In the Hamptons, brokers hire chauffeurs to drive buyers around during the initial showing day. The agents can cover four or five homes in an afternoon across Southampton, Sag Harbor, East Hampton and other areas. With that much ground to cover, no one should have to be focusing on navigating. With a driver, the brokers can focus on their buyers, learning their tastes on the fly, finding out what they do and don’t like. The client gets to put the focus on the house, not on getting lost.
The roads between the towns are bad. About 29,328 cars a day pass east of the Shinnecock Canal on Sunrise Highway, and that’s a 2002 count, says NYSDOT. The Montauk Highway is close to capacity in summer, according to a 2003 town study. In Bridgehampton, there are more than 21,000 cars on the road a day.
A well-planned arrival is a part of the showing experience just like the interior decor or the living room view. What happens in that first five minutes of your customer’s trip to the property shapes the whole trip. To start, hiring a driver makes a broker look professional, instilling more confidence in the buyer. It makes a statement that the broker is going the extra mile to give the client his or her attention.
Some buyers are coming out with the whole family. Bringing family and a partner along a trip has an advantage: the individual partners in a couple or a family can chime in to describe the pros and cons of a particular house. One might notice the bathrooms, another might notice the living space. They can compare the house in front of them with the previous house. When you split up to take separate cars, your team is having conversations that you can’t be a part of, maybe feeling second best, maybe offering negative criticism or points that are awkward to share. You might miss out on the very best comments. Having an agent sit back and direct a chauffeur gives the customers their personal moment of reflection. It’s that time when they just sit, think about what they just saw, and talk it over. The husband and wife, the partners, the grandparents can take stock of what they are experiencing. With a driver at the wheel, all eyes are on the property.
Many serious buyers make the trip by private aircraft to East Hampton, Montauk or Westhampton, skipping the traffic altogether. A chauffeur makes it possible to make an initial showing the moment the plane lands, at exactly the time everyone wants to get going. It’s the difference between looking at the house fatigued, and looking at the house relaxed.
A Showing Schedule That Accounts for Real Travel Times
Thinking about distances and roads is important, and sending the car service the list of homes ahead of time makes sure they can plan a showing schedule that accounts for real travel times between towns. Maybe they will want a second look at the chef’s kitchen, or the media room. A stop like that can run fifteen or twenty minutes over. A chauffeur lets you linger, and gives you the luxury of a scheduled showing that moves in real time.
Before the trip begins, a broker needs to ask themselves who are taking the trip. A buyer and broker might take a top-line executive sedan. For a family or a small team, go for the class and comfort of a luxury SUV. A large group, with a family or a team of multiple buyers and brokers, might be best with a spacious luxury van like the Sprinter. Once you have picked a car that is comfortable and has more than enough space for the group, you can focus on something else.
Clients often want a second look at the homes they liked best. When possible, the return visit should be booked at the same time as the first tour. If not, calling a few days ahead is usually enough, except in spring or summer, when you should ask for a week or more of notice.
A typical trip looks like this. Buyers land at East Hampton Airport and the car service driver is there waiting. There would be a few homes at Southampton and Sag Harbor, with the car waiting at each. For lunch, they can discuss the properties, and afterwards take a second look at their favorite ones. The driver drops the client off at the airport, or at their hotel.
Working with a Car Service
When you are hiring a car service, first and foremost make sure that they serve the Hamptons and have some experience driving around to the area’s towns, beaches and historic areas. The Hamptons has many long, meandering drives that head into wooded areas or along beach fronts. Next, their vehicles need to be properly maintained, so that they can get there safely and on time. You don’t want a driver who’s going to get in the way of you and the buyer. A chauffeur should maintain discretion, delivering people and information with discretion and care.
Licensing and insurance is a more complex subject. Suffolk County generally requires a county for-hire driver license. Your driver will need to take a drug test to be approved, and have to retake the test every twelve months. Next, New York State requires for-hire insurance on any passenger vehicle that takes passengers for money. Make sure they have both.
Part of working with a car service is having to cancel or change your schedule as your client adds or removes houses from the agenda. A good service goes with the flow. Spring and summer are the peak time. During this period, you should confirm that they have enough vehicles available to take care of your group.
The Same Driver
It does not end with the showings. When the tour is over, nothing is stopping you from sticking with the same driver as you go to dinner, visit a local winery or just hang out in town. This makes for a more relaxing, comfortable trip for everyone.
Hiring a chauffeur in the Hamptons is about getting everything out of the way so that you and the customer can focus on the house. A good chauffeur keeps everyone focused, not on the road but on the beautiful houses they are about to look at. When it comes to real estate, work doesn’t get much smoother than this.



