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4 Day Itinerary: What to Do in Nantucket

Last Modified: November 23, 2022

4 Day Nantucket Itinerary

Nantucket has become one of our favorite U.S. destinations and somewhere we plan on going back to during the summer months. Only 14 miles long, Nantucket is a charming place with beautiful grey shingled homes and pristine sandy beaches.

The island is looked after by the Nantucket Historical Association, which has done an impeccable job restoring the original homes and keeping its maritime history intact. What makes Nantucket unique from other places is that every building on the island has the same exterior style, just like they were back in the 1700s.

Most people visit during the summer months to relax on the beach, eat some fresh seafood, and enjoy the upscale atmosphere of the island. This post covers what to do in Nantucket in 4 days, but you can easily visit for just the weekend or stay even longer. No matter how much time you have, it is well worth the trip!

Day 1: Explore the Town

Since we lived too far to drive, we opted to fly to Nantucket. We flew into JFK in New York and took a connecting flight into ACK (Nantucket’s airport). We landed on the island around 2 o’clock that afternoon and took a cab from the small airport to our hotel. The airport also has a shuttle that takes you straight downtown for only $3 per person, but being our first time there, we did not know exactly how far our hotel was from the Greenhound station.

Check Into the Martin House Inn

We booked our stay at the Martin House Inn, a beautiful 1800s mansion that is now a B&B. The Inn is just a few blocks from the center of town and half a mile from the beach. The owner was extremely welcoming. She took the time to give us a tour of the property and even gave us recommendations on things to do and places to eat. Martin House also offers afternoon snacks, complimentary breakfast, and beach towels and equipment for guests to use.

After we freshened up, we made our way up to the Inn’s rooftop. There is a small ladder on the third floor that takes you up to the roof. Once on top, you have 360-degree views of the downtown area. From there, we spent the rest of our afternoon exploring the town.

Lunch at Something Natural

We first stopped at Something Natural for some sandwiches. Of all the sandwich shops we tried, this was our favorite. We liked it so much we went back a second time during our stay. Not only are the sandwiches here made of fresh ingredients, but the portions are much larger than other places we tried. Their prices are also a lot more reasonable here. We tried their turkey sandwich and veggie sandwich with avocado, which both were terrific. Something Natural has a large outdoor area with shaded picnic tables to eat.

Explore the Town

The town is located right on the harbor and is where most people like to stay during their trip to Nantucket since it has everything you could possibly need. The streets are full of wonderful shops and great places to eat. We spent a while walking around the cobblestone streets before heading to dinner.

Dinner at Millie’s

For dinner, we ventured out to Millie’s in the Madaket area. Millie’s was one restaurant that we kept hearing people talk about, so we decided it was the perfect place to go for our first night. It is a Mexican seafood restaurant that is right near the beach. The easiest way to get there is by taking the Wave Shuttle that stops right in front of the restaurant.

We only had to wait about 10 minutes for a table for two and got seated upstairs in the dining room where they had live music playing. There are also two indoor bars and outdoor seating areas. We both ordered their most popular drink, the Madaket Mystery, and some tacos. Their Hitcher Creek fish tacos and Smith Point shrimp tacos were both delicious and came on corn tortillas with a side of rice. Compared to many other restaurants on Nantucket, the price for food at Millie’s is a lot more affordable and just as delicious.

TRAVEL TIP: Taxis and Ubers won’t come out to Madaket later at night. If you don’t have your own car, you will have to take the Wave back to town.

After dinner, we took the Wave back to town and spent the rest of the night walking around the cobblestone streets and admiring the harbor with its million-dollar yachts. The entire downtown was lit and full of people dining outdoors and hanging out along the water.

Day 2: Bike to 'Sconset

Rent a Bike

For our first full day in Nantucket, we decided to rent a bike and wander out to ‘Sconset. This part of the island is known for its quiet beach and quaint village. We started the day out with breakfast in the garden at Martin House and then walked to Young’s Bike Shop in town for our rentals. Young’s has a variety of bikes, cars, and Jeeps to rent. We rented our bikes just for the day, but they also have 1 and 2-hour rentals, 24-hour rentals, and 3-day rentals. What we like about this place is that it has an after-hour bike return. We didn’t feel rushed about getting back at 5 pm before they closed.

Biking around the downtown area takes a little bit of getting used to since the paths are mostly on the roads. Once you get out of the main town, you can get up on the sidewalk. We took the 8.5-mile Milestone Path to ‘Sconset. There is also the more scenic Polpis Bike Path which is a couple of miles long. The path was not too difficult to bike, but we were pretty tired when we reached the town. Thankfully, the Wave has bike racks, and we were able to ride it back to town after our afternoon exploring ‘Sconset.

Visit ‘Sconset

‘Sconset ‘is known for its charming homes and quiet beach. Unlike Jetties and the other beaches near the harbor, ‘Sconset Beach is not for swimming. Since it is on the ocean, it has large waves and an undercurrent, making it hard to swim. However, there is a lifeguard on duty there throughout the day.

‘Sconset beach was one of our favorite beaches in Nantucket. It is much quieter than the ones closer to town, and you can glimpse a lot more marine life. We were able to see seals swimming close to the shore. The beach also had a wonderful breeze, making it perfect for laying out in 80-degree weather.

‘Sconset Bluff Walk

One of the main reasons we came to ‘Sconset was the Bluff Walk. This is a trail that runs about two miles from the center of ‘Sconset to the Sankaty Lighthouse. The Bluff Walk is directly behind some of the larger beach homes with ocean views on the other side.

The entrance to the Bluff Walk is a little hard to find since it is located behind a house. The easiest way to find it is to look for 21 Front Street right off of Broadway. You will walk the gravel path until you reach a marker that says “Public Way”. Walk straight past the marker to where the path officially starts.

We were amazed at just how close the trail takes you to people’s backyards. There were so many beautiful gardens to admire as we walked by. The path is up high on the cliff, so you also get spectacular views of the ocean to your right. After about a mile and a half, the path will bring you out to Broadway. From there, it is another half mile to the Sankaty Lighthouse.

Lunch at Claudette’s

After exploring other parts of ‘Sconset, we stopped by Claudette’s for lunch. Claudette’s is one of the few places to eat in the area, with terrific sandwiches. Their turkey sandwich with “the works” is their number one seller, so we both got one to try. They were pretty busy, but we were able to get a seat outside on the patio.

Afternoon at the Beach

We took the Wave back to our hotel and got ready for the beach. There are several beaches within walking distance of the town. Child’s Beach is a small beach near the White Elephant Hotel. It is right on the harbor, making it the perfect place for little children. The other beaches are Jetties, Galley, and Steps which are all next to each other.

Of all the Nantucket beaches, Steps Beach was our favorite and where we spent most of our time. It is located right next to the private Galley Beach and is less crowded than Jetties. Steps Beach is accessible from Galley or the entrance off of Cliff Road. If you come this way, you will get the best views of the water from the top of the stairs leading to the beach.

What we liked best about Steps Beach is the views of the million-dollar mansions along the cliff and yachts coming in and out of the harbor. We also liked the fact that it was quieter than the other beaches. The weather our entire stay was in the mid to high 70s with some cloud cover, which was perfect for laying out on the sand.

Dinner at the Chanticleer

For dinner, we made our way back to ‘Sconset. There is a highly rated French restaurant there called the Chanticleer that we were both eager to try. It is a high-end restaurant that is hard to get into without reservations, so make sure to call a couple of weeks ahead for a table. Our favorite part was the English garden full of beautiful flowers and seating areas. We got a table under the pergolas that were lit with string lights.

Our overall experience was amazing here. We ordered a bottle of white wine to enjoy before and during dinner. Both our salmon and chicken entrees were delicious and worth the splurge. The staff was attentive and the quality of the food was impeccable. If you are looking for a romantic dinner, this is the perfect place!

Day 3: Cisco Brewery and Lunch on the Harbor

Our third day in Nantucket was pretty overcast, so we decided to spend it exploring the town some more. There were so many wonderful boutiques and antique stores to visit. We found one that we loved off of Main Street that had lots of local artwork. We purchased this beautiful whale carving for our study, as well as some other souvenirs and clothing.

Lunch at Cru

We had decided to visit Cisco Brewery that afternoon but did not want to go there too early so we grabbed lunch at Cru first. Most of the time you need reservations to get in for dinner, but we put our name on the list and only waited 10 minutes to get seated for lunch. We were able to grab seats outside on the harbor. We were excited to try their lobster rolls here, which you can get both warm with butter and cold. The best part of our lunch was watching boats come in and out of the harbor while we ate. Cru has one of the best locations on the island.

Hang Out at Cisco Brewery

After lunch, we took the Cisco van to the brewery. Cisco has its own shuttle service that runs to and from town from Thursdays to Sundays. If you want to visit Cisco other days of the week, you will have to take a taxi or the Wave Miacomet Route. This route takes you about half a mile out from the brewery. They usually charge a $10 cover, but for whatever reason entry was free today!

If you don’t like beer, they also have a distillery with lots of mixed drinks and even wine to choose from. The best part is all the food trucks there. You can get raw oysters, pizza, and items from Millie’s and The Lobster Trap. If you have time, you can also take a tour of the brewery. The best part was the live music there to enjoy. Unfortunately, they are only open until 7 pm, but we hung out for a couple of hours before they closed.

Day 4: Whaling Museum and Historical Sites

Climb the Church Tower

We spent our last day exploring some of the more historical sites. We started at the First Congregational Church, only a couple of blocks from our hotel. The church played a large part in the island’s community and has been around since the early 1800s. We had learned that the tower is open to visitors when we first got into town, but since it is only open a couple of days a week, we were excited to finally climb up.

The entrance to the tower is located in the front of the church. It is only a $5 cash donation to climb, and the volunteers there allowed us to walk around the church itself. There is also a volunteer at the top that is there to answer any questions you may have. We were even lucky enough to get a chance to hear the organist play as they were preparing for a special event.

The climb up takes you through the many levels of stairs to a small room at the steeple. From there, you can see views of the entire island. Along the way, you will be able to see some historical artifacts from the church’s history. The tower windows face in all four directions, and you are able to see all parts of the island. It was absolutely stunning from above!

Breakfast at Black-Eyed Susan’s

Instead of eating breakfast at Martin House, we ended up going to Black-Eyed Susan’s. Everyone had told us this was a great brunch spot. The wait was a lot shorter than we had thought, but we did have to grab some cash as they do not take credit cards. The service was quick and the food was delicious.

Tour the Whaling Museum

From there, we headed to the Whaling Museum on Broad Street. Tickets for the museum are $23, and you can download a free audio guide on your phone that takes you through the exhibits. We were impressed at how big the museum was and were glad we took the time to stop by.

The exhibits talk a lot about Nantucket’s connection with the whaling industry, but they also have a lot of information about the island’s history and influential people. We were also able to see some artifacts from the early settlers. To finish our tour, we climbed the flight of stairs to the observation deck. Although it is not as high as the church tower, you can get great views of the downtown shops and harbor.

Ice Cream From the Juice Bar

We grabbed a quick bite to eat at Provisions, the sandwich shop located downtown followed by ice cream from the Juice Bar. We were excited that there was no line since there usually is. If you do go, make sure to get their freshly made waffle cones. You can either get the cone or a waffle bowl. The Juice Bar has milkshakes and smoothies too, but you have to try their ice cream while in Nantucket. It’s a staple here!

We enjoyed our ice cream while we strolled over to the Brant Point Lighthouse. The Lighthouse is near the harbor, close to the White Elephant Hotel. There were lots of people fishing here and sitting around watching the boats.

The Oldest House

From there, we walked to the Jethro Coffin House before spending the rest of our day at the beach. This house is known as the oldest house on the island and is pretty close to our hotel. It is open for tours several days of the week but was not open when we stopped by. We were able to see it from the outside though.

Dinner at the Lobster Trap

The rest of the afternoon we spent at the beach. We explored Jetties a little bit before walking to Steps Beach to lay down. For dinner, we went to the Lobster Trap. This restaurant is known for its casual atmosphere and large seafood menu. We couldn’t decide what to order, so we ended up splitting a lobster roll and their seafood pasta. The lobster roll was very good but the pasta was my favorite! After a busy day, we went back to our hotel to enjoy some wine in the garden.

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Hey, I’m Ally! Welcome to Cafes and Getaways. I’ll be sharing details on my latest travel destinations, as well as tips and tricks to help you plan your next adventure.

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