There is so much to enjoy on Nantucket, and October is one of the best times to do it – the frenzy of summer is over, everything is still open, days are warm and nights have a hint of fall. Here is a list of some of our favorite things to do, see, eat, and experience on island.


Good Grab & Go Coffee 
Island Coffee Roasters4 Broad Street

Sit & Sip Coffee on a Patio
Handlebar Cafe, 15 Washington Street

Hidden Starbucks
Nantucket Meat & Fish Market21 Old South Road
Because no chain stores are allowed on Nantucket – but here they brew Starbucks!
Also awesome prepared foods, steaks/burgers/marinated meats to grill at home – plus a bit of produce and good wine selection.



Claudette’s10 Main Street, Sconset
Tried-and-true breakfast sandos & iced coffee – take it to the picnic tables behind the Sconset Market or down to the beach. They also serve straightforward sandwiches for lunch.

The Downyflake18 Sparks Ave
The closest thing to a diner on Nantucket – come here for a good hearty breakfast after a long, fun night.

 The Counter on Main Street | 45 Main Street (inside Nantucket Pharmacy)
Nostalgic all-day lunch counter, serving quick breakfast, bagels, smoothies, soups & sandwiches.



Island Kitchen1 Chin’s Way
Excellent sit-down breakfast and brunch with lots of outdoor seating. We love the turkey hash & fresh-squeezed OJ mimosa; try to sit at the covered outdoor bar (off to the left) if it’s open!

Brant Point Grill50 Easton Street
Located at the White Elephant Hotel, this is a higher-end sit down brunch with spectacular views of Nantucket harbor. Reservations recommended; also open for breakfast/lunch/dinner.

or The Whale | 38 Main Street, Nantucket
Hands-down the best patio on Nantucket (which we affectionately refer to as The Blowhole); inventive twists on brunch standards – Sundays only, also open for lunch & dinner


Casual Lunch & Dinner

167 Raw Food Truck | 167 Hummock Pond Road
WORLD’S BEST LOBSTER ROLL! Everything else is good, too. Matt swears by this place. You can buy beer & wine inside the fish shop and post up in the garden for an awesome picnic. May also be the best fish market on island.

The Sandbar at Jetties Beach | 4 Bathing Beach Road
Very casual beachfront bar with straightforward food; one of the best places for oysters – they do buck-a-shuck every day from 3-5, and our wedding band plays there every Sunday from 3-6! Great for kids.

Slip 1414 Old South Wharf
Our friends Tim & Brennan just took over this casual go-to spot and it’s even better than it used to be! Best clam chowder on the island, and a lively all-day bar scene.

The Beet | 9 South Water Street
Healthy, flavorful quick-service or takeout lunch & dinner located in the heart of town.

Pizzeria Gemelle | 2 East Chestnut Street
Run by the fine folks at Ventuno (one of our favorite dinner spots, see below), this is a real-deal wood fired Italian pizza joint. Open all day (usually); you can order online in advance.

Something Natural  | 50 Cliff Road
Provisions | 3 Harbor Square (at Straight Wharf, behind the Gazebo)
Sandwich lovers rejoice, these are 2 places for one of the best you’ve ever had. Something Natural is a couple minute drive west of town and has great soups this time of year, too. Provisions is right downtown and also has the island’s best breakfast sandwich.


Fine Dining

Oran Mor Bistro2 South Beach Street
Our friend Edwin is the chef & proprietor, this is an absolute hidden gem (literally and figuratively!) Consistently the best food on island, without being the least bit pretentious. Amazing wine list and service. Reservations are a must.

Ventuno | 21 Federal Street
Excellent island-inspired Italian food with an outstanding wine list. Have an espresso martini at the lively Back Bar (outside, downstairs behind the restaurant) after dinner!

Le Languedoc | 24 Broad Street
Cozy French-inspired bistro with an awesome vibe. Order the lobster bisque, steak frites, and butter crunch sundae, and thank us later 😉

Drinks & Live Music

Gazebo4 Harbor Square
Post up at this covered outdoor bar, order a mudslide, and enjoy the people-watching!

Cisco Brewery 5 Bartlett Farm Road
One of the most popular destinations on the island, make sure you stop by this beer-garden-on-steroids to enjoy the famous beer & liquor from Cisco and Triple Eight Distillery. There are always various food trucks there, and live music every day. Kid and dog friendly, too.

Chicken Box5 Daves Street
A 5 star dive bar with the best live music on the island.



The Great Outdoors

Fishing Charters

Weather-dependent this time of year, reach out directly to the captain of each boat to make sure they are still accepting charters for Columbus Day weekend. If they are, this is a unique Nantucket experience (plus you get to keep anything you catch.)

Absolute Sport Fishing | Captain Brian Borgeson | 508-325-4000
Albacore Charters | Captain Bob DeCosta | 508-228-5074
Captain Tom’s Charters | Capts. Tom & Jason Mleczko | 508-228-4225

Boat Rental

Our friend Jim has a fleet of small boats you can rent and take out on the harbor! Also weather dependent this time of year – but a great way to see the island from a different perspective.

Island Boat Rental | Jim Mondani | 508-325-1001

Walking Trails

ACK Trails app | The Nantucket Conservation Foundation manages much of the ample open space on Nantucket – download this app to explore trails near where you’re staying. There are many wonderful walks on Nantucket!

Sconset Bluff Walk | One of our favorite easy scenic walks that sets out north from the village of Sconset. You can do just a small portion, or the full 2 miles out and back. Suitable for all ages and abilities. Absolutely incredible views! Click the link for a description and map of the trailhead – it can be a little tricky to find.

Around Nantucket

Nantucket Whaling Museum |  13 Broad Street
Nantucket was the whaling capital of the world in the 18th century, and inspired the likes of Moby Dick and In The Heart of the Sea. The Whaling Museum is a must-visit if you’re into history (or if it’s a rainy day and you have kids to entertain!) Tons of fascinating exhibits and local art, and the centerpiece is a 46-foot sperm whale skeleton that will astound you! Don’t miss checking out the roof deck which offers spectacular 360-degree views of the island.

Downtown Shopping | from Main Street to Broad Street, and Centre Street to Easy Street, plus Straight Wharf and Old South Wharf

Even thought it’s small, you could wander downtown Nantucket for hours checking out all the shops! Chain stores are not allowed on Nantucket (the giant Ralph Lauren store at the bottom of Main Street precipitated that change), so there are plenty of unique options to window shop or buy a souvenir. Columbus Day weekend is closing time for many shops, so there are often lots of sales and amazing deals to be found this weekend.

A few of our favorites to check out are: Murray’s Toggery Shop, Nantucket Looms, Nantucket Bookworks, Force 5 Watersports, Erin Hielle, Kidding Around, Sylvia Antiques & Four Winds Craft Guild, and Centre Pointe.

If you're not having fun on Nantucket, you're doing it wrong...!

Check back here very soon for a compendium of all our favorite things to do, see, eat, and drink on island! 

Until then, here are a few resources to get you going:

Nantucket Chamber of Commerce

Tripadvisor guide to Nantucket

21 Reasons to Visit Nantucket this Fall