I had never fallen in love with a place before until I met Nantucket 28 years ago- and, let me tell you, I fell hard. So hard that I still return each summer- and I truly believe that, if life were perfect, Nantucket summers would last forever. I love this place as if it were family.

The mix of sand, water, flowers, history, biking, walking, dogs, children, food, sailing (and cooler temps) makes me wish for Nantucket summers year-round.

Nantucket is most often and best described as quaint, charming, and magical. There couldn’t be a better description. It is the magical part that has always entranced me- it is that unexplained magic that it worked on me all those years ago as a college student heading for a summer adventure. It captured me -and it still pulls me back with every change in season just like the tide that surrounds its every shore.

I had never visited a place that made me want to cry when it was time to leave but, after spending June, July, and August on Nantucket in 1991, I boarded the tiny plane bound for Boston to connect back home to Atlanta, Georgia and surprised myself by crying for what I was having to leave- the memories that I had created and the experiences I had just had were some that I knew were special and impossible to recreate in any other setting. It was hard to explain to others because it really was a magical time. I was heading home to the south to start the the next semester of college (which is a fun time of life in and of itself) but a big part of my heart was still up east on this tiny sliver of land called Nantucket. I already couldn’t wait to figure out how to get back to it.

Lucky me, it only took about one conversation with one of my college best friends, and we started making our plans to get to Nantucket as soon as May rolled around again and we were out for summer. I returned that summer and the following summer. The third “summer” I lived on Nantucket actually was more like most of the year- I went up in April and came back home in December in time for Christmas. During this time on Nantucket, I worked in the hospitality industry at an Inn.

One of my favorite parts of helping run the Inn was being able to recommend the best restaurants, beaches, activities, etc. to the guests. I loved that part of my job, and I explored every inch of the island that I could to be able to bring the knowledge back to share. I went on tours, ate at allll the restaurants (twist my arm), tasted all the ice cream, rode all the bike paths, played on all of the beaches, and visited every single shop, store, and art gallery. I was everyone’s Nantucket Trip Advisor way before that was even a thing. 🙂

I was asked repeatedly if I could send suggestions to friends who wanted to visit. Over the almost 3 decades of going to Nantucket, I have shared countless “Things to Do on Nantucket” lists. I felt like it was time to also share these tips and suggestions right here with all of you! I hope you find this guide helpful, and I hope you will let me know if you visit my favorite tiny island. It’s lovely and idyllic- and is best enjoyed with friends and family, which is why I am excited to share this with you! If you would like to read more about my experiences on Nantucket, I share more of them here.

How to Get to Nantucket

Depending on your starting point, there are several different ways to get to Nantucket. Just know ahead of time that being patient and flexible will come in handy as you make your way to the island. Nantucket is 30 miles out to sea from Cape Cod and must be accessed by boat or plane. Weather conditions and fog often cause delays and/or cancellations. Just go with it and know that it is part of the gig when getting there. 🙂

My favorite way to get to Nantucket is to fly. If I can, I usually go from South Carolina to D.C. to Nantucket. That is the easiest route from Georgia to Nantucket, if you live close enough to South Carolina. The other choice from Georgia is to fly out of Atlanta into New York, New Jersey, or Boston, MA and then connect to Nantucket. There are also private jet companies that will fly you over. Most recently, I have been interested in hearing more about Fly Louie Public Charter for those leaving New York or Boston. Definitely check flights from your area and remember that patience is a virtue when getting there! It has never been the easiest place to get to, but I kind of like the benefits of that. Ha!

If you prefer to drive, you will want to plan to take the ferry over to Nantucket (there is no bridge that connects from the mainland to the island, which is a common question about Nantucket). The ferries that I am most familiar with leave from Hyannis, MA. I suggest you leave your car on the mainland and hop on the fast Hy-Line ferry. You can go from Hyannis to Nantucket in about one hour on the fast ferry. The slower ferry takes 2 or more hours. If you need to take your car over to the island, you will need to ride the Steamship Authority and make a reservation far in advance to be able to put your car on the boat. I am often asked if guests should bring a car on island…my answer is typically “no”. If you are there to enjoy all that Nantucket has to offer in town and will be staying in town, you will not need a car. Most places in town are within walking distance or there is a shuttle that will take you. Truthfully, there are too many cars on the island which makes for some frustrating driving and parking conditions. You can also rent a car if you need one while you are there.

Where to Stay on Nantucket

The Bed & Breakfast Inns on Nantucket definitely have my heart and so much charm, and I will list my favorites below…but when we go with our family of four, we rent a house in town. My favorite site for finding a home to rent on Nantucket is called weneedavacation.com Of course, VRBO and Air BNB are excellent options, too. We Need a Vacation focuses on the Cape and Islands exclusively.

Favorite Bed and Breakfast Inns

There are a lot of B&Bs to choose from on Nantucket! It is part of the charm of the island, and you can often experience the history of the homes when you stay in the inns. Most of the inns are historical homes that have been converted into guest houses. They are meant to feel cozy and quaint and breakfast service is continental. The laws do not allow them to cook full breakfasts. I will give you suggestions on breakfast, lunch, and dinner options further in the post.

1. The inn where I worked is now called 21 Broad. It has a newly remodeled interior but still retains its historical Victorian exterior. It is the oldest inn (built as an inn) on the island, but it has been updated in the most modern ways. The location is excellent!

2. Greydon House is just down the street from 21 Broad and is beautifully decorated (I used to live in the house between Greydon House and 21 Broad). This inn is gorgeous, the restaurant is attached and beautiful, and the location is excellent!

3. Hotel Pippa- this bed and breakfast is new to the island and housed in one of the many antique buildings in town. The location is excellent!

4. Brass Lantern Inn- this Inn is also excellently located in town! I have watched it grow over the years, and it is a beautiful and cozy space on a convenient street. This inn also has rooms dedicated as “pet friendly” if you are traveling with a dog. There are house rules for pets.

5. 76 Main Street- a beautiful boutique hotel (owned by the same company as 21 Broad) with another excellent location!

Favorite Nantucket Hotels

If you prefer a hotel setting over the quaintness of an Inn, there are several hotels that are convenient and lovely.

My favorite (and everyone else’s) is the White Elephant hotel. This hotel has been an island favorite for so long. There are also cottages that can be rented. The sister hotel is called White Elephant Village and it is separate from the hotel and includes townhouse-style accommodations and a pool. They are both an easy walk (3-5 minutes) into town proper.

Another in-town hotel is The Nantucket Hotel and Resort. This hotel is massive by Nantucket standards and is very family-friendly. My favorite part of the hotel is the charm it brings with the antique firetruck.

One of my favorites throughout the years has always been the Jared Coffin House. It has been going through some needed updates recently, and I am looking forward to seeing it. The house itself has so much grace and history- I am hopeful that the restoration work will bring the JC back to its glory days as a gorgeous historical destination. I will keep you posted!

And, if you would like to stay out of the buzz of downtown Nantucket and in a secluded part of the island, I would highly recommend The Wauwinet. This hotel is truly a haven for a peaceful vacation. Located on a far end of the island, The Wauwinet has hosted many celebrities looking for a getaway that is relaxing and secluded. Even if you don’t stay at the hotel, I definitely suggest going out to their restaurant, Toppers, for brunch. It is one of my favorite places to go for a change of pace.

Favorite Restaurants on Nantucket

Well, you should definitely get comfy and grab a snack for this extensive list. Nantucket is full of fabulous restaurants! My first summer there, my friend Amy and I would choose a different restaurant to try every Thursday night. We had some of the best meals, best laughs, and best first-hand knowledge of all of the best spots. “Where should we eat?” is one of the easiest questions to answer because there are so many right answers, but also one of the hardest because I never know where to start!

Dinner-  I will list the fancier ones first (also harder to get in, so make reservations early). A few take only day-of reservations in person and some restaurants are cash only. These are in no particular order…

1.   Cru- located on Straight Wharf near the boats- make reservations early. This restaurant is typically buzzing with lots of activity inside. Outside on the patio is quieter. I love the interior decoration of this restaurant.
2.   Straight Wharf Restaurant- also has a fun bar for before or after dinner connected to the restaurant. This is one of my all-time favorites!
3.   The Boarding House- on Federal St.- another all-time favorite with fabulous food and creative desserts!
4.   Pearl- this restaurant has the same owners as Boading House- ask about the chef’s table in the garden- Federal St.
5.   Club Car ( definitely go to the piano bar for drinks if you don’t go for dinner)- this restaurant has such an interesting menu full of healthy dinner options. Share plates and try lots of different items. It had a complete change over from its original look/feel/food. It is nothing like its original spot that was a Nantucket staple and favorite- but I truly love the new look and new menu. I think Joe (the late owner and Nantucket icon) would give it his approval and blessing- especially if there is fish involved. Main Street heading toward Straight Wharf
6.   Ships Inn- a favorite that has been around for a long time. Located in a beautiful historical building and a little off the beaten path.
7.   The Galley Restaurant- sunsets are beautiful here- go for drinks and photos if not for dinner.
8.   Chanticleer (one of fanciest) located in Sconset- it used to be coat and tie but has relaxed that rule in recent years.
9.   The Summer House- also in Sconset- quintessential Nantucket
10.   Lola (super hard to get in)- serves Sushi, very small and loud
11.  Company of the Cauldron- always one of my favorites- it is a price fixe menu and has a “supper club”   feel to it. Menus change each night and are listed by the week. A hidden gem, if you ask me!
12. American Seasons- this is usually a local’s favorite restaurant. It has been a while since I have been but I may try it again this summer. It has new ownership and the previous owners opened Proprietor’s. I will let you know what I think if we have a chance to go this summer!
13. Nautilus- on Cambridge St. Day of reservations in person only, I believe. The line for reservations typically forms early. Hard to get in but delicious food. Asian-flavors in quaint setting.

More Casual Dinner

14.  Slip 14- located on Old South Wharf- they have good clam chowder- very, very easy-going vibe. It feels like Florida to me when I go there- my kids always like it.

15.  Black Eyed Susan’s – India Street- it is BYOB. This one is awesome for breakfast if you don’t go to dinner here.  It’s very tiny.

16.  The Brotherhood of Thieves- aka “The Brotherhood” – located on Broad Street- we like to eat outside in the biergarten- inside is tiny and dark downstairs and large and airy upstairs . (I used to live 2 houses down from it at 19 Broad Street when I was in college- also worked at the Inn right next door to it.). This place is very casual, perfect for kids, and can accommodate large groups upstairs. I always like their clam chowder.

17.  Dune- located on Broad St.- dependable- and nice patio seating if you are dining with children.

18.  Proprietors- located on India Street

19. Ventuno- Italian restaurant at 21 Federal St. The back patio is perfect for a night out with kids.

20.  Pi Pizzeria- more than just pizza- try some of their entrees. Very casual, small but mighty. They also have a connected market for take away.

21.  Lola Burger- watch for ducks- valet park- very casual

22.  Millie’s – located in Madaket- this is such a lively and fun place with Mexican-type fare. If you are in Madaket in time for the sunset, go see the beautiful view of the sunsetting over the ocean.

Lunch

23.  Provisions- located behind the gazebo on Straight Wharf- my favorite is the Turkey Terrific (they are heavy on mayo so let them know if you want less 😊)

24.  Something Natural- located on Cliff Road- easy to miss- a half sandwich is the size of a whole sandwich- oatmeal bread is my favorite- the chocolate chip cookies are always good- go early bc it gets crowded fast. You eat outside on picnic tables and the kids always enjoy climbing around in the boat that is in the yard.

25.  Lemon Press- healthy- located on Main Street

26.  The Beet- salads and healthy eats- including beets!

27.  Cru– lively, fun setting right on the Straight Wharf

28.  Cisco Brewery- this place is fun- take the bus out and back so you can sample all of their beers/wines/liquors- usually has live music- they have food trucks for lunch- Millie’s is usually there with their food truck.  Also fun just to go after lunch and just enjoy the drinks.

29.  Culinary School Corner Cafe- super casual and tiny- easy to get things to go. I like their gazpacho- it is hard to get!

30.  Toppers at Wauwinet- take the Toppers Van (it picks up and drops off on Federal Street) and have lunch at the Wauwinet.  Pretty views.  Tucked away.  There is also a boat that takes you out to Toppers at Wauwinet- I prefer to drive or ride in the shuttle. 

If you’re game for driving on the sand, you can take a 4-wheel drive out there and, after lunch, go to Great Point Light House.  You have to stop and let air out of your tires before they will allow you onto the beach.  It is very protected now and so you will need to park the car and walk to the lighthouse.  It is about a mile of walking one way to the lighthouse.  Usually see seals out there- baby osprey are often hatching and so that is why cars have to stop.  

Breakfast

31.  Downy Flake Doughnuts are so good!  The restaurant is basically Nantucket’s version of Waffle House- locals have always gone- but I mostly just love the doughnuts.  There is a separate line for doughnut take-out if you aren’t having full breakfast.

32.  Black-Eyed Susan’s- on India Street– the breakfast is so darn good.

33.  Fog Island Cafe– now called Keepers and located at 5 Amelia Drive. I always loved having a hearty breakfast at Fog Island when it was in town. I look forward to trying Fog Breakfast at Keepers now!

34.  Island Kitchen– newly expanded building with an ever-growing menu, IK has a great breakfast- and I can’t wait to try his doughnuts!

35.  Nantucket Bake Shop- take away/no place to sit.  They also have the best Portuguese Bread on the island, in my opinion.

Treats

36.  The Juice Bar has the best ice cream on the island.  It gets really crowded, and the line wraps around the block, but it’s really good.  It is on the corner across from the Whaling Museum Shop

37.  Sweet Inspirations Chocolate Shop- it has homemade chocolates and they are known for their chocolate toffee and chocolate covered/dried cranberries

38. Cookies from Something Natural are a treat- we especially love picking up their cookie dough and baking our own for a warm, chocolate chip treat!

39. Shhhh…secret candy shop located at Force 5.

PHOTOGRAPHY ON NANTUCKET

Nantucket is such a picturesque island…and while I love taking photos of all of its charm, I also love being able to capture a special trip with a professional photographer who knows the ins and outs of Nantucket. I am often asked who I would suggest for family photos. Without a doubt, I recommend preserving your memories with Rebecca Love of Rebecca Love Photography. You can see Rebecca’s photos of our family and our Strolling Nantucket in Draper James shoot to get an idea of her work. Rebecca is so easy-going and makes family photos stress-free.

ACTIVITIES ON NANTUCKET

BEACHES- In town…Jetties Beach is very popular- it has a restaurant that serves lunch and dinner – family-oriented beach and often very crowded.

Steps Beach is my favorite- no-one used to know about it, but now it has been discovered.  There are beautiful houses along the road leading to Steps.  Great photo from the top of the stairs looking down to beach.  It has no restaurant or restrooms but it is a short walk down the beach to Jetties if you need.

Dionis is farther out and has no facilities but is very tranquil.

The beaches in town are on the Nantucket Sound and the water is calm.

The beaches on the Atlantic side of the island are rougher- waves are bigger and current can be strong.  Erosion has caused a lot of drop-off that can’t be seen…it just drops off sooner than you expect, so just be aware.  Those beaches are Madaket, Surfside, Cisco, Nobadeer, Sconset.  I haven’t listed all of the beaches, because the island is one big beach with different sections having different names…but those are the most well-known.  Just be careful in the water on the Atlantic side- much rougher than the water in the Sound.

Biking out to Madaket with a picnic to catch the sunset is one of my favorite things to do.

LIGHTHOUSES- Nantucket has 3 lighthouses that are equally beautiful!

Brant Point- in town- cute little lighthouse- also beautiful houses around it…walk down Hulbert Ave. and look at all of the gorgeous homes on the water.  Hulbert is a long street but comes out near Jetties Beach- you can turn right and walk to Jetties if you are on Hulbert.

Sankaty- in Sconset- also amazing homes along the water…sadly several are falling into the water now. 

Great Point- the one I mentioned earlier near Wauwinet- must have a 4 wheel drive to go to this lighthouse.

Sailing on Nantucket

SAILING- my favorite sailboat is the Endeavor.  Capt. Jim has been doing this forever.  

You can also charter a Hinckley through Harborview Sailing.

Shearwater Excusions has a dinner cruise/sunset cruise– it is bring your own food and beverage. See our Sunset Cruise with Shearwater.

Whale Watching-  also through Shearwater Excursions (Shearwater has many options for guided water activities- be sure to see them all at the link above.)

SHOPPING- I’d say just go in them all. 😊  The art galleries are beautiful, too.  One of my favorites is Cavalier Gallery on Federal Street.  One of my favorite shops is Murray’s Toggery Shop– it has been around for many, many years and is a staple of Nantucket. Murray’s is where you can get the original Nantucket Reds. Another one of my favorite shops to go in and take the kids is Town Pool. They have a very creative, interactive, enjoyable shop! Putt putt is upstairs- but each year there is something new and different! I also love to pop into Nantucket Looms, Lion’s Paw, and Current Vintage, Flowers on Chestnut, Vis-a-Vis, and Peter Beaton. I strongly encourage you to go in them all- there is fabulous shopping on Nantucket!

BIKE PATHS- Nantucket has great bike paths- you can ride for miles.  We usually rent bikes at Young’s, but there are several bike rentals. I love the bike path that takes you to Madaket. It is so pretty to ride through the moors and wildflowers. Grab a map from the bike shops and decide which paths look like what you wish for. Most end up at the beach. The most difficult path is probably the Polpis Road path- and the good news is that you can catch the shuttle back from any of the bike paths if you have decided riding a bus better suits you. 🙂

WALKING PATHS ON NANTUCKET

Tupency Links off of Cliff Road is a pretty place to go to walk- follow the paths and you will end up looking at the ocean.  Use bug spray- deer ticks are common on Nantucket.

Head out to Sanford Farm for walking trails- this is a great place to walk your dog.

Go for a walk on the ‘Sconset Bluff- (no dogs allowed on the trail)- follow from town and walk toward Sankaty. The trail closes before the lighthouse due to erosion, but this is one of my favorite walks.

LIVE MUSIC- there are 2 bars on Nantucket that have bands each night- – The Chicken Box and The Muse.  Just in case you want to relive your college days.  All bars have to close at 1:00 a.m.

BEST ACTIVITIES FOR KIDS ON NANTUCKET

My favorite activity with my kids is going to the beach each day. Of course, you also have shopping, biking, walking, and stopping for ice cream. But here are a few other ideas that are at the top of my list…

Critter Cruise. Kids and parents board the boat and then fish in the Harbor. My kids loved this- especially seeing the lobster and catching a fish! Such a fun activity for the littles! Be sure to bring sunscreen and snacks!

At Jetties Beach, you can rent kayaks, paddle boards, sailboats, and wind surfers through Jetties Sailing Center. Cisco Beach also has rentals/surfing.

Endeavor Sailing is a fun trip around the harbor for adults and kids. Captain Jim keeps everyone entertained. You can find the Endeavor on Straight Wharf.

If you are traveling with toddlers, there is a nice little shady garden area at the Nantucket Atheneum to have snacks and let them run around in circles. I always loved this little hidden gem in town when my kids needed a break from being in the stroller.

Stop by Pete’s Fish Tales for a chance to say hello to Pete and see him making fish prints. Sometimes, he even lets the littles (and not so littles) try making their own!

Of course, there is Children’s Beach which is such a great spot for the younger set. Children’s Beach has an area for the kids to wade/splash/swim but, even better, there is a playground and a green space area for running, chasing, playing frisbee, or just watching. There are children’s activities that you can also sign up for- such as yoga classes and entertainment.

Older kids (teens and up) may enjoy deep sea fishing that you can charter on Straight Wharf.

Dreamland Theater is also an option for movie buffs. There are 3 theaters- and Dreamland is also the best place to go for a public restroom when you are in town.

See below for ways to explore Nantucket’s history with kids…

FAVORITE WAYS TO LEARN THE HISTORY OF NANTUCKET

Favorite Tour Guide on Nantucket is GAIL’S TOURS- take this tour and learn about the different areas of the island, the whaling history, and local folklore. Gail was the first tour I ever took and she remains my favorite!

The Whaling Museum is so interesting to see- there is so much history on that little island. The museum shop has lots to offer for souvenirs. Head to the top of the museum for a nice view and a pretty place to relax for a minute. Kids love the giant whale skeleton!

First Congregational Church– this is the church I love to attend when I am on the island. On a clear day, head to the First Congregational Church (be ready to offer a small donation) and climb the steps and look out at Nantucket from the steeple. The views are beautiful and there is always someone there to answer questions about the history of the church or Nantucket. It is right in town and easy to find on Center St.

Hadwen House– a beautiful and grand Greek Revival home of a former whaling merchant turned silver salesman. There are 2 houses side by side that look like twins on Main St. at Pleasant St. Hadwen House is the only one of the two that is open to the public.

Thomas Macy House– this beautiful home still resembles life in the 1800s inside. It is a great one to tour to get a feel for Nantucket life during this era.

Nantucket’s Oldest House– this tour offers a glimpse into the early life of Nantucketeers. I always enjoy showing my kids how life used to be and letting them visualize the old-fashioned lifestyle without our present-day amenities. Be sure to go upstairs to see the bedrooms and go outside to sample the garden harvest. My kids love the currants they first tried here. Side tip- if you are ready for lunch after visiting the Oldest House, Something Natural is only a short distance away.

Old Mill– there is a cool windmill on Prospect Street that was built in the 1700s. It has been well-preserved and guides will explain the history and how the mill works. On most days, kids can help grind the corn. It is definitely a step back in time!

Nantucket Shipwreck and Lifesaving Museum– this museum pays tribute to those who worked to help others who were shipwrecked on Nantucket and offers a glimpse into the difficult lifestyle of sailing. You will find fascinating stories and heroic efforts.

Maria Mitchell Association– (Maria is pronounced Ma-RYE-ah) – the first female astronomer, Maria Mitchell became famous for her discovery of a comet. Within the association, there is an observatory and a small aquarium among other interesting areas.

Let me know if I can help with any questions that you have. If you visit Nantucket, tell me what you love and what your favorites are! There are always places and things to do that I haven’t included because their are so many things to do and see. But, wherever you find yourself on the island, enjoy the change of pace and the combination of historical and modern all in one place. Nantucket is a charmer, that’s for sure!