The weather-beaten, hand-painted sign nailed to a tree on State Road in Vineyard Haven is about the last tangible memento on the Island harking back to Bill Clinton’s time of troubles. For me, it remains a living symbol of the Monica-mad summer of 1998. The lettering on the lobster-trap-sized placard is faded but the defiant take-that-Ken-Starr message remains unequivocal: “Hoorah for Bill.”

When Mr. Clinton — now a globe-trotting hostage negotiator — met with Barack Obama for 40 minutes in the White House Situation Room Tuesday, the topic was the insular, hermetic government of North Korea. Since the former president was fresh from a 63rd birthday dinner at the Chilmark home of Ted Danson and Mary Steenburgen, it is quite possible that another insular (but far from hermetic) place was also discussed.

If Mr. Clinton offered his Democratic successor any advice on how the sitting president should relax during his upcoming one-week Vineyard vacation, Obama should file it next to Dick Cheney’s helpful memos on how to find loopholes in the Constitution. The Clinton summers on the Vineyard (aside from the Big Chill of 1998) were a manic whirlwind from golf outings with Vernon Jordan at Farm Neck to impromptu strolls along Main street Vineyard Haven and to a social round of cocktail parties, dinners and fundraisers that would have exhausted Ernest Hemingway during his Paris days.

Just as Mr. Obama has rewritten the Clinton playbook on how to achieve health-care reform, he has a chance to do the same when it comes to enjoying the true essence of the Island in August. The secret of the Vineyard is the ability to do absolutely nothing amid beautiful surroundings. Mr. Obama has gone the house guest route before (staying in Oak Bluffs with his close friend and adviser Valerie Jarrett in 2004 and 2007), but this is the first time that he is here answerable to no one but time and tide and, oh yes, the Secret Service.

Most presidents are too tightly wound to ever let go — think of Lyndon Johnson racing around his ranch in a Cadillac convertible or George H.W. Bush roaring around the waters off Kennebunkport in his cigarette boat, the Fidelity. And I am not suggesting that Mr. Obama should completely shuck off his responsibilities by trying to use the suitcase containing the nuclear codes as a flotation device on Tisbury Great Pond. But there are psychological benefits that come with pretending — even for just a week — that the Obamas are just another typical laid-back American family spending upwards of $35,000 on their vacation.

Mr. Obama may have the right stuff (but maybe not the right staff) to pull it off, since he is island born (Hawaii) and island raised (Indonesia). He boasts the political self-confidence to come to this Democratic enclave (as opposed to, say, the Outer Banks of the swing state of North Carolina) and the personal self-confidence to dare replicate the Clinton choice of an Island idyll. Now comes the test of whether Mr. Obama, the most self-contained of modern presidents, has the capacity to power down.

I have been Island-bound for the last two weeks, carefully preparing with each beach visit, for the arduous journalistic responsibility of covering the vacationing Obamas. When Pulitzer Prizes are at stake, you simply cannot start too early on a sand and saltwater regimen. But I am willing to give up the prize and the testimonial dinner in my honor for the joy of living in a country where the President embraces lassitude.

In fact, as a patriot I fantasize about a White House press briefing by Robert Gibbs (or his vacation replacement) that goes something like this:

Q: Could you give us a read-out on the President’s day?

A: Aside from a 15-minute national security briefing this morning, the President, as far as I know, did absolutely nothing.

Q: What do you mean “absolutely nothing?”

A: He had lunch with the First Lady and his daughters and joined them on the beach. I’m told he had a book with him, but that he mostly held it in his lap and looked out at the water. He also dozed a bit.

Q: What’s the book? Is he dozing over a briefing book on health care? Is he abandoning the public option?

A: No, it’s something he found on the book shelves at Blue Heron Farm. I think it was Vanity Fair.

Q: Is it the issue of the magazine with the Sarah Palin story? Is he worried about reelection?

A: No, I believe it is the 19th century novel by William Makepeace Thackeray.

Q: What is the President doing this evening?

A: He’s having dinner with his wife and the girls. And I think they plan to play some board games. There are also unverified rumors about a jigsaw puzzle.

Q: C’mon. Stop holding out on us. Has he had another beer with Skip Gates? When is he going to Valerie Jarrett’s for dinner? And when’s tee time with Vernon Jordan?

A: They’re all friends of the President and they understand his need to have some unstructured time with his family.

Q: This doesn’t make sense. Do you expect us to believe that the President is on vacation doing nothing?

A: Absolutely nothing is the phrase of the day.

Q: What are you hiding from us? Are we about to go to war with Iran?

Who are we kidding here? Presidents cannot just disappear into the early morning fog off the water. Although it is true that the Secret Service has tested everyone’s gullibility by (ssshhh!) taking down the sign on South Road for Blue Heron Farm. During World War II, the British tried similar deceptive tactics with directional signs to thwart a German invasion.

Every president is surrounded by aides eager to wring the maximum political advantage from every muscle movement by the Leader of the Free World with the possible exception of a POTUS sneeze. So it is all but certain that memos have already been prepared arguing that Obama can solidify the Midwestern agricultural vote by making a Saturday morning cameo at the West Tisbury Farmers’ Market. There is also probably White House talk about Obama holding a stimulus-package round-table while on the Island boosting the virtues of the Vineyard’s diversified economy built around fruit pies, cut flowers and lobster rolls.

If Obama ventures out in the evening — as he surely will — he should be aware of the peculiar journalistic tradition that might be called Vineyard off the Record. Back during that fateful summer of 1998, my wife and I attended a large dinner party that featured the feuding Clintons in their first public appearance after the President made his belated televised confession. Our host Steve Rattner cautioned us (and the few other journalists on the guest list) that the dinner was completely off the record and writing about the Clintons’ awkward night out would be a breach of every conceivable code of honor. So imagine my chagrin the next morning to turn on CNN to see Alan Dershowitz burbling about his dinner with Bill Clinton. He got the scoop — and I learned that reporters are the only ones who can actually keep a secret on the Island.

Even with Hurricane Bill (somebody at the Weather Service has a warped sense of humor) heading in this direction, Barack Obama has one week to make the Vineyard his own. While it is an exaggeration to say everyone on the Island is a Democrat (Mississippi Republican Sen. Thad Cochran is defying clichés by vacationing here), the goodwill here towards the new President is pretty universal. And if anyone attacks Obama for his elitist vacation habits in the midst of a recession, just remember that FDR readied himself to fight the Depression by cruising the Caribbean on Vincent Astor’s yacht.

Walter Shapiro is a columnist for PoliticsDaily.com, for which this article was written. He has been a summer renter on the Vineyard since 1994.