First Timer’s Guide to Nantucket (With a Toddler!)

THE DL: I had always wanted to go to Nantucket and knew once we moved to NYC it was a must! Over the years after reading books, seeing social media and pinterest posts of the quaint island I wasnt sure it would live up to the hype but it did. We also always knew we wanted to bring kids when we did this trip which after going reaffirmed this is a great family or girls trip or bring your parents on a trip! It is pricey but was totally worth it.

Things to Know

• The flight from NYC is ONLY 45 minutes, so quick and easy!
• We went late June which was “offseason” and it was actually perfect
• Nantucket is more kid friendly than you think
• The bus is free for the year and run pretty much all over the island
• Rental cars are pretty pricey and really only needed if you are staying out of the downtown
• ACK is tiny, like one conveyer belt, like one room for gates. You will get off on the tarmac FYI
• The flower boxes and just overall look and feel is out of a story book!
• The downtown is a lot of cobble stones so can be a little tricky with a stroller if you go off the sidewalks

How to get around

• We got a Driver to pick us up from the airport we used Island Experience and they were super great

• We did a Rental Car the last couple days of our trip and used Nantucket Rentals, also great

• Most of the cars are like broncos or jeeps, we did a sahara jeep with 3 adults and a toddler and plenty of space and it fit all our luggage.

Public Transportation:

• Wave Bus is Free for 2026 and runs pretty frequently, we honestly just had a lot of stuff traveling with a toddler so did a driver to get to our Air BnB and then rental car last part of the trip.

Where to stay

Ok when looking originally I thought stay out by one of the beaches, after talking to a lot of people they said stay close to downtown and this was the best advice. We were in walking distance of the downtown and the some of the beaches and walked back and forth multiple times a day with no issues. Unless you are planning to just do beach all day every day I think this is the best base spot or else you will be doing a lot of driving because restaurants are limited outside of the downtown.

Hotels people like: Nantucket Hotel, White Elephant, Faraway hotel but you have to book all these SO far in advance so heads up

Where to eat

So many good options, so little time! Even being in Nantucket for a week there were so many other spots we didn’t get to try (Brotherhood of thieves, Sea Grille, the Pearl, Or the Whale etc. to name a few). My top 5 we did try and would go back:

• Cru – indoor seating was better to me than outdoor (lobster roll and oysters were both top 2 for me, also martinis were fab)
• Galley Beach – the views are what make this spot so good, food was good but a little overpriced
• Sandbar at Jetties – again views here over the quality of food, chill beach bar vibes
• Bar Yoshi – cocktails to food all so good and fun outdoor seating vibes
• Proprieters – The food was so unique and fresh here, also a cute townhome setting

Where to drink

Coffee/Matcha

• Lemon Press
• Handle Bar
• Surfside 45 (smoothie)
• Roastd

• Cocktails
  • Galley Beach
  • Gazebo
  • Sister Ship
  • Cisco
  • Cru back bar
  • Jetties

Copy my Itinerary for the Week!

For context, we had my mother in law with us so we were able to enjoy a few toddler free moments which you will see in this schedule. However, Nantucket is SUPER kid friendly and you can do most of this with a kid, we did!

Day 1

• AFTERNOON
  • Land at ACK – TINY tiny airport, like 1 baggage lane and like 1 gate
  • Driver picked us up and then check into Air BNB (stay downtown)
• EVENING
  • 5 PM – Walk to dinner in town for some sushi
    • Nicer Vibe – Lola 41 or more chill do Bar Yoshi
  • Grocery Shop on the way back for the week
    • Shop + Stop, Picked up Wine at one of the stores nearby
  • Evening of mahj + firepit at the house

Day 2

• MORNING
  • Coffee and breakfast – lemon press (go early it gets packed) or black eyed susans for breakfast
  • Shop around the downtown 9:30-11:30 
  • Lunch – Galley beach bar reservation (you can bring little ones in the day, its a tasting menu at night. You can still bring them but will have to pay for a full tasting menu per spot at the table).
• AFTERNOON
  • Steps Beach (literally next door to lunch), but make sure to get a picture from the top of the steps
  • Mud slides at the gazebo or ice cream from the juice bar on the walk or ride back
• EVENING
  • Dinner resy at CRU (book as soon as they open 4-6 weeks out)
  • Finish with Drinks at the back bar
  • Evening Out Options
    • Gazebo (25+) and its a tiki hut with mudslides (closing at end of 2026)
    • Club Car, Gaslight (music) or Sister Ship for cocktails
    • Chicken Box (for younger casual crowd, late late pool bar vibes)

Day 3

• MORNING
  • Coffee – Handle bar
    • Get nitro cold brew here on tap
    • (low key yummy pastries + GF options)
  • Check the town schedule before going, there was a fun kids music class going on and nantucket film festival
  • Lunch – Something natural for sandwiches, its a cute house on some property a little bit out of downtown or you can go to provisions in town with same menu.
    • Get the Turkey sandwhich the ones with stuffing and cranberry
• AFTERNOON
  • Rent Bikes!
    • So many options so find whats best for your group. Also so many bike paths all over town.
    • Most you have to pay for at least a half day, we didnt find any hourly options.
      • Youngs + Easy Riders were both reccomended to us
• EVENING
  • Dinner at Proprietors
    • Low key one of the more unique dinners we had, cute old home and everything was so fresh!
    • Get the shrimp stuffed mushrooms, that was my fave

Day 4

• MORNING
  • Coffee and breakfast sandwiches – born and bread bakery (blackberry matcha) 
  • Go when the open or else prepare for a long line on weekends 
  • 11: 00 AM – Book signing with Elin Hildebrand (check dates before you go)
    • We lined up an hour early and were 50 out of the 100 tickets they give out
  • Lunch – straight wharf fish (or to go counter here) or Sayles seafood
• AFTERNOON
  • Beach (explore or go to one close by – ladies, steps, jetties etc)
• EVENING
  • Dinner at Nautilus
    • We walked in and got a bar seat
    • Service was slow but food was yummy
  • Post dinner drinks

DAY 5

• MORNING People recommended Island Kitchen but we ended up picking up some pastries around time
  • 10:30 – Whaling Museum 
    • Actually kid friendly, go to the discovery room and rooftop
• AFTERNOON
  • Lunch at Millie’s Madatuket and sit upstairs for views
  • Hang at the Beach
• Pick up snacks before hand or pizza and head to a beach like steps with a good sunset on the way home for causal vibes
• Dinner at Galley Beach (if you are kidless!) or one of the spots listed above you didnt get to try

DAY 6

• Chill Day – We used this to just wander, drive around the island, beach etc.
• Lunch – Bartlett farms for key lime pie and other essentials and head to Cisco/Ladies Beach
• Afternoon Hang – Cisco Brewery
• Dinner at the food trucks on site or Raw 167

DAY 7

• MORNING
  • Breakfast 45 surfside for burritos and Nantucket bake shop 
• Spend the Day at Sconset
• Bluff Walk
• Sconset Playground
• Lunch – Claudettes take to the beach (anything with their horseradish sauce)
  • Stop at Sconset Market for cookies or muffins
• AFTERNOON
  • Fly out of ACK (dont get there more than an hour early, its so tiny!)