Full disclosure: Though I “actually” grew up in New York City, I “practically” grew up on Cape Cod. With my grandparents calling it their year-round home since my dad was a kid, my childhood trips to the Cape from the icy chill of mid-February to sun-soaked summers that last long after Labor Day,  have always held a special place in my heart.

My Life-Long Love Affair with Cape Cod

I love the stories my father tells of his summer adventures as a kid in the Cape. These started when he was picked up on the last day of school, the car still running, packed to the brim with everything his Boston-based family would need for a summer on the Cape.  Not once did they step foot off the island – why would they – until the first day of school in the fall. 

The Cape has decidedly changed since then, yet much of it remains the same. And that’s where its allure and beauty lie. Nestled among trendy new restaurants, bars, boutiques, and luxury hotels, are long-standing family-owned bakeries, cute old single-story shingle cottages with their steep pitched roofs, and decades-long traditions like evening bandstands.

From the best hotels to little-known brunch spots; must-walk main streets, and the best beaches alike; here is my insider guide to visiting beautiful, charming Cape Cod—no matter what time of year.

The Best Places to Stay On the Cape

Image Courtesy of Ocean Edge Resort

Cape Code is peppered with quaint inns and seaside resorts that all evoke the unmistakable charm of the Cape.  Though I am lucky I get to stay like a local at my family’s house, my career as a travel writer has afforded me the luxury of experiencing some of the best hotels on the island.

Chatham Bars Inn

By far, the crème de la crème, The Chatham Bars Inn, located right on the beach, is within walking distance to one of the best main streets on The Cape.  Here you have the choice of staying in either the main house or one of their many shingle-style cottages situated along the property’s bluff. Built, in 1914 as Cape Cod’s first luxury hotel, it underwent a $100 million renovation in 2015 and perfectly retained its deep history while being given a modern update.

Ocean Edge Resort

Another mainstay that attracts locals and tourists is Ocean Edge Resort, where you can stay in a huge suite in the main mansion or a condo-style room in the villas on the property. If you’re looking for a golf vacation, Ocean’s Edge has a fabulous course. And when you’re not golfing? The hotel plays host to a private beach where you can swim and nap in seclusion or take advantage of the fully staffed service if cocktails and small bites by the water’s edge take your fancy. I also highly recommend dining at the hotel’s Ocean Terrace, a sprawling bar and restaurant overlooking Cape Cod Bay. And, with heaters installed you can enjoy the view and the delicious food year-round.

The Best Breakfast Spots on The Cape

Image Courtesy of Snowy Owl Coffee Roasters


A local gem, Grumpy’s is a family-owned old-school roadside coffee shop and cafe. I fondly remember sitting at the counter with my grandfather and his retiree friends having breakfast at the ripe old hour of 6 am, and I’ve continued to go back over the decades since—and brought friends along with me to experience this institution.  And I can say with certainty that they do a killer breakfast, the best in the Cape hands down. If you’re after a homestyle comfort meal of coffee, eggs, French toast, or pancakes, this is your place. Don’t be deterred if you see a line of people waiting outside. It moves quickly and is well worth the wait.

The Red Cottage

For the best home fries on The Cape, head to The Red Cottage restaurant for a homestyle and homemade breakfast where the classic breakfast potato side dish is the main attraction. You’ll likely have to wait, and the parking lot quickly overflows into side-of-the-road pullovers, but there’s a reason that so many people continue to stand in line for this epic hearty breakfast meal. Insider tip:  Whether you try it as a sweet addition to your meal, or simply want to take it home to indulge, don’t leave without picking up a loaf of their old-fashioned homemade cinnamon bread to go.  

Snowy Owl Coffee Roasters

An honorable mention goes to Snowy Owl Coffee Roasters, which opened in 2015 as a cozy coffee house. They brew delicious coffee, tea, matcha et al and have a variety of grab-and-go breakfast pastries, local chocolates, and sweet bites that promise to delight.  Our back is an apothecary-and-herb-style store that sells everything from crystals and incense to herbs and plants.

The Best Lunch Places on The Cape

Image Courtesy of The Mercantile

Spoon and Seed

Another newish addition to the Cape Cod culinary scene Spoon and Seed offers house-made fare infused with local ingredients in support of the community. The menu is eclectic and of the moment, without feeling overly trendy. Selections range from a brussels sprout salad with squash and chickpeas to a vegetarian orecchiette with “mushroom bacon,” and all offer combinations that you never would have expected, but now can’t imagine life without. 

The Mercantile

For a grab-and-go option that will send you off to the beach with the absolute best sandwich in town (although you are also welcome to swipe a seat inside) head to The Mercantile, a mainstay of Dennis Village. . Though they have classic menu items like a BLT,  Blarney,  a vegetarian’s dream), tuna melt, Italian sub, or their epic broccoli salad you can also craft whatever it is your heart desires. This is deli eating at its finest, with a family-owned familiarity that has been maintained since its inception. Not in the mood for lunch, I suggest snapping up one of their killer muffins or breakfast pastries that, while offered all day long, certainly will not last long.

The Best Restaurants for Dinner on The Cape

Image Courtesy of Cuvée at the Chatham Inn

Harvest Gallery and Wine Bar

No matter what season you’re visiting, Harvest Gallery and Wine Bar will not only be open, but also packed. It’s a fun place in the summer, to be sure, but such a cozy option in the winter as well. They have a huge selection of wine and beer, and killer wine flights that ensure that you don’t have to choose just one. The food is just what you would expect of a wine bar, and everything is delicious—from charcuterie plates to flatbread pizzas, salads, sandwiches and fish. Though their entrées are fabulous, it’s really all about the appetizers, so consider it an insider tip and order as many as you want to share with the table.

Cuvée at the Chatham Inn

If you’re looking for a more formal dining experience, head to Cuvée at the Chatham Inn. It is Cape Cod’s only Relais & Châteaux restaurant and opens all year-long, though their days and times vary depending on the season. The menu is seasonally inspired and locally sourced with an emphasis on fresh fish, lobster and wagyu beef.  Order, off-menu, the 7-course tasting menu or be seated at the chef’s table for an unbeatable experience.

The Best Beaches on The Cape

As a small island—it doesn’t take long to drive from one end to the other—it goes without saying The Cape is surrounded by fantastic beaches. While some are more crowded than others, and some have more amenities, you really can’t go wrong when it comes to picking the perfect sandy spot. A couple of my faves:

North Beach Island

Right off the coast of Chatham and only accessible by boat or water taxi, North Beach is one of the emptier beaches on The Cape. There is nothing on the island besides the beach itself, so make sure to pack all that you might need.  The effort is worth it to travel to Cape Cod and  find a beach where you might not see another human is quite magical.

Corporation Beach

I’m also quite partial to Corporation Beach in Dennis because it’s where I went the most growing up  but it is also one of the most beautiful. It’s almost like a lagoon at high tide, with a crescent-shaped shoreline on the bay side of the island. At low tide, the beach extends seemingly forever, making it a great place to come at night for kite flying and dinnertime picnics.  Not to say it’s not also wonderful during the day to be able to spread out with your friends and family, especially with its stone jetty and pebbled inlets which make it a great place to swim as well as walk and explore. 

Where to Get the Best Lobster Roll on The Cape

Ok, if you didn’t get a lobster roll, did you even go to New England? Hands-down the best lobster roll is at Sesuit Harbor Café. Though the dates vary slightly, this seasonal restaurant is open roughly from the end of April through the end of September, weather permitting. All dining is outdoors, and you walk through a tiny shack and into a pebbled dining area right on the harbor. The picnic tables are first come, first served, and all alcohol is BYO.  Needless to say this place is packed for breakfast, lunch, and dinner – with those seeking the best lobster rolls on The Cape. What’s more, they also have a killer raw bar if you fancy throwing back a few oysters. .

Where to Go for Sweet Treats on Cape Cod

As a true New England town, The Cape is loaded with homemade ice cream parlors and old fashion candy shops. I can say with authority, after trying nearly all of them, that the best ice cream parlor is the Ice Cream Smuggler. They’re seasonal (they all are on The Cape), though the season is long. The Smuggler offers 27 homemade ice cream flavors and 4 frozen yogurts and has been family-owned since its first season in 1979 (by three separate families, all friends of one another through the generations). One of the few ice cream parlors on The Cape that has that true throwback feel and continues to churn out the same great quality of ice cream as they have for decades. Two other must-mentions for a sweet treat at all hours are Nancy’s Candy of Dennis and the Chatham Penny Candy Store. While Nancy’s is a bit larger, offering everything from homemade fudge to penny candy; gifts and toys, it and the Penny Candy Store located further out on the island offer that nostalgic choose-your-own-adventure scooped candy that make adults feel like kids and kids feel like they live in a Willy Wonka wonderland.

My Favorite Places to See, Shop, and Explore on Cape Cod


Cape Cod is all about the neighborhood main street, each town taking on its own unique personality. For a classic walk that’s filled with penny candy store nostalgia and updated New England shopping head to Chatham and walk through the town’s staple T-shirt company, Chatham Clothing Bar, past preppy The Black Dog, and stop for lunch (and a cocktail) at the Wild Goose Tavern when you need a break or to re-fuel. In contrast, for a whimsical, artistic, and larger-than-life stroll, drive out to the tip of the island and take a walk through Provincetown. There, you’ll find not only the Provincetown Art Association & Museum, a celebration of the town’s history as America’s oldest active art colony, but also the Lobster Pot, which offers up lobster in more ways than you’ve ever even seen —and will likely ever see again. After that, go vintage shopping at Marine Specialties, which celebrates the town’s colorful history in more ways than one. Be sure to stop in as many art galleries as you can, peppered throughout the town, to immerse yourself in Cape history and culture. 


Story brings a touch of high-end style to New England with elevated contemporary fashion from established and emerging designers. Instead of shopping for vintage-style cutoffs, nautical tees, or Breton stripe sweaters, you can stock up on floral mini dresses, puff-sleeve tops, knit tanks, and more. More of a bookworm? The quaint Brewster Book Store is a great place to visit and has an inspirational selection for every type of reader. Take the whole family and fan out once inside, wandering through fiction, historical biographies and children’s chapter books all housed in a classic Cape Cod shingle-style house that you could—quite literally—picture yourself living in. 

Bike Trails 

To experience a truly unique repurposed space head to the Cape Cod Rail Trail. Built on the site of the old railroad which used to transport passengers and freight throughout the 1800s, its closure around 1960 prompted The Cape to try to find a creative use for the winding, mainly flat, trail. The rail-trail covers a total of 25 miles that will take you through siix towns from South Dennis to Wellfleet. There are different entry and exit points throughout, making it a great activity for everyone from kids to avid riders.