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Travel Guide: 4-Night Nantucket Itinerary in Late September

Well, friends, we planned on spending our anniversary this year having a romantic dinner overlooking the cliffs of Positano, drinking wine in a small cottage outside of Pienza with views of the rolling hills and vineyards, and gazing at the canals of Venice, but that obviously didn't happen. When we learned in early July that the EU wasn't going to be allowing U.S. tourists to cross the borders, we sadly canceled our Italy trip, and began to come up with a new plan. Because our anniversary and Josh's birthday are so close together, this time of year is our favorite for traveling. But with the uncertainty of the world, we decided it was easiest, safest and most worry-free to stick with something more local, and something we were familiar with. And honestly, it turned into such a memorable trip.

Photo by Georgie Morley Photography.
Photo by Georgie Morley Photography.

The most we've ever stayed on the island of Nantucket is two nights, and for quite a while, we've wanted to stay even longer just to really experience the island without feeling rushed, or like our time there was fleeting (and two days definitely felt that way). We've also been wanting to go back to Martha's Vineyard because it's been a few years since our last visit. So, for this trip, we decided to spend four nights on Nantucket and three nights on Martha's Vineyard.

We knew visiting these islands would be safe because since getting through peak tourist season in the region, cases weren't spiking, masks were required, and we're also familiar with the areas. We knew what to expect once there, and also planned to be outside almost all day, every day. We also picked a hotel that advertised very strict COVID policies in case we were rained out for a day and needed to stay inside. Much like our week-long stay on the Cape's mainland this past July, it was just a different kind of trip, but one we were really excited about.

For this post, I'll be focusing on our time spent on Nantucket to give you some ideas that will fill up a four-day itinerary nicely, while still allowing you some relaxation at your rental or hotel. In my upcoming post, I'll share our time on Martha's Vineyard.


We somehow lucked out with a really good off-season/mid-week rate at The Nantucket Hotel, which was a surprise because it usually goes for about $700/night for the cheapest rooms, and we definitely did not pay anywhere near that. And guys, this place was amazing. First and foremost, they were taking a lot of COVID precautions and we felt really safe while there. In addition, everyone working was so kind and friendly, and they go out of their way to make sure you're comfortable. They also provide you with everything you need for a day at the beach, including umbrellas, coolers, towels, etc., so no need to lug all that stuff with you on the ferry. It's centrally located in the main town area, and easily walkable to all the downtown shops, restaurants and Brant Point lighthouse. When we arrived, we found out our room was upgraded to a suite, which had a really spacious living room, separate office area, a bedroom that was also huge, and guys, an amazing corner private deck that had seating furniture, a full dining table set and chaise lounges. It was incredible, and the fanciest hotel room we've ever gotten. The hotel also offers free ferry pick-up/drop off, and a breakfast included in your room rate during select months (September being one of them). For breakfast in the age of COVID, every morning you made your way to the on-site restaurant to pick up your individually boxed morning treats, which was usually yogurt, fresh granola, fresh fruit and a delicious muffin, and you were welcome to enjoy it in your room, or out on the hotel's front porch. We brought ours back to our own private deck every morning, and it was a great way to start our day.


Nantucket has three lighthouses: Brant Point, Sankaty and Great Point, all of which are gorgeous and unique. Brant Point lighthouse is the first you'll see as you approach the island on the ferry. It has its own little beach where you can watch the ferries come in and leave for the day, with plenty of space to spread out, and has a beautiful wooden bridge leading up to the actual structure. It's also very walkable from town (and even closer to The Nantucket Hotel), so if you just come to Nantucket for a day, you can easily visit. And I highly recommend that you do.

Sankaty is the next easiest to get to, and it will require you to take a visit to Siasconset, or 'Sconset, as the locals call it. I'll go more into 'Sconset later because I love this cute little town, but let's talk about how beautiful Sankaty is. It stands tall in an open field with swaying grass, and the red and white stripes make it even more beautiful. We love coming out here because it's pretty peaceful, and there are tons of opportunities to take some great photos. It's especially lovely in the golden hour before sunset.

Photo by Georgie Morley Photography.

Photo by Georgie Morley Photography.

Photo by Georgie Morley Photography.

Lastly, Great Point is one that requires more work to see, and this trip, we decided to make it happen. In order to visit Great Point lighthouse, you have to either have or rent a 4WD vehicle that can go over sand, and have an OSV (Over Sand Vehicle) permit to get out there. Guys, this was such a fun adventure, and I can't recommend it enough. So, let's get into why I loved this so much.

Great Point lighthouse was covered in fog when we first arrived, making it even more dreamy.

If you look at a map of Nantucket, the little skinny peninsula all the way on the upper right is where Great Point is. And since it's not the easiest area to get to, it's very quiet and secluded. This year, we decided to bite the bullet and pay to rent a Jeep for the day to go there, and it's probably my all-time favorite memory from all our trips to Nantucket.

A few things to know: When you rent your Jeep, ask if it comes with all the permits you need to enter Great Point. Also, even though your rental will likely come with all these permits, know that you'll still have to pay a hefty $50 fee to enter the park. It's a steep price to pay for just a day, but if you can swing it, it's so worth it. Thankfully, we budgeted for this in advance. When we arrived as of September '20, they were requiring you to purchase your permit in advance online. If you arrive and haven't gotten it yet, you can do it on your phone, and then show it to the folks at the gate.

Before you start your Great Point adventure, you'll need to deflate your tires in order to drive over the sand. Your rental company will be able to go over how to do this, and provide you with a tire gauge. I'll be honest, Josh did this part for us, but he said it's pretty easy to do, and it takes about 10-15 mins for all four tires. And then, you're off to explore. You'll start to drive on some sandy "roads" through the dunes before you follow a sign for the beach, and then you literally just start driving along the ocean to get to the lighthouse. Once you've visited the lighthouse, you can drive back to the beach, park, hang out, go swimming, eat lunch - and do whatever you want to do. The beach area is huge and even if it's busy on the day you go, I can't imagine you'd feel cramped. In September, we often had it to ourselves, but even during peak season, I've read it never feels crowded. 

Once you're done for the day, and you're through the gate to exit, you'll see the tire inflating station on your right. There may be a line because there are only two stations, so you can pull over on the side of the road and wait if needed.

The Nantucket Hotel gave us a cooler full of ice to bring with us that day. We stopped at Something Natural for our
all-time favorite sandwiches, chips and cookies for lunch.

We spent just under four hours out there, and I honestly could have spent the whole day. Jeep rental prices on Nantucket are not cheap, so I suggest staying out there as long as you can to make it worth your while. They're open from 9a-6p daily. 

'Sconset is an adorable little town about 8 miles away from the main town area, and even though it's rather small and quiet, there's some really unforgettable things to do.

To get to 'Sconset (assuming you didn't bring your car to the island), you can take The Wave public bus, bike out (the bike path is paved, rather flat and really nice) or rent a car or moped for the day. Once you arrive, you'll be greeted by a little breakfast/lunch cafe and a market in case you want to grab some food or snacks. 

Besides Sankaty lighthouse, the Bluff Walk is the most popular thing to do, and I highly recommend it. I believe Google now knows where to take you to start this because it's not easily found otherwise (the last time we did it a few years ago, we had to follow random instructions on a local's blog to find the entrance point). The Bluff Walk is basically a path along the cliffs of 'Sconset Beach, and you, quite literally, are in the back yards of some of the most gorgeous homes. But yet, it's 100% a public walking path. So, you get to take in ocean views, while also imaging what it's like to live there since you're so close to multi-million-dollar beach front homes. I believe it's about a mile 1-way, and it's a very easy, flat walk. You'll start by walking on a shell-lined path in-town, and then it will turn into the back yard adventure. Once you're done (it will just suddenly end), you can either take the road back to see the front-views of the houses, or reverse your Bluff Walk to get back to town.

How you start your Bluff Walk.

Part of the Bluff Walk - see what I mean about walking in back yards?

Behind the market, there's this really adorable little white foot bridge that has a nice view of the ocean. I don't know why, but I love this little thing so much, and it also makes for cute photos.

Surprisingly, we've never actually walked on 'Sconset Beach, but from what we've seen via the Bluff Walk, and the foot bridge, it's rather beautiful if you have some extra time. 

'Sconset is also known for having gorgeous rose-covered cottages, so it's actually really fun to just wander the streets if they're in full bloom (summer months, usually) and day dream about living in an English countryside cottage. 

Madaket is probably my favorite beach on Nantucket, and it's also known for big waves, turquoise water and gorgeous sunsets over the water. There isn't much to do in this town besides the beach, and one of my favorite restaurants, Millie's. It's residential otherwise, but the beach and Millie's are definitely worth coming out here. The Wave bus does go out to the beach during the summer months through Labor Day. I'd recommend coming out here for sunset if it's going to be a clear night. The beach is rather long with plenty of space to spread out. At the end of September, we had a huge chunk of the beach to ourselves for a few hours while we waited for sunset. 

Does anyone else love the curl of a wave as much as I do?

This shows you the scale of the waves as they crash - they really are huge.

The water at Madaket always is this beautiful and serene turquoise color.

We've only ever been to Cisco Brewery once before, and had kind of avoided it since because it was just really crowded, and we could never get a table. Being that we were here at the end of September on a weekday, we thought we'd try it again, and we had much better luck. During COVID, they had some really great updates (that I honestly wish they would stick with even after the virus is a distant memory), which included only allowing as many groups in per picnic tables (so no standing crowds), and you could only get up to get food from the food trucks or to use the bathroom. Wait staff would take drink orders and bring them to you, and carry iPads or iPhones to pay at your table. It was so nice. They also started to make canned cocktails, and I definitely have a thing for their Nantucket Blue - I'd recommend giving that one a whirl. Their beers are also really nice, and they have a winery as well (which I haven't ever tried). Josh loves their Nor'easter Bourbon. All tables are outside, and during non-COVID times, you're able to go inside the buildings to do tastings of their beer, wine and spirits.

Nantucket beaches are some of my favorite of all the Cape and Island beaches. I've done a post in the past about Nantucket for Beginners/Day-Trippers, which likely will repeat a lot of info in this post. But if you're looking for more info on Nantucket beaches, I would scoot on over here. One beach we visited for the first time ever this trip was Surfside, and it was a tough contender with Madaket for my favorite. I think the waves may have been even bigger, and I just found myself totally at peace here. 

Surfside Beach.

Always running toward the waves.

... and usually getting caught by them.

Step's Beach is closer to town, and has great views from above before you take a staircase down to the shore.

Walkway at Step's Beach during sunset.

I'm going to refer you to that same beginner's guide here for my favorite stores downtown, as well as more information about the entire downtown/wharf area. The shops are absolutely lovely on Nantucket, and if you're on the island for a few nights, it's definitely worth it to budget an afternoon to explore this whole area. I especially suggest wandering the back streets to take in all the gorgeous historic homes  because they're absolutely stunning. 

I was in love with this house (and especially the door).

Can you spot the seagull?

September hydrangeas are still beautiful hydrangeas.

I love morning walks at the wharf before it gets really busy.

I'm probably not the best person to ask about restaurants, simply because we have to be really selective on where we eat with Josh's vegetarian/bordering-on-vegan diet. I eat seafood, so I always have options, but with it dominating most menus, for Josh, it can be tough to find places to eat because we've noticed a lot of places still don't always have a good vegetarian entree option. 

But, after having done a lot of research, I can point you in the right direction. For a more upscale meal overlooking the water, start by looking into Strait Wharf, which, as you guessed it, overlooks the wharf. Summer Galley, which sits right on the stretch of beach next door to Step's Beach, is an open-air restaurant that's pretty pricey, but you pay to dine on the beach as you watch the sunset over the water. 

We tend to eat really casually while on the island, and our favorites are Brotherhood of Thieves (I especially love their puff pastry lobster bisque), Sea Grille, Pizzeria Gemelle for really great authentic-style pizza takeout and Something Natural for sandwiches. All those places are pretty casual, with the exception of Sea Grille, which is a bit more upscale (and shout out to them for always having a really nice vegetarian entree for Josh). 

And, because this is me we're talking about, ice cream is a must. Juice Bar is my absolute favorite, and probably my all-time favorite waffle cone. My go-to is strawberry in a waffle cone with chocolate sprinkles. When I took my mom to Nantucket, she said it was some of the best ice cream she's ever had. Jack + Charlie's is one that we tried for the first time during this visit, and we really liked it as well. Not quite as good as Juice Bar, but a worthy opponent, and we really enjoyed it.

And there you have it - how to spend a perfect 4-nights on Nantucket. As much as this little island has become even more popular over the past few years with social media, I still find it to be just as charming, authentic and naturally beautiful as the very first time I've been. I still feel as though I've stepped back into time when I arrive, and it maintains its old-world charm season after season. 

As much as I was hoping this would cure my craving to spend more than two nights here, it actually made me want to desperately, just once, trade our week on the Cape's mainland for a week on the island during peak season. I absolutely love the beaches on the Cape, but I would love to go swimming in those big waves at Madaket or Surfside when the water is warmer (in late September, especially this year because of our early cold snap, it just was too cold). So, added back to my bucket list is a peak-season week-long stay on Nantucket. It's so incredibly expensive, and I honestly don't think we will ever be able to afford it, but let's just say I'll be scouring travel sites for deals for the rest of my life. Or, until we win the lottery.

Have you ever been to Nantucket? What was your favorite thing you did?


Nantucket Sweater: Annie and the Tees
White Button-Front Tank: Old Navy
Everything else is old and no longer available (including both striped dresses)

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  1. Absolutely beautiful. So jealous.