Perhaps the first ship to leave for Connecticut was the Mermaid.  Capt. Shirley sailed the Mermaid from Annapolis Royal on Oct. 13 and was supposed to be bringing Acadians to Connecticut.  But it arrived at Massachusetts on Nov. 17.  I haven't found whether or not it made it to Connecticut.
     A ship called the Two Sisters was supposed to take 280 Acadians to Connecticut, but was replaced by the 166 ton ship, Elizabeth.  Captained by Ebenezer Rockwell, it left Annapolis Royal on Dec. 8 with the 280 Acadians.  Three Acadians died on the way, but the ship finally arrived at New London on Jan. 21, 1756 with 277 Acadians.
     The following day, 173 Acadians from Pisiquid, Grand Pre, and Mines arrived. (This is from Brasseaux.  Does this include the Dove mentioned by Lauviere below?)
     Capt. Samuel Forbes sailed the 87 ton sloop Dove from Boudrot Point (Minas) on Dec. 18, 1755.  His "cargo" of 114 Acadians arrived in Connecticut on Jan. 30, 1756.   Lawrence specifically mentioned the Dove in an Aug. 11, 1755 letter where he says "if it is not very inconvenient I would have you send the Sloop Dove to Annapolis to take on board part of the inhabitants there destined for Connecticut to which place that vessel belongs." [Selections from Public Documents of the Province of Nova Scotia, p. 273]
     The next group didn’t arrive until May 1756. The 139 ton sloop Edward, captained by Ephram Cooke, had left Annapolis Royal at 5 a.m. on Monday, Dec. 8, 1755 with 278 Acadians.  A bad storm blew it off course and and it docked in Antigua. While there, many died of disease (smallpox). Eventually the Edward made it to Connecticut on May 22, 1756 with only 180 Acadians.  (Brasseaux says 260 Acadians)  LaFreniere states that almost 100 had died of malaria.  When they got to Connecticut, what little belongings they had were burned so that the disease wouldn't be spread.
     According to Al Lafreniere, the Connecticut gazette noted that another unnamed sloop that left Minas on Nov. 30, 1755 with 173 exiles made it to Connecticut, arriving on Jan. 22, 1756.  The captain (Worster) may have been John Worster.  Noted in Winslow's Journa, John Worster left Fort Cumberland on Oct. 27, 1755.  The other ships to Connecticut sailed from Annapolis Royal and Minas, but some of the Connecticut Acadians came from other areas of Acadia.  Running behind the other ships, it could be that he was assigned to pick up the remaining Acadians from the isthmus and elsewhere.  Since Osgood shipped out 732 Acadians, and only 600 are "identified" ... this may be where the other 132 ended up.
     In 1763, 666 Acadians petitioned to be sent to France, but were denied. Some of them subsequently migrated to Saint Domingue to face hard labor and tropical weather. Some of these survivors eventually made it to Louisiana. Of those Acadians who stayed in Connecticut, 240 chartered a boat (the Pitt) in 1767 and sailed north (to the St. John River Valley, in New Brunswick or Quebec). There is some evidence that some Acadians remained in Connecticut.