Winston Flowers Going Above and Beyond to Make Valentine’s Day Deliveries

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winston flowers Avant Garde Gathering

‘Avant Garde Gathering’ arrangement by Winston Flowers. / Photo Provided

Between blizzards and blistering wind chills, Boston’s weather has been wreaking havoc on local businesses left and right—restaurants, shops, museums, etc.—that have been forced to close on snow days, cancel events, and so on.

But the best of these businesses are powering through, proving why they are so beloved in the community. One of these is Winston Flowers, a local family-run favorite since 1944, which this week is busy making all sorts of updates to ensure that their customers’ Valentine’s Day orders make it to their destinations on time and in one piece.

“Ordinarily, we have a central location on South Hampton Street in Boston,” explains co-owner Ted Winston. “On Valentine’s Day, this year, half of our deliveries will go out on Friday for people who want to send something out early for businesses and whatnot, and the other half will be delivered on Saturday. We’ll have approximately 10,000 deliveries over the two days.”

Typically, the delivery process is very straightforward. Deliver the bouquet to the recipient, done.

Because of the bitter cold weather, however, as well as the traffic issues that Boston and the suburbs have been dealing with, Winston Flowers is renting more than 100 SUVs instead of the usual cargo vans they use for deliveries. To deal with the severe lack of parking available due to snowpiles, the company also hopes to double up the usual amount of manpower as well—rather than having one driver per vehicle, there will be two people, one to stay at the wheel, and the other to run out and carry the bouquets from SUV to doorstep.

Making sure the the flowers arrive in prime condition is also a factor that Winston Flowers is working on.

Ted points out that because Valentine’s Day is Saturday, a lot of people who receive flowers on Friday will want to take them home to enjoy for Presidents Day weekend and into School Vacation Week. For these recipients, Winston is working with customers to come up with plans on how best to transport their bouquets from office to home. Knowing that their “creme-de-la-creme” bouquet is three feet tall and 30 pounds, they understand that bouquets are heavy and awkward to carry to and on the T even regardless of weather. For their signature bouquets, Winston is arranging with customers the possibility of picking up the arrangement from their office at the end of the day on Friday and redelivering the flowers to their home Friday night or Saturday. Full service indeed.

“We’re also taking into consideration special packaging that protects the flowers as much as possible, knowing that if it’s 10 degrees out, there’s only so much you can do,” Ted says. “It’s a combination of special packaging with really having a lot of dialogue with the sender and recipient so that ultimately the bouquets get to their final destination without getting affected by the cold.”

How to get the flowers imported into Boston at all has been a challenge too. Half of Winston Flowers’ Valentine’s Day supply comes from Holland, the world leader in flower distribution. To make sure that canceled flights didn’t delay flower deliveries during Boston’s successive snowstorms, Winston rerouted deliveries to land in New York—mainly JFK International—and then sent trucks to pick up the flowers and drive them up to Boston.

In case you’re wondering, a lot of Winston’s roses come from Ecuador and Colombia, which are usually flown to Miami and then trucked up to Boston. Fortunately this Miami route has been relatively unaffected by the bad weather, Ted says.

All in all, adding up the cost of protective wrapping, doubling up on manpower, and renting SUVs (which cost three times as much as the regular vans), Ted estimates that Winston is spending an extra $75,000 this Valentine’s Day season.

But he says it’s worth it for maintaining their customer base and acquiring new ones.

“We consider it a successful holiday if everyone who orders from us gets beautiful product, and if they want to do business with us again,” Ted says. “If it’s a successful Valentine’s Day, then it’s well worth that expense.”

Ted points out that this is also an opportunity for Winston to show people the company’s dedication. His brother, co-owner David Winston, cites their strong workforce as an integral part of surviving this week. According to David, even when MBTA didn’t run on Tuesday, more than 150 Winston employees still showed up to keep the process moving.


Winston Flowers has locations in Back Bay, the Financial District, Chestnut Hill, Concord, Hingham, and Wellesley. Check out their Valentine’s Day collection online at


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How to Pick the Right Bouquet—and Make It Last

We asked David Winston of Winston Flowers what kinds of arrangements are appropriate for whom, and how to care for those flowers after delivery.

winston flowers Twilight Gathering

‘Twilight Gathering’ arrangement by Winston Flowers. / Photo Provided

Picking an appropriate flower arrangement:

Taking care of your bouquet:

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