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Jeff and Joan Talmadge continue to lead the WeNeedaVacation team celebrates 15 years!

For 15 years, has been helping vacationers find their ideal vacation rentals on Cape Cod, Nantucket and Martha’s Vineyard. The company has grown significantly since 1997, when it began with just two employees (who also happened to be the founders) and fewer than 50 listings. Currently, WNAV employs ten, and the site lists over 3500 Cape and Island vacation rentals. To help vacationers plan the perfect Cape and Islands vacation, the site includes events, restaurants, activities, shopping and beaches via the online Vacation Planner. And for homeowners, one aspect that has never changed over the 15 years is the personal attention and hands on approach in guiding and assisting those who list their homes for rent on the site.

Jeff and Joan Talmadge
Jeff and Joan Talmadge

After 15 years, founders Jeff and Joan Talmadge continue to lead the WNAV team. We wanted to catch up with them to learn a little bit more about WeNeedaVacation, and what Joan and Jeff love about Cape Cod and the Islands.

What inspired you to start WeNeedaVacation?

Two disjointed events. First, we bought our second home in East Orleans in 1996 with the understanding that we would have to rent it to pay the mortgage. The first summer, we had no problem booking it by the end of March, using a realtor and various classified ads in the Boston Globe (remember those?) and alumni magazines. But in the following season of 1997, vacation rentals had become more sluggish. Out of the blue, we received a direct mail ad from, one of the pioneers in the online vacation rental industry. We tried their introductory offer, and it worked like a champ.

At the same time, Jeff, a software consultant, attended a conference that touted Microsoft’s brand new tools for developing interactive, data-driven websites. Websites at that time, including, were mostly just text and links to other pages - not interactive. These new tools opened up the possibility of users interacting with websites, asking questions and getting answers – stuff we take for granted today. At the conference, Jeff vowed to redirect his consulting practice towards interactive websites, and he realized that he’d have to build one just for the practice.

With Jeff’s technical expertise and Joan’s writing and editing skills (she had been an educational writer and editor for many years), we started building what became Had it not been a business success, Jeff would probably still be building websites for others!

How did you come up with the name WeNeedaVacation?

We had tried many options, but even in 1997, many website names were already taken. A friend suggested that we use an up and coming practice of using a sentence, not just nouns or verbs. Joan came up with the name, and we wish we had a dollar for every chuckle we’ve received over the years. Folks love the name and often say, “Boy, do we!"

What’s it like to own a business with your spouse?

Great question. It’s not for everyone, for sure, but it’s been perfect for us. We are two very committed, yet different people. We differ in what skills we bring to the company, how we view the business, and, on occasion, even its main priorities. But we’ve always cherished our diversity of perspective and genuinely respected each other’s views. Nor do we ever get bored hearing the other talk about work! Neither of us could have done this alone, and we’re grateful for the chance to build something so meaningful together.

What is your ideal day on Cape Cod?

An early morning walk. A round of golf at Captains. An afternoon walk on Nauset Beach. A seafood dinner on our deck overlooking Pleasant Bay.

Do you have a favorite spot to go for a walk?

We sure do: Nauset Beach near our house. In the early days of the business, we referred to those walks as our “board meetings” – time away from the humdrum, computers and phones, when we could reflect and try to steer our little ship in the right direction.

Nauset Beach, Orleans Cape Cod
Nauset Beach, Orleans Cape Cod

Cape Codders and Islanders celebrate their daffodils, cranberries, oysters, scallops, lobsters, and clam chowder. Which of these is your favorite?

Wow, that’s a tough one. For Joan, clam chowder – the national dish of Cape Cod, with all the restaurants competing for the best recipe. Her favorite, however, is made by her brother-in-law, Roger Smith. For Jeff, it has to be lobster, boiled, of course, with drawn butter galore.

Jeff, do you own a pair of Nantucket Reds*?

I certainly do – two in fact -- and of course, they are Murray’s Toggery originals, direct from Nantucket’s magnificent Main Street.

Joan, do you have a Nantucket Lightship Basket**?

No, but if anyone would like to give me one, I’d happily accept it!

What are you most proud of about

Starting our own business from scratch, which allows us to promote and assist homeowners and businesses alike in this very special part of the world. Also, developing a terrific, loyal and capable staff, having two of our three kids work for us, and seeing what we built develop as it has over the last 15 years. It’s been a blast.

Congratulations on 15 years of helping vacationers find the perfect vacation rentals on Cape Cod, Nantucket and Martha’s Vineyard!

*Nantucket reds are a style of trouser that was originally created by a local shop on Nantucket.

**Retired whalers who manned isolated lightships originally created Nantucket Lightship baskets in order to pass the time. They are now popular souvenirs.

About Susan Hutchins

About Susan Hutchins: I joined the WeNeedaVacation team in 2012 and write website and blog content as well as promote through social media. Having grown up spending summers on Nantucket, I have a strong connection to Cape Cod and the Islands. I now live in New Hampshire with my husband, two children, and golden retriever, and we are frequent visitors to the Cape. I love running local road races, the Brewster in Bloom 5K being a favorite. My family enjoys biking on the Cape Cod Rail Trail, hiking in Nickerson State Park, and relaxing on the beautiful beaches (usually a dog friendly one!).