Quick note on what you’re getting here: I travel a lot with my dogs. I’ve flown, road-tripped, trained, ferried, and even Uber’d with them. I’ve used every item I mention. And yes, I’ve made mistakes so you don’t have to. If you want to see how my lessons stack up against another seasoned pet nomad, check out ValidTravel’s candid rundown of dogs that travel—real-life hits, misses, and a few weird wins.
Meet My Two Co-Pilots
Bean is my 12-pound terrier mix. She’s small, bold, and thinks every bag is hers.
Milo is my 32-pound cattle dog mix. He’s sweet, clever, and hates hotel elevators. Honestly, same.
They both travel. But they don’t travel the same way. That’s where the gear and the rules really matter.
By the way, if you’re more of a cat-carrier type or just curious how our feline friends strut their stuff on the move, there’s a cheeky French photo journal called Je montre mon minou that reveals the ups, downs, and unexpected laughs of letting a kitty tag along; it’s short, visual, and might spark ideas (or at least a grin) before your first cross-city cat hop.
Flying With a Small Dog: The Sleepypod Air Saved My Trip
I’ve flown Alaska and Southwest with Bean in a Sleepypod Air carrier. It fits under the seat and still lets her curl up. That carrier breathes well. The mesh doesn’t cave in. It also has these smart little pockets that hold treats and a flat leash.
The airport part isn’t that bad. TSA makes you take the dog out of the carrier. I keep Bean in a Ruffwear Front Range harness so I can hold her close while the bag goes through the scanner. She shakes a bit when the bins clank. I get it. I do a quiet “touch” game with a soft treat to calm her. Nothing fancy. For a broader checklist of pre-flight prep and in-air etiquette, I cross-referenced the American Kennel Club’s ten tips for traveling with your dog before our first trip.
On the plane, I zip the carrier most of the way. I leave a tiny opening by my feet so my fingers can reach her nose. Weird trick, but it helps. The PA system is loud. Chewing a tiny bully stick keeps her busy at takeoff. My vet okayed a gentle calming chew for long flights (we used Zesty Paws Calming Bites once on a three-hour leg), but I don’t do that every time.
What I love:
- The Sleepypod Air actually fits under slim seats. I’ve done aisle and window.
- The padding is thick. Bean sleeps hard in it.
What’s meh:
- If I’m in a hot gate area, the carrier gets warm. I use a small cooling towel inside. Not wet, just cool.
- Southwest boarding with a dog and a carry-on plus coffee? It’s a circus. Ask the gate agent for a helper tag. They’ll smile, but it helps.
Would I fly with a bigger dog? I wouldn’t. Cargo is a no for me. Milo sticks to car trips and trains.
Road Trips With a Medium Dog: The Kurgo Harness and a Hammock
Milo rides in a Kurgo Tru-Fit crash-tested harness with the seat belt tether. It clicks in fast. It doesn’t twist. That matters when you pull off for gas and a sudden skateboard rolls by and your dog acts like it’s the end of times.
I tried a cheap hammock. It ripped. The Orvis seat cover with anchors and wide side flaps? That one lasted. It keeps the doors clean when Milo jumps in with muddy paws. I toss a towel over the middle for extra grip. Simple fix. Works.
Water and snacks go in a Yeti Boomer bowl on the floor. It doesn’t slide. I also carry a MalsiPree leak-proof water bottle for quick sips at rest stops. For treats, Milo loves Bocce’s Bakery soft chews. Easy to break, not crumbly.
We’ve done Portland to Boise, and LA to Joshua Tree. Windows cracked. Classic rock on. Milo settles after 15 minutes if my voice stays calm. Planning those longer hauls, I skimmed Kiplinger’s concise guide on retirement road trips with pets to pick up a few human-comfort hacks that actually translate well for any age driver. If I get tense, he gets tense. Funny how that mirrors kids, right? Those 400-plus-mile stretches made me curious about species stamina in general, and ValidTravel’s breakdown of how far a horse can travel in a day gave me a fun benchmark while mapping stops.
Next spring I’m eyeing a loop around the Great Lakes with a pit stop in Michigan; everyone says the river trails in Ann Arbor are a dog’s dream. While plotting that leg I also looked up some strictly-human evening options and found this detailed nightlife guide, AdultLook Ann Arbor, which breaks down late-night lounges, easy-going patios, and other spots where you can unwind while your four-legged co-pilot recharges back at the hotel.
Hotel Nights: Kimpton “Yes,” Random Fees “No”
Here’s the thing: hotels can be friend or foe.
Kimpton has been great. No pet fee when I’ve gone. They gave us a mat and bowls at check-in more than once. Milo loved the lobby pets. Bean loved the elevator buttons. She likes pressing things with her nose. It’s a whole thing.
Marriott and Hyatt vary. I’ve paid $50 to $150 in pet fees for two nights. Sometimes worth it for location. Sometimes not. I ask at the front desk for a corner room by the stairs. Less foot traffic, fewer barks. This cuts surprise “woofs” by a lot.
For a regularly updated list of pet-friendly hotel chains and their current fees, I often start my search at ValidTravel, which keeps a handy cheatsheet that’s saved me from a few pricey surprises.
I bring a Diggs Revol crate for Bean when we drive. It folds, but it’s still a chunk in the trunk. In a rental car, it fits if I plan. When Bean’s crated in a hotel, she settles faster. Milo sleeps on a Rumpl blanket. He spreads out like a pancake, sighs once, and he’s out.
For floors, I use Musher’s Secret on paws in winter. Hotel salt on sidewalks is rough. Boots? We tried Ruffwear Grip Trex. Bean marches. Milo moonwalks like he’s on butter. So boots are a “sometimes” thing.
Trains, Rideshares, and Odd Little Trips
Amtrak let me bring Bean in her carrier on the Cascades line. She stayed under the seat, slept the whole way, and only woke when a kid dropped a juice box. Staff was kind. Rules were simple: small pet, short ride, stay in carrier. Easy.
Uber Pet has worked in San Diego and Seattle. I message the driver to say “tiny dog in a carrier,” and I bring a blanket. One driver had allergies but was okay with the carrier shut. Fair call. I tip more for that.
Ferries? Bean stayed on the car deck with me on a Washington ferry. Wind, salty hair, happy dog. Milo sniffed every spot and then napped. Good day.
My Real Go-To Kit (Stuff I Actually Use)
- Sleepypod Air carrier (Bean’s plane and train bag)
- Kurgo Tru-Fit harness with seat belt tether (Milo’s car safety)
- Orvis seat cover hammock (full back seat, door flaps)
- Ruffwear Front Range harnesses (both dogs, daily use)
- Yeti Boomer bowl + MalsiPree water bottle (spill control)
- Dexas Popware collapsible bowl (backup)
- Wild One leash (nice feel, easy clean) and Earth Rated poop bags
- Musher’s Secret paw balm (winter sidewalks)
- Rumpl blanket (hotel “home base” smell)
- Diggs Revol crate (hotel and family stays)
The Stuff That Let Me Down
- Cheap hammocks with plastic clips: they snap and slide. Annoying and unsafe.
- Soft carriers with floppy sides: they collapse on a small dog’s face under a seat. Bean pawed and whined. Never again.
- Clip-on car window fans: cool idea, weak power. They rattled and spooked Milo.
- Leashes with fancy bungee handles: they felt great… until Bean slipped a hand loop while I fumbled a coffee. I went back to a plain grip.
Food, Tummy, and… You Know, Poop
I pre-pack meals in Stasher bags with labels. AM and PM. If we change time zones, I shift by a few hours each day. If I switch food on the road? That’s when we get “situations.” I bring a small roll of paper towels and a spray cleaner in