"I have loved cars my whole life and wanted to share my passion for special automobiles with our guests to enjoy."

- Charles Mallory, Founder of Delamar Hotels

A Classic Getaway

Indulge in the epitome of luxury with Delamar Hotel's chauffeured classic car experiences, a peerless journey into sophistication and elegance. Elevate your stay by selecting from our exclusive fleet of vintage and modern collector cars from Delamar Hotels founder Charles Mallory's personal collection. Your voyage awaits where opulence meets history and every moment becomes a timeless memory.

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the side of a black car

1941 Cadillac Series 60 Special Fleetwood

This beautiful machine was the-top-of-the-line offering for Cadillac and the epitome of high-style luxury during the first few years of World War Two. This model offers unmatched styling, first-generation fully automatic transmission, fine wood accents, and a luxurious mohair interior accented by leather trim. It was the choice of Hollywood elites and captains of industry. Smooth, quiet and opulent, you will enjoy the exceptional ride and build quality of yesteryear.

a black car rolls royce in front of a building

Rolls Royce Phantom 7 Drophead Coupe

The Rolls Royce marque has been synonymous with wealth and heads of state since 1911. This car turns heads like no other! Large and in-charge and opulent, the Phantom is possibly the last of a rare and magnificent breed of no-holes barred motorcars engineered and designed to the very highest standards. It’s huge and heavy but don’t be fooled, it has high performance capabilities. Ask your chauffeur to put the top down and be transported to another carefree latitude. The boat deck inspired rear roof cover will make you feel you are floating in a fabulous yacht. This is a marvelous machine to cruise down Greenwich Avenue while waving like a royal from the back seat.

southport map


Let our chauffeur share with you some of the most iconic coastline vistas in all of Fairfield County. On this drive you will see the quaint Village of Southport Harbor with its manicured homes and gleaming yachts of the Pequot Yacht Club. Continue to Sasco Hill Road and pass by the stately homes as you press on to the exclusive Country Club of Fairfield. Sasco Hill Beach is wonderful background to hop out for a selfie with the classic car and an unforgettable view. From there, retrace your steps to Southport and see the Pequot Library, a Richardsonian Romanesque icon and on the National Register of Historic Places for more than 70 years. Continue to the famed Beachside Avenue with some of the most ritzy real-estate in all of Connecticut. Your driver will then make way to The Inn at Longshore, the historic 168-acre “Jewel of Westport,” an inspiration to F. Scott Fitzgerald’s The Great Gatsby affording magnificent views of both the Saugatuck River and Long Island Sound. From there you will pass the Westport riviera of Compo Beach as you wind your way to the Greens Farms neighborhood with its awe-inspiring architecture and manicured lawns.  Soon you will return to your enclave at Delamar Southport Hotel where your chauffeur will open the door for you in our courtyard to be seen by the curious guests in the Artisan patio. 

a man and woman sitting on a blanket in front of a car


Our driver will take you on a scenic route around town and stop at a scenic spot for a picnic in collaboration with Mark & Graham that features products such as a premium picnic basket, variety of wine picnic tables to choose from and a waterproof blanket from their expertly crafted picnic collection. Select from our autumn inspired menu, curated by Executive Chef Frederic Kieffer. Unplug and rediscover the poetic simplicity of dining en plein air; a treat for all five senses.

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$360 for one person, $450 for two people, $540 for 3 people
This experience is approximately 2 hours

Timeless Coastal Charm


Enjoy riding in style around our local Connecticut shoreline. Select from one of two very different yet equally stunning Collector cars: our award-winning and evocative 1941 Cadillac Series 60 Fleetwood.  Or perhaps ride top-down in the over-the-top 2011 Rolls Royce Phantom Seven Drophead Coupe, the undisputed king of the road. 

a bride and groom kissing in a car


Elevate the charm and elegance of your special wedding day by choosing one of our remarkable classic cars for your grand entrance. At Delamar, we understand the importance of every detail when it comes to creating the perfect ambiance. That's why we offer a curated selection of timeless and impeccably maintained classic cars, designed to add a touch of sophistication and nostalgia to your wedding celebration.

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