I’ve been hearing about Nantucket for my whole life.
My parents went there on their honeymoon and the stories they told about it made it sound like such a magical destination.
At the start of the year, Andrew and I were talking to my parents about doing a family trip and when Nantucket was suggested, we knew it’d be perfect for a long weekend getaway.
We spent three days (technically four, if you count a travel day) on the island in June and it was truly such a happy trip for us all.
From delicious meals to views that will instantly calm your nervous system, the island truly dazzled us and I’m already down to plot a return trip.
Here’s our Nantucket weekend guide, featuring the exact itinerary we followed during our summer visit.
Nantucket Weekend Guide: How to Spend Three Days on the Island
For this trip, we selected a long weekend that worked for everyone in early June.
We flew out first thing Thursday morning and left on Sunday morning giving us three full days on Nantucket.
Day 1: Settling in
10am: Drop bags at hotel
We called our hotel ahead of time to confirm we could drop our bags off while we waited for our rooms to be ready.
In a surprising turn of good luck, we were able to get into our rooms right away!
We stayed at The Carlisle House Inn on this trip and I can’t recommend it enough.
It is super charming and just a short walk to all of our dinners downtown.
We also liked that it is on a side street, so it was very quiet in the evenings compared to some of the other options we considered.
Our first stop was Born & Bread Mercantile, where we picked up coffees to help keep the energy high from our early travel day as we walked around.
12pm: Lunch at Lemon Press
After strolling for a bit, we chose to check out Lemon Press for lunch, which I had bookmarked thanks to recommendations from my community.
They were able to seat us right away upstairs around noon on a Thursday.
I ordered the chicken shawarma and a beer from a local brewery. I loved the fresh flavors and everyone else enjoyed their food as well.
3pm: Blue Book tour
After a bit more wandering through the main town my mom and I split off from my dad and Andrew to embark on a bookish activity.
If you’ve followed me for a while, you’ll know I love reading and Elin Hilderbrand has quickly become one of my favorite authors.
My book club actually did a whole Nantucket trip last year (I was out of town for Nora’s wedding, so I wasn’t there) but they had recommended the Blue Book tour and I’m so glad they did!
Not only did we get some fun tidbits about Elin’s life and insight into the inspiration behind the people and places in her novels, but it was also a fantastic tour of Nantucket!
We drove all around the island past the Nantucket Hotel, Sankaty Lighthouse, and more. It was a blast!
Heather, our tour guide and Elin’s sister, did an excellent job and we ended with a toast of prosecco at the famous Chicken Box bar.
6pm: Early dinner
Our first dinner of the trip was at Ventuno, a lovely Italian spot on Federal street.
The inside was beautifully decorated and every detail was perfect even down to the cute menu fonts.
I even made a comment about it to our server and we learned that the owner has a graphic design background—how perfect!
We ordered the olive marinate and ciabatta to start, and then I got the fritto misto and the risotto with scallops.
The whole experience was great and we really liked our waitress and the sommelier who helped us choose wines to pair with our meals.
Since we had a long travel day we turned in early to prepare for our next day.
Day 2: Exploring the Island
8am: Quick breakfast
We enjoyed breakfast at our hotel every morning on Nantucket.
Breakfast was included with our stay at the Carlisle House Inn and the simple continental breakfast worked perfectly for us.
Most mornings I opted for the waffles with some fresh raspberries…I am very much still thinking about this combo.
For the second day I highly suggest making plans to check out the Sconset neighborhood on the east side of the island.
With that said, you could plan to pick up breakfast from the market there or grab something in town before hopping on the Wave shuttle out to Sconset.
10am: Sconset Bluff Walk
Up first on our second day was to do the Sconset Bluff Walk.
This extremely scenic walk takes you along the coastline and also involves weaving in and out of the backyards of some of the island’s richest residents.
A nice hot girl walk where you also get to peep on gorgeous properties…count me in!
We had a nice lunch planned after the Bluff Walk so I ended up wearing a tank top, maxi skirt and sneakers.
This was definitely doable but if we didn’t have those lunch plans I probably would have been more comfortable in a cute workout set.
The bluff walk goes halfway to the Sankaty Lighthouse and you can either continue the walk along the roads or turn back.
My parents decided to turn back but Andrew and I kept going and ended up with a nice view of the lighthouse.
We definitely took our time on the way there but had to book it on the way back to make our lunch reservation in the main town of Sconset.
Pro tip: I’d recommend giving yourself two hours to do the whole walk so you can take your time, stop for photos and have a buffer for any afternoon plans.
Also, there were some adorable little entrepreneurs selling lemonade right by the lighthouse—it was refreshing and only $2 so I definitely recommend it if they’re open the day you go.
12pm: Lunch at The Chanticleer
My parents love The Chanticleer and make a point to come for lunch when they visit the island.
We sat out in the rose garden and it was a gorgeous setting.
I ordered the moules frites—the sauce was nothing short of decadent and the fries were plentiful and cooked perfectly.
My only complaint about our meal was that they were out of every beer that I would have wanted to order to go with the mussels.
I thought this was odd given it was Friday at lunch time, but the food itself was still great.
2pm: Afternoon at Cisco Brewers
What lunch lacked in beer, we made up for just a few hours later.
After lunch we took the Wave shuttle back towards the main part of town.
Andrew and I got off a few stops early and took an Uber to check out the island’s only brewery.
Cisco Brewers is massive and has a few different sections including a brewery and distillery.
There were also lots of food trucks the day we went including one for sandwiches and even a la carte oysters.
You can check their website and Instagram to see which trucks will be there when you’re visiting.
We tried a couple of the IPA’s and pale ales all of which were great, while listening to live music and watching the World Cup.
They were even setting up for Shwayzee (!!!) to perform (deep 2012 lore for me) but we didn’t want to be late to our dinner reservation so we left before he went on.
6pm: Dinner at Lola 41
Fun fact, I actually looked into booking Lola 41 for my dad and I when we went to Palm Beach but the reservation timing didn’t work out.
I’m so glad we added it to the list for this trip though, because this meal was another crowd favorite.
We each got some small plates and specialty rolls (mine was the asahi) and we shared the shrimp friend rice which was amazing.
They sat us outside under the tent and it felt like the place to be seen on the island!
There were lots of bachelorette parties and large gatherings so definitely look into this spot if you need a big group reservation.
8pm: After-dinner drinks
After wrapping up our meal, Andrew and I headed to The Gazebo to try their famous mudslides.
Sadly I heard this will be their last summer, so if you don’t make it there for the 2026 season, you can also grab a quick drink at Queequeg’s or Town (they’re right next to each other).
A summer night on Nantucket is so fun, so no matter where you go I think you’ll have fun popping out for an extra cocktail or glass of wine to continue to soak in the vibes.
Day 3: Downtown day
10am: Whaling Museum and farmer’s market
We happened to be in town on a Saturday when the farmer’s market was running so we made sure to walk through.
There were so many vendors from artists to knitters and of course lots of fresh produce and homemade foods for sale.
From there we went to The Whaling Museum, which showcases Nantucket’s history as a whaling town.
We learned so much about whaling and the history of it on the island over four centuries.
The museum features a 46-foot sperm whale skeleton suspended in the main gallery, which is definitely the focal point.
You can also walk through a restored candle factory from 1847 that is part of the museum.
Lastly, the museum boasts a relaxing rooftop that gives you sweeping views of downtown and the harbor so be sure to check it out before you leave.
12pm: Lunch at Straight Wharf Fish
On the Blue Book tour, Heather mentioned how much she loved the lobster rolls from Straight Wharf Fish, so we made sure to circle back here for lunch.
We all ordered lobster rolls (warm if you were wondering) and sat outside on the dock overlooking the wharf.
I’d highly suggest sitting outside if you can grab a seat in the shade, otherwise the inside was super cute too!
2pm: Exploring downtown
We had the whole afternoon free to do whatever we wanted, so Andrew and I both bought Nantucket sweatshirts from 3 Girls and a Dog.
We also (ambitiously) tried two more local bars—Brotherhood of Thieves and Or, The Whale.
Brotherhood is a classic, old school tavern that had a friendly vibe to it. We just grabbed one beer at the bar, but you could tell that people come here and stay for hours.
The timing worked out great to pop into Or, The Whale because the kitchen was closed on Saturday between 2-5 so we were able to sit at a table outside with our drinks.
We both tried the Kelly Kapowski, which was light and refreshing—much needed on a surprisingly warm early June afternoon.
6pm: Dinner at The Proprietors
Our final meal of the trip at The Proprietors impressed us all.
Proprietors is a shared plates restaurant, so keep that in mind when you book your reservation.
We loved the smoked olives with sourdough crackers, the beef tartare, the vol-au-vent and the funnel cake to name a few.
But I really think it’s hard to go wrong at this place!
8pm: Sunset on the beach
To close out the trip, Andrew and I walked back to Brant Point Lighthouse to watch the sun set on the beach.
We saw the sun go down as sailboats floated past us and the ocean breeze kicked up.
Day 4: Travel day
We caught a morning flight out of Nantucket Memorial Airport to come back home.
Other spots that were recommended that we didn’t get to on this trip:
Breakfast/lunch spots:
- Black Eyed Susans
- Wicked Island bakery
- Provisions
- Milie’s
- Something Natural
- Walter’s (lobster roll)
Dinner spots:
Bars:
- Sandbar
- Sister Ship
- Chicken Box
- Galley Beach
- Rose & Crown
- Queequeg’s
- Club Car (live music)
- Gaslight (karaoke)
If we had one more day on the island I would have prioritized:
- having a meal or drink at either Galley Beach or Sandbar at Jetties Beach
- a night out at The Chicken Box!
- trying a few more breakfast spots including Black Eyed Susan’s or Wicked Island Bakery
Getting to Nantucket
Flying
We chose to fly to Nantucket for this trip, but my parents have driven to Cape Cod may times too.
For this trip we were just visiting Nantucket and not the cape, so we wanted to maximize our time on the island.
The non-stop flight from Newark was only about 90 minutes—just prepare yourself for a smaller plane.
Ferry
You can also take a ferry from the mainland to get to Nantucket! Drive yourself to Cape Cod and then hop on one of the ferries.
They run from Hyannis, Harwich Port and New Bedford, and they run more consistently between Memorial Day and Labor Day.
Getting around Nantucket
Walking: Nantucket is very walkable, and that was how we got around for the most part. I’d just advise you to bring flats, as there are lots of cobblestone streets.
Wave shuttle: Download the app for the shuttles to check the schedules! I was actually pretty impressed by the (free!) shuttle system and if we had more time I could have seen using it more.
Uber and taxis: We took a taxi from the airport to our hotel and on the way back to the airport we called an Uber. They’re usually available within 10 minutes or so.
I hope you enjoyed browsing our itinerary for a long weekend on Nantucket island!
Any questions about our trip? Leave them in the comments.
yours,
Austen
