What to Do on Nantucket to Avoid the 15 Worst Rookie Mistakes (2024)

In sharing what to do on Nantucket, I thought it would be best to start with what not to do first.

Allow me to explain.

My brief trip to Nantucket with a friend of mine was not one of my finer moments.

From the opening of this farce to the final act, it was practically a textbook example of what not to replicate on a trip.

In just eight hours, we experienced comical misfortunes ranging from farcical ferry flubs to a lame lobster roll finale on a dark, isolated boat deck.

Fortunately, the issues we faced had nothing to do with the island lacking in any way.

In fact, after this teaser visit, I can say that Nantucket is my favorite destination in all of New England.

Instead, our hilarious hardships had everything to do with poor planning and a healthy dose of bad luck.

Funnily enough, the magnetic pull I feel toward this enchanting island was my impetus to write this guide.

Frankly, I wish I’d come across a road map like this one to keep me on course, but I found no such thing.

Instead, I feel it’s my duty to shield you from my silly slip-ups, most of which could’ve been avoided.

Here’s hoping this guide will set you up for a successful stay on Nantucket – and provide a few laughs along the way!

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A Brief Word on Nantucket’s Appeal

Captivating Nantucket is a 14-mile-long island located 30 miles south of Cape Cod in Massachusetts. It feels exceptionally exclusive, particularly compared to neighboring Martha’s Vineyard.

As such, it’s an extremely popular summer destination for the East Coast’s wealthy elite.

Even the name “Nantucket” itself connotes exclusivity. Derivative of a Southern New England Algonquian word, it’s loosely translated to mean “far away land” or “in the middle of waters.”

Nantucket has great historical significance as well, previously serving as the whaling capital of the world from 1690 to the 1800s.

In addition, the island is home to over 800 meticulously-restored pre-Civil war homes, more than anywhere else in the United States.

There’s something mystifying about this place, from the soft sweeping plains to the fog blanket that periodically rolls in, shrouding the island in mystery.

A visit to Nantucket feels vaguely nostalgic, like discovering a secret passageway into a beloved childhood storybook.

This island has something truly special to offer, if you only know how to let it in.

15 Common Mistakes & What to Do on Nantucket Instead

Mistake #1: Underestimating the Travel Situation

Before determining what to do on Nantucket, you’ll first need to understand the challenges associated with getting there.

Getting to Nantucket is not simple, especially in comparison to other places in New England.

To reiterate, Nantucket is an island, so driving there is obviously out of the question.

Although I was aware that it was a bit out of the way compared to Martha’s Vineyard, I underestimated just how long it would take to get there.

(Not to mention, we also hit an unexpected bump in the road, so that caused further delays.)

What to Do Instead

If I’d taken the time to calculate the travel time (and anticipate hiccups), we would’ve done the trip very differently.

Instead of winging it and hoping for the best, I recommend sitting down and calculating how much time you’ll spend traveling. This will help you figure out how much time you actually have to spend on the island.

First things first, there are only two ways to reach Nantucket: by ferry or by plane.

Traveling to Nantucket by Ferry

Since we were coming from Connecticut, we went the ferry route.

We actually based ourselves in Cape Cod and then took the ferry back and forth each day. On the first day, we visited Martha’s Vineyard, followed by Nantucket the next day.

SPOILER ALERT: I would not recommend traveling this way and will explain what to do in Nantucket instead in the next section.

In any case, there are two ferry options you can choose from: high-speed or traditional.

Pricing will depend on your port of departure, but the high-speed option is about twice as costly as the traditional ferry alternative.

You can check out the current ferry schedule here to plan your trip.

We took the cheaper traditional ferry that departed from Hyannis.

However, looking back, I definitely would’ve sprung for the high-speed ferry to Nantucket.

From Hyannis, the traditional ferry journey takes 2h, 15m each way.

However, our trip was even longer, due to unforeseen circ*mstances.

Unfortunately, we were informed of a medical emergency on board about 15 minutes after departing from Hyannis.

As a result, we had to turn around and head back to Hyannis, where we waited about 20 minutes until the issue was resolved.

Sadly, I don’t have any more information on what happened and I sincerely hope the passenger in question was okay.

Traveling to Nantucket by Plane

If you’d prefer to avoid the ferry, you can fly into the island’s one airport instead, Nantucket Memorial Airport.

This public airport is located on the south side of the island. You can read more about traveling to Nantucket by air and what airlines you can expect here.

To give you a quick example, Jet Blue offers convenient, nonstop flights from New York to Nantucket in just under an hour.

FUN FACT: Nantucket is nicknamed the “Gray Lady” due to the thick fog that often rolls in from the sea and veils the island. As a result, flights to Nantucket are often delayed, so be prepared for a potential interruption to your plans!

Mistake #2: Assuming You Can Squeeze Everything into a Day Trip to Nantucket

Underestimating the inconvenient travel situation to Nantucket can drastically cut your time short on the island.

That brings us to our next big mistake on this list – not properly allocating your time here.

One of the biggest blunders I made was falsely assuming we could squeeze everything I wanted to do into a day trip.

(I’m honestly laughing and shaking my head as I write this.)

Now, I’m not saying you can’t possibly do Nantucket in a day.

However, if you’re taking a traditional ferry and there’s a lot you want to see/do, you’re setting yourself up for failure.

Let’s take a peek at the math, shall we?

Since we took the traditional ferry from Hyannis, our round trip was supposed to be 4h, 30m (2h, 15m each way).

However, the medical emergency I mentioned set us back almost an hour, so it was really a 5h, 15m trip.

Although we got on our first ferry at 9:15, we didn’t actually arrive in Nantucket until just before 12:00 PM, due to the delay.

In addition, the last ferry was leaving at 8:00 PM, so we really only had eight hours to see everything.

Plus, we didn’t actually have eight full hours, since we wanted to arrive at the port a little earlier than the ferry departure time.

PRO TIP: If you’re doing a day trip and you want to have dinner on the island, I suggest sitting down at a restaurant no later than 6:30 PM.

What to Do Instead

I highly recommend avoiding what we did and spending at least one night on Nantucket island instead. This will ensure you can have a relaxing dinner, rather than rushing to catch your ferry.

I’m hoping to do a proper Nantucket trip in the future, so I’ll update this section with my hotel recommendation(s) then!

Mistake #3: Assuming You Can Walk Everywhere on the Island

Of all the blunders I made on this trip, I’d say the biggest faux pas was not having a car.

Although Nantucket is a relatively small island (compared to Martha’s Vineyard), it feels much larger when you’re exploring on foot!

Now, many bloggers will tell you that you can easily travel to Nantucket without a car…

…and they’re not wrong.

That said, they probably weren’t lugging around a twenty-five-pound backpack stuffed with camera gear/outfit changes like I was.

So, if you’re a content creator with a lot of gear like me, walking will probably wear thin quickly.

(Not to mention how frustrating it was when both our phones died and we couldn’t charge up in the car.)

What to Do Instead

Personally, I would highly suggest arranging for a car.

Now, there are two different ways you can approach the car situation (one of which I wasn’t aware of previously).

You can either transport your car on the traditional ferry or you can rent one on the island.

Do keep in mind that bringing a car with you – while convenient on the island – can be a hassle in its own way.

For one, it’s not cheap to transport your car and it’ll cost you around $400 round trip.

In addition, you’ll need to book this in advance, so if you’re planning a last-minute trip, this won’t be feasible.

You also won’t be able to take a high-speed boat, as cars are only permitted on the traditional ferries.

Personally, I think renting a car is the best option, particularly if you’re not dead-set on having your own vehicle.

This way, you can avoid the additional ferry fees and the headache of having to book months in advance.

You can learn more about the car rental options on the island here.

However, keep in mind that you may not be able to rent a car as easily in the off-season (such as the winter). I recommend reserving your car ahead of time to ensure you’re all set while on the island.

PRO TIP: If you love beaches, consider renting a Jeep or an SUV with a beach driving permit. This will give you the ability to drive right over the sand!

Mistake #4: Planning the Trip at the Last Minute

Due to travel complications and the potential need to arrange for a vehicle, I would not suggest planning your trip at the last minute.

You also don’t want hotel planning to be an afterthought, particularly if you’re traveling during the high season (Memorial Day to Labor Day). Hotels book up pretty quickly on the island during peak season.

What to Do Instead

The more you can plan in advance for potential obstacles, the smoother your trip will go. Personally, I’d suggest giving yourself at least a month or so to sort out the details of your getaway.

Again, if you’re planning to take your car along on the ferry, you’ll need to arrange this months in advance.

Keep in mind that you’ll need to provide the year/make/model/license plate number of your vehicle when you make a reservation. In addition, all vehicle reservations are non-transferable.

Mistake #5: Attempting to Plan a Trip Around a Tight Budget

While we’re on the topic of planning a trip, I want to be very transparent about something:

Nantucket is not a budget destination.

From hotels, to restaurants, to gift shops, expect to pay a premium. While hotel prices tend to decrease in the shoulder season as I mentioned, this destination is still by no means cheap.

Therefore, determining what to do on Nantucket will largely be dictated by what you have to spend.

In fact, according to this budgeting website, you can expect to pay an average of $182/day while on Nantucket.

What to Do Instead

Rather than imposing an unrealistic budget onto your itinerary, calculate what the actual costs will be up front. Then, explore all of your options in advance to make the trip as financially feasible as possible.

Here are some things to consider to keep costs manageable:

• 

  Seasonality – The best (and cheapest) time to visit Nantucket is during the shoulder season (spring and fall). During these months, the island isn’t mobbed by crowds and you won’t pay a grossly-inflated price for a hotel. March to April is ideal for a springtime trip, whereas September (post-Labor Day) to October is perfect for an autumn adventure.

• 

  Hotel Costs – Booking your hotel months in advance can help you save some cash. Alternatively, if you have some flexibility with your travel dates, you may snag a great last-minute deal. Just don’t cut it too close or you may miss out on booking your desired accommodation!

• 

  Restaurant Options – Research local dining options to get a sense of what typical meal prices are. You may need to limit or eliminate your Starbucks trips for a bit to set aside some money for restaurants.

Mistake #6 Not Taking Advantage of a Bike Rental

…Or at least that’s what I’ve heard from countless bloggers discussing what to do on Nantucket.

I still have yet to do it, which is another mistake I made on this trip.

However, I’m definitely inclined to believe that it’s the top method of travel, particularly when it’s warm out.

Just the idea of the wind whipping through my hair as I glide past the charming pre-Civil War constructions puts a smile on my face!

Although I was tempted to rent a bike, the thought of wearing my ginormous backpack while biking wasn’t appealing.

That said, most of the bikes come equipped with cute baskets. (I just don’t think my pack was fitting into one of those!)

What to Do Instead

Fortunately, it won’t be difficult to find a bike rental on Nantucket and two wheels will take you to most spots on the island.

Plus, bike rentals typically cost between $20-$30 for the day, so they’re not too hard on your wallet, either!

There are a number of bike rental services around the island that you can use. You can read more about some popular shops in the area here.

Mistake #7 Anticipating Sunny Days & Clear Skies

As gorgeous as Nantucket is, it’s not one of those destinations with near-constant sunshine and blue skies.

After all, not everywhere can be Greece!

Conversely, the “Gray Lady” is notorious for cloudy days and heavy fog, as I mentioned earlier.

What to Do Instead

Although gray skies are far from ideal to most people, they’re no reason to get upset. First off, they can make for some really cool and moody photography.

Secondly, even if the morning appears dreary, it doesn’t mean it will stay that way all day. In fact, Nantucket weather can really shift pretty drastically on an hour-by-hour basis.

So although I’m always a proponent of checking the forecast in advance, do keep an open mind.

Oh, and bring along a raincoat and umbrella, just in case.

Mistake #8: Underestimating How Chilly it Gets at Night

As you’ve probably gathered by now, the weather here can be pretty unpredictable.

That said, one thing that you can predict is that it will pretty much always feel chilly at night.

Although the daytime temperature was in the seventies during September, I was shivering by nightfall and changed into pants.

What to Do Instead

Your best bet for coping with the erratic weather patterns is to come prepared.

I suggest always packing a sweater/light jacket (even in the summer) as well as different footwear options to prepare for all scenarios.

As a general rule of thumb while packing, you can typically expect summer temperatures that are slightly cooler than mainland Boston.

Winter temperatures, on the other hand, are usually slightly warmer than mainland New England.

Mistake #9: Winging it with Food

Although it may not seem like a big deal, I’m still kicking myself over the foolish food faux pas I made.

To provide some context, I’m a huge lobster roll fan, as evidenced by my adventures in Kennebunkport, Maine.

In fact, I’m such a fan that I took the time to research the best lobster roll on Nantucket island before the trip.

After reading countless blog posts, I determined that the clear winner was CRU, an oyster bar with rave lobster roll reviews.

I was sold.

In fact, I was so pumped about it that my mouth was literally watering as we walked around Nantucket.

Unfortunately, what I neglected to do, however, was check which days Cru was actually open.

Much to my surprise (and dismay) a few hours before dinner, I discovered that the one and only day they close is Wednesday.

Of course, Wednesday also happened to be our one and only day on the island, so I bet you can guess how that turned out!

Major fail.

After looking into some alternative options, we discovered that a bunch of seafood restaurants close on Wednesdays in Nantucket.

Honestly, I have no idea why. I’ve heard of restaurants going dark on Mondays and even Tuesdays, but a mid-week closure was something I never anticipated.

So be advised if you’re traveling to Nantucket mid-week!

What to Do Instead

While deciding what to do on Nantucket, be sure to take a look at the area’s best dining options.

This is especially important if you’re the type of person that has crippling anxiety about making last-minute restaurant decisions.

Here’s what to consider when researching restaurants:

• Menus
• Pricing
• Days/hours of operation
• Pandemic-related limitations/procedures

I will say, however, that there’s actually a silver lining to this story!

We did manage to find delicious lobster roll at Easy Street Cantina right before hopping on our evening ferry.

Sadly, I don’t have a picture of this culinary creation, as we ate it on the deck of our dark ferry (oblivious to the new no-food-on-board policy).

Sigh. Live and learn, as they say.

Mistake #10: Skipping the Island’s Lighthouses

If you’ve been following along with this blog for a little bit, then you already know I’m obsessed with lighthouses.

In fact, I’ve dedicated an entire blog post to all of the lighthouses in Portland, Maine.

So it should come as no surprise that lighthouses were at the top of my list for what to do on Nantucket.

Honestly, you’d really be doing yourself a disservice by not visiting at least one lighthouse on your trip.

What to Do Instead

I suggest mapping out the lighthouses you’d like to visit in advance. Since they’re all located at different points on the island, this will save you time on the trip.

Here’s some handy information about the island’s three lighthouses:

• Brant Point Lighthouse – This cinematic gem was established in 1746 and is one of the oldest operating lighthouses in the United States. It’s also the easiest to get to and the first one you’ll spot from the ferry, as it’s right near town. Since it’s only about a 20-minute walk from the ferry, I suggest hitting this one first.
• Sankaty Head Light – This unique lighthouse was first built in 1850 and is easily recognizable with its red and white stripes. It’s located in Siasconset, on the opposite side of the island from the Brant Point Lighthouse. Many people will visit this beauty as they complete the Sconset Bluff Walk (more to come on that later).
• Great Point Lighthouse – This lighthouse was originally built in 1784, but was destroyed by a fire in 1816. It was then rebuilt one year later, only to topple down in a storm in 1984. Finally, it was rebuilt again in 1986 and still remains standing today. Great Point Lighthouse is located at the northernmost point of the island at Great Point. In order to reach this one, you’ll need to rent a Jeep with an over-sand vehicle permit and 4-wheel drive. However, Great Point Lighthouse is currently closed due to the pandemic, so you’ll need to put this one on your future list for now.

Unfortunately, due to limited time, we were only able to visit one lighthouse on our trip. Since we stayed around the center of the island, Brant Point Lighthouse was the easiest one to visit.

Although we originally planned to check out the Sankaty Head Light as well, we never made it to the east side of the island, sadly. To reiterate, this is why I previously emphasized the importance of having a car!

However, let me just say, Brant Point Lighthouse did not disappoint!

Although the lighthouse itself is more of a bug light, the beautiful boardwalk leading up to it makes for some really cinematic shots.

How to Get Here:

The addresses for the lighthouses are as follows:

• Brant Point Lighthouse – Easton Street, Nantucket
• Sankaty Head Light – Baxter Road, Nantucket
• Great Point Lighthouse – GPS Coordinates: 3901° N, 70.0483° W

Mistake #11: Skipping Nantucket Boat Basin

Skipping Nantucket Boat Basin is one of the rare mistakes on this list that we didn’t make!

The Boat Basin is a full-service marina located in the historic Nantucket Harbor. Here, visitors can enjoy access to pet-friendly docks, 240 boat slips, and luxury amenities.

What to Do Instead

These waterfront accommodations offer full kitchens, spacious decks with dock views, and complimentary access to bicycles and a beach shuttle to explore the island more easily.

I certainly wish we’d taken advantage of this!

You can learn more about these charming accommodations and book a stay here.

How to Get Here:

Mistake #12: Skipping the Sconset Bluff Walk

What if I told you it was totally acceptable to stroll behind people’s homes to discover stunning coastal views and flower-covered properties?

Well, this is exactly what you’ll do on the Sconset Bluff Walk.

This scenic walk can be accessed along a public footpath that runs behind private homes.

Sure, it may feel a little obtrusive to walk through people’s yards, but it’s a super common island practice! Just be respectful and aware of the fact that you’re walking behind private properties.

I honestly can’t tell you how many blogs gushed over this walk when I searched for what to do on Nantucket. Bloggers insisted that it’s the number one thing to do while on the island.

Unfortunately, this was the main thing I most wanted to do on our trip – and one of the many things we didn’t have time for.

In any case, I’m not at all bitter that we missed out on this opportunity! (Is it obvious?)

What to Do Instead

Make sure to build this special two-mile trail into your itinerary. I know I will next time!

From what I’ve read, it can be a bit tricky to locate the starting point, as it’s not clearly marked.

However, most of the resources I found said to begin the walk on Front Street.

As a reference, the path you follow will take you roughly two-thirds of the way to the Sankaty Head Light. For more details on this scenic stroll, check out this helpful resource.

Mistake #13: Skipping Cisco Brewers

As a beer fan, I’m also bummed we missed out on Cisco Brewers, Nantucket’s award-winning brewery.

Established in 1995, Cisco Brewers is Nantucket’s first and only craft brewery offering coastally-inspired beers.

Under normal circ*mstances (i.e. pre- and post-pandemic times), Cisco Brewers offers food trucks, live music, and an energetic beer garden.

From what I’ve read, they have great-tasting beer and a lively atmosphere.

FUN FACT: This popular brewery also has locations in Boston, Massachusetts and Portsmouth, New Hampshire!

What to Do Instead

How to Get Here:

Mistake #14: Rushing Through the Trip

One of our worst offenses on this trip was trying to cram a “checklist” of activities into eight short hours.

Nantucket is a destination you’ll want to savor slowly, whether strolling along the Sconset Bluff Walk, bike riding along the coast, or indulging in the island’s best lobster roll.

It’s not the type of place where you’ll find loud nightclubs, rowdy beaches, and a fast-paced lifestyle.

Unfortunately, our trip was the polar opposite of relaxing.

If anything, it felt rushed and hurried.

As a result, I feel like I didn’t experience the true spirit of the island and the beautiful atmosphere surrounding it.

What to Do Instead

Slow. Down. Don’t cram. Don’t over-plan.

Have an itinerary or at least a general idea of what to do on Nantucket, but spread it out over two or three days, at least. Breathe in the ocean air. Feel the breeze against your skin. Admire the island’s plentiful hydrangeas. Make lasting memories beyond your devices.

Nantucket can be your much-needed escape from the chaos of everyday life if you simply let it be.

Mistake #15: Forgetting Your Camera

It may seem contrary to my preceding point, but Nantucket is a photogenic destination that you’ll definitely want to document.

From the charming lighthouses, to the cedar-shingled homes, to the beautiful sandy beaches, there are photo opportunities around every turn.

Definitely do not forget to take your camera along!

What to Do Instead

Make sure to bring plenty of extra camera batteries because you’ll likely be snapping away here.

In fact, if I’d collected more content, I would’ve created an Instagram guide, similar to my post on Palm Beach island.

Hopefully I’ll have the chance to do so in the future.

Until then, each of the sections in this post that include pictures are all areas I recommend capturing on camera.

Although I clearly made more than my fair share of mistakes on this island, Nantucket has undoubtedly captured my heart and mind.

In all honestly, it’s rare that I discover a U.S. destination that I immediately want to return to. However, I’m already plotting a return trip for later this year!

Next time, I hope to savor a longer, slower experience under Nantucket’s spell – and hopefully make a few less blunders along the way!

I sincerely hope Nantucket will mesmerize you, too, and that this guide will help you avoid some common first-timer mistakes.

Have you ever been to this hypnotic island? If so, I’d love to hear your personal suggestions for what to do on Nantucket in the comments below!

Also, if you’re looking for additional inspiration for your New England trip, be sure to check out my companion posts:

• 10 Fun Things to Do in Kennebunkport
• The Prettiest Lighthouses in Portland for Your Charming Maine Vacation
• The 1-Day Acadia National Park Itinerary You’ll Want to Steal
• Most Instagrammable Towns North of Boston
• 10 Dreamy Gardens in Connecticut You Can’t Miss
• Where to Experience the Magic of Woodstock, Vermont in Winter

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