The Day Tripper’s Guide to Nantucket

Nantucket, MA is an island rich with history, fresh seafood and scenic ocean views. Perhaps you know of the Island from Herman Melville’s “Moby Dick,” or its annual and internationally renowned sailboat race, Figawi. Authentically historic, there’s a feeling of nostalgia in the Island’s breeze, and its 18th century roots are shown off in the shops nestled close together with hand-painted signs clanking above the entryways, tiny alleys cluttered with shoppers, and chunky cobblestone walking paths.

With the help of our friend Abby Capalbo, we’ve assembled a quick and easy guide for those planning a day or weekend trip to the ACK (a local nickname derived from the Nantucket Airport’s call letters).


Nantucket has a dress code all its own – preppy, relaxed and beachy. Double-check that you’ve packed plenty of items to protect you from long days in the sun. This includes a hat to shield your face, and a full bottle of sunscreen.

Then, stuff your suitcase with all the essentials for small island exploration: a camera to capture the lighthouses, wharf, beaches, and cobblestoned streets; comfy shoes to walk and bike; and, believe it or not, a wrap to cover up when it gets cold along the water. Since the island is often fog-bound, the chances of getting chilly – even in the hot summer months – are high. They don’t call Nantucket “The Grey Lady” for nothing!


Those visiting the island should ride as the locals do – on two wheels! Rent a beach cruiser for the day to get a true sense of the island. There are over 30 miles of bike paths, all of which offer a unique way to explore.


Whatever your goal, there are plenty of must-sees and delicious eats to indulge in during your time in Nantucket. First stop: the art galleries located near the harbor and Old South Wharf. Visit to see amazing collections of landscapes and coastal scenes by local artists.

Next, wander back in time with a trip to the Whaling Museum, located in the original candle-making factory in Nantucket. The museum is over 80 years old and currently includes an exhibit on the legend behind Moby Dick. Back in its prime, Nantucket was once the hub for the whaling industry and has maintained the look and feel of this time period since the industry declined in the 1850s.

Once you’ve had your fill of history, pop into the Club Car for a drink to refuel and perhaps even a tapa while you’re at it. This Nantucket staple is in a refurbished railway car, featuring California Cuisine and a menu full of your seafood favorites.

Close your day with a stop at Bodega on Candle Street for light shopping of all the housewares you can imagine – candles, table settings, throws, you name it.

There’s a reason people fall in love with the ACK. Above all, our recommendation is to make it your next day trip and experience the charm firsthand.


48 Hours on Martha’s Vineyard

What would you do with 48 hours to spend in the sun and on Martha’s Vineyard? We asked local influencer Annah Todd for her recommendations on how to make the most of your time on the vineyard.

Martha’s Vineyard is one of those rare well-known vacation destinations that not only meets your expectations – it actually exceeds them. To take full advantage of the island itself, you will need a car, and if you can, find your way onto a boat. The travel to Martha’s Vineyard itself is an easy 40-minute ferry ride from Woods Hole or Falmouth, and there are lots of ferry options depending on when and from where you are coming.

Martha's Vineyard

Photography shot by Jack Callahan

I visited Martha’s Vineyard for a weekend at the beginning of June. The weather was perfect for breezy linen tunics and flowy silk dresses – and we even managed to squeeze in some time at the beach! Below are my recommendations for the best Martha’s Vineyard activities. If you can, stay longer than a weekend.

Cliffs and Beaches

Aquinnah, MA

The clay cliffs of Gay Head are striking. Unlike anything I’ve seen on the east coast before, the cliffs are a vibrant terracotta color. They are protected, but you can get a stunning vantage point from the Gay Head Lighthouse.

Annah Todd on Martha's Vineyard

Photography shot by Jack Callahan

For an even better view, I recommend walking down to Moshup Beach.  Moshup Beach is public so depending on the time of year you visit, parking may or may not be an issue, so consider the time of day and season. The cliffs and beach are located on the most western point of the island, resulting in an unbelievable sunset.

Annah Todd on Martha's Vineyard

Photography shot by Jack Callahan

Chappaquiddick Island

Chappaquiddick, MA

Rent bikes and take them on the small Chappy Ferry, to Chappaquiddick from Edgartown.

It’ll cost you $6/person round-trip and the ferry ride takes about five minutes. The ferry’s slogan is endearing and fitting: “Back and forth between two worlds – 527 feet apart.” Almost 1,000 acres of land is preserved on Chappaquiddick Island by The Trustees of Reservations, and the island truly feels like an entirely different place than the bustling streets of Edgartown. While you cannot really go wrong with anything on Chappaquiddick Island, East Beach (otherwise known as Leland Beach) in the Cape Poge Wildlife Refuge is my absolute favorite. With salt marshes, 14 miles of trails, and seven miles of remote beach, I highly recommend packing a snack and enjoying the isolated and peaceful excursion.

Annah Todd on Martha's Vineyard

Photography shot by Jack Callahan

Ice House Pond

West Tisbury, MA 02568

I would never have found this swimming spot if an old friend who summers on the Vineyard hadn’t told me about it. He described it as “unusual and difficult to get to,” so naturally, I knew we had to check it out. Ice House Pond is a secluded pond inside Martha’s Vineyard Land Bank Commission preserve and it’s a well-worth trek off the beaten path. When you arrive, parking is extremely limited (only four spots). Since there is no beach at the swimming hole, it’s a destination more reserved for adventure seekers than families, but there is a perch where you can slip into the crystal clear freshwater and enjoy a long swim. The pond’s name comes from its industrial past: the Vineyard Ice Company, from 1908 to 1953, ran an ice-harvesting operation out of the pond.

Annah Todd on Martha's Vineyard

Photography shot by Gretchen Powers

Back Door Donuts

5 Post Office Square, Oak Bluffs, MA 02557

I was hesitant to try Back Door Donuts, I will admit. Everyone told me to go, and frankly, I’m more of an ice cream kind of girl rather than donut. However, I acquiesced and found myself waiting in a 40-person line one evening, and boy, was it worth it. Open only at night (7:30 PM – 1 AM), the donuts were incredible. The kind woman working behind the counter recommended the apple fritter but after seeing the magnitude (they are approximately the size of a football), I opted for the classic chocolate glaze. Worth every bite.

Behind the Bookstore

46 Main St, Edgartown, MA 02539

While I cannot vouch for Behind the Bookstore’s food offerings, I can tell you that their espresso drinks are fantastic. We went right when they opened, around 7 AM, and ordered cortados and sat under the tent. The sun was so bright and the foliage around the tent was so lush, it had a very ethereal feeling to it.

Annah Todd on Martha's Vineyard

Photography shot by Jack Callahan

Creative tips for traveling with kids

Low-tech entertainment for your next family vacation

As the season of family road trips and airplane travel approaches, it’s a good idea to have some fresh strategies ready to keep kids happy and occupied. Tablets and phones can be great in a pinch, but we love creative and interactive activities. Here are a few favorites:

Ask the kids to document the trip with an instant-print camera

Ocean Photos
You know, the old-fashioned kind. Introduce your kids to the joy of snapping a photo and waving it around in the air as you eagerly wait to see what develops.

Pro tip: You’ll want to ration the film – maybe even hide some extra in your bag – so you don’t run out before you’ve even left the driveway.

Create a collection with free (or nearly free) found items

Travel Bag
Anything from rocks, to sea glass, to coins, to flowers for pressing. Next, decide on some creative ways to catalog where you found each item and what it reminds you of.

Pack a journal/scrapbook with supplies

Butterflies on a Book
Give your child a journal for doodling, writing, and pasting in their photos. A blank book plus a glue stick, stickers, crayons and colored pencils for the younger set, and markers for older kids are all a good start.

Bring along a family mascot

Golddish in a Bowl
Pack something meaningful, but not priceless, like a photo of a pet who couldn’t make the trip or silly knickknack from home. Tote them along for funny photo ops and share their journey with family and friends.

Play some travel-friendly family games

Remember I-Spy? License-plate bingo? 20 questions? All of those car-trip classics are just as fun for kids now as they were back then, and they have the added benefit of engaging little imaginations.

Refresh your memory on how to play, and discover more games you may not know.

If you have the space, pack UNO, Go Fish, and Travel Yahtzee for more options.

Make a big deal out of little thrills

Kids are experts at this. The hotel elevator, the frog in the grass by the parking lot, the tiny swing set at the playground (rather than the over-the-top rides at the amusement park).

As every parent knows, the things you expect to make an impression are often not what kids are still talking about months and years later. And really, that’s part of the magic.

Step back whenever possible and let the kids take the lead. You may find it’s the key to your best vacation memories.

What are your suggestions for keeping everyone happy on a family trip?