The Key to a Family Holiday in Cape Cod, Massachusetts

Advisor - Nicole Sansone
Curated By

Nicole Sansone

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  • USA

  • Massachusetts

  • Cape Cod

  • Beaches

  • Domestic Travel

  • Family Travel

  • Nature Escapes

  • Slow Travel

  • Weekend Getaways

  • Coastal

  • Small Town

  • Sunsets

Advisor - The Key to a Family Holiday in Cape Cod, Massachusetts
Curator’s statement

A week-long break to the Cape is a family summer tradition for many New England families. There’s plenty of activities to keep you busy, that is if you can pry yourself away from being a beach bum till sunset. Today it continues to be a popular vacation destination for families from all over, choosing the region for its fair weather, privacy and recreation. Both adults and children alike indulge in the welter of experiences that this legendary peninsula has to offer.

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Where to stay in Cape Cod, Massachusetts

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Ocean Edge Beach Resort

Captain Freeman Inn

This sea captain’s mansion-turned-breezy boutique hotel is located within walking distance to the beach.

Pelham House Resort

The Pelham House Resort is a truly one-of-a-kind hotel in Dennis Port, Massachusetts. With a private beach, an oceanfront rooftop restaurant, a beachfront pool and an array of luxury amenities, it captures the best of Cape Cod to ensure a genuinely unique and fun guest experience. 

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Things to do in Cape Cod, Massachusetts

The Key to a Family Holiday in Cape Cod, Massachusetts - Things to do

When in Cape Cod, you’ve a bounty of activity, but you may also just want to stay at your resort. The private bayside beach club at Ocean Edge Beach Resort provides chairs, umbrellas and food and drink service from the beach bar overlooking the bay. You can rent kayaks and paddle boards for an additional cost. At low tide you can walk down miles of beach taking in the waterfront homes in Brewster. You must also see at least one sunset over the bay! You can enjoy a private bonfire and s’mores on the beach right at sunset too.

The mansion lawn is a fun spot for adults and kids. Food and drink, lounge chairs, fire pits and games are set up with live music to enjoy on the weekends. Play a game of golf and tennis at the resort, with lessons provided, or pickleball. 

When venturing outside of the hotel, set up a private oyster tour and indulge. The Cape Cod trail is close by too and lovely for an afternoon bike ride. Check out the Cape Cod Museum of Natural History too. In addition to museum exhibits, you can walk the trails over the marsh and to the beach. There is a butterfly exhibit in the summer and a mud kitchen for toddlers to go crazy. And when you’re in a mood for a chill evening, drive out to the Wellfleet Drive-In Theater for an outdoor movie experience. 

Boozy Libations 

A compilation of breweries like the Cape Cod Beer, Devil’s Purse Brewing Company, Hog Island Beer Co. and the Provincetown Brewing Company are also available. More of a vino lover? Check out the Truro Vineyards, Cape Cod Winery and First Crush Winery


Shopping in Chatham or Provincetown is a must to outfit in your Sunday best. While you’re at it, sign up for the Arts Dune Tours for an experience of a lifetime exploring the dunes of the National Seashore Park. 

You can also go whale watching from Provincetown and charter a fishing trip. Kayaking and clamming trips are quite popular as well in this marine heaven of a destination. 


When in Cape Cod, the beaches can be quite diverse ranging from bayside options to the ocean side. For bayside beaching, head out to Mayflower Beach in Dennis and Skaket Beach in Orleans. For stunning ocean-side beaches Nauset Beach in Orleans, Cahoons Hollow Beach, as well as Marconi Beach in Wellfleet are lovely choices for an afternoon of water activity and suntanning. Beachcomber is the bar & restaurant that overlooks Cahoons Hollow Beach, and is another great spot to visit if you're looking for a space with beach views.

Day trips 

Take the high-speed ferry to Nantucket or Martha’s Vineyard. Boston is only a 1.5 hour drive away.

Eat & drink in Cape Cod, Massachusetts

The Key to a Family Holiday in Cape Cod, Massachusetts - Eat & drink

Ocean Edge: This resort offers a plethora of culinary experiences including a terrace bar, beach bar, and lawn, including spectacular room service too. 

JT’s Seafood: A local’s favorite eatery featuring the freshest ingredients from the bay. 

Brewster Fish House: Curator’s favorite restaurant set in a charming cottage and serving curious twists on traditional seafood dishes. 

FIN: High-end restaurant in Dennis that serves sustainable seafood dishes. 

Impudent Oyster: Craving some oysters? You can’t go wrong here!

Chathams Bar Inn: One of the most beautiful addresses in Cape Cod, this location features several world-class dining spots including a private organic farm. 

Sesuit Harbor Cafe: A laidback clam shack in Dennis that serves delicious lobster rolls. 

Chapin’s: Indulge in fish & chips at this Dennis restaurant. 

Grumpy’s: A hearty restaurant in Dennis perfect for an all-American breakfast and/or lunch. 

The Local Scoop: Need a refresher? How about a cone of ice cream in Orleans? This space is owned by a friend of my mom's, and it's one of the best local digs. Honey lavender (made with local honey) and lemongrass are my favorite, not your typical ice cream flavors. The Cape Cod pops are great too. 

Ice Cream Smuggler: Homemade ice cream shop featuring the classic flavors as well as some new ones.

Advisor - Nicole Sansone

Travel Advisor

Nicole Sansone

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