Jonathan Bennett

Jonathan Bennett

Your Host

Jonathan Bennett

Your Host

His striking good looks may have made Jonathan Bennett an object of affection for the “plastics” in Mean Girls as the heartthrob Aaron Samuels, but his talent and commitment to the craft are what have led him to becoming one of the most sought after actors in Hollywood. The GLAAD Award winner and five-time nominee broke new ground at Hallmark Channel starring in and executive producing The Holiday Sitter, the network’s first gay-led romantic comedy. Fans have dubbed him “The Gay King of Christmas” for his many hit holiday movies on the network including The Christmas House franchise and most recently, Christmas on Cherry Lane. The talented actor also hosts the ratings powerhouses Halloween Wars, and Cake Wars on Food Network, Time Square New Year’s Eve and Battle of the Decades on Discovery Plus. His work to bring more LGBTQ+ storylines to television and movies earned him the Equality Visibility Award. Other fan-favorite roles include taking on the iconic character Van Wilder in National Lampoon’s Van Wilder: Freshman Year, as Steve Martin’s antagonistic son-in-law in Cheaper By the Dozen 2 and roles on popular shows such as Station 19, Law & Order: SVU, Fantasy Island and more.



Schedule - Sail 1

  • Tuesday, Nov 5

    Hallmark Sail-ebration
    with Hallmark Channel Stars
    6:00 PM - 7:00 PM
    Pool Deck

  • Wednesday, Nov 6

    Bingo
    Presented by Bingo Blitz
    10:00 AM - 11:00 AM
    Stardust Theater

  • Wednesday, Nov 6

    Hallmark Photo Ops
    11:30 AM - 2:30 PM
    Grand Pacific

  • Wednesday, Nov 6

    A Very Merry Christmas Match
    with Hallmark Channel Stars
    5:30 PM - 6:30 PM
    Pool Deck

  • Wednesday, Nov 6

    Ugly Christmas Sweater Party & Contest
    with Hallmark Channel Stars
    9:00 PM - 10:00 PM
    Pool Deck

  • Wednesday, Nov 6

    Talent Panel
    The Groomsmen Trilogy
    10:15 PM - 11:15 PM
    Stardust Theater

  • Thursday, Nov 7

    Finding Mr. Shipmas
    Hosted by Jonathan Bennett
    5:30 PM - 6:30 PM
    Pool Deck

  • Thursday, Nov 7

    Holly Jolly Pajama Party Presented by Dearfoams
    with Hallmark Channel Stars
    8:30 PM - 10:00 PM
    Pool Deck

  • Friday, Nov 8

    Hallmark Photo Ops
    11:30 AM - 2:30 PM
    Grand Pacific

  • Friday, Nov 8

    Christmas Sing-Along
    3:30 PM - 4:15 PM
    Pool Deck

  • Friday, Nov 8

    A Scene for the Season with Hallmark Screenwriters
    5:30 PM - 6:30 PM
    Pool Deck

  • Friday, Nov 8

    Hallmark Christmas Ball
    with Hallmark Channel Stars
    8:30 PM - 10:00 PM
    Pool Deck

Schedule - Sail 2

  • Sunday, Nov 17

    Hallmark Sail-ebration
    with Hallmark Channel Stars
    7:00 PM - 8:30 PM
    Pool Deck

  • Monday, Nov 18

    Photo Ops
    with Hallmark Channel Stars
    11:30 AM - 2:30 PM
    Grand Pacific

  • Monday, Nov 18

    A Very Merry Christmas Match
    with Hallmark Channel Stars
    5:30 PM - 6:30 PM
    Pool Deck

  • Monday, Nov 18

    Ugly Christmas Sweater Party & Contest
    with Hallmark Channel Stars
    9:00 PM - 10:00 PM
    Pool Deck

  • Tuesday, Nov 19

    Finding Mr. Shipmas
    hosted by Jonathan Bennett with Erin Cahill & Sarah Drew
    5:30 PM - 6:30 PM
    Pool Deck

  • Tuesday, Nov 19

    Hallmark Christmas Ball
    with Hallmark Channel Stars
    8:30 PM - 10:00 PM
    Pool Deck

  • Wednesday, Nov 20

    Photo Ops
    with Hallmark Channel Stars
    11:30 AM - 2:30 PM
    Grand Pacific

  • Wednesday, Nov 20

    A Scene for the Season
    with Hallmark Screenwriters & Hallmark Channel Stars
    3:15 PM - 4:00 PM
    Stardust Theater

  • Wednesday, Nov 20

    Festive Feud
    with Jonathan Bennett, Taylor Cole, Sarah Drew, Erin Cahill & Wes Brown
    6:00 PM - 7:00 PM
    Stardust Theater

  • Wednesday, Nov 20

    Holly Jolly Pajama Party Presented by Dearfoams
    with Hallmark Channel Stars
    8:00 PM - 9:15 PM
    Stardust Theater