Make Room for Side Trips: Adding Adventure to Your Vacation
You’ve planned your trip, mapped out the big events, and are ready to make the most of your vacation. But as you follow your schedule, you realize something surprising: there’s extra time between your main attractions.
What should you do with that unexpected free time?
Enter the side trip.
What is a Side Trip?
A side trip is a smaller adventure tucked within your larger vacation. It can last anywhere from a few hours to a couple of days and adds an extra layer of fun to your journey. The best part? Your “home base” stays the same, so you can venture out without the stress of packing up and moving on.
Some side trips are spontaneous—a delightful discovery when you realize you have free time. Others can be planned in advance to take full advantage of your location.
Here are three types of side trips, complete with real-life examples to inspire your next getaway.
1. The Extended Side Trip
This type of side trip can last a full day or even several days. It often requires advance planning to coordinate transportation, timing, and activities.
For example, on a recent multi-generational family trip to Maui, several of us wanted to visit the WWII Valor in the Pacific National Monument, including the USS Arizona Memorial. The catch? It’s on the neighboring island of Oahu, about 100 miles away.
To make it work, we booked a day trip through the tour company Viator. They handled the flights, ground transportation, and scheduling, so we could focus on enjoying the experience. We were up before dawn to catch our flight and didn’t return until late at night, but it was absolutely worth it. Having everything pre-arranged meant we could pack the day full of unforgettable memories without worrying about logistics.
2. The Classic Day Trip
This is your traditional one-day adventure—a short excursion that gives you a refreshing change of scenery.
On a recent trip to Ashland, Oregon, we attended a play at the Oregon Shakespeare Festival on a Friday evening. With the weekend ahead and no need to return to work until Monday, we planned a Saturday visit to Crater Lake National Park.
Knowing it would be cold, we dressed appropriately, and the snowy landscape turned out to be stunning. Although the park’s road was partially closed, we still reached the lodge and enjoyed breathtaking views of Crater Lake draped in fresh snow.
The day didn’t end there. On the drive back down the mountain, my parents suggested stopping at the Rogue River Gorge, a viewpoint they’d visited years before. It was a short detour—less than an hour—but the fall colors and rushing water made it spectacular. In a way, it was a side trip to our side trip!
3. The Mini Side Trip
These quick stops, often spontaneous, add a touch of local flavor to your travels.
On the way out of Ashland that Sunday, we decided to spend a couple of hours at Weisinger Family Winery. When we arrived, the team was shoveling grape clusters into the press by hand due to a broken forklift. Watching the process and chatting with the workers gave us a glimpse into the winemaking world—and added a unique and personal memory to our trip.
Why Side Trips Matter
Whether you have a few hours or a few days of free time, side trips can transform your vacation. They allow you to explore hidden gems, interact with locals, and uncover experiences you didn’t plan for—but will never forget.
So next time you travel, embrace the gaps in your schedule. Plan a side trip or leave room for spontaneity. These small adventures often become the highlights of your journey, adding richness and depth to your overall experience.
Originally posted in 2017. Updated in 2024.