Some people say that you’re never supposed to look back unless it is to see how far you have come. And while I do agree that putting too much time into the past takes away from this gift of the present, I also believe that if we never reflect we never really give ourselves a chance to grow. So here, with my 20 for 16… I’ve got a look bACK at some of my happy places… a reflection at some of the harder times… and the thoughts of what goes into making blACKbook and travel blACKbook what it is today. Thank you all for following along.

1. 3E Entrepreneur Escapes

January || Nantucket



There are few things that make me happier than connecting people… I went to school for journalism, so this whole solo business person venture has never been my forte.. but as I have grown into an entrepreneur, I realized the only way to do it and do it well, was to surround myself with other like minded individuals and help each other and grow together. The first 3E Entrepreneur Escape that I cohosted with Meg Blair and Jason Bridges and Justin Taylor on ACK was such a cool way to bring together 30 entrepreneurs from on island and off, to talk about work, wealth and wellbeing all while being surrounded by the beauty of our Grey Lady. It was also the first time that I was able to bring my favorite branding strategist Jasmine Takanikos to the island … and I am so grateful that we have been able to host her three more times since then! (And for the first ever BrandHuman Experience next weekend!) Check out the recap of the first ever 3E Entrepreneur Escape from our friends at Yellow Productions below

2.  travel BLACKBOOK: #SoStowe Girls Getaway

January || Stowe, Vermont



I grew up as one of three girls, was in a sorority all four years of college, and keep a super close group of strong women around me daily, so creating a womens weekend away to one of my favorite resort towns made my heart sing. Thus, welcome the first ever blACKbook retreat with the #SoStowe Girls Getaway. After spending much of November and December in the Green Mountain state and falling love with the authentic mountain town of STOWE, I partnered with my amazing friend Lisa Haggerty of Well Heeled and The Yoga Barn to curate a women’s retreat that represented how I would stay, play, sip, shop and get active here. It was a pretty amazing to bring 16 incredible ladies together and I am so grateful for the opportunity to partner with Field Guide Stowe, Tradewind Aviation, Cork, Edson Hill and more on the wonderful weekend! (So much so that I will be back up in Stowe next month!) See how blACKbook vaca’s in Stowe below:


3. travel BLACKBOOK: #7thHeavenSBH in St Barth’s

February || St. Barth’s, FWI



Spirited. Magical. The Nantucket of the Caribbean… Whatever you want to call it, St Barth’s has that island mystique that sucks you in and you never want to get spit out. My #ACKpartyhosts cohost David Handy and I headed from the ACK to the SBH for a week of fun and sun and our fair share of rose. Highlights of the #7thHeavenSBH trip included lunch at the newly designed beach dining spot at Le Toiny, dinner and a show (and a few costume changes!) at Le Ti, live music at Baz Bar, and of course, celebrating the seventh anniversary of our dear friends Terry and Marla Sanford with this insanely fun Nikki Beach Sunday Brunch. (As seen above!) Take a peek at the dozen do’s when it comes to St. Barth’s Below:


4.  travel BLACKBOOK: #GoingPlacesTogether… to Qatar

March || Doha, Qatar



If you told me a year ago that one of the places I would travel to in 2016 would be Doha, my first question would have been, Doh, where? One of the craziest experiences of my year was checking out Qatar through Qatar Airways. Traveling with a group of media influencers from around the Northeast, we headed on a 36 hour journey to the middle east, to tour the home of the 2022 FIFA world cup and take the inaugural flight from DOHA to Boston with Qatar Airways. Definitely one of the most incredible flight experiences I have ever had…  from the pajamas and champagne upon arrival to the LED lights to the way the cabin is pressurized… I truly felt better than I have ever after a trip when we landed that 14 hour flight in Boston! If you haven’t checked out  Qatar Airways, see what they are all about below.


5.  travel BLACKBOOK: California (Road Trip) Love

April || California Coast



I am always a big fan of a good road trip… and while we drove from The Cape to Charleston in 2015, we decided to check out the west coast for our big 2016 Spring Trip. Little did many of my blACKbook followers know, during this time away was also during the two anniversary of my mothers passing. Before she died, my mother had done a road trip of the US and her favorite part was Northern California. I wanted to dip my toes in the same part of the ocean that she did and also wanted to see the coastline that had left such a vivid imprint in her mind. While in the Golden State, I wrote this piece about what I’ve found out about life since her death… It was probably one of my favorite things I wrote this year… You can read it below.

Two Years Forward…

6.  The Nantucket SLEEPover

April || Nantucket Hotel 



One of my very favorite parts about blACKbook is connecting the women that I work with together… So when I partnered with The Nantucket Hotel for their first full year as a blACKbook member, I wanted to give these amazing entrepreneurial women in the community a chance to experience the beautiful downtown property first hand and give them the back story, told by none other than the owner Gwenn Snider (who owns the hotel with her husband Mark!) We savored some beautiful yoga in the studio, toured the hotel with Gwenn and got the details on how this epic building came to life in 2012 and even the stories into how she picks out the bedding, pillows, sheets and more! The night finished off with great conversation and connections around their fire pits. Definitely a serious highlight to have these twenty women be able to come together before the season really kicked in.

Nantucket Hotel

7.  Spring Street Style Shoot

Daffodil Weekend || Nantucket

daffy-2 daffy

The 19th #blACKbookstyle shoot happened to be on one of the coldest days of April with one adorable Nantucket couple modeling the latest in ACK Street Style for Daffy Weekend. (You probably recognize that handsome gent, Nick from behind the bar at CRU and now one of the new owners of Sandbar at the Jetties, and his beautiful girlfriend Julia, the sommelier at CRU!) It was freezing… it was windy… it was typical Nantucket… but oh boy, these two brightened up everything throughout that grey lady day! Always love what my style photographer Maria of Charlotte Carey Photography and the floral queen Betsey Brooks Floral & Design are able to collab with me on! Click below for the full shoot:


8.  Printed blACKbook Launch Collab

May || Station 21


donelan-3 donelan-2

This is probably one of my treasured celebrations in 2016, as it is pretty crazy how a decade on Nantucket changes your life… Here is it goes… 10 years ago this May, I was waitressing at Galley Beach. The very first table I waited on was the chef, W Scott Osif, the co-owner, Geoffrey Silva and the maître d, Marco Coelho. It was Marco’s birthday… And I remember nervously unwrapping a beautiful bottle of champagne sent over to him as a gift…. from this great guy named Joe Donelan.   I could have never imagined that a decade later, I would be launching my PRINTED Nantucket blACKbooks with Marco at his newest restaurant, Station 21… And toasting to it with this great guy, Joe Donelan … and his Donelan Family Wines.  Thank you for all the strength and support over the years. I truly love this island and the community here and am so grateful to call this place home.   Here’s to good wine, good reads, and good friends that out here, become our island family!


9.  First Ever #ACKpartyhosts Pop Up Fashion Show!

May || Samuel Owen Gallery


tastemaker-2David Handy of David M Handy Events, Lindsay Walsh of RJ Miller Salon and I have been known to create some buzz and excitement around Fashion. (We collaborated on three Beauty & The Beach Fashion Shows at Galley Beach from 2013 to 2015!) And this year, we decided to change up the pace… and give people a surprise with a stylish kick! So we created an art show opening at Samuel Owen that revolved around cool drinks during Wine Fest and then secretly added in a Pop-Up Fashion show, featuring all our blACKbook SHOP members! For all those who weren’t in attendance, we had our friends at Yellow Productions film the entire thing! Check out their recap below…

10.  Miss blACKbook heads to KRIPALU

June || Lennox, Massachusetts


I checked myself into a three day retreat at Kripalu, locked up my phone and computer during my time there and spent the weekend without any technology. I lived to tell the tale. It was a very humbling and very necessary weekend to realize how much I was completely relying on my phone, social media and my computer for much of my life during May… and I cannot recommend this retreat enough to the many bloggers and digital strategists I know.. it’s so important to reflect and step back once in a while and to TRULY do it without any devices. You can read my full story below… and I know the reason that I was able to succeed during the summer of 2016, was because of this reboot in June.

HELP! Self? Breathe… Flow

11.  MANtucket Gets ACKtive

June || Nobadeer

Charlie Merrit (aka, MANtucket blACKbook) knew this summer that he wanted to stay fit, he wanted to have fun… and he wanted to document his experiences in Video Blogs… We kicked it off Daffy weekend with his Sconset Recap… and then added some more fun with his first ACK SURF SCHOOL lessons with our buddy Gaven Norton… (Make sure you watch his video above!)

MANtucket second annual SPIKEBALL Tourney

July || Fishermans

MANtucket took it to the beach again, this time for the second annual Nantucket SPIKEBALL tourney… And while he may have lost the actual title on the beach that Saturday… he definitely won some love with his ACK Spikeball preview as seen above. (And judging that we are already getting emails about next years tourney, we can be safe to say that SPIKEBALL is the beach game that is here to stay!)

12.  CISCO Trashion Show

July || Cisco Brewers


trashion-showWhen it comes to collaborative events… you know I am always game. So when Jay Harmon of Cisco Brewers approached me to put together the fashion component of the first ever Cisco Brewers TRASHION SHOW… I couldn’t say yes fast enough. One, because I (like pretty much everyone else I know in the world) loves Cisco and the Brewery and the vibe that this amazing place gives off. Two, because I knew that the event would give back to the community and raise funds and awareness for the ACK Clean Team and to keep our beaches some of the best in the world…. and three, because there is nothing more fun and festive that the week of the 4th on ACK and what better way to add in some fashion to it and do it with a scouting trip to the DUMP?! We connected with a dozen models and a dozen makers, who all created some of the coolest style spreads that I have ever witnessed! Again… for those that missed out, our friends at Yellow Productions captured the day so perfectly and I am so grateful to be a part of this annual amazing event.


CJ LAING SCONSET || August || Siasconset, Massachusetts


JOEY WOLFFER of STYLELINER || August || Nantucket Boat Basin


ELEVATE & EDUCATE || October ||White Elephant’s New Ballroom


I am a connector. It is my superpower (as our friend Trish Fontanilla told us we all needed to find our personal super power last January at the 3E Entrepreneur Escape!) And this summer and fall, I hosted three events with some amazing women that really touched my heart. We kicked it off with the opening of CJ Laing’s newest boutique in Sconset and I invited a dozen women to share in some bubbly and some delicious Claudette’s as we talked about life as an entrepreneur on ACK and beyond. A few weeks later, the extraordinary JOEY WOLFFER of Styleliner came out to the island and we hosted her on a Nantucket Mermaids charter as she told us her back story into becoming her own personal brand. (You have to check out her store, which began as a traveling boutique on wheels with The StyleLiner) Finally, in October, to showcase the brand new White Elephant Ballroom, I bought together my favorite branding strategist Jasmine Takanikos, the super savvy wealth management advisory, Gianna Armano, and healthy entrepreneurs, Evie O’Connor and Rachel Afshari to talk about self branding, self care and self worth with twenty women in attendance. This Elevate & Educate event was another “a-ha!” moments where I recognized how much I love bringing in continuing education to the island community. (And for those here next weekend, you should check out the BrandHuman Event at the Nantucket Hotel!)


September  || Dharma Yoga



Joann Burnham of Dharma Yoga has been a huge influence on my life here on ACK. She has helped me find my love for yoga, figure out how to make time for self care, and she is also the cofounder of the Nantucket Yoga Festival (which is always one of the biggest highlights of my summer season!) This fall, she brought back the amazing Tao Porchon Lynch to our island for a September weekend workshop that really made my heart smile. Tao is 98 years young and the world’s oldest yoga teacher. She is the epitome of grace and positivity. Tao makes you really think about how everything is possible and her stories that run the gamut from her modeling days to her encounters with movie stars and Ghandi to her time on America’s Got Talents and beyond. She inspired me to really think about how I am living my day to day life. These are the weekend that truly make me so grateful for the opportunities our Nantucket community offers us. Click below for the latest article about Tao in the New York Times!

Tao In The Times!

15.  travel BLACKBOOK: to the other island

October || Martha’s Vineyard



Ever feel the real need to just get away and feel anonymous? I get that at the end of a Nantucket season. So when I had the opportunity to check out the latest Lark Hotel in Martha’s Vineyard… I jumped on the first Hy-Line ferry for a quick escape. I love when people ask what the difference between Martha’s Vineyard and Nantucket is… because they are truly apples and oranges. (Or Vineyard grapes and Nantucket cranberries!) Either way, MVY has a certain charm to it that you will find… from the way the island is so expansive, to how each town has its own identity and even to the way that the place is filled with makers, creatives, farmers and more! With my friend Emme, we were able to explore a few Grey Days on the other island while staying at Summer Camp… a fun and fresh take on a larger hotel in Oak Bluffs. We biked (in the hardcore wind!) shopped around (loved SLATE!) and ate at a few super delish places including 20ByNine which is such a cool bar serving American Beer and Whiskey and some of the most beautiful charcuterie plates I have ever seen! Check out all the Lark Hotel Properties by clicking below:


16. travel BLACKBOOK: ACK of the mountains

October || Aspen, Colorado



Ever arrive at a place you’ve never been and immediately feel at home? That was the sentiment I had as soon as I got to Aspen, Colorado. While I’ve had many friends tell me that I would love this Mountain Town, I had no idea what was awaiting as I flew over the Rockies and landed in this beautiful resort village. I was thankful to tour the town during a slower week, during when the fall met winter, and during a time when I didn’t have to share the hikes, the bars or the streets with too many other visitors… Who has been to the Maroon Bells!? Pure amazingness! Just an extraordinary little village… one I can’t wait to go back to.

17.  travel BLACKBOOK: Vacationland

October || Kennebunkport, Maine



October sure was a month filled with many escapes… including a stay at one of the most unique properties I have seen in a long time. Say hello to Hidden Pond in Vacationland! What a beautiful little oasis this place is, located in the picturesque seaside town of Kennebunkport. Collborating on an instagram tour with the Kennebunkport Resort Collection, I finished off October with a Maine Escape to catch the tails end of the foliage and the last weekend of this seasonal resort. After a weekend of dining around and checking out the town, my favorite part ended up being dinner at Earth and the donuts that you will 100% be dreaming about for months after. Check out where we stayed by clicking below:


18.  travel BLACKBOOK: Venice… and the Reboot

November || Venice, California



Ever feel like you need a little creative boost? Head to California. I swear the vibes in that Golden State are pure magic. With the need for a reboot, I decided to book three weeks away in my favorite town that I found through the April Cali Road Trip… To Venice Beach. Living right off Abbott Kinney, I took a page out of my blACKbook to spend some time focusing on my brand and where to go from here. See I think the hardest part about being an entrepreneur is trying to figure out time to pause and build your brand again. So I took a few weeks off from social media, put the computer down and picked up my first love again (a Sharpie pen and a blank Moleskin journal) and began to work on where to go next. It was a transformative November… and while I know I’m an East Coast girl in my heart, my head is often telling me that I am solar powered and West Coast destined… and who doesn’t love that Cali weather!? Stay tuned for more Venice Vibes as I travel back to that part of the country this winter… and until then… make sure if you’re ever in Venice that Gjelina’s, Gjusta, and Intelligencia are on your super short list.

19.  HAPPY (strollin’) PLACE

December || Nantucket



I mean… is STROLL probably the most fun weekend of the year of Nantucket!? I am a believer that this is the case. Think about it… it’s like Halloween in December, everyone is trying to outdress each other and no sweater is too ugly for this weekend. Visitors are in the most festive of moods and the weather over the past two years was nothing short of spectACKular. Santa arrives via Coast Guard, the streets are filled with carolers and Christmas Trees and there’s enough holiday cheer at the restaurants to satisfy every diner and drinker. Just sayin’… #ACKstroll is where it’s at. If you don’t know, now you know… for 2017!

20.  travel BLACKBOOK: saying YES to Nosara

December || Costa Rica



I am so happy to write that I ended 2016 making sure to build the foundation of something new and exciting with a travel BLACKBOOK experience that not only helped me grow, but also elevated an amazing group of women around me. The first ever blACKbook wellness retreat to Nosara, Costa Rica was a week that I will never forget. From the amazing yoga to the awesome surfing, the pristine beaches to the low key nightlife, this place is seriously a wellness heaven. While our full feature will be out later next week, I am excited to report that our experiential blACKbook excursions and retreats will be a big part of our coming year. Take a peek to see where we stayed by clicking below:


Thank you all so very much for following along with blACKbook. Thank you for the likes, the loves, the good vibes, the comments and the support and love for Nantucket (and beyond!) that makes me jump out of bed in the morning. I think it’s a pretty amazing thing when your job and your joy can come together… here’s to more of that… and here’s to a healthy, happy and magical 2017!
xx Holly