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Going on vacation is fun! Planning a vacation…not so much.
I love to travel, and I love to plan a vacation for myself. But when you're on the hook to build an itinerary that satisfies your own interests, your spouse's, and the interests of your parents who are road-tripping with you…the stakes get high and the pressure is on.
Long story short: planning a multi-generational road trip is an extreme sport of balance, timing, and action.
When my wife and I decided to drive down from Winnipeg to Minneapolis with my parents to see Tim McGraw, The Chicks, and Lady A at Target Field, the concert was the only locked-in item on the calendar.
The rest of the weekend? Entirely in my hands.
My instructions were somehwat vague: "Let's do some shopping" and "We want to see the sights."
To make things more interesting, I was behind the wheel of my dad's full-size Dodge RAM. This meant navigating an unfamiliar city with tight downtown parking, interstate speeds, and cross-border conversions in a vehicle that was not my own.
Because I run this tech website and host a national TV segment about tech and gaming, I'm often telling people about the benefits of letting AI "take the wheel" for trip planning. So, I decided to take my own advice.
Instead of spending hours cross-referencing travel blogs, parking garage clearance forums, and mapping apps, I put Amazon's new generative AI-powered Alexa+ and the Echo Show 11 to the test.
The biggest takeaway? While I thought planning on my Echo Show 11 at home would be the end of the prep work, I frequently tagged in the Alexa mobile app on the go for last-minute tactical advice.
Here is a rundown of what it's actually like to let an AI helper co-pilot plan a cross-border vacation.
1. Solving Highway Friction in Real Time
Cross-border driving comes with instant mental friction. The second we crossed into North Dakota, I realized the truck's digital instrument cluster was still locked to kilometres per hour.
Trying to calculate 70 mph on the fly while navigating unfamiliar merges isn't ideal.
Instead of pulling over to swipe through layers of steering wheel menus on an unfamiliar truck dashboard, I opened the Alexa app on my phone:
The Prompt: "Alexa, how do I switch the digital speedometer display from km/h to mph in a Dodge RAM?"
Within five seconds, it gave me the exact button sequence on the left steering pad to toggle the digital gauge. No scrolling forum threads, no PDF owner's manuals.
On the seven-hour drive to Minneapolis, it was equally helpful for scouting regional fast food we don't have in Winnipeg (yay, Culver's: definitely try the deep-fried cheese curds) and finding easy fuel stops with wide berths along the route.
It also kept family debates moving. While discussing our upcoming stop at the Albertville Premium Outlets, we asked Alexa+ for the store directory, current hours, and whether there were special savings for Canadian shoppers, which pointed us toward immediate signup perks at spots like Skechers and Gap.
2. Crafting an Itinerary With Minimal Guidance
The main test for Alexa+ was turning vague family requests into a tight, geographically sensible schedule. Rather than giving me rigid template results like older voice assistants, the new generative model understands layered criteria.
The Prompt: "We're staying in Minneapolis/St. Paul. We love regional history, unique guided tours, and need dinner nearby with easy parking for a full-size truck."
The result was a weekend that flowed without backtracking:
- The Gangster & Architecture Morning: It mapped our morning starting at the Wabasha Street Caves Tour for 1930s mob history, followed directly by downtown St. Paul's federal building (where John Dillinger went to trial). Inside the Landmark Center, we also caught a great music exhibit hosted by a local arts organization.
- Tornadoes, Mining, and Mansions: It steered us to the Minnesota History Center (specifically flagging the historic mining and 1965 Fridley tornado exhibits) before routing a walking path along Summit Avenue past F. Scott Fitzgerald's historic home.
- Stress-Free Dining: It recommended Forepaugh's Restaurant, pairing historical ambiance with incredible multi-course dining (the blue crab pasta and artisan gelato lived up to the hype) while routing us to high-clearance parking at the RiverCentre ramp. I also hinted that I wanted something "Ghosty" and this place is supposed to be haunted.
- The Historic Trolley Connection: For our pre-concert morning, it found the Minneapolis Trolley Tour departing from a historic mansion, letting us grab a light lunch on the grounds before heading to Target Field.
I went back and forth to refine some stops, which was one of the most natural parts of the experience. I didn't have to use a robotic cadence; I could ramble, self-correct midway through, or cut in if a suggestion missed our personal vibe.
On the road, the real lifesaver was parking and transit advice. Alexa+ helped us assess whether taking a massive truck downtown was worth the headache versus hailing an Uber. For the Vikings pre-season game and the Tim McGraw concert, it even calculated how many blocks we should walk away from the stadiums to dodge heavy rideshare surge pricing.
3. How Alexa+ Actually Differs for Canadians
For years, smart assistants have felt transactional: set a timer, play a song, report the weather. The leap with Alexa+ on the new Echo Show 11 comes down to memory and continuous conversation.
Aside from local colloquialisms like knowing what TimBits are, Alexa+ was also mindful of Canadian pricing/exchange rates and helping us get the best bang for our buck when considering the possible tours and experiences we could enjoy.
It's also nice to talk to a smart speaker without feeling like you're talking to a robot. You don't need to repeat setup details every time you speak. Saying "Remember we have the big truck" ensures subsequent requests for dinner spots or parking naturally filter out tight underground garages with low overhead clearance.
Geeking Out Shop
Amazon Echo Show 11
Smart Display
This upgraded smart display is built on Amazon's AZ3 Pro processor and Omnisense sensor fusion platform. At home before the trip, using the bright 11-inch screen to visually map out travel days, review route forecasts, and coordinate family schedules made pre-trip planning collaborative rather than a solo chore. You can speak like you're having a normal conversation and get things done using Alexa+ on the Echo Show 11.
- Canadian Availability & Pricing:
- Included with Prime: Amazon Prime members in Canada receive unlimited access to Alexa+ at no additional cost across Echo devices, the Alexa mobile app, and Alexa.com.
- Free Chat Tier: Non-Prime users can access a web/app-based text interface to try out research and planning workflows.
- Standalone Subscription: For households without Prime wanting full voice-driven ambient AI features across all household devices, it is available for $27.99 CAD/month.
Now that I've trusted Alexa+ to help me plan a trip, I would absolutely do it again. It surfaced stops that weren't on my radar (like the pre-season NFL game or the walk down Summit Avenue) while leaving enough room for me to customize the details.
Alexa+ got me 90 per cent of the way there. And truly did an amazing job of putting things on my radar I absolutely would've missed, like the Schubert Club Music Museum, a free experience where you can go hands-on with instruments from around the world while learning about the musical and artistic history of the Twin Cities.
Whether you're gearing up for back-to-school schedule chaos or trying to keep three generations happy on a cross-border road trip, having an assistant that understands real-world context turns tech into genuine peace of mind.
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