Our anniversary trip to Bermuda — and why every parent needs a trip like this
Okay, hear me out. I know what this site is called, not to mention that I’ve built an entire brand around the idea that travel with kids is not only possible but incredibly meaningful.
And yet, when my husband and I hit our 10th anniversary, we leaned into a promise we’d made each other 11 years prior. Off a desolate little beach in Bermuda, just after he’d proposed and while we were blissfully floating in the Atlantic, we suggested that we’d come back to celebrate 10 years of marriage. And so we did.
We left our kids with grandma and grandpa for a handful of days while we carved out time for only ourselves. It. Was. Heaven. Afternoon naps. Decadent and drawn-out dinners. Beach visits without a floatie or sand shovel in sight. Fruity cocktails on repeat. And unexpectedly, time and space that naturally led to the type of core conversations that set the foundation for the next 10 years.
If you’ve been craving a similar escape, go ahead and hit copy and paste on our getaway. (It was that good.)
Where We Stayed: The Rosedon Hotel
The Rosedon is an adults-only boutique hotel in Hamilton, and it is exactly what you want when you’ve temporarily offloaded your parenting responsibilities for a few days. It started life more than 100 yeas ago as a private home and the original residence is now the lobby and restaurant, perched at the front of the most beautiful garden property.
Thirty-two guestrooms – every one with colorful and charming aesthetic – wrap around a chic pool outfitted with the sort of luxe striped and fringed shade umbrellas that elicit a frozen cocktail order. Outside each guestroom, you’ll find a private seating area. Inside, the coziest beds and ceiling fans complement the chirping of island birds, all of which sent us into the deepest sleep I’ve had in ages.
And as if that weren’t enough, the on-site restaurants alone are reason to make The Rosedon your homebase. There’s Huckleberry, a proper fine dining experience on the grand front porch. Nearby, tucked among the greenery, Clarabell’s serves up oven-fired pizza and cocktails. The pool bar delivers chill DJ tunes on the weekend, as well as full vibes. And for mornings, there’s a coffee and food truck setup called Bagels & Brew that is the perfect, zero-effort way to ease into a day with nowhere to be. (Book direct through the hotel’s website for free daily breakfast, which was amazing!)
The location is also ideal – you’re steps from electric car and boat rentals, downtown Hamilton, and Miles Market, a gourmet grocery that’s perfect for grabbing beach snacks and sunscreen before you head out for the day.
What to Do
Beach hop. Bermuda’s pink sand beaches are real and they’re as dreamy as every photo you’ve ever seen. Horseshoe Bay is the most famous and the most vibrantly pink, and you’ll find rental umbrellas and lounge chairs as well as a small bar serving up drinks and a few beach bit options. But the real move is to wander far to the left side of this lifeguarded beach and follow alcove after alcove until you’ve found yourself a completely private stretch of sand.
Rent a tiny electric car. Traditional rental vehicles aren’t available to tourists on the island, but you can rent a one- or two-seat EV and zip around at your own pace. We picked ours up from Current Cars, right across from the hotel, and kept it for a 9–5 stretch, plenty of time to explore. Given that the entire island is only 21 miles long, we never even needed to charge it. It’s one of those unexpectedly fun logistics that offered us the flexibility to go wherever, whenever for a day.
Get out on the water. This is non-negotiable. On our first trip we rented a 13′ Boston Whaler boat and found our own deserted beach from the water. This time we booked a half-day boat rental through KS Watersports (also across the street from the hotel; everything is wonderfully close) and headed out toward Nine Beaches and a shipwreck. Bermuda’s water is a genuinely unreal shade of turquoise.
Visit the caves. We skipped these on the return trip but did them on our first visit and they stuck with me. Bermuda has a beautiful cavern system, it’s a cool, otherworldly way to spend an afternoon, and apparently they now offer massages inside the caves, which, I mean. File that under things you cannot do at home with your children.
The Swizzle Inn. This historic bar is the birthplace of the Bermuda Swizzle: rum, juices, tangy, refreshing, and exactly the kind of thing you order by the pitcher on a slow or rainy afternoon. (Go on and order the pitcher. You’re on vacation.)
Stroll St. George. The island’s most historic and colorful town is absolutely worth an afternoon. Historic reenactments, cute shops, good food, and the kind of charm that makes you want to take pictures of everything.
Getting There: Easier Than You’d Expect
This was genuinely the most surprising part of the trip. Bermuda is less than a two-hour flight from multiple East Coast airports, which means this is not some epic international undertaking — it’s closer than many domestic destinations.
We flew BermudAir, and I want to talk about this for a second. Every plane is configured in rows of four, meaning there are no middle seats. On top of that, you’re served free drinks in actual glassware and fresh, Bermuda-made chocolate chip cookies the size of your face. It felt less like a regional airline and more like someone had decided air travel should just be… pleasant? (Three cheers all around; we kept looking at one another and wondering why every airline couldn’t operate like this.)
On that note, the Bermuda airport itself is new, compact, and easy to navigate. But the thing that really got us: you clear U.S. customs in Bermuda before you leave, which means you land back stateside and just walk out. No customs line. No waiting. Just home.
BermudAir currently flies direct from several East Coast U.S. cities and Canadian destinations, so if you live along the eastern edge of the states, checking your options is an absolute must. We connected after flying Delta into Baltimore.
The Bottom Line
I don’t say this lightly coming from this particular corner of the internet: some trips are better without your kids. Not because your kids aren’t wonderful. But because you existed before you were a parent, your relationship existed before you had children, and it deserves to be tended to somewhere beautiful with good food and pink sand and no one asking where the snacks are.
Bermuda is that place. And it may actually be one of the few destinations that genuinely feels more convenient for two. Those teeny EV rental cars don’t seat more than two, for instance. Even so, it didn’t keep us from noodling when we’d be able to get back, with the kids in tow…
