While each of our guides aims to offer simple advice in a format that's easy to navigate and share, we recognize that not all travel enthusiasts can translate that information into an actionable plan. We also understand that not everyone has the bandwidth to take on the details of planning a trip. If you would like to purchase a turnkey itinerary that outlines a four nights in Gloucester and then goes further to identify exactly how to structure a two week road trip across the northeastern seaboard, click here to purchase our New England Itinerary: Cape Ann to Bar Harbor.

Where are we going?

Cape Ann is otherwise known as "The Other Cape."

Thirty miles from Boston sits the lesser-known eastern Cape Ann, and the quaint coastal communities of Rockport, Essex, Manchester-by-the-Sea and Gloucester, which will soon celebrate its 400th anniversary as America's oldest seaport. The area greets you with charming cottages, sandy beaches and seaside eateries like many have grown to expect of New England’s rocky coastline.

When should we go?

Ideally July to September

August in Massachusetts tends to be a sure thing weather-wise, but Labor Day weekend if you can arrange a visit to catch the Schooner Festival, it’s pretty spectacular.

How do we get there?

We fly direct from MSP to Boston. Then drive 40 miles north to Cape Ann. It’s easy, no ferry rides or small planes to catch. You’ll be on a beach within an hour of landing in Boston.

Where do you stay?

We love this place so much we purchased a rental property, but I still love a family staycation at the Beauport Hotel in downtown Gloucester. I equally adore a romantic getaway to the historic Emerson Inn by the sea in Rockport. If you are searching for properties, Atlantic Vacation Homes is a great resource for summer rentals. Accommodations on Rocky Neck will put you in the heart of America’s oldest working art colony in Gloucester.

If your preference is to stay in a hotel there are several good options along the back shore of Gloucester. The Atlantis Oceanfront Inn and the Ocean House Hotel at Bass Rocks are both within walking distance to Good Harbor and overlook the Atlantic Ocean. If a smaller hotel is more your style, look at Addison Choate in Rockport. It’s an historic inn that has a lot going for it for only seven rooms.

What should we do?

The ocean is your playground

There are several incredible beaches in the area but my personal favorite is Good Harbor, with its endless tidal pools for young children to explore, waves strong enough for boogie boarding and evening surf lessons with Surfari Gloucester, when the beach quiets down. It’s best to bring a picnic dinner while your kids learn to surf. I suggest the lobster rolls from nearby Charlie's Place or Surfside Subs, both tasty options and the best deal around. Treat the surfers after their lesson at the nearby Long Beach Dairy Maid -- just be sure to ask for a "kiddy" or be prepared for the largest cone you’ve seen in your life. 

7 Seas Whale Watching is an unbelievable experience with guaranteed sightings and Cape Ann Whale Watch takes you out with marine biologists on board. Alternatively you can charter a daytime fishing excursion with Yankee Fleet to reel them in alongside folks from the popular National Geographic Show "Wicked Tuna." Really, you'll likely see them shooting while you're out on the water. If you’re prone to sea sickness you can buy your sea bands at a nearby pharmacy and do what the fisherman say and, “keep your eyes on the horizon.” I also suggest you consider taking a schooner ride aboard the Lannon or the Ardelle out of Gloucester, very family friendly and extra special at sunset.

The Gloucester Maritime Center is full of touch tanks and fascinating exhibits on the marine life of Cape Ann. The Cape Ann Museum holds world class art by artists who flocked to the area in the summer like Winslow Homer, Edward Hopper and Fitz Henry Lane. Once you explore the coast or catch a Cape Ann sunset, you'll know why! The museum has a terrific children's art room with interactive opportunities, a gift shop full of woodblock print masks and adorable children’s tees, as well as a summer exhibition that's always worth the trip! While we’re talking museums, The Beauport Museum on Eastern Point in Gloucester is the summer home of the first interior designer in the US, Henry Davis Sleeper in the early 1900s. Incredible!

Other parts of Cape Ann worth exploring would be Halibut Point State Park in Rockport. It’s extraordinary, made up of granite estimated to be 440 million years old. There are hiking trails and tide pools, and it’s ideal for picnicking. If you go, you’ll want to visit nearby Lobster Pool for a fun eat-in-the-rough, family friendly meal. 

Where should we eat when we’re there?

Let’s start with the best beach food, and it’s not seafood! Check out the Italian bakery Virgilios and the classic sandwich shop, Destinos. You haven't had a real Italian sub until you try the "St Joseph" at Virgilios or the "Italian with the Hots" at Destinos. Both delis offer catering, take-away and a whole lot more than bread.

Our favorite breakfast spots in Gloucester include Sugar Magnolia's, Mom's Kitchen, George’s and The Atlantis on the Back Shore. Two Sisters Coffee Shop is another amazing breakfast spot with delicious Italian style hearty breakfast offerings like, fishcakes, lobster eggs Benedict, Anadama bread and linguisa.

For lunch, the best chowder can be found at The Causeway. Huge chunks of fish like you’ve never had in a chowdah before. The east coast is rife with local seafood spots offering fresh off the boat delights and plenty of local charm. You’ll find everything lobster at Lobsta Land overlooking the Great Marsh. It’s very family friendly and they make fabulous cocktails. Go for the catch of the day. Another favorite for seafood, including those famous lobster rolls and delicious clam chowder, is Charlie’s Place. Grab some take away delights to enjoy for a picnic on Good Harbor Beach. Finally, en route from Gloucester to Rockport, Willow Rest is another amazing spot for gourmet beach food.

In the evening, stroll down Rocky Neck in Gloucester with gallery after gallery to pursue on your way to dinner on the deck with the kiddos at The Studio. The Gloucester House restaurant is also a wonderful family-friendly place to soak up the working waterfront, perfect after your whale watching adventure.

You’ll find true sea-to-table amazingness, like fish stew, at Feather and Wedge in charming downtown Rockport. A stone’s throw from world renowned concert venue with pitch perfect acoustics and retractable curtain that lifts onto the ocean. A feast for the senses. Date night is best served at the lovely Franklin Cafe in downtown Gloucester, or over a plate of authentic Italian at Tonno.

Where can we grab a drink?

Short and Main, The Franklin or the Beauport Hotel in downtown Gloucester make great cocktails. The Lone Gull is perfect for an afternoon latte, Caffe Sicilia has your real Italian coffee, and Cape Ann Coffee has a great drive-thru on the way to Good Harbor Beach. 

“This is a coffee town -- for anyone missing Dunkin' Donuts, there's practically one on every block! I'll take a Big One "regulah" please!”

Tell us something we don't know?

Much of the award winning film Manchester by the Sea was actually filmed in Gloucester. There’s a joke around here….Manchester by the Sea, Gloucester by the Smell. Although when we’re in Gloucester and we smell fish, we’re just happy that the fishermen are keeping Gloucester’s working waterfront alive and full of healthy sustainably caught seafood. Stop by Steve Connelly’s Seafood on your way out of town for lobstahs-to-go. Perfectly packed in seaweed and ready for the plane ride home.

Where can we shop?

Antiquing in Essex is second to none. You'll find treasures galore at Andrew Spindler Anitques & Design, with 17th - 20th century antiques from the homes of sea captains and art collectors in Cape Ann. And while you’re in Essex, be sure to take a scenic cruise with the Essex River Cruises and Charters, and if possible go for the optional tidal beach clambake!

In Gloucester you’ll find a cluster of great shops on Main Street, the first of which is a feast for the eyes, Bananas. Hands down it’s one of the most fun vintage stores you'll ever experience. Always worth a trip to pick up some baubles and delight in the artfully decorated window displays. The kids will also love Toodleloos, old fashioned toy store.

If you need an extra layer for the whale watch or sunset cruise, don’t miss the Gloucester fishermen’s mainstay, Nelson’s of Gloucester. For all things surf and sea, head to Gloucester’s Surfari!

The Brass Monkey has the best Cape Ann/Boston sweatshirts and baseball hats. The Bookstore of Gloucester has excellent beach reads and delightful sea-centered children's books that make great gifts. You’ll find the most delicious homemade bread, local gifts and woodblock print cards at Alexandra's Bread Shop. And finally, hop on the Mystery Train for a flashback to your youth with rows of albums, rare vintage music finds and a super knowledgeable staff to help you find the soundtrack to your Gloucester visit.

What should we take with us on the trip?

Cape Ann is very casual so you can leave your fancy clothes at home and just relax by the sea. I suggest a few easy-breezy cotton dresses from Mille. Versatile enough for the beach, and easily dressed up with these amazing Mercedes Salazar earrings for the evening lobster bake. I’m also obsessed with the nautical jewelry made by Chloe Sevigny’s sister in law for Serpentsea, and the bangles from Ivory Reed (pictured below) which pair perfectly with any summer seersucker.

Pack all of the stripes! Especially a sweater for the sunset sea breeze and a raincoat for the boat, just in case. You’ll want sunscreen, terry coverups, and a good picnic/cooler bag. On this trip you’ll also need the perfect beach tote. If you don’t have one that you love, then just pick one up while you’re on the island. My favorite (pictured below) is made from retired spinnaker sails that once blew in the Atlantic Ocean. They can be customized (one week turnaround) by local maker Regina Loiacano of Again and Again, or you can pick out your favorite from the Beauport Hotel gift shop.

What’s the one can’t miss item on your itinerary?

Salt heals everything and you will never regret spending the day with your family at Good Harbor Beach. Just get to there by 9 am for parking because the lot fills up fast on a "beach day!" And remember please don't feed the seagulls!

What will you do differently on your next trip?

We love Gloucester and spend most of our time centered there, but we always try to explore further in Cape Ann on every visit. Essex is always fun for fried clams at Woodman's or Farnham’s, and the best antiquing around. Assuming of course you can convince your children it's “just a detour” on the way to Crane’s Beach. Crane’s was most recently captured in a breathtaking scene from Greta Gerwig’s remake of Little Women. And if you go you’ll want to allow a few hours to explore the sprawling mansion and gardens at Castle Hill. Further down the road you'll find Russell Orchards with endless berry picking, fall apple picking and the best apple cider donuts on Cape Ann. Manchester's Singing Beach is also lovely, and so is Coolidge Point -- an unbelievable place to park a picnic, rock climb and fly a kite in the sea breeze. The fresh air and simple life is waiting.