Where to Wander: The Art of Choosing When and Where to Travel

As a family, we often find ourselves reflecting on the fleeting nature of our vacation time.

With kids growing up so quickly, the question lingers: How many summer breaks do we have left before they head off to college? The pandemic taught us the value of family adventures and the joy of traveling together. Now with school commitments and extracurricular activities on the agenda, finding time for travel can be a challenge. Like many families, we’re restricted to school vacations, making it all the more important to make every trip count.

Deciding on the Perfect Destination

Choosing the ideal travel destination involves a mix of logistical considerations and personal preferences. Here’s a glimpse into our decision-making process:

  1. Timing is Everything: The time of year can make or break a trip. For instance, we once dreamed of visiting Tanzania for winter break, only to realize it wasn’t the best timing for witnessing the Great Migration. We will save that for a summer trip. We also factor in the length of our trip. A week for spring break means a different approach compared to the multiple weeks we might have in summer. There are some places that we would want to plan for a longer visit either because of the challenge of getting there, or the vast amount of things we want to explore at that particular destination.

  2. Age and Interests: Our kids’ ages, abilities, and interests play a crucial role in shaping our travel plans. We waited until the kids were old enough to snorkel and had a solid understanding of animal species before heading to the Galapagos Islands. We also look for specific opportunities that align with their interests, such as sporting events for Jackson, or the opportunity to see animals up close for Lila. Such considerations ensure everyone gets the most out of the trip.

  3. Special Events and Opportunities: Sometimes, our travel plans are influenced by unique events. For example, a trip to Paris was a no-brainer when the Olympics were in town.

  4. Balancing Commitments: We also consider our current life commitments. How will this particular trip fit in with the other activities in our lives? If we’re in need of a relaxing getaway, a beach vacation might be more suitable. If we’re feeling adventurous, we might opt for something more activity-packed.

 
Paris 2024 Family Photo

2024 Olympics in Paris

 

Brainstorming and Inspiration

Once we have a framework, the fun begins with the ‘Big Brainstorm’. We throw out all the dream destinations, from places we've always wanted to visit to suggestions we have heard about through our friends or on social media. As a doctor, I have access to a fantastic network of physician moms who share incredible travel ideas within a dedicated Facebook group for travel inspiration. These unique suggestions often lead to some of our most memorable trips.

From our brainstormed list, we start narrowing down options based on logistics—seasonal factors, travel time, and duration. We also consider budget aspects, such as high-season pricing or special events that might affect our experience. If possible, we leverage travel points or special deals to make the trip more affordable.

Family Vote and Final Touches

After narrowing down our options, we hold a family vote to choose the final destination. We discuss what each of us are most looking forward to during this vacation, and any special activities or sites we’re excited about. This helps in planning and booking essential activities far enough in advance, ensuring we balance relaxation with adventure. We strive for a mix of planned and spontaneous experiences to keep the trip enjoyable for everyone.

Making Plans

Choosing to attend a popular special event or bucket list destination can sometimes make booking plans challenging. When something big is happening, or a lot of travelers are interested in a particular place, the cost of flights and hotels increases, and also makes getting reservations more challenging. We navigate this with a little creativity and flexibility in order to still make our dream tip happen. In these cases we also try to make our plans as early as possible to allow the most flexibility.

An example of this occurred this summer when we decided on including a visit to the Paris Olympics in our plans. I knew that flights were going to be expensive and limited. I hoped to use our transferable credit card points in order to minimize the airfare cost for our family of four to travel. As I began to look at options more than a year in advance, I realized that flying directly to Paris was really expensive and there were no award flights using points available. I considered whether I could use points to fly to a different nearby city in Europe that could be a short transfer away. Ultimately I was able to book our family on a British Airways flight to London using our points, and reserved the Eurostar to Paris a few hours after arrival. This ended up being a great strategy, not only was I able to use our points instead of using our travel budget for the flights, we ended up adding a stay in London to our itinerary which allowed us to enjoy the summer’s hottest concert.

Needing to Pivot

We have also had situations where we settled on a destination and plan, then needed to switch our plans due to circumstances beyond our control. Our first experience with this was during COVID when we opted for a domestic road trip to national parks rather than flying to Europe. We ended up really enjoying the trip even though it was not our originally planned itinerary. This happened again this past year for spring break, we had voted on a private catamaran trip to visit Dry Tortuga National Park in the Florida Keys. I have always been interested in seeing the park, and we would have had the opportunity to stargaze there in the evenings. After booking our trip I received a call from the Captain that we would need to change our itinerary. I was disappointed because while we were excited about being on the catamaran, however part of that excitement included our itinerary in the Keys.

During our particular vacation dates, the Captain was obligated to sail in the Bahamas as soon as we departed. He offered us the opportunity to sail around Abaco instead. He shared that he thought that this itinerary was even better than what we had planned, and that we could still do many of the same activities we had looked forward to, with the exception of visiting Dry Tortuga National Park. We discussed it as a family, considering whether we wanted to plan a different trip and save the catamaran experience for when we could visit the Florida Keys. Ultimately we made the decision to go to the Bahamas because we were really looking forward to the catamaran experience. We ended up absolutely loving Abaco and realized that the opportunity to switch our trip ended up making the trip and destination one of our all-time favorites. Staying positive and thinking about what was most important in the experience (in this case being on the catamaran) allowed us to enjoy the change in plans.

 
Abaco Family Photo on the water

Sailing Around Abaco on a Catamaran

 

Embracing the Adventure

Deciding where to go can be one of the most challenging parts of travel. With so many possibilities and limited time, it’s crucial to engage everyone in the decision-making process. By being mindful and enthusiastic about our destination, we make our family trips truly special.

So, how do you choose your vacation spots?

Share your strategies and favorite destinations—let’s inspire each other to make the most of our family travel time! 👇

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From Anticipation to Adventure: Sparking Excitement for Your Upcoming Travel