Generations of travelers have made Cape Cod one of New England’s most iconic vacation destinations. The hook-shaped peninsula on the eastern end of Massachusetts is revered for its sandy beaches, family-friendly fun, and active LGBT community. It’s at its best in summer, when skies are sunny and the weather warm —though still a milder escape from the mainland heat.

Inspirato Members stay in the club’s Eastham Place residence, an estate that encompasses two homes and can accommodate up to 18 people. Located near the charming town of Eastham, this residence has a semi-private swimming pond in its backyard. Alternatively, members can stay at Inspirato’s resort partner, Chatham Bars Inn, a classic Cape Cod getaway perched on its own private beach.

A Cape Cod vacation is full of delicious seafood, bike rides along scenic trails, and long days in the water. With Inspirato, members can do all of that and even more. Keep reading to see our picks for the perfect five-day itinerary in Cape Cod.

The house was terrific -- spacious, with a great patio overlooking Jemima Pond. The location was convenient for local beaches, but also very secluded and private. Whale watching trip and dune tours are a must! Our concierge was extraordinarily attentive and helpful during the week -- this is a place we would definitely return to.

Tim GriffyInspirato Member

Day One

Morning

Start your first day on the Cape with coffee and a breakfast sandwich at Sunbird Kitchen in Orleans. The honey- and lavender-filled scones are to die for.

Afternoon

Pack a picnic lunch and head out to First Encounter Beach for the afternoon. This peaceful stretch of sand played host to the first meeting of Pilgrims and Native Americans in the New World.

Evening

Make your way back to Orleans and enjoy dinner at Mahoney’s Atlantic Bar & Grill. With the freshest fish, shrimp, scallops, and clams, Mahoney’s is a seafood lover’s dream come true.

Day Two

Morning

Pick up rental bikes and take a ride along the Cape Rail Trail. This 22-mile paved trail traverses the “elbow” of Cape Cod and can be accessed right near your Inspirato Residence.

Afternoon

After cycling to heart’s content, unwind and relax at home with a private in-residence massage. At all Inspirato Residences, club members have an on-site concierge to arrange details, and they will be happy to recommend top therapists in the area and make an appointment.

Evening

Unleash your inner child and enjoy pizza with a side of mini-golf and arcade games at Red Barn. Be sure to check out the attached gift shop for classic Cape Cod souvenirs.

Day Three

Morning

Head “down” to the Cape to Wellfleet and tuck into breakfast at PB Boulangerie Bistro. Part bakery, part bistro, this beloved gem feature pure French fare – don’t miss the classic pastries.

Afternoon

At the very tip of Cape Cod lies Provincetown, famous for its whale-watching. Let an experienced naturalist guide bring you up close and personal to these majestic marine giants.

Evening

Back in town, continue your seafood tour of New England with the succulent calamari and exquisite cod at Jimmy’s HideAway, a favorite haunt of both visitors and locals alike.

Day Four

Morning

After a leisurely breakfast in your residence, paddle and play in the nearby pond. Inspirato’s on-site team can help arrange boat or stand-up paddleboard rentals.

Afternoon

Cape Cod is home to thousands of acres of protected sand dunes. Let Art’s Dune Tours show you this unique landscape, along with its historic lighthouses and fascinating shoreline wildlife.

Evening

You can’t visit the cape without indulging at least once in a mouthwatering lobster roll. The Lobster Pot in the heart of Provincetown serves heaps of the delicious crustacean on toasted bread.

Day Five

Morning

While away the morning at Nauset or Marconi Beaches. Nauset stretches for 10 beautiful miles along the Atlantic, while Marconi features nature trails and a historic telegraph station.

Afternoon

Wander the quaint streets of seaside Chatham, where the art galleries and antique shops entice you to take home a memento or two from your time on the Cape.

Evening

Conclude your incredible Cape Cod adventure with a private chef-prepared meal in your Inspirato Residence. Raise a glass to the memories made and start planning your next vacation to the Cape.

Whether Inspirato Members are visiting Cape Cod for five days, a whole week, or just a quick overnight, they have a bevy of things to do and see — and they also have their Member Care team and on-site Destination Concierge to handle all the details. Learn more about Inspirato in Cape Cod and hundreds of other destinations around the world, and how the club changes the way members vacation.

2 Comments

  • donna reynolds says:

    looking for a home in Oct 6 2018 for a family wedding at chatham bars inn. At least 4 bedrooms in chatham or harwichport. Date starting oct 5.

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