You arrive at Delamar Southport, a three-storied building with preserved 19th century architecture and elegant white columns. Walking up the antique marble stairs into the stylish lobby featuring works of Connecticut artists, you’re welcomed with a smile and a crisp glass of bubbly. A relaxing, lavish New England stay in the historic coastal village awaits.
Inside your guestroom, the gas fireplace roars, and a warm blanket sprawled over the bed invites you to get cozy underneath the soft linens. A freshly baked pair of coconut almond cookies awaits at the bed’s tableside. The bright burnt orange walls feel warm yet playful, conveying a sense of individuality, with views of the town just steps away.
Once the sun sets over the Long Island Sound, Artisan Southport, tucked away in the lobby, blends curated cocktails with fresh ingredients and garnishes alongside farm-to-table inspired entrees led by Executive Chef Frederic Kieffer. Have a seat at a bar stool at the lively bar to chat with the bartender shaking up a sweet and refreshing Dela-Margarita with caramelized pineapple. Or tuck yourself into a table in the intimate dining room, met with white tablecloths and flickering candles. When the weather is perfect for fresco dining, the courtyard is bustling with laughter and chatter among the lush plants lining the terrace.
SATURDAY MORNING — EXPLORE THE QUINTESSENTIAL NEW ENGLAND VILLAGE Lace your sneakers and head into downtown for a light stroll. Start at the wooded Southport Park, with guided walking trails through the woods, stepping stones, wooden bridges, and a log treehouse for a rest.
You might even hear a quiet bustle and see deer frolicking amongst the trees.
Continue the walk exploring Southport Harbor while taking in the breathtaking views of the sailboats docked along private marinas and yacht clubs. The town center offers historic charm, with tree-lined streets and centuries-old Georgian, Victorian, and Federal-style mansions with rose bushes adorning the front yards.
For a pick-me-up, stop by G Cafe Bakery for house-roasted coffee and espresso blends and a selection of breads from Berliner— a blend of rye and wheat flour with a dense, moist crumb and tangy flavor— or a hand-pressed prosciutto panini paired with a warm cup of the soup of the day. For a sweet finish, Atelier BE Chocolat offers a private tasting of the gemstone chocolates paired with coffee, tea, or a glass of prosecco.
Upon your return to the hotel, ask the concierge about a unique book experience in partnership with the historic Pequot Library. The Blind Date with a Book is perfect to save before bed or pack in your suitcase for the trip home.
LATE MORNING TO AFTERNOON — REST AND RELAXATION It isn’t a rejuvenating vacation without a solo trip to the spa, and The Spa at Delamar Southport is perfect for alleviating stress and bringing calmness to the body. Whether guests enjoy a deep tissue massage or a quick sauna session, they will leave feeling revived.
With a pearl clutch in hand and a purple satin dress, pinkies are raised with a hot cup of Earl Grey. The hotel’s collaboration with MacKenzie-Childs, a luxurious home decor and ceramics brand known for its checkered patterns, brings a Plum Check Collection to the afternoon lunch table, with finger sandwiches like everyone’s favorite cucumber dill cream cheese and vanilla cream puff pastries, carrot cake, and more delicacies served on the tableware.
SATURDAY NIGHT — DINNER AND A SHOW Once the sunset fades and dusk has arrived, depart for dinner at Dandelion in Westport, with the hotel’s door-to-door shuttle making the journey seamless. Sophisticated yet welcoming, Dandelion brings vibrant Mediterranean flavors to the table. After the last drop of Cabernet Sauvignon leaves the glass, it’s time for the Westport Country Playhouse, bringing beloved stories to the stage from producers of all backgrounds.
SUNDAY MORNING — A SLOW DEPARTURE Draw the blinds as the natural light fills the room for a slow morning relaxing in hand-embroidered robes in bed. Wander down to the Artisan’s complimentary breakfast buffet spread along the bar. Enjoy decadent, fresh-baked pastries like chocolate almond croissants and petite blueberry muffins, plus scrambled eggs topped with chives alongside breakfast potatoes and crisp bacon. Before leaving town, stroll through the town square shops, for a perfect parting gift.
Southport is a quiet escape from life’s noise and an idyllic place to spend the holidays, with peaceful walking trails, fireside glasses of wine, and boutique shopping all within walking distance.
From the soothing sound of sailboats by the dock to the beautiful architecture of historic homes, guests are transported to a picture-perfect corner of New England.
