Nantucket | Planning the Perfect Day Trip

We just returned from a wonderful week on Nantucket.  We went later in June than we normally do and surprisingly ended up with rather chilly and gray weather for the bulk of our trip.  It was perfect for long walks and bike rides, eating chowder for lunch, wearing sweaters over sundresses, snuggling under blankets while eating outside at our cottage and for lighting lots of candles in the evening.  We did have a few gorgeous cloudless, blue sky days which we happily spent on the beach.  It was a welcome reprieve from the crazy hot and humid summer we are having in Cincinnati.  I have shared lots of my Nantucket favorites in past posts (here, here,  here, here and here) so I thought this time I would do a little something different....

So many of the island visitors are day trippers.  Nantucket is the perfect place for a day trip but I think it helps to have a bit of a plan when you arrive.  Jimmy and I first visited Nantucket in the fall when Andrew was a baby.  I remember coming off the ferry and walking up and down Main Street while Andrew slept in his stroller and not really knowing what else to do with ourselves. We were young and it was a time before smart phones, blogs, google and the instagram frenzy that seems to surround the island nowadays.

Even though Nantucket is small, trying to figure out the best way to experience the island and maximize a day there can be a little daunting, especially if it's your first visit.  So... if I only had a day to spend on Nantucket, here is how I would spend it.  For each of these scenarios, I would arrive as early as you can and leave at sunset or later.  Only choose the high speed ferry for a day trip! Book in advance.  Both Hy-Line and The Steamship Authority offer high speed ferries.


Day Trip #1: Sailing + Shopping
When you arrive make a bee-line away from all the shops around the wharf.  Everyone goes in there first. Best save those for later in the day if something catches you eye.  Grab breakfast and coffee from the Hub on Main Street.  Their croissants are incredible (I recommend the ham and cheese) and I love their iced coffee!  Walk down Main Street, Centre, Federal, N. Union, India and Broad. Some hidden gems: Saturday mornings is the Farmer's & Artisan Market (Cambridge and N. Union), The Hospital Thrift Shop (India), Bookworks (Broad St. their children's section is dreamy), Flowers on Chestnut, Nantucket Looms (Main Street), and Antique Depot (S Beach St.).

After shopping for the morning, go and grab a picnic lunch from Provisions (The Turkey Terrific is my favorite. My brother's is the Curry Chicken Salad.  The Straight Wharf Fish Shop also has awesome sandwiches and lobster rolls if you want something different).  Take your picnic with you down the wharf and meet up with your Captain for a sailing trip on the Endeavor!  It's a 2 hour ride around part of the island.  You'll get the most gorgeous photos and it's just so much fun. You get a chance to escape the crowds and make a special memory.  You'll need to make reservations in advance for the 1:00 sail. 

After sailing, walk down S. Water Street (good spot to grab souvenir t-shirts if you want them) toward Broad.  The Sunken Ship is great store for hats and souvenirs too.  Get ice cream from the Juice Bar (an island visit MUST) and don't skip the waffle cone!  Walk with your ice cream to see Brant Point Lighthouse and then head back into town for dinner. There are tons of amazing dinner spots.  Straight Wharf, Boarding House, Ventuno, Greydon House, Cru, Galley Beach, Ship's Inn are just a few.  If you are feeling a little windswept and tired and want to be super casual, I'd suggest Brotherhood of Thieves.

Then catch a sunset ferry back to the mainland!

Day Trip #2: Beaches + Lighthouses

Walk to Affordable Rentals (short walk!) to pick up your jeep.  Get all the details from them on how to get to Great Point.  They are super friendly and they have the best priced rentals for a single day.  On the way out of town stop at Wicked Island Bakery to stock up on treats for a brunch picnic on the beach.  This is the island's best bakery. No contest.  Then head toward Great Point.  Crank up the music and enjoy your amazing drive on the beach!  Stop and enjoy a brunch picnic and walk towards the light house.  Even if you don't make it all the way, it's still breathtaking.  Say hi to the seals and then make your way back.  You can easily spend a few or more hours doing this.

For lunch head to the Summer House Bistro in Sconset.  Then keep your car parked and walk through town toward the Buff Walk.  It's well hidden, so ask directions if you need it. Walk the whole way to Sankaty Head Lighthouse.

Hop in your Jeep and head back into town for a late afternoon pick me up at the Juice Bar and walk to Brant Point Lighthouse.  To end your day, drive out to  Madaket to see the sunset (you'll need to take the 10pm ferry back if you do this!)  Grab dinner from the Millie's Take Out window (this is the restaurant you'll see right by the beach) before heading down to the beach.  This is an annual tradition for us!

 Hopefully those are some helpful ideas!  You can also rent bikes and explore the island that way which is what we did on a day trip several years ago and it was amazing!  You can't really go wrong with anything, just remember to reserve things in advance because it is very busy in the summer months!

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