How to Get to Nantucket

A Nantucket trip is not for the travel faint of heart. Departing from Little Rock (first trip post-surgery!), the trip involved three plane changes as only a few airports fly into Nantucket. Since the island is only 14 miles long and 4 miles wide, it’s not exactly a travel hub. You can access Nantucket via air by flying in through major New York airports (LGA, Newark, JFK), Boston Logan Airport, Philadelphia, as well as smaller airports on specialty airlines, such as Cape Air through Hyannis, MA. If you’re in the mood for a boat ride, you can also access the island by taking one-to-two hour ferries from Hyannis, MA, Martha’s Vineyard, and Harwich Port, MA. It all sounds daunting for such a small island, but let me tell you, it’s worth the travel delays and cancellations you might endure.

Arriving in Nantucket is like taking a step back in time. With no stoplights to speak of and strict development and preservation laws, many of the island’s homes and structures date back over a hundred years to when Nantucket was a hub for the whaling industry. The commercial center of Nantucket is the cobblestoned downtown area near the harbor where streets are lined with boutiques and quaint restaurants. The 19th Century charm is off the charts and the summer landscaping can’t be beat. Seriously, the combination of bright florals and shingle cottages is postcard-worthy. Keeping my fingers and toes crossed that Mitchell St. and I meet again, preferably when I have a home on it 🙂

Where to Stay

Though a lot of Nantucket real estate is residential, the island has some noteworthy resorts that are just as cozy as having your own island retreat.

The Roberts Collection

Southern Tide graciously provided our lovely accommodations at The Roberts Collection, a collection of cottages (the oldest of which dates back to 1846!) smack-dab in the middle of the Downtown Historic District. If the Victorian details and charming antiques aren’t picturesque enough, take a walk around the serene courtyard with hydrangeas nothing short of e.v.e.r.y.w.h.e.r.e. It’s like they knew it was my favorite flower or something. The best upside to The Roberts Collection is the location. We were literally steps from all that downtown had to offer – breakfast, shopping (anyone catch my map dress on IG stories?), boating, you name it.

White Elephant

A collection of cottages, spa, and restaurant on the water overlooking Children’s Beach, White Elephant is a Nantucket staple for both for accommodations and dining. Brant Point Grill is a gorgeous spot to enjoy weekend brunch with a view of the harbor. Pro tip: Make a reservation as it’s definitely a hot spot!

Greydon House

A relatively new addition to Nantucket hospitality, Greydon House is a 20-room luxury boutique hotel that opened in the fall of 2016. Fun fact – the hotel structure combines a former island doctor’s office building that was built in 1850. The hotel includes fun amenities such as an aperitif cart that roams the halls for guests to enjoy in-room pre-dinner cocktails! Because space is limited, call for reservations months in advance to ensure booking!

Sip, see, and savor the flavor in Nantucket

Lighthouses Galore

Glance through any guidebook or blog regarding Nantucket and you’ll most likely come across one or several images of the Brant Point Lighthouse. Located near Jetties Beach, the Brant Point Lighthouse is the second oldest lighthouse in the country and has been in service since 1746. Another picturesque lighthouse to visit before departing? The Sankaty Head Lighthouse with its famous red stripe. It’s a bit further from town, but the Siasconset landscape and views are unbeatable.

Setting Sail with Endeavor Sailing

I love getting a new perspective of a city which is why I thoroughly enjoyed getting on the water with Endeavor (even through the sprinkles and cooler weather!). If you’re looking to rent a boat while on the island, Captain Jim is happy to be your fearless leader behind the wheel of his 31 ft. sailboat. He’ll also teach you some crazy fun sea shantys that begin with “What do you do with a drunken sailor?” Trust in the activity. It’s a win.

The boat brings people together. -Captain Jim

Nantucket Whaling Museum

Since Nantucket was once the hub of the whaling industry in the 19th century, it’s no wonder that the island’s Whaling Museum is filled with interesting fun facts, exhibits, and maritime history. The coolest part? A 46-foot sperm whale skeleton hung from the ceiling. I got major Moby Dick vibes touring the museum which is no surprise considering Herman Melville was a Nantucket tourist!

Cisco Brewers

If you do anything in Nantucket, just visit Cisco for the love of God. I had the pleasure of attending a casual welcome party at Cisco Brewers during my first night on the island, hosted by Southern Tide and OCEARCH, an insanely cool shark conservation nonprofit that is teaming up with the apparel brand and a partnership that first blossomed at Cisco Brewers a few years back between the two companies. The brewery is actually a winery/brewery/distillery combination with lots of casual outdoor seating for enjoying a drink after a day at the beach. Cisco Brewers is definitely the place to be seen on the weekends in Nantucket and gets huge crowds on holiday weekends. The grounds host a variety of food trucks offering up local cuisine such as lobster rolls, freshly shucked oysters, crab legs, mac & cheese egg rolls (yes you read that correctly) and more. I’ll spare you the rest so as not to spoil your dinner.

If you went to Nantucket and didn’t go to Cisco, did you really go to Nantucket? -Chris Heyn, CEO of Southern Tide

Shop til you Drop

Nantucket makes spending every penny in your bank account veryyy easy. A few areas concentrated with amazingly beautiful apparel, accessories and trinkets makes for successful outings and depleted wallets one Shift dress at a time. Shout out to my Bracey girls for staying to meet me at the Shift store (the cutest contemporary apparel featuring over 75 brands) during our Southern Tide party. Y’all made my day!

The Juice Bar

Peruse Nantucket instagram mentions and there’s a solid chance you’ll come across a snap from The Juice Bar, a Nantucket institution. There’s a catch – The Juice Bar, while serving an array of smoothies and juices, is actually famous for it’s homemade ice cream. Not so healthy, I realize, but my scoop of mint chocolate chip was DEFINITELY worth the cals.

Jetties Beach

Southern Tide Seersucker Bikini

During my first afternoon on the island, I headed straight to Jetties Beach, only a short drive from downtown and a little more relaxed and scenic for those wanting a chill beach day. Before dipping my toes in the sand, I made sure to devour my first Nantucket lobster roll for lunch at the Sandbar Jetties Beach. That may sound like a lot of food before flaunting a bikini but…YOLO.

Surfside Beach

WHALES. We saw whales on our last morning here in Nantucket! It was the best farewell we could have asked for, alongside the best last lobster roll that I inhaled at the beach shack a few yards away. Surfside is super chill and laid back, ready for anyone to bike to its shores and spend the day whale watching from its warm sands.

Millie’s

Never have I ever devoured a queso, guac and salsa trio quite like I did at Millies, a crowd favorite eatery on the island. It’s the age old problem of eating too much during appetizers and thus, being too full to do your entree justice. But alas, my lobster quesadilla and I did some work. I highly recommend Millie’s for dinner, especially if you’re with a big group. Eat outside at their long picnic table and drink/laugh the night away. I loved the convo I had with a local on the island. Holly is the mastermind behind Nantucket BlACKbook, a modern day guide to Nantucket that highlights advocacy of certain local companies instead of advertising. She’s also full of woman power.

Women are now the breadwinners, so find someone who will elevate you in everything else. The future is female, obviously. – Holly Finigan

‘Sconset

If you visit Nantucket, you must take a stroll around Siasconset, aka ‘Sconset. The floral-covered houses and adorable cottages are enough to make you visit the local real estate office. Yeah…probably never wanted to do that before, but this eye candy is unlike anything you’ve ever laid your eyes on. The area’s beach is notoriously less crowded than the beaches closer to downtown, and the bluff views are otherworldly. The neighborhood is also home to Sconset Market, a local market famous for their homemade goods such as granola and other sweet treats.

Meet Interesting People

This may sound obvious, but meeting interesting people doesn’t always happen on each and every trip. One of my favorite aspects of Nantucket is its people, no matter if they are seasonal or there for the long-haul. They have an entrepreneurial spirit about them that I admire greatly. From Southern Tide supporting OCEARCH’s marine research mission to Holly’s collaborative nature to the Sunday Market greeting cards I bought where 50% of proceeds go towards the Sailing Stork Fund, it was immediately apparent to me that I was witnessing an island that was full of special inhabitants. Not only did they create businesses for themselves, but they go a step further in supporting other businesses and incorporating causes that drive them to make good for an abundant future.

It’s in your best business interest to do interest and make good for an abundant future. – Chris Fischer, Founding Chairman of OCEARCH

I want to give a special shout out to the people I quoted above, alongside my new BFF Kahdel, ready to be at your service for all of your transportation needs. We learned that hiring a car & driver is much easier to do on the island than waiting on an Uber ride, to only most likely get canceled.

I love the opportunity here. You can be somebody on this island really fast as far as being successful goes. I took an idea, meditated on it, and made it my dream. From that dream, I made it a reality. -Kahdel

Kahdel Transportation Services: 508-648-9619

Nantucket, you were a dream to visit and I can’t wait to return, travel delays be damned!