Haute Secrets Boston: Herb Chambers, President of The Herb Chambers Companies

If you live in Boston, Herb Chambers is certainly a household name.

The car mogul owns and operates the largest automobile dealership group in New England with 57 locations, but what you may not realize is that he wasn’t always in the car industry. Prior to entering the automobile business, Chambers was the founder of A-Copy America, which became the largest office copier dealer in the world. In 1983, he merged that company with what became Ikon Office Solutions, later acquired by Ricoh.

It wasn’t until 1985 when Chambers decided to seek another business challenge. As a car enthusiast, he purchased his first dealership in New London, CT.  Since then, he has grown The Herb Chambers Companies to 57 automotive dealerships throughout Massachusetts and Rhode Island. He has a staff of more than 2,500 employees and annual sales over $2.7 billion.

Herb ChambersPhoto Credit: Herb Chambers

With more than 18,000 automobile dealers in America, Herb Chambers is ranked the fourth largest privately owned dealership group.

Some of the exclusive cars you will see on his lots include a 2017 Lamborghini Aventador S Coupe, Rolls-Royce Dawn Convertible and Bentley Mulsanne Speed Sedan.

We caught up recently with Chambers to find out what he loves most about Boston.

Where were you born: Dorchester

Neighborhood: Dorchester (He now resides in Boston and Connecticut).

Occupation: Business owner [President of The Herb Chambers Companies]

Favorite Restaurant: Davio’s Northern Italian Steakhouse 

Best Sushi: Red Lantern 

Best Italian: Strega

Best dessert: Out of Bounds

Best place for a romantic date: Sorellina

Best Sunday brunch: Bristol Lounge at Four Seasons

Best place for a power business meeting: Davio’s Northern Italian Steakhouse 

If you have out of town guests, which hotel would you recommend? Four Seasons Hotel Boston

Favorite shopping venue/boutique: Armani 

Favorite Charity Event: Camp Harborview’s Beach Ball and Mass General Hospital’s Storybook Ball

Favorite Cultural Event: Boston Pops

Best Steakhouse: Davio’s Northern Italian Steakhouse

Best Pizza: Regina Pizzeria in the North End

Best Lunch: Davio’s Northern Italian Steakhouse

Best Massage: Four Seasons

Best Museum/Exhibit: Museum of Fine Arts

Describe Boston in three words: Vibrant, comfortable, safe 

All-around favorite spot in Boston:  Newbury Street

Best Aspects of Boston: Great restaurants, great business opportunities, the Charles River and Boston Harbor