About When I Wander

Estimated read time 6 min read
Estimated read time 6 min read

Welcome to When I Wander…

All About Us – Hi! I’m Portia, a homeschooling mom who has transformed into an intrepid travel guide. My mission? To inspire and lead families on their own travel adventures.

Born in the heart of Chicago and now flourishing in the sun-kissed lands of Central Florida, I have turned my city-girl roots into an undying love for nature and the road less traveled. My journey, extending over three decades, has taken me across scenic routes, idyllic coastlines, historic landmarks, and bustling metropolises in more than half of the United States and several international destinations. Along the way, I have garnered invaluable knowledge and wisdom that I share through my travel tales and tips on our family travel blog here.

About Us - littles at Mt. Diablo

At the heart of my adventures is my family – my supportive husband of 29+ years and our five delightful children. Most often, you’ll find our youngest two, Parker & Piper, featuring in our current explorations and narratives.

Art and CultureAshevilleBeachesBudget TravelCaribbeanCascaisChicagoCruise CabinsCruisesDay TripsDealsDiningDisneyFreeGardensHistoricHolidaysHotels and ResortsHurghadaIstanbulItinerary PlanningKissimmeeLas VegasLifestyleLisbonLondonLuxury TravelMallorca (Majorca)MiamiMuseumsNew OrleansOcalaOrlandoParisParksPhotographyQuotesScience and NatureShoppingSummerTravel InsuranceTravel SafetyUniversal Studios OrlandoVacation RentalsVirgin Voyages

Welcome to our corner of the world, where we celebrate affordable adventure and the creation of indelible memories. From hiking through serene landscapes to capturing the vibrancy of urban life, our passion for exploring pushes us to venture beyond the beaten path.

We relish finding amazing deals and free activities, and sharing our insider tips on locating the best value accommodations. By joining us, you’ll learn how to stretch your dollars without compromising the richness of your travel experiences.

Our travel philosophy orbits around seven key principles:

  • We go with the flow, capitalizing on the right travel prices.
  • Advanced booking of accommodations to avoid skyrocketing prices.
  • Utilizing loyalty programs and rewards for irresistible freebies.
  • Opting to drive for most destinations within a six-hour travel time.
  • Prioritizing affordable attractions and planning for “can’t miss” splurges.
  • Making the most of memberships to gain free access to numerous travel attractions.
  • Never forgetting essentials like baby wipes and sunglasses!

Over the years, we have identified a handful of reliable travel resources that have helped us save money and plan effectively:

Booking Flights: We swear by  Google Flights or Momondo for comparing prices and setting alerts.

Accommodations: We typically stay in mid-range or boutique hotels with loyalty programs.  That way we earn ourselves free stays to help extend our vacations and getaways for free.  Learn more about earning your free stays here.  For vacation rentals, our preference is VRBO  and Marriott Homes & Villas.

Travel Insurance: We feel pretty strongly about this, travel insurance is a MUST for international trips, and if you still aren’t sure why, check out our Travel Horror Stories. We recommend comparing your options with Squaremouth , learn more here

Local Attractions:  We utilize memberships to help us see more when we travel. NARM members get free or discounted access to reciprocal member Art museums, Arboretums, Historic Sites, and Nature Centers throughout North America. AHS reciprocal membership includes gardens throughout the U.S. and Canada. ASTC membership gives reciprocal access to Science Centers and Museums. America the Beautiful National Parks Pass allows entry into National Parks for $80 annually.  You could spend less than $300 for all 4 memberships depending on your local museums and have access to hundreds of museums, parks, and gardens.  Memberships often pop up on Groupon so always look there first.


Save more with loyalty programs, read how to get more free flights and hotels here.

Professionally Speaking…

Professionally, I’m a Florida Travel Agent with nearly two decades of experience in crafting perfect getaways. From my early days as a reservationist to my current career, I’ve always gravitated towards travel. I specialize in turning once-impossible experiences into achievable realities.

Whether you’re setting sail for the Caribbean or planning a magical trip to Disney World, I’ve got your back. With my extensive knowledge of Florida’s hidden gems, I’m well-equipped to guide you in making the most of your trip.

As an ardent advocate for affordable travel, I appreciate the invaluable experiences and lifelong memories that come from exploring new places. The thrill of witnessing an iconic landmark for the first time or sharing an unforgettable moment with loved ones is a feeling like no other.

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How Our Travel Inspiration Can Guide You From Daydream to Your Own Adventure

We get it; the world is a huge, beautiful place with limitless opportunities for exploration. But how do you go from dreamy travel photographs to actually stepping off a plane into you very own adventure? This is where we come in. Our family travel blog is intended to be your go-to resource for turning travel ideas into actionable plans. Here’s how it’s done:

Step 1: Identify Your Travel Inspiration

What’s Calling You?
Our blog features a myriad of destinations, activities, and cultural experiences that can serve as your travel muse. Whether it’s a secluded beach in the Caribbean or a bustling market in Bangkok, we help you identify what’s calling your soul.


Step 2: Set a Budget

Counting Your Adventure Coins
We offer practical advice on budgeting for your dream trip, including cost breakdowns for various destinations and travel styles. Our downloadable budget templates make financial planning a breeze.


Step 3: Research, Research, Research

Becoming an Informed Explorer
Our in-depth guides provide all the information you need to become an informed explorer. From visa requirements to local customs and free things to do, we help you get ready.


Step 4: Create an Itinerary

Your Adventure Blueprint
Our sample itineraries offer a balanced mix of activities and downtime, giving you a blueprint for your adventure. Plus, our tips on itinerary planning ensure you make the most of your time.


Step 5: Make Travel Arrangements

Booking Your Dream Into Reality
We guide you through the maze of flight bookings, accommodations, and activity reservations, offering insider tips on how to snag the best deals.


Step 6: Pack Smart

The Art of Packing
Our packing guides are tailored to various types of trips, ensuring you have exactly what you need.


Step 7: Prepare for Departure

The Final Countdown
Before you jet off, we help you tie up all the loose ends. From setting up an emergency contact to double-checking your reservations, we ensure you’re fully prepared with everything you need to know.  Feel free to reach out with any questions you have.


Ready for Your Own Adventure?

We believe that travel is more than just seeing new places; it’s about experiencing new cultures, meeting new people, and growing as a person. So why stay stuck in the daydreaming phase? With our blog as your guide, you’re fully equipped to turn your travel inspiration into your own unforgettable adventure.

For the travel enthusiasts, we offer a curated selection of travel merchandise on Amazon, Society 6, and Fine Art America. Our product range includes travel-inspired clothing and accessories, all selected to ensure the perfect blend of style and functionality.

Your next adventure starts right here. Welcome to our travel world.

Portia O’Laughlin

That Cruise Life / An Affiliate of Cruises and Tours Unlimited
Florida Seller of Travel Ref. No. ST15578

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Thanks for wandering with us…