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A Road Trip Mini-Moon Guide to Watch Hill, Rhode Island

By Cathleen Freedman | Photography by 


Christie and Bobby Tonnessen were looking forward to their April 17,2021 nuptials at the Coral Beach Club when the pandemic inevitably put a halt to their best-laid plans. By July 2020, they canceled the event. After the discombobulating experience of postponing a wedding during COVID-19, they figured they should stop planning for the wedding and instead start planning for a road trip.

Rhode Island was one of the few states without travel restrictions and has always been a special place for the two. “It was safe, reliable amidst the summer restrictions, and most importantly, FUN,” Christie admits. “In between dining outdoors, sunning on the beach, and biking through the winding back roads eyeing our dream homes, we did a shoot capturing our road trip where we focused on celebrating our engagement instead of worrying about our canceled wedding plans.”

Now that the world is both vaccinating and re-opening, we’re all due for a getaway! Curate a playlist, roll the windows down, and drive to Watch Hill with Christie and Bobby.


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Where to Stay

The couple reserved a room at the historic and recently restored Ocean House, which is the seaside getaway Bobby would stay for holidays with his family. Bobby’s grandfather, Bob Callahan, is even the Artist-in-Residence and painted the watercolor portrait on the luxury hotel’s Christmas card. The interiors of the Ocean House are reason enough to visit. “Bobby and I talk endlessly about homes, and interior design is a passion of mine,” Christie says, “so, not surprisingly, we fall more in love with the gorgeously designed hotel with every visit.”

For those looking to stay in downtown Watch Hill, Christie suggests the Watch Hill Inn, which is also owned by the Ocean House. Guests have access to the main hotel’s amenities and can enjoy the gorgeous beach, restaurants, and spa. The Weekapaug Inn is another favorite with picturesque views of Quonochontaug pond.


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Where to Dine

Venture into town and visit the storied, family-owned Olympia Tea Room for lunch and dinner. Sit beside all the locals in-the-know at this beloved Watch Hill landmark.

The Ocean House property features so many fantastic dining options that Christie confesses they hardly left the hotel for dinner! “If you’re lucky enough to secure an ocean facing room with a terrace,” she adds, “we highly recommend doing at least one room service meal so you can take in the view distraction-free and just enjoy the company.”

Dress to the nines and try the Oyster Club in the nearby town of Mystic. Guests of the Ocean House and Watch Hill Inn are allowed to borrow the properties’ new Mercedes, which is perfect for a detour to Stonington, Connecticut. The sixty-three-acre Stone Acres Farm has sprawling gardens, fit for alfresco dining. Stone Acres is a year-round working farm, but during the summer, they open a pop-up restaurant with seasonally inspired and locally sourced meals.

For a seaside picnic, pick up sandwiches and coffee from Ten Sandwiches. Plus, their grab-and-go options are ideal for the road trip back home!

What to Do

Christie and Bobby began each day taking in the Rhode Island scenery on wheels or on foot. The hotel provides bikes for guests, so you can traverse backroads with ease. A stroll to the lighthouse includes a stunning geographic vantage point: you can see Fishers Island, Block Island, and even Long Island along the way. Try to scout out all of the stunning celebrity cottages as you go— Watch Hill is practically a second home for stars like Taylor Swift and Conan O’Brien.

Head downtown and cross off  “Visit the Nation’s Oldest Wood-Carved Horse Carousel” from your bucket list. Whether or not you ride this historic merry-go-round from 1876, keep walking until you reach Bay Breeze Interiors. “Bay Breeze Interiors is a chic, quintessential New England antique shop with the most incredible colonial chest of drawers, sea glass lamps, antique mirrors and more nautical-inspired vintage treasures,” Christie dishes.

Christie and Bobby also stopped by Manufaktura and wound up adding a few last-minute additions to their wedding registry. She notes that “We left that day with dog bowls for our future golden retriever puppy who, at the time, wasn’t born yet, but we learned he was on his way!”

When they weren’t exploring or shopping, Christie and Bobby relaxed on the beach, played croquet, and enjoyed the hotel spa. If they could add another day to their itinerary, the first two places they would spend the afternoon are at the Jonathan Edwards Winery and the Saltwater Farm Vineyard.


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What to Pack

First and foremost, any New England road trip calls for a nautical tote bag. “When going from antiquing to the beach, and everything in between, you never know what you’ll need to throw in your bag so best to keep it simple and chic,” Christie wisely advises. We’re personally partial to this monogrammable Boat & Tote staple.

No Rhode Island-bound suitcase would be complete without proper sweater-wear. “In classic New England fashion, a striped knit pullover is not to be left behind as the evenings can be a little chilly,” Christie asserts, “and it’s the perfect piece for a sunset beach picnic or pop of champagne.” Consider an Addison Bay pullover to achieve that effortless coastal look.

Needing a little more help planning your honeymoon? Take a look at our tried-and-true travel guides. While you’re at it, you may also want to get a head start on your packing list—put together your dream registry with us and get ready for a romantic (and well-styled) getaway.