Between 1914 and 1921, William and Maggie traveled to and/or lived in St. Augustine and Daytona, Florida. The details on his time in Florida are fuzzy and still need further research. I found William and Maggie in a city directory in St. Augustine in 1914 , as well as a statement from her sister-in-law Della Groves Swank about them living in Florida. Della's divorce testimony states that her husband Charles was visiting his sister (Maggie) in St. Augustine, FL in 1914.
In September of 1918, William and Maggie were back in Swissvale. William's World War I Draft Registration Card states that they were living on Schley Avenue, at the same address as Maggie's brother George. Under "Description of Registrant" it states "left index entirely gone, also 1st & second joint of second finger left hand." I don't know how or when his hand was injured.
Neither William nor Maggie can be located in the 1920 Census in either Pennsylvania or Florida (or anywhere else). In July of 1920, Maggie is visiting in Braddock, PA when her niece Leah dies, and the obituary states that she is from St. Augustine, FL. I also have a photocopy of a picture from an unknown family member of William's boat "Marian C" in Daytona in 1921. Marian was the name of both Maggie's mother and niece.
Sometime around 1925, William and Maggie moved to Cape May, New Jersey. The Monessen Daily Independent mentions Marian Cubbage (Maggie's niece) visiting them in Cape May in July of 1925.
According to newspaper reports in the Cape May Star and Wave, William Speedy, age 52, went out alone on Saturday morning, 7 August 1926 to fish and did not return that evening. He only had some lunch and water with him. It is believed that his boat "Merion" sank and he died when an electrical storm swept through the area. About 3 weeks later on August 28th, the Cape May Star and Wave reported that a piece of the wreckage, with "Merion" painted on it, was found by the Coast Guard.[8, 9] Click on either article to enlarge for reading.
My grandfather, William Arthur Cubbage, was named after his uncle, William Arthur Speedy. He was 13 years old when his uncle died. Maggie, also know as "Aunt Mag", moved in the with Cubbage family in Monessen, PA a few years after Captain Speedy's death. As far as I know, his body was never found (there was no death certificate issued). There is a tombstone for William A. Speedy in Russell Cemetery in Braddock, PA.
The image of the Speedy's boat (above) was found in a photocopy from an unknown family photo album (my father believes it was from Marian or Babe Cubbage, both nieces of Maggie). This page also had a photo of Captain Speedy, some articles that appear to be from Pittsburgh newspapers, "Behold the Fisherman" poem, a handwritten poem "Dead at Sea," and another newspaper article about waiting for fishermen who were lost at sea. A family member must have complied these into the album and I wonder if the pieces were at one time Maggie's. I wish that we had the originals of these photos and articles!
I also wonder if Maggie or another family member wrote the poem "Dead at Sea." Below is a quote from the article in the center above, and sums up what it must have been like for his wife Maggie.
"Of all the agonies that rack the human heart, such waiting is the cruelest. The uncertainty of
hope deferred plunges the heart into a constancy of the bitterest grief. Better far to know the
worst than to hope on and on, without even the poignant consolation of knowledge of the
dear one's fate."
My family talks about Captain Speedy whenever we visit Cape May, especially when we stop at the Fishermen's Memorial. Family lore is that Captain Speedy and Maggie lived on Washington Street. I think it's time to plan another trip to this beautiful beach town and do some local research to see if I can find out more about them!
 "Pennsylvania, Births and Christenings, 1709-1950," index, FamilySearch (https://familysearch.org: accessed 05 Aug 2013), William Arthur Speady, 24 Jan 1874.
 "Pennsylvania, County Marriages, 1885-1950," index and images, FamilySearch (https://familysearch.org: accessed 05 Aug 2013), William A. Speedy and Maggie A. Schwenk, 1899.
 "St Augustine, Florida, City Directory, 1914," Ancestry.com. U.S. City Directories, 1821-1989 (https://ancestry.com : accessed 05 August 2013), William Arthur Speedy.
 Allegheny County, Pennsylvania, Court of Common Pleas, Case No. 700 April Term 1916, Della E. Swank vs. Charles W. Swank, Transcript of Official Notes of Testimony, 17 May 1916, Department of Court Records, Pittsburgh.
 "United States, World War I Draft Registration Cards, 1917-1918," index and images, FamilySearch (https://familysearch.org : accessed 05 Aug 2013), William Arthur Speedy, 1917-1918.
 Undated clipping, ca. 1920, from unidentified newspaper; photocopy privately held [address for private use] NJ, 2011.
 "Out of the Files, Twenty Years Ago, Monday July 13, 1925," The Monessen Daily Independent (Monessen, PA), 13 July 1945, p. 7, col. 3; digital images, Ancestry.com (http://www.ancestry.com : accessed 5 August 2013).
 "Fisherman Still Missing," Cape May Star and Wave (Cape May, NJ), 14 August 1926, p.1; photocopy of clipping, privately held [address for private use] NJ, 2011.
 "Searching for Speedy's Body," Cape May Star and Wave (Cape May, NJ), 28 August 1926; photocopy of clipping, privately held [address for private use] NJ, 2011.
 1930 U.S. census, Westmoreland County, Pennsylvania, Monessen, population schedule, enumeration district (ED) 65-98. sheet 5-A, p. 106 (stamped), dwelling 119, family 163, Charles A Cubbage; digital image, Ancestry.com (http://www.ancestry.com : accessed 5 August 2013) citing National Archives publication T626; imaged from FHL microfilm 2341891.