Classic Car Rental

Are you looking for a memorable ride?


Part of Shake and Stir LLC

Big Drop Top has a parent company in Shake and Stir Bar Trucks.  We own two lovingly converted big Chevy Trucks from the early Fifties that are now spectacular Bar Trucks.  Please have a look at our website at  

Making Memories

Making Beautiful Cars Available for Special Occasions


Wedding? Reunion? Photo Shoot? Do you want to make a lasting impression? Limos are ubiquitous and even a beautiful Rolls Royce has become commonplace at weddings.  Arrive in one of these distinctive land yachts and everyone is smiling .  

My Favorite Cars


What were they thinking 50 years ago?  They never heard of fuel efficiency, but they certainly understood luxury, comfort and power.  The Imperial Crown above has 16 motors (who needs power vent windows?), not including the big 440 under the hood.

Where Are We?


We just launched this business in Wilton, CT.  We are booking now for summer 2020 in Connecticut and Westchester County.   In the fall we will have the cars available in the Richmond and Charlottesville, VA area.  

How We Work

A Simple Business

We rent our own elegant luxury classic convertibles in pristine condition for weddings and special occasions. We will have a professional driver at the wheel and we can accommodate special requests such as champagne on ice, decorations etc.  In certain situations we may rent the car out as a self driver for a weekend or longer as long as insurance and a deposit are in place.  

What We Charge

We rent these vehicles out for a 3-hour minimum commitment for $500 which includes the driver (but not the special requests). We can negotiate if the customer needs the car for longer than three hours. Rentals include 50 miles of travel with each additional mile charged at $1.50 per mile. We will get the car to its assignment within 20 miles of its garage in Wilton CT . Delivery charge beyond that radius is charged at $1.50 per mile. 

No Worries

 These vehicles are  kept in tip top shape. If there is a maintenance issue, we will do our best to have a comparable vehicle as a backup.

Payment is expected upon booking. If the rental is cancelled at least 2 weeks before the event, 50% of the payment will be refunded.  A full refund will be made if that day is rebooked by another customer.  


1970 Oldsmobile 98

We bought "Kathleen", our Oldsmobile 98 Convertible in 1994 and have had many great memories; weddings, parades, Nantucket vacations etc. We have probably maxed out with 10 neighborhood kids going for ice cream.  The Oldsmobile 98 was the cheaper alternative to the Cadillac.  They share the same frame, engine etc, but the luxurious touches are not quite Cadillac.  She has been remarkably reliable and easy to maintain.  It is an incredibly smooth and comfortable ride.  We can even hook your tunes up so the song you want is playing when you pull up. 

Kathleen has been in over a 30 weddings for nieces, nephews and friends.  She always seems to make people smile and she has never let us down. 



1966 Imperial Crown

"Hope" just joined the family in the spring of 2018.  There were only 514 of these cars made, so you may not recognize this beauty.  Imperial was the luxury division of Chrysler, designed to compete with GM's Cadillac and Ford's Lincoln divisions.  The goal was to offer even greater luxury than those brands at a 15-20% price premium.  I guess that strategy missed the mark, given the disparity in production numbers. Nevertheless, they are remarkably luxurious vehicles.  Fans of Mad Men and Pawn Stars might recognize these cars.

We are awaiting the "birth records" from Chrysler's Historical Records group to confirm that this car was originally owned by Bob Hope, the comedian.  I have been told that two early production 66 Crowns were delivered to 20th Century studios in Hollywood.  One (see picture to the right) became Mr Drysdale's car in the Beverly Hillbillies while the other (in Regal Blue with black leather interior)went to the show's executive producer, and Imperial celebrity spokesman, Bob Hope.  


Check out our Movie Star Cars

Our 1970 Oldsmobile 98 appears at 1:15...and steals the show

Hope gets her 15 Minutes of Fame in Charleston

California Sportswear Maker Travis Mathew  hired her in November for a new product line launch

About Us

Barry Hines

My wife Leslie and I have raised our three kids in the Northeast. We have always had rescue animals.  The current lineup; two dogs, three donkeys , a cat, and thousands of honeybees.  

Tired of  limos and white Rolls Royces as the predictable choices for wedding vehicles?  Make a lasting impression with our distinctive beauties

Contact Us

Drop us a line!

Big Drop Top

901 Ridgefield Road, Wilton, Connecticut 06897, United States

(203) 919-1799

Open today

08:00 am – 07:00 pm