Nantucket Travel Guide: The Best Itinerary for a Weekend Trip on the Island

Our first trip post-quarantine was a weekend trip to Nantucket. We went without the kids and during this time where masks and social distancing are required. I received a lot of questions after posting photos from the trip on my Instagram, so I decided to share what it’s like on the island, as well as my recommendations for anyone interested in going for two to three nights and isn’t taking or renting a car. There are lots of fun things to do on Nantucket but I’m only listing my top picks for when your time on the island is limited. I know a bunch of people who are heading there in August and September – hope this helps!

Nantucket: Getting There

There is a Steamship Authority ferry that holds vehicles but it takes 2 hours from Hyannis, so I’d only take that one if you are staying for a full week or longer and really want to hit up a bunch of different beaches around the coastline of the island. Also, it’s tough to get a reservation on that boat.

We parked our car in a lot across from the ferry terminal/dock (it was $30 per day) and took the Hy-Line passenger-only fast ferry, which takes one hour. The Steamship Authority also offers a fast ferry; they are similar but offer different departure times throughout the day so you can select a time that works for you. If you’re driving up from south of Massachusetts (say, from CT or RI), you may want to look into Seastreak, which takes 1 hour and 40 mins from New Bedford, MA. Seastreak also leaves out of the NJ/NY area.

Just be warned that Fridays to ACK and Sundays back to Hyannis are packed and the traffic is usually insane. We did a Thursday morning (no traffic heading down to The Cape) until Saturday afternoon and the ferry heading back to Hyannis at 2:15pm was practically empty!  

In regards to social distancing, folks waiting to get on the ferry were spaced 6-ft apart and eating or drinking inside of the cabin was not allowed. Unfortunately, once we were docked, all passengers were standing in line very close together waiting to get off. If you are not in a rush, I suppose you could wait until everyone is off and then get up and walk off.

Nantucket: Where to Stay

Because we’re just getting out of quarantine and hotels and inns are open again, you may luck out and find some last-minute availability at an okay price. Normally during the summer, places would require a two- to three-night minimum and this is the first summer (ever!) where I saw almost all of the hotels offering one night, if desired!

If traveling without children and without a car, I’d look into the following:

21 Broad

The Roberts Collection

Hotel Pippa

White Elephant (will likely be the most expensive option out of these recos)

Jared Coffin House (this is where we stayed this time; it’s a historic home dating back to 1845; nothing fancy but our room and bathroom were both spacious, the location is perfect and continental breakfast and bicycles were included)

If you’d like to stay somewhere other than an inn, a nice spot for couples traveling with or without kids (and also without a car), is The Nantucket Hotel & Resort. This resort is also within walking distance to downtown and some of the spots I’m going to recommend below. I have yet to stay there but I’ve heard of so many positive experiences. They are one of the few places that has a pool on the property and offers shuttles to the ferries and beaches (in case you’re with little kids who can’t walk too far).

About Nantucket Dining During Covid & Required Social Distancing:

One of the reasons I love Nantucket is for the abundance of places offering great food. The biggest disappointment is going to a new vacation destination and having to settle on eating mediocre food the entire time.

Most of the Nantucket restaurants have either set up an expanded outdoor dining area and/or seating folks at tables spaced apart inside. Some spots are only taking reservations the week-of (or not at all) and some don’t have online booking. Again, assuming you’re not going to ACK for a full week, I’ve listed a small number of dining spots that would be my top picks. Take a look at their websites prior to visiting to see how/if they are accepting reservations and make them for as many places as you can.

Day 1 Itinerary (let’s assume it’s a Friday):

ARRIVE: Take a morning ferry that gets you on the island by 11am and walk to the hotel/inn and ask them to hold your bags if the room isn’t ready yet.

LUNCH: Order lunch from Gaslight’s restaurant window and eat outside (pray for good weather!).

SHOP: Settle into your room and then walk around downtown and pop into some stores. Since there are so many amazing boutiques, it’s a good idea to divide your shopping trip into two parts (especially if your significant other is trailing you! Ha!). See the must-visit shops below.

COFFEE BREAK: Board & Bread downtown (opened last spring; serves nugget ice cubes and jumbo straws with its iced drinks). Lemon Press is another spot people like for an acai bowl or a drink.

Nantucket Home Downtown

PHOTO OPP TIP:  From Board & Bread, walk up Centre Street, to the left side of the Jared Coffin House, and you’ll see the amazing home (where I’m posing, below) that has hydrangeas completely filling up the yard around the brick driveaway and on either side of the front entrance.

Freshen up back at the hotel.

DINNER: Eat an early dinner outside at one of the following spots:

  • The Proprietors
  • Galley Beach (during Covid they are offering a prix-fixed only, which includes one app and one entrée for $79 per person. If you can swing it, the atmosphere on a warm, clear night is very special. Book your reservation for an hour before sunset.)
  • Brant Point Grill (the restaurant at the White Elephant hotel where you can eat on their open-air deck or on the lawn overlooking the harbor)
  • Dune
  • Millie’s (a fun rustic dining spot out in Madaket that everyone loves; you’ll have to bike or Uber there though)

I used to love American Seasons, which is in a little house on Centre St. (has a tiny outdoor patio), but I haven’t been there since a new owner took over. May be worth trying since the menu still looks amazing. I’ve also heard good things about Italian restaurant, Vertuno, which is only serving dinner outside (no indoor option at all). If you are staying for longer than a weekend, I’d add The Chanticleer in ‘Sconset to your list and sit outside in the gardens. Must catch a ride there and back.

Galley Beach Nantucket Sunset Photo
Galley Beach Nantucket Sunset

SUNSET:  If you aren’t already seated at Galley Beach, take the 14 minute walk up North Beach Street to that spot. It’s a quiet walk and there are plenty of cedar shingle beach houses to ogle.  There’s a public pathway to the beach, right next to the restaurant. Catch the beautiful sunset and then take a stroll on the sand to the left until you hit the public staircase that goes up to the Cliffs neighborhood. This is an exclusive area of the island and home to many gorgeous family compounds.

Staircase down to Steps Beach

PHOTO OPP TIP: There’s a stunning driveway lined with hydrangeas on both sides. If you’re willing to be a little bold and stand at the end of the driveaway, you’ll capture a very pretty pic like this one that I posted on my Instagram feed.  Without giving the exact address away since it’s private property, head to the street entrance to Steps Beach and you’ll find it around there.

DESSERT: An ice cream come from The Juice Bar. The long line will annoy you (it’s especially long once the sun has set and because of the 6-feet apart rule) but where else are you going to go late night on the island during Covid?

Must-Visit Shops (all hyperlinks go to their IG accounts):

There are lots of other shops that I haven’t even mentioned that you may love! There are plenty of adorable t-shirt/souvenir-type shops all around and some are worth popping into as well.

Day 2 Itinerary:

BREAKFAST: (if you want something other than what your inn may be providing): Black-Eyed Susan’s, which has an outdoor dining area and opens at 7am. Since there likely will be a line, I’d get there as early as you possibly can.

ACTIVITY: Ride bikes up to ‘Sconset, following the bike path from town. ‘Sconset, short for Siasconset, is a fishing village on the east end of the island. It’s home to the cutest little cottages (many with amazing flowers growing up the sides and over the roofs), a post office, grocery store and some spots to grab lunch or dinner.

There’s also a lovely luxury hotel, The Summer House, if you’re looking to get away from the action of downtown.  I’ve stayed in one of their cottages before – they are tiny but it’s a unique experience and they have a picturesque pool, right by the ocean.

Biking to ‘Sconset will take you 40-45 minutes each way and please note that the ‘Sconset bike bath doesn’t start until you’re a little bit outside of the downtown area. As you head that way, there are streets without sidewalks and ones where you have to walk your bike instead of ride it (for safety reasons). Anytime we weren’t on the bike path, we hopped off and walked the bikes. I would not attempt this ride with little kids in tow. Since ‘Sconset is not to be missed, just take a 20-minute Uber there if you can’t bike it!

Impressive Row of Hydrangeas

PHOTO OPP TIP: If you walk your bikes up Orange Street from downtown Main Street at the onset of your excursion, the long row of hydrangeas lining a white picket fence can be found at the corner of Plumb Street.

LUNCH: Grab some sandwiches from Claudette’s Sandwich Shop in ‘Sconset (a local told us that he always orders either the turkey salad or meatloaf sandwiches; they do not disappoint!) and eat them over on ‘Sconset Beach, just down the little hill to the right of Claudette’s.  

PHOTO OPP TIPS:  Walk up the stairs of the white bridge that leads to the Bluff Walk. It’s a narrow stone walkway with cottages on both sides. Stand on the bridge looking down or in the middle of the walkway and you’ll get a very cute pic.

‘Sconset Cottage

Also, if you head down the street on the right side of Claudette’s, you’ll come across a little patch of grass and benches. All around there are the cottages with amazing gardens. You’ll find the homes with little rambling raspberry roses  around there (look for Mitchell Street, especially, which is where I posed with my bike) but note that some of the climbing ones wilt by mid-July. There are some other homes with roses lining their fences and those should be in bloom all summer.

COFFEE BREAK: Stop at Handlebar, which you can hit up once you’re back from ‘Sconset on the way back to your hotel (it’s also next to The Lovely boutique – might as well pop in there too!).

Quick nap back at the hotel.

DINNER: Try one of the restaurants I listed above.

Day 3 Itinerary:

BREAKFAST: Grab some pastries at your hotel or at one of the coffee shops.  

SHOP: Take an hour or two and visit all of the remaining stores that I mentioned!

LUNCH: Something Natural, which is walking distance from downtown and has outdoor picnic tables if you want to eat there. Something Natural is on my list because I’ve seen tons of positive online reviews and my friend and island-lover, Alyssa (The A-List blog), can vouch for the deliciousness of their extra-large sandwiches.  

If not, Provisions has a great Turkey Terrific sandwich.

ACTIVITY: If you aren’t catching an afternoon ferry departure and are leaving late that evening, ask your hotel to hold your bags and take an Uber out to Cisco Brewery for some drinks (you can get lunch there too) and/or hit up a beach in the late afternoon. There are so many great beaches along the coastline of Nantucket. From downtown, you can walk to Children’s or Jetties Beach (good options if you’re short on time) but those two aren’t usually the fan favorites compared to other ones like Cisco, Surfside, Madaket, Tom Never, etc. If you have a good amount of time to spare, I say head to Cisco Beach after the brewery (don’t try to walk it though) or look at the surf report and pick one where you can watch the surfers.  Some of them are a trek though!

I could make this travel guide much more extensive since I know there is so much more to see and do on the island BUT I’m hoping this is a good start for anyone who hasn’t been in awhile (or ever!).  Have fun and pack a bunch of cute masks!

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A brand marketing/PR exec and new mom based in Boston; sharing my thoughts on fave destinations, gift ideas, décor, style, beauty and more. Read More

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