You’ve made your flight reservations or plotted your route for vacation. Now what? Once you arrive at your destination, do you know what you want to do? Or, does it seem like you do the same types of activities over and over when you travel? It’s easy to develop a travel itinerary rut. Not to worry, here are 9 unique itinerary ideas that will have you traveling like a local and enjoying destinations like never before.
1. Catch a Local Theater Performance
Whether it’s a community playhouse or an experimental black box production, local theater offers insight into regional culture and talent. Additionally, it’s always a fun way to spend an evening or afternoon.
Before you travel, research local theater groups or performances that may coincide with your visit.
I’ve had great luck finding entertaining shows, everything from a moving WWI Christmas play in Asheville, North Carolina, to a laugh-out-loud audience participation mystery in Charleston, South Carolina. Community theaters have been a favorite itinerary idea. Best of all, the tickets are usually comparatively inexpensive, making catching a local show an affordable option as well.
2. Attend a Local Sports Event
From minor league baseball to high school football or roller derby, local sports are full of energy, hometown pride, and a fun, budget-friendly night out.
Plan ahead and check out the team schedule so that you can add a fun sporting event to your list of itinerary ideas. This is a great way to immerse yourself in the local culture and support the home team while you’re visiting.
3. Browse a Farmers' Market, Attend a Festival, or Artisan Fair
Farmers’ markets are filled with local produce, handmade goods, and a strong sense of community spirit. They’re also great places to chat with locals and find delicious goodies to enjoy while you’re there. Likewise, local festivals and artisan fairs offer visitors a unique glimpse into the community and the people who make it special.
I’ve made it a point to visit several towns during festivals, and by adding these events to the itinerary, it’s provided extra fun for touring these destinations. Furthermore, festivals deliver an added level of excitement and memories you’ll cherish for years to come.
4. Join a Local Walking Club, Group Walk, or Walking Tour
Many communities host walking groups that welcome visitors for casual strolls, scenic routes, or themed walks. It’s a great way to explore at a local’s pace and maybe make a few new friends.
If you don’t find a walking group, visit the town website to learn about a walking tour. Many towns offer self-guided tours via their website or an app. You can hit the pavement for fun, exercise, and for an up-close, personal look at your destination.
5. Listen to Live Music at a Neighborhood Spot
Skip the big concert halls—look for pubs, cafés, or patios where local musicians play. You might discover a new favorite band in the most unexpected place.
Plan your evening meal to include a little musical accompaniment. One of our favorite travel serendipities was finding a cozy winery in Rabun Gap, Georgia, that featured musician Teddy Baker. Baker once played with Paul Davis, who had several hits on the radio back in the late 70s and early 80s (I Go Crazy, Cool Night). Ironically, we ran into him again a few years later at another winery in Cleveland, Georgia.
There is something special about enjoying live music on your journey. That music becomes a soundtrack to the trip and makes the memories all the more meaningful.
“Don’t pack your schedule too tight. Leaving a little wiggle room gives you the chance to stumble upon those unexpected gems, maybe it’s a cozy café down a quiet lane or a local you meet who points you toward a hidden treasure. Some of the best travel moments aren’t planned.”
Anna Marie
6. Take a Creative Workshop or Hands-On Class
Pottery, painting, beekeeping, cooking, baking—local classes let you try something new while connecting with the area’s culture and artisans.
There is an array of classes to choose from, which allows you to be as creative as you wish. Many businesses cater to out-of-town guests who are looking to experience a class that is unique to the area. Do a little research before you arrive to make sure you snag a spot in a class that excites you. You might even end up with something delicious to take with you or a special handmade souvenir.
7. Ride a Historic Trolley, Heritage Train, or Commuter Ferry
These often-overlooked transport options offer scenic views and a laid-back way to see the area, especially if they’re used more by locals than tourists.
You really can’t go wrong with transportation, especially if it is an out-of-the-ordinary mode of transportation. Not only will it be a great itinerary idea, but it will make the trip more exciting.
8. Find a Kid-Friendly Local Gem (Even if You're Not Traveling with Kids)
Visit a small children’s museum, ride a vintage carousel, or stop by a local farm with animals. These places are charming, often affordable, and full of heart.
They’re also crowd pleasers for tiny travelers. It’s always a good idea to include itinerary items that let youngsters play and immerse themselves in their new surroundings, too.
9. Check Out a Quirky Local Museum or Exhibit
Doll museums, neon signs, vintage toys—you’ll find the weird and wonderful tucked into almost every town. Museums are great for rainy days and great stories.
I love finding the most unusual museums because so often I come away with a new understanding and appreciation for the subject matter. The Medieval Torture Museum in St. Augustine, the Kool-Aid Musuem in Hastings, Nebraska, the Louisville Slugger Museum in Kentucky, and the Cork Butter Museum in Ireland are just a few of the standouts from my explorations. You simply can’t go wrong with a local museum on your itinerary.
More Great Itinerary Ideas
These itinerary ideas aren’t just about filling your schedule—they’re about finding the soul of a place. So leave a little room in your travel plans for spontaneity and surprise. You never know what you’ll discover waiting for you that will make you say, ‘Pull over and let me out!’
Have you ever stumbled upon something unexpected while traveling? Share it in the comments—I’d love to hear!
Listen on the go!
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