24 Hours on Nantucket: A Pet Friendly Itinerary

From Boston proper, Nantucket is about 2.5 hours away.  The ferry terminal, located in Hyannis, takes about 90 minutes to get to.  Once aboard the (fast) ferry it takes about an hour to cross over to Nantucket!  Nantucket is often listed as a “must visit” island & as soon as you disembark the ferry you can see why! You are greeted by quaint cobble stone streets, lined with boutiques, cafes, restaurants & gift shops.  It’s a great place!

BUT, it’s an expensive place!  Once peak summer season ends on Nantucket, it is slightly more affordable to visit, so we tend to take an overnight trip ‘down the Cape’  in October.  The fall colors are beautiful and the price point is a bit lower!  The only downside of visiting during the off-season is some restaurants & shops choose to close for the Fall/Winter.  I still think it is totally worth a visit!

Here is a look at our 24 hours on Nantucket!

Brigette & I usually do best when we travel with just one another.  Sometimes adding a third wheel can really throw off our vibe, but for this trip, we weren’t the planners, we were the passengers!  Matt booked our ferry tickets, hotel, Jeep rental & all of our activities.

Who’s Matt?

He’s my best friend, my emergency contact, the person I call when I’m in a pickle (read: I’ve just nearly chopped my thumb off, my car battery is dead, I need money wired to Sri Lanka, I can’t find my phone…the list is long).  Brigette & Matt have also known each other for ages and share a mutual affinity for both speaking like pirates & a certain curse word.  Matt loves Nantucket, and was excited to plan our itinerary!

As you can see, Matt travels with precious cargo.  MEET BENNY!

Well, since little Benny was accompanying us and our cottages were pet friendly, Brigette brought her little monkey too!  MEET NEELY!

And, here I am channeling the dog whisperer…

Back to our itinerary! An early morning wake up, quick drive & ferry ride later, we arrived on Nantucket.  Our chariot swooped us up at the ferry terminal and we headed to the Cottages at the Boat Basin to see if we could check in early.

I can’t say enough how great the Cottages at the Boat Basin are!  Not only is the property meticulously maintained, but they also go above and beyond for the furry guests!  Both Neely & Benny were welcomed with this gift bag full of swag & a personalized name tag with the Cottages listed as the contact.  A seriously awesome touch!

Luckily, one of our cottages was ready, so we unloaded our bags before heading out.  We had an aggressive amount of luggage amongst us considering we were only on a 24 hour trip.  #overpackers

Now back in the Jeep, our first stop was checking out the view from the highest point on Nantucket.  A great look out point & perfect for a quick photo-op.

A drive by shot of Sankaty Light.

Our next stop was to check out the Cranberry bogs, but sadly the bogs were dry due to a drought, so the photos we hoped to capture looked pretty underwhelming. So much so, I won’t add them here.

Alas, we still had lots to do.  From there we headed to Smith’s Point.   While it’s super fun to drive on the beach, this is for confident drivers only!  If you don’t know how to drive over-sand, this may not be the activity for you!  Getting stuck in the sand out there will really put a damper on your 24 hours on Nantucket!

Next, a MUST VISIT when you are on Nantucket! Cisco Brewery!  Cisco Brewery is comprised of several different cottages, that all surround a big courtyard with picnic tables, food venders, and open spaces.  Each little cottage contains a bar where you can try different beers & wines and ciders, all made right on site! An added bonus is that the Brewery is dog friendly!  So, our 4-legged friends were able to stay with us!

During the summer, several different food vendors set up shop around the property, but since our visit was in the offseason, the only option that afternoon was a dumpling hut.  So, we did what anyone would do when faced with consuming several beers on an empty stomach.  We ate dumplings, very overpriced dumplings, whilst crouching around a tiny stool.

We left Cisco with just enough time to grab some snacks and wine (of course) from Bartlett’s Farm, before catching the sunset from Ladies Beach.  The photos will speak to just how beautiful the Nantucket sunset can be!

Once the sun ducked below the horizon, we headed back to the Cottages to “get ready” for dinner.  After a long afternoon consuming adult beverages, we mutually agreed we’d forgo the whole getting ready for dinner/wardrobe change process.  We put the puppies to bed for a bit, and headed to dinner at Lola 41.  The Crab Rangoons are life changing.

We had more drinks & a lovely chat with the nice couple sitting next to us at dinner.  We hit the point in the night where we were faced with a tough decision.  Go back to the cottage or bar hop for a bit…

Can you guess the outcome?  We painted the town for a bit longer.

The morning came too soon.  We sluggishly packed up and shuffled our hungover bodies back to the ferry terminal.  A little cold sea air on the ferry ride home helped ease our pounding brains.

Neely was a little embarrassed about the outfit his Mom made him wear…

If you are ever in the Boston area, we’d highly recommend a quick trip to Nantucket!  Even if you choose not to stay overnight, you could still execute a similar itinerary.



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  1. Josie

    April 3, 2017 at 3:57 am

    Great post! very useful for people who travel with there pets I love the idea but where I live there is sadly not very many pet friendly places 🙁

  2. Katie @ Zen Life and Travel

    April 3, 2017 at 8:21 pm

    I love that Matua Sauvignon Blanc : )

  3. The Travel Ninjas

    April 4, 2017 at 4:00 am

    This is so cool. My bother won’t go anywhere with out his dogs, so he doesn’t travel as much as he’d like. I’m going to share this with him to show how awesome a time he could have in a gorgeous area. Thanks for this post, its so helpful.

  4. Paula - Gone with the Wine

    April 6, 2017 at 11:49 pm

    Looks so beautiful out there! I have never been in that part of the country, but I wish to explore more that coast too soon. I’m especially interested in those lighthouses! 🙂 It is always good to have those life time friends who will do anything for you, and you would do the same for them. Many of my travels are related to meeting my friends and gives travelling a whole new meaning.

  5. Carmen Baguio

    April 7, 2017 at 12:55 am

    I need to plan a trip to this area of the northeast. The scenery looks postcard perfect and oh so relaxing. I need this in my life!!!

  6. Only By Land

    April 7, 2017 at 7:44 am

    For you, Matt is like my brother Chris, I’ve called him so many times in difficult situations and he’s always there!. The personalized swag bag for Benny was awesome! The brewery looked a fun place for the afternoon, did Benny try some beer and dumplings as well?

  7. Punita Malhotra

    April 8, 2017 at 5:02 am

    A nice, relaxing do-nothing day at Nantucket…sweet cottage, sandy walks, lovely boat ride away from the buzz of city life. And how adorable are those paw-print ribbons on the brown paper bag! Wish there was a weekend getaway like this close to my city..but no beach anywhere close.

  8. Simon - SiDash Travels

    April 9, 2017 at 11:42 am

    Great post. Really enjoy your writing style 🙂 Nantucket sounds like my kind of place 🙂 Somewhere to drink lots of different beers and enjoy said drinks on stunning beaches 🙂 looks like a great place to visit and I’m glad you all and the furry friends had a great trip 🙂 thanks for sharing.

  9. neha

    April 9, 2017 at 1:33 pm

    Beautiful. I am going to forward this piece of information to some of my friends who have pets. Often pets become a part of the family but it is challenging to take them everywhere with you. So, this itinerary will be a hit with the pet lovers

  10. Izzy

    April 10, 2017 at 2:08 am

    As a Bostonian, I totally approve of the Massachusetts love. Glad to see a pet itinerary! I know a ton of friends who need help when it comes to accommodating their furry companions. And will be sure to check out Cisco Brewery this summer!

  11. Danik

    April 10, 2017 at 10:28 am

    I was so upset by not visiting Nantucket as I did my road trip around New England. Now looking at your photos and reading the posts, I have sure missed a lot. Must get back to that area soon. Great write up guys and safe travels 🙂

  12. Dave

    April 10, 2017 at 6:32 pm

    This is definitely a great way to spend a day in Natucket, I love that place!

    And adorable pups!

  13. Jas from My Suitcase Journeys

    May 31, 2017 at 10:34 pm

    What an awesome post! Seems like a beautiful place to visit – although 24 hours would definitely not be enough for me. Added this to my bucket list. Thanks for sharing!

  14. maegan

    June 1, 2017 at 4:17 am

    Such a great post! We travel with our 2 spaniels as well and it is always top priority to find those dog friendly locales! Your babies are adorable BTW.

  15. the lazy travelers

    June 1, 2017 at 1:46 pm

    LOVE nantucket and how cute is benny?!!? we’ll have to find a pup to join us when we make our own trip…

  16. Genie | Gallivanting Bean

    June 7, 2017 at 1:35 am

    omg all the puppers are soo cute!

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