlin’ Across America

“Fresh air” was the name of the game for family fun this year once traveling and vacations resumed. From national parks and hiking to sandy beaches and more, we shared a TON of outdoorsy vacation ideas:

  • Angelica from Toddlin’ Across America skipped the theme parks and shows in Branson to check out hiking, water tubing and more in her How to Plan a Nature-Filled Family Trip to Branson, MO story.
  • Jessica from Bring the Kids shared what all she’s learned from hiking with her family of SEVEN in her Hiking with Kids: 10 Easy Tips story.
  • Our Club members shared their favorite hiking spots in this National Take a Hike Day: 9 Member-Favorite Hiking Trails story.
  • Our Club members also had a LOT to say about which 18 Florida beaches they consider to be the best of the best in the aptly named What Are the Best Beaches in Florida? story.
  • Nearly our entire corporate brand team contributed tips to this National Park Trips: Best Family-Friendly Tips by Park story, while copywriter Tori Ferrante shared her helpful, smaller-scale learnings with this 6 Tips for Your Next State Park Trip post.
  • And last, but certainly not least in the fresh air camp, local journalist Rona Gindin served up 12+ ways to enjoy Central Florida without stepping foot in Orlando’s theme parks in her story: Top 12 Things to Do in Central Florida Right Now (That Aren’t Theme Parks).

Cue the Schoolcations & Work/Play Trips

Brenda (right) helps her son (left) with his homework assignments.
Brenda of @she_plusfive

The silver lining for virtual school and homeschooling? The introduction of “schoolcations,” which happily combine school and vacations together, with spacious villas to get work done, poolside recess, after-school mini golf, field trips to the beach and ice cream on school nights.

Even working from home opened up to working from not-at-home with work/play vacations chock-full of changes in (still productive) scenery and inspiring views:

  • Homeschooling mom of five, Brenda of @she_plusfive, shared tips on how to mix school with fun at our South Beach Resort in her How to Take a Schoolcation: Myrtle Beach Edition story.
  • Kimberly, a motherhood and lifestyle blogger, mixed birthday celebrations, virtual school and working from resort tips—all at our flagship Orange Lake Resort—in her post, Work & Schoolcation Tips for Families: Orlando Edition.
  • Angelica from Toddlin’ Across America is no stranger to taking homeschooling on the road. She’s been mixing schoolwork and travel adventures long before 2020 and shared her eight best tips in this Homeschooling While Traveling: 8 Ways to Keep Learning on the Go story.
  • And Jennifer Probst has mastered the art of working from home and … working while vacationing. She’s done it for years as a New York Times best-selling author that craves new destination inspiration when she’s writing, as she shared in her guest post: How to Work While Traveling.

Relearning How to Fly

Ashley's kids posing in the airport terminal.
Ashley Haby’s family of @southernsudsandsimpleliving

There wasn’t any pixie dust involved, but there was a whole lot of social distancing, new boarding procedures and empty middle seats. And as more and more travels and vacations picked up again, with new safety measures and precautions in place and in mind, we gathered up tips about flying during COVID-19:

  • Ashley Haby, mama of four from @southernsudsandsimpleliving, shared how she and her husband decided they were ready for airplane trips again and how they tackled flying with kids during the pandemic in her story Flying During COVID-19: A Family’s Experience.
  • And Checking In travel blog contributor, Sarah Conroy, wrote all about tips for flying with babies, toddlers and kids (yes, all with hand wipes) in the story Tips for Flying with Kids This Holiday Season.

Reopened Theme Park Visits & Safety Reviews

Featured author, Jessica Salina, with husband, Anthony, in Epcot World Showcase-Japan Pavilion get photobombed by Remy from Pixar's 'Ratatouille.'

And we even (thoroughly) navigated the new masks-on, temperature checking, hand sanitizer-a-plenty world of Orlando theme parks! With our flagship Orange Lake Resort and Corporate Headquarters located so close to all the magic, our team eagerly checked out the new safety measures, crowds (or lack thereof), ride line and seating procedures, safe Character interactions-from-afar and more at some of the (reopened) happiest places on Earth:

  • What It’s Like at Disney’s Magic Kingdom & Epcot Right Now post
  • What It’s Like at Disney’s Animal Kingdom & Hollywood Studios Right Now post
  • What It’s Like at Universal Orlando Right Now post
  • What It’s Like at SeaWorld Orlando Right Now post
  • 2020 Central Florida Theme Park Guide post

Visiting Some of Our Favorite Resorts with Friendly Faces

Karen and her family at Emerald Bay State Park with the gorgeous forest, mountains and lake as a backdrop.
Karen and family of The Mom Trotter

When we weren’t busy checking out all those Orlando theme parks, we got the great pleasure of visiting some of our favorite resorts across the country with new friends and families, as well as some of our regional team member experts:

  • Jessica shared how to have a super active (and very safe) Arizona vacation in her guest blog, Scottsdale Vacation Tips: How to Plan a Family Adventure.
  • Karen from the Mom Trotter made her very first stop on her family’s cross-country RV trip to our Tahoe Ridge Resort. Read all about her time exploring the Tahoe area in her post, Things to Do in Lake Tahoe: What to See, What to Eat & Where to Stay.
  • Clarissa of Passports and Parenting reminded us how important quality one-on-one time is as a mom with your kids, even on vacation! She shared all about her special time with her kids, with her husband back at home, in her story, Traveling Solo with Children: One Mom’s Take on One-Parent Vacations.
  • As a long-time local and the activities and engagement manager at our Scottsdale Resort, Jeff Gee knows a thing or two (or 10, actually) about the Scottsdale, Arizona area. His Top 10 Best Things to Do in Scottsdale post is a must-read if you’re headed that way in 2021.

There Were Travel Tips a Plenty (Yes, Even in 2020!)

Raff with her family in the villa.
Raff and family from @raffinee and the Raff Out Loud blog

We also got to share some really helpful, real tips and travel tricks from moms and dads, and even a professional weddings and lifestyle photographer, who all know a thing or two about family travel:

  • Raff, of @Raffinee, and her wife Micaela tackled potty training … on vacation … with THREE three-year-olds. Hear how it went (and what all they loved about staying at Orange Lake Resort as a family) in her How to Potty Train While Traveling guest post.
  • While packing up her adorable family of five for a Seattle-to-Florida trip that included swimming, Disney World and more, Mia got to writing down her top tips for How to Pack Up the Whole Family for a Cross Country Vacation in her September story.
  • Danny, husband, dad and voice behind Accessible Vacations, shared his story, his favorite ways to vacation while in a wheelchair and his best Tips for Traveling with Disabilities story.
  • And Sara Martin, longtime photographer, shared How to Take Great Family Photos on Vacation, even if you’re just traveling with your cell phone camera, in her guest blog.

Celebrating the Holly Jolly Holiday Season with Safe Travels & Cheer

Author, Amanda Nall (right), and her family look at the string lights and enjoy being surrounded by holiday decor.
Amanda of That Inspired Chick

And, of course, we celebrated the holidays together! Some things change, but holidays, family travel and fun are always in season in our book. Our favorite Halloween, Thanksgiving and Christmas stories included:

  • Tina Meeks of @herlifesparkles reminisced about her family’s super special Halloween-y staycation in her story, The Perfect Texas Staycation: Our Family’s Visit to Falladays.
  • We gathered a ton of Cooking on Vacation tips from Club members, a foodie author and our Editor-in-Chief for when it’s time to take your Thanksgiving feast on the road.
  • We shared a very special story about Give Kids the World Village’s Night of a Million Lights Holiday Event.
  • Texas mom, Amanda Nall from That Inspired Chick, shared her 5 Ways to Decorate for the Holidays While on Vacation post (as well as a little look-back at her family’s visit to Jollydays last year at our Villages Resort in Flint, Texas.)
  • Amanda from our Oak n’ Spruce Resort shared the Top 7 Holiday Experiences in the Berkshires you won’t want to miss when traveling to Massachusetts during December in her post.
  • Then we made our way from the Berkshires to Hill Country, Texas, where Chris, guest engagement manager, shared his Texas Hill Country: Top 7 Things to Do During the Holidays expertise, right from his desk at our Hill Country Resort.
  • Yes, we went back to Disney World! This time, we checked out all the Holiday magic they had in store … and then wrote a story all about it. Check out Walt Disney World: 16 of the Most Magical Holiday Happenings to see Santa, hot chocolate, hidden Mickey Christmas cupcakes and more.
  • And for all you Hallmark Christmas movie fans out there, we shared an exact one-day itinerary for How to Visit the Biltmore Estate in Just One Day during Christmastime, so you can see and do it all while still feeling like a commoner-turned-princess at this not-to-be-missed mega-mansion.


Exterior image of our New Orleans resort in the twilight hour.

Yes, we opened our newest resort in December! Our New Orleans Resort is our first city destination, and we could not be more excited to welcome you to the Big Easy in 2021:

  • Sticking with that whole excited thing, we shared this post about, well, all of our NOLA excitement: Our New Resort in New Orleans: 21 Things We’re Most Excited About.
  • And we took a sneak peek at the newly renovated interiors and even shared a video from our general manager, Mike Larose, in this Special Inside Look at Our Resort in New Orleans story.
  • Plus, there’s so much more NOLA fun to come in the new year … stay tuned!

Looking Ahead to 2021 Adventures

Author, Jessica Averett, and her family sit on the ski lift in winter apparel and ski gear.
Jessica and family of Bring the Kids

And to wrap this Year in Review up on a mega high note, we’re already looking forward to next year’s travels and family fun:

  • We partnered up with Jessica from Bring the Kids again on how to Plan a Family Ski Trip: 8 Tips for Your First One
  • Danny from Accessible Vacations shared all about how he and his wife, Val, became Holiday Inn Club Vacations members with us in 2016 and what their journey through timeshare has been like in their (super real and super funny) story, What Vacation Ownership is Like: The Gift of Family Vacations.
  • And last, but not least, Chris Johnston came back to finish our year out with a fun New Year’s travel resolution: to visit more national parks! Her guest blog, National Parks: How to Start a New Family Travel Tradition, is a must-read if you collect national park passport stamps or if you’ve always wanted to start, but didn’t know where to begin.

Phew! It’s been a great few months of telling your travel stories, even if travel looked a little different this year. If you’d like to write for our travel blog in 2021, please contact us and share your story! We’d love to hear from you.

Until then, from our Checking In family to yours, Safe Travels and Happy New Year!

Sally Butan, of The Butan Clan, celebrates New Year's Eve with her family in a Signature Collection villa at New Orleans Resort in Louisiana.
Sally and family of @thebutanclan celebrate New Year’s Eve in a Signature Collection villa at New Orleans Resort

All information is subject to change. This article is a curated guide and is neither sponsored nor considered an official endorsement. Please be sure to check information directly with any/all tours, guides or companies for the most up-to-date and direct details.

Our guest bloggers are compensated for their writing contributions and honest opinions.

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Close-up of Jennifer Harmon in front of a colorful wall.

Jennifer C. Harmon

Jenn was the founding Editor-in-Chief of the Checking In travel blog and is now President of the creative agency, Content Unicorn. She’s a storyteller and proud maltipoo dog mom to Bode McNugget, and she loves coffee, wine, writing, cycling and traveling. Jenn and her husband, Anthony, have mastered the art of the long weekend couples’ getaway (sans kids). And while it’s too hard to pick just one type of “favorite vacation,” her three-way tie would be a snowboarding trip, going to Hawaii or sailing with Disney Cruise Line.