• About
  • Travel Resources

One Day in a City

24 Hour Travel Itineraries to Make the Most of a Day in a Destination

  • United States
    • California
    • Pacific Northwest
    • New England
    • Midwest
    • South
    • West
    • New York
    • Hawaii
    • Florida
  • Europe
    • Austria
    • Croatia
    • Czechia
    • Finland
    • France
    • Germany
    • Greece
    • Hungary
    • Iceland
    • Ireland
    • Italy
    • Netherlands
    • Poland
    • Portugal
    • Romania
    • Russia
    • Scandinavia
    • Slovenia
    • South Korea
    • Spain
    • Turkey
    • United Kingdom
  • More Destinations
    • Canada
      • Quebec
      • Vancouver Island
    • Caribbean
      • Dominican Republic
      • Puerto Rico
      • Jamaica
      • St. Maarten / St. Martin
      • St. Thomas
    • Central & South America
      • Argentina
      • Colombia
      • Mexico
    • Australia & New Zealand
      • Victoria AUS
      • Queensland AUS
      • North Island NZ
      • South Island NZ
    • Asia
      • Cambodia
      • India
      • Japan
      • Jordan
      • Nepal
      • Singapore
      • Taiwan
      • Thailand
      • Vietnam
    • South Pacific
    • Africa
      • Kenya
  • Girls Trips
  • Cruise
  • Travel Tips
    • Travel with Babies & Toddlers
    • Couple Travel
    • Solo Travel
    • Packing Tips
    • Gift Guides
    • Work and Travel Balance
One Day in a City > Destinations > United States > New England > Visiting Nantucket in the Off Season and My Modern Family

Visiting Nantucket in the Off Season and My Modern Family

November 2, 2020 By Gina
Posts on this site may contain affiliate links. Read the full disclosure here.

Pin
Share
Tweet
0 Shares

Experiencing the Nantucket local way of life with my super cool Uncle Dean

The Nantucket lighthouse...getting ready to greet tourists. But not yet.
The Nantucket lighthouse…getting ready to greet tourists. But not yet.

I visited Nantucket at the beginning of April while the air still had a harsh crispness to it, the flowers weren’t yet in bloom, and the downtown area only had about half of its shops open for business. There were many signs saying “Closed for the Winter, see you next year!” There weren’t any ladies prancing down the cobblestoned streets in Lily Pulitzer dresses with Nantucket Lighthouse baskets dangling from their arms. The beaches were void of people and a frigid wind bit at the cheeks of anyone daring to walk along the shoreline.

Yet I loved it.

Nantucket's empty downtown during low season.
Nantucket’s downtown during low season – not a person in sight.

The island was beginning to unfurl itself from a sleepy winter as it prepared for summer and the hordes of tourists that were soon to come, and you could feel the action and excitement beginning to fill the air as restaurants were stepped in once again by crews getting them back into top form, and shops ran one last “everything is 50% off sale” to clear merchandise before bringing in new items for the summer crowds.

I was on the island to visit my Uncle Dean.

I haven’t spent much time on the east coast of America. Growing up all my family’s vacations were to the west coast from Minnesota (or we stuck around the Midwest). So when I got the chance to go to Nantucket recently to visit my uncle and his fiancé with my mom for her birthday weekend I jumped at the chance.

I’m the oldest of four children. I adore my siblings and if you knew my sister, Coley, you would understand why I’ve never fully felt like I was the “oldest” in my family. Despite Coley’s incessant responsibility and poise in the wake of my childhood and teen dramatics, I was still technically the oldest. But unlike most oldest siblings though, I never had to wonder much what it would be like to have an older sibling. My poor Uncle Dean filled that role. I say “poor” because at only three years older than me and five years older than the next round of cousins (all of whom are girls) we were always trying to get in his space and probably tormented him through most of his teenage years, as we all treated him like an older brother and was keen on getting him in trouble at every turn and teasing him about every girl he spoke to. I remember calling him “Brother Dean” instead of “Uncle Dean” much to his annoyance for much of my 9th or 10th year of life.

Being only three years older than me (my mom is the second oldest of ten children) I always felt so lucky to have an uncle that was so close to my age – which I used to brag to my friends about. Well, let’s be honest, I still brag about it, even though my husband can’t seem to grasp the fact that I have an uncle so young.

“So you’re going to Nantucket to visit your cousin?” Tom inquired when it got closer to my departure date.

He’s my uncle!” I shouted. “We’ve been together for four years. Shouldn’t you know this by now?”

“Yes, yes,” Tom agreed. “I just forget sometimes. It’s weird!”

“Not that weird,” I retorted. Hello, Modern Family!?

Ok, my family’s not that modern; my grandparents just had a lot of children.

Much to my glee, my Uncle Dean started dating Kate, who has a great sense of humor and is super sweet to my uncle. She is also a writer, so needless to say, I love talking to her as I feel she actually understands why I keep/love writing.

Kate is also close in age to me so it was wonderful to get to visit her and my Uncle Dean (plus her totally delightful younger sister who also lives in Nantucket) and get a taste of how the locals live on the island. Both Dean and Kate worked in the restaurant industry and that’s what brought them out to Nantucket, a known culinary haven, though recently Kate has transitioned back into writing again. This was the reason my mom and I visited Nantucket a couple weeks before the tourists are due to arrive because once they do, we’d never get to hang out with my uncle while visiting. He’ll be the throes of restaurant life for most of the summer.

In Nantucket, you get to eat gourmet cuisine in adorable places like this.
In Nantucket, you get to eat gourmet cuisine in adorable places like this.

My Uncle Dean is admirable in that he’s someone who’s lived life his way, sometimes against the grain. These days, he seems to be living a pretty great life living and working as a chef in one of the epicenter’s of the food world, ready to exchange vows with the love of his life. It’s weird because I still remember playing Nintendo in the basement, just wanting his friends and him to think I was cool. (Pretty sure they never did.)

Dean and Kate showed us their favorite parts of the island, plus as foodies they introduced us to some of the most amazing food on the island. Dean, being a chef, also made us a delicious meal in the charming little bungalow they rent. The food was incredible, but what was even more neat to see was the way the entire community of Nantucket comes together and acts as a small town during the off-season. Everywhere we went on the island, Dean and Kate often saw people they knew. Even if they didn’t know the person, if they were on the island this time of year, everyone treated each other like a neighbor. It warmed my heart and – just like when I visit the town where my mom and uncle grew up – it makes me wonder what I’m doing in massive and unattached southern California.

The brewery on the island is one place locals like to hang out, drink, and play games. It's a super fun, laidback place in the off-season.
The brewery on the island is one place locals like to hang out, drink, and play games. It’s a super fun, laidback place in the off-season.

I’m not leaving California, though… at least not anytime soon. So I’m happy to be able to experience this way of life with my uncle and soon to be aunt, the latter of whom grew up on the dynamic east coast.

One of the best parts of visiting my uncle with my mom, though? Seeing the connection that’s between him and my mom. This is an over 20 year age difference, people (dear mom, please don’t be mad at me for mentioning that number) and yet they share a bond that is deep and is so siblingish – that it truly reminds me age is but a number. Dean may be only three years older than me, but he is without a doubt my mom’s brother. And he is, like many of my uncles, someone I look up to and admire. Each of my many uncles I admire in a different way, and in Dean’s case it’s that he followed his heart all the way to the beautiful island of Nantucket, where his cooking is enticing people into the restaurant he works at just as his current home entices many people from all over the world to visit it every summer.

My mom and Dean braving the frigid evening wind to walk on the Nantucket beach. Kate and I decided it was too cold and went back to the car. (What can I say - I'm a California girl now.)
My mom and Dean braving the frigid evening wind to walk on the Nantucket beach. Kate and I decided it was too cold and went back to the car. (What can I say – I’m a California girl now.)

About Gina

I'm a former travel agency marketing director turned freelance travel writer. My editorial and copywriting work has been published on and in USA TODAY, Travel + Leisure, the Travel Channel Cities app, TripSavvy, and many more online and print publications. I especially love sharing my knowledge of traveling with limited vacation time, making the most of cruise ports of call, and vacationing with kids. I also enjoy sharing my favorite travel gear and products to make traveling easier!

About One Day in a City

One Day in a City: Start Here
Hi! I'm Gina, a former cruise and tour marketing director turned independent travel writer who helps those short on time make the most of their travels, even if you just have 24 hours to spend somewhere. Read More...

Travel Writing

Gina Tarnacki Writing

Top Travel Tips

Travel Resources and Websites to Make Your Vacation Easier

Travel Inspiration

One Day in a City: Start Here
I have over a decade of experience working in the travel industry and use what I've learned to help you take control of your travels and design YOUR best trip with however much vacation time you have. Start Here...

Recent Posts

  • One Day in Mykonos: Perfect Itinerary + Tips for Cruisers
  • How to Feel Like a VIP on Your Cruise Vacation
  • Why Cruises are one of the Best Vacations with Kids
  • Take a Cruise to These Epic Wine Regions
  • Family Packing Tips: 8 Do’s and Don’ts on What to Pack for a Cruise

Search for a Destination…

Contact
Advertise
Content Writing Services
Privacy Policy, Disclaimer, and Disclosure

Copyright © 2025 · One Day in a City is a property of Ports and Pen Media LLC.

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites. Certain content that appears on this site comes from Amazon. This content is provided 'as is' and is subject to change or removal at any time.