In the Driver’s Seat: A Fall Weekend in Southport, Connecticut

Far-flung travel is fabulous if you have the time (and budget!) to make it happen. But if you’re looking for a quick and easy getaway, allow us to remind you of the beauty of the weekend road trip. In this recurring series, we ask seasoned travelers to share all the details of their best recent trip, from the car they drove to the clothes they packed—and, of course, the must-visit locations on their itinerary.

There’s something special about escaping into the calm of Connecticut.

After a year of rigorous wedding planning, my husband and I quickly learned there was no way we were going to have a full-blown honeymoon immediately following our official celebration. It’s not that we couldn’t make it work, but logistically it didn’t make sense. We were new puppy parents, there was no way we could have brought enough clothes to make it from New York to New Orleans to Italy, and most importantly, we were simply exhausted. So we decided (like a lot of modern couples of late) to push our official honeymoon into next year and instead unwind with a low-stakes “mini moon” as we eased into our new, postnuptial reality.

Considering we live in Brooklyn and just celebrated our marriage in New Orleans (by no means a quiet or quaint city), we knew we were hoping for a getaway that was romantic but also tranquil. It turned out Southport, Connecticut was the answer.

Where to Stay

When it came to pick a destination for our mini moon, my husband and I wanted to stay close to home, since we’re new parents of an almost one-year-old Lab mix. And after spending over a week away for our wedding, we wanted to get a few days of downtime while ensuring our pup could tag along. I was also dying for a proper fall getaway and dreaming of crisp weather and ombré foliage. Southport specifically attracted us with its proximity to the water, gorgeous surrounding architecture, and quaint small-town vibe. We chose to stay at Delamar Southport (one of four Delamar hotels in New England and northern Michigan, with two more arriving in 2024), a charming (dog-friendly!) boutique hotel in the area with farm-to-table restaurants and mini-moon-appropriate excursions. The suites are roomy and feel like home—perfect for winding down at the end of a busy day exploring.

What We Drove

Delamar Hotels

A perk of staying at any Delamar property is that you technically don’t need to drive anywhere. At every Delamar location, guests can opt to be chauffeured in luxury cars from owner Charles Mallory’s pristine personal collection. That includes Rolls-Royces, Bentleys, 1941 Cadillacs—you name it. It’s an extra special touch that makes driving up and down the tree-lined streets all the more special.

What I Packed

When it came to packing for this trip, I didn’t want to think too hard about what to wear every day—I just wanted to feel cozy. That meant bringing along my favorite oversize sweaters (like a knit number from Anine Bing I basically live in every autumn), wide-leg jeans (comfortable but still elevated), and walkable moto-inspired boots or my platform Ugg mules. I wanted to keep my beauty routine pared back as well, and spend less time getting ready and more time exploring, so I brought the essentials: my Rhode skincare kit, Haus Labs concealer and Rare Beauty blush, and easy treatments like Milani’s Fruit Fetish lip oils. My smaller carry-on luggage from July and oversize duffle bag from Away held everything I needed.

Carry On
July Carry On
Credit: july
The Medium Everywhere Bag
Away The Medium Everywhere Bag
Sydney Ribbed-Knit Turtleneck Sweater
Anine Bing Sydney Ribbed-Knit Turtleneck Sweater
Citizens of Humanity Beverly Boot
Citizens of Humanity Beverly Boot
Eyra Boots
Jane Sunglasses
Elisa Johnson Jane Sunglasses
The Rhode Kit
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Where to Eat

la plage westport

Delamar Hotels

La Plage

La Plage is one of the best dining experiences I’ve had in New England, full stop. Obviously, seafood is the center of the menu (the restaurant’s name is French for the beach, after all), and rotating seasonal dishes like squash risotto, seared scallops, and luxe seafood towers help maintain a steady influx of regulars. During the summer, seats on La Plage’s patio are obviously in high demand, but an evening visit during autumn is still moody and romantic. Even if you’re skipping dinner, it’s worth popping by the bar for their divine espresso martinis and a few bites of dessert. While technically in the neighboring town of Westport, it’s only a 10-minute drive from Delamar Southport.


a table with candles and glasses

Delamar Hotels

Dining at Artisan feels like stepping into your own dining room—where standout chefs just happen to be preparing the night’s meal. The menu is a thoughtful curation of farm-to-table cuisine including homemade gnocchi, pumpkin ravioli, chicken foie gras meatballs, and crispy duck confit. Staying for dessert—whether the fresh ricotta donuts or lemon verbena crème brûlée—is simply a must.

Bonus Spot: BE Chocolat

If you have a major sweet tooth (like me), then a pit stop at the neighboring BE Chocolat is a must. Award-winning master chocolatier Benoit Racquet crafts artisanal Belgian chocolates in unique flavors such as limoncello, pink sesame, and vanilla bourbon. Make sure to buy two boxes: one to eat as a late-night snack back at the hotel and another to take back home as a souvenir.

What to Do

A sunset boat ride for two

a bench sits in front of a marina full of boats

Delamar Hotels

A bottle of champagne, the setting sun, and a top-tier view of the Long Island Sound? What more do you need? Grab your favorite coat and bundle up for a predinner boat ride for two (or up to six, if you’re feeling social).

A romantic picnic

a person sitting on a blanket in front of a car

Courtesy of Bianca Betancourt

I highly recommend using the Delamar’s chauffeur service and planning a picnic for two while the weather still allows. We sat out by the water (no too far from La Plage) and had delicious meals (think Scottish salmon and roasted chicken with autumnal squash) handcrafted by the team at Artisan for a relaxing lunch. Whatever you do, make sure to order the apple tart and crème fraîche if it’s in season.

A couple’s spa day

delamar hotels spa

Delamar Hotels

Delamar Southport specifically is working to expand its spa offerings by the end of this year, with new relaxation rooms and saunas being added to the property for guests searching for a winter escape. Until then, the hotel still offers top-tier massages and facials, incorporating luxury products from Biologique Recherche and Valmont into the treatments.

Headshot of Bianca Betancourt

Culture Editor

Bianca Betancourt is the culture editor at, where she covers all things film, TV, music, and more. When she’s not writing, she loves impulsively baking a batch of cookies, re-listening to the same early-2000s pop playlist, and stalking Mariah Carey’s Twitter feed.