Sometime in the steamy haze of August in Sarasota, we glanced at the calendar and had a thought that felt almost magical: Wouldn’t a New England Thanksgiving be perfect?
With most of our family based in New York and Connecticut, it didn’t take long for that idea to turn into a plan.
And just like that, we were off to the races.
Spreadsheets were created. Lists multiplied. Google searches became a daily ritual. We found ourselves asking all the important questions:
Are there really dog-friendly rest stops?
Do Love’s Travel Stops actually have fenced areas?
And what about those pet fees—$50, $75, even $150 per night?
What we quickly learned is this: no matter how much you plan, you don’t really know a place until you’re standing—or sleeping—in it.
So if you’re considering making the drive from Florida to the Northeast with your pup, come along. We’re sharing what worked, what didn’t, and how to make your trip more fun than frustrating.
First Things First: The List (Yes, the Big One)
Before locking up the house and loading the car, a final checklist is everything. Maybe we went a little overboard—but honestly, it paid off.
Beyond the basics (ID tags, meds, food, water, and a bed), here are a few extras that made a big difference:
- An extra favorite toy (things will get lost)
- Multiple water bowls (keep one within reach for a quick drink at a rest stop)
- Bottled water for easy access
- Plenty of treats for morale—yours and theirs
Setting Up the Car for Comfort
We invested in the Ruff Rover seat cover, which works like a hammock across the back seat with a firm base so your pup won’t slide into the footwell. That alone made the ride safer and more comfortable.
On top of that, we added a memory foam bed with raised edges—perfect for head resting and keeping toys contained. And of course, a seatbelt attachment for the harness.
It turned the back seat into a cozy little travel lounge.
Leg 1: Sarasota to Savannah (The Reality Check)
About six hours—totally doable, right?
For our first night, we decided to go budget and booked a Red Roof Inn right off I-95 in Savannah. No pet fee sounded like a win.
It wasn’t.
While the location was convenient, the property had clearly seen better days. There was a lot of activity in the hallways, constant door slamming, and overall it just didn’t feel clean or comfortable.
Lesson learned: sometimes “no pet fee” comes at a cost.
On the way home, we gave Savannah another shot and stayed at a Staybridge Suites in the historic district—and what a difference.
It was very clean, a bit lively and welcoming. There was even a social hour at the bar, a solid breakfast, and a park nearby for easy dog walks. Yes, there was a pet fee—but it was absolutely worth it.
Leg 2: Savannah to Richmond (Finding Our Groove)
This stretch is about seven hours, and after our first experience, we made a quick pivot.
We canceled our Red Roof reservation (no hassle, thankfully) and rebooked at a Hampton Inn in Richmond.
It was exactly what we needed—clean, friendly, and reliable. Early coffee, a great , free breakfast, and a small grassy area with a pet station made traveling with our dog easy. You’d never even know pets were allowed, which says a lot.
On the return trip, we treated ourselves to a stay at The Jefferson Hotel in downtown Richmond—and it was unforgettable.
This place is pure old-world luxury. Think grand lobby, holiday decorations everywhere, (in December) and a true VIP welcome for dogs. We enjoyed cocktails in the lobby with our pup, had an incredible meal, and were even upgraded to a beautiful suite.
Yes, it’s a splurge—but if you need a reset mid-trip, this is the place.
A Cozy Pause in Philadelphia
From Richmond to Philadelphia is a shorter, four-hour drive, and by then we were craving something that felt a little more like home.
We booked a small Airbnb in Fishtown, and it was perfect. A full kitchen, easy street parking, and first-floor access made traveling with our dog simple.
After days on the road, being able to scramble eggs and make toast felt like pure luxury. No pet fee, and under $200 for the night—it was a great value.
The Final Stretch
From Philly, we made our way to Connecticut, navigating a bit of traffic near the George Washington Bridge, and arrived mid-afternoon—tired, but happy.
For the rest of the trip, we stuck with Hampton Inns. By then, we knew exactly what we were getting: clean, consistent, and easy.
A Word About Rest Stops
Not all rest stops are created equal.
We found that county-run stops were the most reliable—clean facilities, grassy areas, picnic tables, and pet waste stations.
Love’s Travel Stops advertise dog parks, but in our experience, they were small chain-link enclosures with rough gravel—not ideal, especially for smaller dogs.
Was It Worth It?
Absolutely.
It was an experience we wouldn’t trade for anything. The memories, the adventure, the time together—it all mattered.
Would we do it again?
Maybe… but next time, we might look into flying with our pup. Services like private pet-friendly air travel are starting to feel comparable in cost once you factor in hotels, food, and sheer travel fatigue.
Final Thoughts
If you’re planning a road trip with your dog, here’s the truth: it’s not always easy—but it is worth it when you do it right.
Plan well, stay flexible, and don’t be afraid to spend a little more for comfort and cleanliness. It makes all the difference.