A recap of President Obama's Martha's Vineyard summer vacation

The First Family went out to dinner often and stayed out late but shied away from public encounters. Golf was the primary activity.

President Obama exits a car at Martha's Vineyard Airport on his way to Marine One. It is safe to assume he did not leave his golf clubs behind. Pool photo Steve Myrick/Vineyard Gazette

President Barack Obama and his family boarded Marine One at Martha’s Vineyard Airport and departed the Island about 6:20 pm, Sunday evening. For the most part, the average Islander, at least those not able to lay out $10,000 to be present at a Democratic National Committee fundraiser in Chilmark, did not see the president. Even the press pool barely caught a fleeting glimpse as they tagged along to Island golf courses and restaurants, struggling to generate copy, most of which ended up being about Vineyard scenery and weather. 

So how did President Obama spend his 16-day Martha’s Vineyard vacation? Here is an unofficial synopsis:

This vacation, Edgartown and Oak Bluffs split the prize for most favored dining destination.

  • The Obamas ate in Edgartown three nights (L’Etoile, Detente and Chesca’s).
  • The First Family dined in Oak Bluffs three nights (Jimmy Seas Pan Pasta, Down Island, and Red Cat).
  • There was one trip to Vineyard Haven (Beach Road) and one trip to West Tisbury (State Road), which may earn a bonus point since Mary and Jackson Kenworth operate both restaurants.
  • Obama photo opportunities were as rare as an August weekend reservation on the Steamship Authority’s 8:15 am boat from Vineyard Haven to Woods Hole — almost nil. One-on-one encounters with year-round Islanders were equally rare beyond a few glimpses on the golf course and a handshake or two at Mink Meadows.
  • The Obama vacation house abuts The Trustees of Reservations (TTOR) Menemsha Hills property, a 211-acre preserve that overlooks Vineyard Sound. There were three official walks: President Obama and Michelle Obama began the final day of their Martha’s Vineyard vacation with a short walk together on a trail near their rented house in Chilmark, according to a White House official; President Obama, Michelle Obama and Malia Obama, their oldest daughter, went for a short walk on a trail near their residence, according to a White House official; and the President and Malia Obama went for a short walk on a trail near their residence.
  • The Obamas made four trips to a private stretch of south-shore Edgartown beach. The initial trip was to a beach owned by the Kohlberg family. After that, the White House was mum on beach ownership, and the press pool only mentioned a dirt road.
    The road less traveled leads to a series of private beaches that stretch between Edgartown Great Pond and Oyster Pond. Property owners include the Flynn family, for generations the largest landowners of Pohogonot Farm and surrounding property at Jobs Neck and Edgartown Great Pond, Andrew and Pamela Kohlberg, children of Jerome Kohlberg, owner of the Vineyard Gazette, Robert Levine, and Richard L. Friedman, the real estate investor and former host of President Bill Clinton when he vacationed on the Vineyard. Jerome Kohlberg was a financier widely acknowledged as a leveraged buyout pioneer, first with Bear Stearns and later Kohlberg, Kravis, Roberts, formed in 1976 to pursue such deals, in which a group of investors buys all the publicly held stock in a company and takes it private, financing the purchase mainly with debt. Mr. Kohlberg founded his own investment firm, Kohlberg & Co., run by his son and headquartered in Mount Kisco, N.Y.
  • POTUS and FLOTUS attended a private party at Lola’s in Oak Bluffs, arriving after 11 pm and staying for about one hour.
  • On Monday, August 15, President Obama attended a Hillary Victory Fund event at the Chilmark home of Hank and Carol Goldberg. Approximately 60 people were expected to attend. Attendees contributed $10,000 to attend and hosts contributed $33,400, according to one source. The President spoke for about 10 minutes at the fundraiser and stayed for about one hour.
  • The First Family watched the annual fireworks display Friday night in Oak Bluffs with friends at White House senior advisor Valerie Jarrett’s vacation rental home adjacent to the Lookout restaurant. The motorcade left at 11:42 pm, the press pool reported. Of course, no member of the press actually saw the president so his presence is unconfirmed.
  • The official summer reading list, according to the White House: “Barbarian Days: A Surfing Life” by William Finnegan, “The Underground Railroad” by Colson Whitehead, “H Is for Hawk” by Helen Macdonald, “The Girl on the Train” by Paula Hawkins, “Seveneves” by Neal Stephenson. No official word on whether the president finished any of the books on his list.
  • President Obama played golf on 10 days of his vacation. Farm Neck Golf Club in Oak Bluffs was his favored course (six outings), or perhaps it was the most accommodating. Memberships at the very private Vineyard Golf Club in Edgartown (three outings) reportedly sell for $350,000, and one can expect that at that price a member golfer, even a Democrat, does not want to give up his or her tee time, even for a president. POTUS made one trip to Mink Meadows Golf Club in Vineyard Haven, a much more relaxed, public nine-hole course.

    For the most part, President Obama played golf with basketball players, investment bankers and lawyers. The No. 1 member of his foursomes was Cy Walker (seven games) followed by Alonzo Mourning (five games).
    Here is the lineup:
    POTUS golfed Sunday at Farm Neck Golf Club with Chris Paul, lawyer Cy Walker and Joe Paulsen. Chris Paul is a point guard for the L.A. Clippers. Mr. Walker is the cousin of White House senior adviser Valerie Jarrett. Joe Paulsen is a White House aide.
    POTUS golfed Monday at Farm Neck with NBA superstar Steph Curry, his father and former NBA great Dell Curry, and Cy Walker.
    POTUS golfed Wednesday at the Vineyard Golf Club with businessman Glenn Hutchins, founder and CEO of Silver Lake Partners, a Silicon Valley private firm that invests in technology companies, and part owner of the Boston Celtics, and basketball players Ray Allen and Alonzo Mourning.
    On Thursday POTUS played Mink Meadows Golf Course with Ray Allen,  Cy Walker, and Alonzo Mourning.
    On Friday, POTUS played golf at Farm Neck with Robert Wolf, former president and CEO of UBS Investment Bank, and Chris Paul and his brother, C.J. Paul.
    POTUS golfed Sunday at Farm Neck Golf Club with Alonzo Mourning, Cy Walker, and insurance executive Mercer Cook.
    Monday POTUS golfed at Vineyard Golf Club with Alonzo Mourning, Cy Walker, and Chicago businessman Marty Nesbitt.
    On Wednesday it was back to the Vineyard Golf Club, where he was joined by Marty Nesbitt, Alonzo Mourning, and Cy Walker.
    On Thursday, POTUS golfed at Farm Neck Golf Club with seasonal Chilmark resident, producer, writer and comedian Larry David, Robert Wolf, and Jonathan Lavine, co-managing partner at Bain Capital and managing partner and chief investment officer of Bain Capital Credit.
    POTUS played his last round of golf on Sunday at Farm Neck with Glenn Hutchins, Robert Wolf, and Cy Walker.

  • Mr. Obama and his family vacationed on the Island every year since his 2008 election with the exception of 2012, when he was campaigning for re-election. Chilmark is their favored vacation spot.
    In 2009, 2010, and 2011, the first family rented Blue Heron Farm in Chilmark, a 28.5-acre compound on Tisbury Great Pond. In 2013, the first family rented a house in Chilmark just off South Road. The location necessitated a road closure that left some Island residents grumbling about the inconvenience.
    In 2014, 2015 and 2016 the Obamas stayed at the home of Joanne Hubschman on Gosnold’s Way off Prospect Hill Road, which overlooks the north shore and Vineyard Sound. The seven-bedroom, nine-bath, 8,100-square-foot house sits on a 10-acre lot and features 17 rooms in total, expansive water views of Vineyard Sound, an infinity pool and hot tub, and a dual tennis-basketball court.