How to Swing a Month at the Beach (Yes, You Can!)

The same culture shift that is making working at home (or anywhere there’s Wi-Fi) a norm is prompting adventurous souls to choose where they make their home.

Here are two inspiring stories:

Beth and Jim: Trying on a Better Quality of Life
(Right, with kids, Amy and Brodie)

The vision: “We were looking for a small town community that wasn’t small town—that had some culture,” Beth says. “We go to church and wanted a living breathing exciting church like ours in Baltimore. There’s a great church community here and that was a huge part of our decision.

We wanted to be near ‘stuff’. We love the wildlife on Sanibel and we can go to Fort Myers and get whatever you need or want and you have access to the airport and city and shopping. And, really, just about everything you need is here on the island.”

The plan: “Vacationing somewhere and living there are often two different things,” Beth says. “Our plan was to rent for three months. We were going to try to spend about a month just settling in and seeing how we felt about hot summers and bugs and the community.

We decided from the get-go that, even if we hated it, or decided it wasn’t what we thought it would be, it would still be a nice vacation. Our worst-case scenario: we came down and enjoyed three months on Sanibel and went back home.”

What happened: Lots of fun, along with some trial by fire. “Toucan House (reviewed below) was a great home base,” Beth says. “You can walk to the beach and bike all over the island on 30 miles of paved paths. The entrance to the Wildlife Drive in J.N. "Ding" Darling Wildlife Refuge is just four miles from the house. The end of the wildlife viewing loop comes out at the entrance to the neighborhood where we were staying at Toucan House. We bought a federal Duck Pass and every time we came home, we’d detour through there free instead of taking the main road.”

During their stay, a Category 4 hurricane and two tropical storms roared through and the island was evacuated. “We decided we’d seen the worst of it and we still loved it,” Beth laughs. “After about a month, our kids were done with the vacation thing. So we started looking to buy.”

Bottom line: “We’d always go away to these vacation spots where other people were living the life we wanted to be living and we got to a point where we thought, ‘Why can’t we do that too’?

We waited until the right time in our lives. It was kind of the perfect time to jump because our kids weren’t into the high school groove yet. But they were old enough.”

With the kids settled back into home schooling, Beth and Jim found new gigs on the island. Jim started a computer consulting business and has become the local computer guru for small businesses owners and returning sunbirds. Beth works part-time for her favorite clothing store, Fresh Produce.


Inge and Gustavo: A Winter Haven for Retirement

The goal: After retiring from high-powered corporate careers, this couple wanted the best of both worlds: a warm weather refuge from the wintry cold of Pennsylvania.

The plan: Gustavo (Gus) and Inge started a love affair with Sanibel Island started with a day trip.

“We decided to spend a month here to see if we really liked it for daily living,” Inge says. The next year they rented for two months. The third year was the charm: “We planned to rent for three months and that’s when we bought,” she says.

What happened: During each visit, the pair took their time settling in. They joined the library and Inge volunteers at the Sanibel-Captiva Conservation Foundation.

On daily bike rides the couple chatted with locals who were happy to share their experiences living on the island. “We didn’t feel rushed. It gave us time to explore and get a lay of the land. I think I explored every neighborhood on the island before saying, ‘Yes, I like the one we’re staying in now. It feels right,’” says Inge.

Call it luck or kismet -- the couple’s new home is virtually across the street from Toucan House (reviewed below), where they rented for three years!

The bottom line: Today, Inge and Gus spent half the year on Sanibel Island.

“I think renting a home exposes you to the area, the people and amenities more than staying in a hotel or a condo because you’re out in the open. You relate to people in a broader way than you would in a hotel,” Gus says. “I can’t think of a better way to make the transition.”

In a state full of sunny beaches, Sanibel Island has proven to be an ideal fit for these two former world-travelers.

“It’s a pretty unique little place,” says Gus. “We have a pretty broad range of foreign visitors -- French, German, English, Spanish -- who are interested in wildlife conservation and did the same thing we did. There’s a real cosmopolitan feel, even though we’re all dressed in shorts and tee shirts and sandals.”

4 tips for making it work

1. Take your time.
“I think I explored every neighborhood on the island before saying, ‘Yes, I like the one we’re staying in now. It feels right,’” says Inge. “We didn’t feel rushed, so we felt like we made a better decision.”

2. Get out and about -- and listen.
“Exploring on a bicycle gives you a whole different picture than riding around in a car,” Gus says. “The people we met who were out gardening invited us back for drinks. We got a much better feel for the type of people who were already living there and we also got inside information on Sanibel’s neighborhoods. Once you tell them you’re buying, boy, they come out of the woodwork with help! Our neighbors helped us with all kinds of recommendations.”

3. Get involved.
One of things Inge and Gus love about Sanibel Island, Florida, is its active community. “There’s more of an interest in doing vs. going out and dressing up,” Gus says. “There’s a lot of intellectual power here,” adds Inge. At Monday morning current events discussions, “you had better have read the New York Times.”

4. Face reality.
Inge and Gus visit during high season when the local population swells from 6,200 to 21,000. “You really have to plan that you’re not traveling on and off the island during certain times of day. There are two main roads, so the traffic can be horrendous.”

As prospective year-round residents, Cindy and John wisely choose the off-season -- three months squarely in the middle of peak hurricane season. They wanted to know exactly what they were getting into. And even in the middle of paradise, “If you’re working, it’s still real life,” says Cindy. “Your plumbing still falls apart. Your kids still get sick.”

TOUCAN HOUSE

Tucked in to a cluster of palm and sea grape trees on a large corner lot, this three bedroom (1,900-square foot) home has the airy feeling of a tree house. Here, the toucans peek at you from inside a mural-sized painting and whimsical handcrafted replicas perch throughout the house.

With its cathedral ceiling and sprawling multi-level deck and two screened porches (locally referred to as lanais), Toucan House manages to feel both expansive and cozy. Inside, rustic stripes of unfinished wood mix with intense tropical colors, original art, inlaid tile and handcrafted treasures from the couple’s travels.

There’s a loft bedroom at the top of spiral stairs. A fully stocked kitchen opens off the living room. The large screened lanai with wicker furnishings runs almost the length of the house. (The loft bedroom has its own private lanai.)


Sylvia and Joe’s personal recommendations

Jerry's Foods We love having breakfast in the sunlit cafe at Jerry's Foods grocery store. The menu is diverse, you can watch beautiful tropical birds in their cages surrounded by lush landscaping while you eat and you can eat in your bathing suit and a cover-up.

Lunch on Useppa Island Pristine and private Useppa Island is steeped in legends of pirates -- like Gasparilla, who’s said to have held women captive on Captiva Island (hence, the name) and buried treasure nearby. The boat ride and lunch at The Collier House (where you might spot a celebrity) makes a lovely afternoon.

Biking through Ding Darling It’s just minutes from Toucan House and we spot something new on every trip. One day, we’ll see a dozen Roseate Spoonbills roosting in the trees like big pink balls of cotton candy. Another day, there’s an armadillo scooting down the road.

Full review and photo tour of Toucan House

Next Month: Planning a Family Reunion

Maybe it’s the times. Maybe it’s just time. More and more people are planning family reunions in one large vacation rental home or a cluster of homes close to each other. Next month we'll scout out the best family reunion sites.

Stay tuned!