The Generational Planning Divide: Millennials vs. Baby Boomers

From needing a travel agent to book a trip to spontaneously booking one because of a TikTok, trip planning has changed dramatically over the years. Today, blogs, social media, and AI are all making it easier for the average traveler to plan their next adventure. However, traditional media still has a place in all this innovation.

I wanted to explore how travel planning and needs vary across generations—and how that should shape your marketing strategy. We’ll look at some stats and compare my experience planning a trip as a millennial to how my baby boomer parents planned theirs. We’ll break down how long it takes, how enjoyable the process is, and ultimately, how to effectively reach both generations.

• Empty nesters with more disposable income
• Prefer all-inclusive deals and are willing to pay more
• Some still use travel agents for expertise
• Hesitant to embrace social media and AI for travel planning
• Prefer longer vacations since they have the time
• Enjoy road trips for flexibility
• Prefer traditional hotels
• Rely on print ads and word-of-mouth recommendations

• The primary travel demographic today, traveling more than any other generation
• Prioritize experiences above all else and are willing to pay for them
• Prefer Airbnb over traditional hotels for a local feel and more space for family or group travel
• Tech-savvy, using social media and the internet to plan trips efficiently
• Take longer vacations than Gen Z but shorter than Baby Boomers

I’m 29, and I like to thoroughly plan a trip before arriving at my destination. My boyfriend, on the other hand, is more spontaneous, so I ironically scheduled some time for him to be spontaneous. Like many millennials and Gen Z travelers, we prioritize experiences—so activities like hiking, skiing, and sightseeing were high on our list.

We chose Colorado for its activity potential and started with the basics:

• Booked hotels via Expedia (although we do like Airbnb’s occasionally, we found some pretty good hotel deals)
• Reserved a car
• Booked flights

Then came the fun part—planning activities. We had been to Boulder before and wanted to revisit the Flatirons, Estes Park, and Rocky Mountain National Park. We also wanted to ski/snowboard and explore Colorado Springs.

I decided to try ChatGPT for building an itinerary. I gave it the prompt: “Can you help me create a 6-day itinerary for a trip to Colorado? We’d like to spend 1 day in Boulder, 1 day skiing near Boulder, 2 days in Colorado Springs, and 1 day in Denver before we fly out. We like to hike and be outdoors. We enjoyed the Flatirons and Estes Park last time but are open to suggestions.”

Two well-targeted Instagram ads served the day after I started planning led to last-minute itinerary changes:

• Immersive Gamebox (offering a Squid Game experience) replaced Meow Wolf
• Holey Moley, a 3-course mini golf experience, replaced the RiNo Art District

For ski resort selection, I turned to Reddit. Users recommended Loveland over Eldora for its quieter slopes and better pricing. Reddit also tipped me off to choosing the three-seat side of the Pikes Peak Cog Railway for the best views—and to grab a donut at the summit!

In the end, I planned this entire trip using AI, Instagram ads, and Reddit in under 6 hours. We traveled in mid-March and had an incredible experience: hiking in the Rockies while it snowed, skiing, and sipping some of the best hot chocolate thanks to ChatGPT’s recommendation. Immersive Gamebox and Holey Moley were both a lot of fun, so I’m glad I was served those ads. The Pikes Peak Cog Railway was my favorite part—and yes, the three-seat side was absolutely the better side.

This process was so smooth that I’ll likely use it as a starting point for all future trips.

My parents, in their early 60s, are active travelers who enjoy historical sites, road trips, and bringing their bikes along for mobility. My mom can’t hike as much as she used to, so biking helps her see all the sights. Being retired, they have the freedom to travel during off-peak times for fewer crowds and better prices. They enjoy their comforts; my dad is a certified hotel diva and keeps a spreadsheet ranking every hotel he’s ever stayed at. As you can imagine since I am a product of them, they like to plan out their whole trip before getting to their destination.

1. Picked a Destination: They decided to head west and used their atlas to plan a route. After they heard we were going to Colorado, they set their sights on that as their primary destination.
2. Gathered Resources: Ordered visitor guides from states they would be driving through and cities they would be exploring like Colorado Springs.
3. Used CVB Websites: Read itineraries from Visit Colorado Springs for ideas.
4. Booked Accommodations: Planned a 12-day trip, booking hotels along their route using Expedia.
5. Planned Activities: Chose to visit Rocky Mountain National Park, Garden of the Gods, Pikes Peak (after asking me which seats to book on the cog), and Mesa Verde National Park to see the Pueblo Ruins
6. Meal Planning: My dad used Yelp to check out a few local restaurants but didn’t make any reservations.
7. Mapped Road Trip Stops: Planned additional stops for sightseeing using paper maps.

Their trip was well-researched, allowing them to explore at a leisurely pace while following their planned route. They had a fantastic time and saw everything they wanted to see! They also really enjoyed the planning process. After they returned, I showed them how I planned my trip, they said they might be open to using Chat GPT in the future since it provided solid results but would miss the fun of reading through and doggy earing pages of interests in the visitor guides and marking up the maps. So sometimes saving time isn’t all it’s cracked up to be if you really enjoy the magic of the planning process.

Our planning styles were drastically different, but both resulted in successful trips tailored to our preferences. Over time, I imagine more travelers will likely adopt a hybrid approach, blending digital tools with traditional resources.

Both traditional and digital marketing methods play crucial roles in reaching travelers across generations:

• Visitor Guides: Print guides appeal to older travelers, while downloadable versions may cater to slightly younger audiences. Having the visitor guide or the visitor guide request form easily accessible is key. Providing additional links or buttons on these pages may help them explore around the site.
• Blog Content: Tailor content to different demographics, such as:
  • Active seniors: Comfort-focused itineraries, historical sites, easier hikes and bike routes, and all-inclusive options
  • Millennials: Budget travel tips, family travel tips, pet-friendly spots, unique activities or experiences
• SEO & AI Influence: Ensure blogs have accurate, well-structured information to be picked up by AI tools like ChatGPT. Use conversational language that’s well understood by the user, offering bullet points and helpful links within the blogs and pages.
• Digital Ads: Well-targeted ads influenced my trip—proving that smart targeting is key. I saw these ads within a day of starting my planning and was immediately drawn because my boyfriend and I love Squid Games and I dominate in mini golf. Focusing on specific demographics and locations can help but targeting for specific audiences who engage with a page, products or social media, additionally, adding in interest targeting or experimenting with some of the AI integrations can greatly help get you in front of the correct eyes.
• Social Media Presence: Pinterest remains a go-to platform for trip planning (especially among women), while TikTok and Instagram Reels drive discovery for younger travelers. So, keep posting organically, and it doesn’t have to be professional content. Unpolished can be a best practice.

Whether you’re a traveler or a CVB, understanding generational differences in trip planning can help create stress-free travel experiences and effective marketing strategies. If you’re about to plan your next adventure, I hope this gives you some new ideas. And if you’re in the travel marketing space, consider this an inside look at how your audience is making travel decisions! Happy travel planning!

Ashley Maddix

Digital Advertising Strategist