My Ideal Nantucket Weekend Itinerary

Ohhhhh Nantucket, my favorite place in the US (truly!) I have been to this island I think 8 times in the past 5 years, and it never seizes to amaze me (and make me squeal upon landing!) There are a number of amazing guides out there (many of which say a lot of the same thing, but rightfully so), so I thought instead I would put together my ideal 4 day itinerary, down to which nights I think are good for what, etc. This has come from some trial and error, and also a lot of advice from some fun locals & summer folk alike (shoutout to my client Tami who is I text each season to find out what to be on the lookout for!)

Let me preface and say I am packing a lot in with this itinerary. This is the itinerary I would ideally follow if I was going to Nantucket one long weekend this whole summer. If I was in Nantucket for a longer period of time, I would definitely be spacing this schedule out. If you follow the below, you may be tired but you sure would have had a great time!

Late morning arrival

Grab a sandwich from Provisions or lobster roll from Straight Wharf Fish

At Provisions, I am partial to the Turkey Terrific (Thanksgiving in a sandwich, and it’s freaking good) or The Other Turkey, plus always a bag of Nantucket Crisps! And then right next door, Straight Wharf opened up a more casual spot that serves up amazing lobster rolls (+ onion rings!)

Mudslides at Gazebo (& it’s Gazebo’s last season!)

The Gazebo is closing after this season (RIP!), so you must get one of their famous mudslides one last time!

Shop around town

So many great spots! Some of my favorites include:

• Commonwealth - consignment store that has amazingly priced hidden gems

• Bon Ton - antique store

• For Now

• Mitchell’s Book Corner

• Milly & Grace

• Doen

• Ralph Lauren

5pm - Take the Wauwinet Lady to The Wauwinet

One of my favorite Nantucket hacks when you want to spend some time on a boat but don’t want to pay $$$ charter prices, is to book dinner at The Wauwinet and do the boat transfer add-on. The Wauwinet Lady is a 20 passenger boat that goes from the White Elephant to The Wauwinet (a 50-minute journey with beverage service!), and the round-trip boat service is only $35 per person. You must book this in conjunction with either a lunch or dinner reservation at The Wauwinet’s restaurant, Topper’s, but the food and experience are great so it’s worth it.

6pm - Dinner at Topper’s at The Wauwinet

Topper’s is the restaurant at The Wauwinet, and it is the only AAA 5-Diamond restaurant on island. They have a prix fixe menu, a wonderful ambience, and you can hang out in the chairs on the lawn afterwards to watch the sunset.

9pm return to town & optional nightcap

Once you get dropped off via boat back in town, the world is your oyster! I personally love Proprietors for a good cocktail or The Club Car for their live piano nights (that encourage singing along) set in a 19th-century train car. I absolutely love The Club Car but do recommend avoiding Fridays or Saturdays if you want to avoid crowds/lines!

Coffee at Handlebar & morning walk around town

My go-to spot on island to grab a fun latte to take with me on my morning walk.

Lunch at The Chanticleer in Sconset

Next head to Sconset and start with brunch at The Chanticleer, which is one of the most romantic & charming restaurants on island (in arguably the most charming corner of Nantucket!)

Sconset Bluff Walk

The Sconset Bluff Walk is one of New England’s most beautiful coastal walks. You pass a number of grey-shingled cottages while also walking along the cliffs bordering the ocean. You feel like you are stepping back in time which I love!

Pre-dinner drinks at Ethos Wine Bar

Ethos Wine Bar just opened last year, and it has quickly become one of our faves! The decor & intimate setting make it feel like your local neighborhood spot, while the elevated wine list & food (please try the grilled cheese) make it feel like you discovered a hidden special gem. Walk-ins only!

Dinner at The Nautilus

One of my favorite reservations on island… and one of the hardest! They have inventive Asian-inspired cuisine (you must get the blue crab fried rice!), great cocktails and always a buzzy atmosphere. If you have a large group, reach out to them to book the Captains Table — we did this on a bachelorette and it was perfect.

Ventuno Back Bar

If you still have steam left, head to Ventuno’s back bar for a lively outdoor drinking scene. Their indoor bar is fun as well!

Breakfast sandwiches from Born & Bread

The best breakfast sandwich in Nantucket IMO (I don’t know how I have never taken a photo). They are closed on Sundays and Mondays so make sure you go one of the earlier days. I like the BB Egg Sandy and any of their baked goods. Worth the line!

Bike ride to Millie’s for lunch

Biking is one of the essential forms of transportation in Nantucket, and the well-defined bike paths make the ride from town to Madaket (around 6 miles) one of the best! Reward yourself with queso, tacos & margs at Millie’s upon arrival.

Beach day at Madaket Beach

After lunch, spend some time laying on the beach & swimming at the beach right outside of Millie’s!

Dinner at Cru

A scene-y Nantucket classic, a dinner reservation at Cru on a Saturday around 8pm is a coveted one. The see-and-be-seen lively atmosphere is part of it all, but also the cocktails, lobster rolls, seafood towers, harbor views & more are equally enticing.

Cru Back Bar

There is a long line outside of Cru to get into the back bar on any given night, so you would be silly to not head right back in there after dinner and enjoy a fun night singing along to classics & drinking more Crucombers.

Cisco Brewers for lunch & live music

No trip to Nantucket is complete without an afternoon at Cisco! I personally prefer to not go on Saturday when the line can get long and it can get way too packed. The beer is great but the cocktails also have a following. They have food trucks/stands ranging from Millie’s to oysters to lobster rolls & more. Live music, outdoor picnic tables, always a good time!

Sunset drinks on the beach

Close out the best weekend in Nantucket while drinking with your toes in the sand at either Sandbar (casual) or Galley Beach (fancier)!

Dinner at Bar Yoshi

Old South Wharf is so charming, and Bar Yoshi has an intimate setting with water views and delicious sushi & noodle dishes. Also their bar across the way, Bar O, serves the same menu but in a more quaint bar setting that places FUN music. Love this as an option if you have had a day and would like to keep the fun going!

Ice Cream at Juice Bar

It’s a must!

Cheers,

Chelsea