Kelly's Last Sail Before the Veil: Part I

Holy cow. This past weekend was incredibly unforgettable, and special, and momentous. Kelly and her bridal party-- made up of myself as the MOH and her three closest friends-- celebrated her Bachelorette weekend in just the COOLEST way possible, and I'm so excited to share our weekend with you all. But first, I need to set the scene...

Did you have that friend growing up whose house you were always at, and whose family basically adopted you as their own; took you on their family vacations and wouldn't be surprised at all to find you at their house, even if your friend wasn't home? For Kelly, that friend is Rosie. They have been best friends since the 1st grade and are essentially family for better or worse. My family loves Rosie, and Rosie's family adores Kelly. So when I emailed Rosie, along with Kelly's two very best friends from college Claire and Brianne, in January to start brainstorming Kelly's bachelorette, Rosie was quick to reply that she and her Dad really wanted to make this celebration the most special for Kelly; they very generously and thoughtfully offered Rosie's dad's boat for the weekend, and what resulted was-- I think-- the best weekend of Kelly's life.

Friday morning, Brianne and Kelly left New Hampshire around 8am and drove down the shore to scoop me up, and we continued on to Boston to pick up Claire. Keep in mind that Kelly had no idea where we were going or what we would be doing. We told her that Rosie would be meeting us at our destination, which made sense because Rosie would be flying from her new home in Puerto Rico (or so Kelly thought).

As we drove, Kelly could tell that we were headed for the Cape, and she was psyched!! We arrived in Falmouth, MA and told Kelly that this was one stop on our journey. She couldn't understand what was coming next because "there's nothing else after the Cape!!" There was a slight hiccup with the dinghy on the boat so Rosie and our Captain for the weekend, Scott, were a little bit delayed leaving Connecticut; we told Kelly that Rosie's flight was delayed and that we would explore Falmouth while we waited for her to fly in.

This turned out to be pretty serendipitous because after an incredible lunch at Alejo, a Mexican restaurant, we wandered into Lilly Pulitzer where Kelly found her rehearsal dinner dress! We continued to shop, rode a carousel (because why not?) and reveled in all of the congratulations and best wishes that Kelly received on the street!

First thing we did, though? Adorned Kelly with some adorable bridal accoutrements! Look at Claire here flexing those bridesmaid skills.

After lunch and exploring downtown Falmouth, Rosie was about an hour out, so I quickly looked up restaurants on the water that were close to the ferry lot where we would park our car for the weekend. I ended up finding a place called Pier 37 Boathouse that looked like the perfect outdoor bar for us to grab a drink and hang by the water. Again, very serendipitously, this ended up being the perfect spot for Rosie and Captain Scott to pull up with the most perfect reveal. I snapped this picture of Kel because she had no idea what was about to pull up to that dock right behind her...

(Don't mind our toast in the beginning to Yappy Fred and the Yum Yum Gumball Regime... the name of our server's now defunct band.)

Kelly was SHOCKED. And so very pumped. We quickly paid our tab, grabbed our luggage, and Claire, Brianne, and I planned to go park the car at the ferry lot and Uber back to the dock. That's when the very, very nice dock attendants told us that we could leave our car (for free!) at Pier 37 for the weekend. They were so excited for us, our bride to be, and the adventure we were about to embark on-- it was so sweet.

So we left the car, boarded the boat, and that's when Kelly found out that we were headed for.... Martha's Vineyard!! Rosie (who happens to be a restaurant owner) had the most incredible charcuterie spread and champagne waiting for us, and we set sail for the hour-long cruise to Edgartown on our floating home for the weekend. I'll let the pictures (some of which were taken by the multi-talented Captain Scott) do the talking here:

We pulled into the BEAUTIFUL Edgartown Harbor right at sunset, and almost could not have planned it better.

If Kelly wasn't already THRILLED, the burgee that Rosie had made for her really put her over the edge, as you can tell.

After settling on to our mooring and sending Captain Scott to shore for the night, general bachelorette games, antics, and hilarity ensued, along with some night-swimming off the boat. Claire and her husband Phil very thoughtfully coordinated a hilarious video from the groom, Tom, answering questions about he and Kelly that we then asked Kelly to see if their answers matched. Kelly laughed, she cried-- it was hysterical (and also not suitable for sharing ;) ). We eventually settled into our cabins for the night ready for the beautiful day on the island that lay ahead. Part two coming soon!


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