Gallery

Fan Pier Park in the Seaport area of Boston, MA.

Fan Pier Park in the Seaport area of Boston, MA.

Acorn Street in the Beacon Hill area of Boston, MA

Acorn Street in the Beacon Hill area of Boston, MA

Acorn Street in the Beacon Hill area of Boston, MA

The Boston Public Gardens

The Boston Public Gardens

Caitlyn and Anthony have taken many trips together, with their first being to Niagara Falls in Canada in 2016.

Caitlyn and Anthony took a trip to NYC in 2017 where they said I Love You for the first time in front of the tree at Rockefeller Center.

Caitlyn and Anthony took a trip to Kennebunkport and Ogunquit Maine to celebrate their 1-year anniversary in 2017.

Caitlyn and Anthony visited San Diego in 2018, and "joked" that they wanted to move there.

Caitlyn and Anthony traveled abroad together for the first time to Ireland in 2019.

Cliffs of Moher

Blarney Castle

Caitlyn and Anthony saw the Ice Castles in New Hampshire in 2021.

Caitlyn and Anthony visited Newport, RI to celebrate their 5-year anniversary in 2021.

Caitlyn and Anthony visited Charleston, SC in 2022 where he would surprise her by proposing.

Caitlyn and Anthony took a relaxing trip to Punta Cana in 2023.

Caitlyn and Anthony celebrating Caitlyn's love of strange animals at Spring Day 2017 at Bentley University.

Caitlyn and Anthony before their Senior Formal at Bentley University in 2017.

Caitlyn and Anthony on Bentley University's traditional Senior Trip to the Bahamas in 2017.

Caitlyn and Anthony graduating from Bentley University in 2017.

Caitlyn and Anthony have attended many sporting events over the years, the first one being a Celtics game in 2017.

Caitlyn and Anthony attended a Padres game in San Diego in 2018.

Caitlyn surprised Anthony with tickets to a Patriots game for their 5-year anniversary in 2021.

Caitlyn and Anthony attended their most exciting game ever when they watched the Red Sox defeat the Yankees in the 2021 Wild Card Game.

Caitlyn and Anthony have attended the Cape Cod Brew Fest every year they've been together, the first time being in 2017.

Halloween 2016 as Wendy Peffercorn and Squints from the movie The Sandlot.

Halloween 2017 as 'Taco Belle.'

Halloween 2018 as Mermaid Man and Barnacle Boy from Spongebob Squarepants.

Halloween 2019 as Colonel Sanders and the chicken inspired by KFC.

Halloween 2020 as a farmer and a pig.

Halloween 2021 as Hugh Hefner and a playboy bunny.

Halloween 2022 as 'Hawaiian Punch.'

Caitlyn and Anthony with their favorite son Otis down the Cape in 2020.

Caitlyn and Anthony included their furry friend Otis in their Friendsgiving celebration in 2021.

Otis was forced to take Christmas Card pictures in his least favorite sweater in 2021.

On February 25, 2022, Anthony proposed to Caitlyn at the Pitt Street Bridge in Charleston, SC.

Caitlyn showed her angry side (probably from Anthony making fun of her) during an intense game of mini golf down the Cape in 2017.

Caitlyn and Anthony down the Cape at The Black Cat in Hyannis in 2021.

Caitlyn and Anthony down the Cape at Alberto's in Hyannis in 2021.

Caitlyn and Anthony down the Cape at Tugboats in Hyannis in 2022.

One of Caitlyn and Anthony's favorite activities is cornhole, which they play every Thursday in a league at one of their favorite bars, The Seapoint. They have won the league (and Das Boot) 5 times.

Caitlyn and Anthony attended their friends' wedding together in 2021.

Caitlyn and Anthony attended their friends' wedding together in 2021.

Caitlyn and Anthony attended his sister and brother in law Jacqui and Paul's wedding together in 2023.

Caitlyn and Anthony attended their friends' wedding together in 2023.

Caitlyn and Anthony attended their friends' wedding together in 2023.

Caitlyn and Anthony celebrated NYE together in 2019.

Caitlyn and Anthony rang in 2023 during one of their NYE Bashes at their apartment in Southie.

Caitlyn and Anthony celebrated their third anniversary at The Top of the Hub in Boston in 2019.

Caitlyn and Anthony in the Boston Common after celebrating their six-year anniversary together by going to the restaurant, Moo...Beacon Hill.

Caitlyn laughing at something stupid Anthony said during their Friendsgiving celebration in 2021.

Caitlyn dragging Anthony to go apple picking on a football Sunday in 2020.

Caitlyn and Anthony at their engagement party with friends at one of their favorite bars in Boston, MA called The Hub Pub in 2022.

Caitlyn and Anthony at their family engagement party at Bay Pointe Waterfront Restaurant in Quincy, MA in 2022.

Caitlyn and Anthony when they first toured the wedding venue they ended up choosing, Water's Edge Resort and Spa in Westbrook, CT in 2022.