Captain Farris House

Aerial view of Provincetown, MA with boats on water with houses along beach

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Your 36-Hour Itinerary on Cape Cod

With so much to see and do, your 36-hour itinerary on Cape Cod will only get you started. But if you follow our carefully curated itinerary and first-hand experience here, we’ll guide you to the best ways to spend your few days and nights here.

For some, the Cape is an island, though technically attached to the mainland by two bridges that span the Cape Cod Canal. For others, this long and slender spit of sand that juts out into the Atlantic Ocean is simply a peninsula. But no matter what you call it, Cape Cod is a destination that merits multiple visits to unearth its scenic beauty.

You could spend days, weeks, even months exploring Cape Cod and never see it all. With 11 lovely towns and villages, miles of scenic bike trails, and dozens of sandy beaches fronting Cape Cod Bay to the north and the Atlantic Ocean to the east, every hour you spend here reveals something beautiful.

As innkeepers on Cape Cod, we’ve devoted a lot of time to finding just the right balance of sights to see and things to do to recommend to guests of our bed and breakfast in historic Bass River. We like to combine a little bit of exploration and a dollop of local color, with a pinch of retail therapy thrown in for diversion. Don’t worry, you’ll still have plenty of time to relax and enjoy our fresh local seafood and farm-to-table cuisine.

Day 1

Traveling from north, south, or west, to get to Cape Cod you must come over one of the bridges. As soon as you reach the apex over the Cape Cod Canal, roll down the windows and smell the salt air. It’s best to get an early start to your day, so plan on arriving before lunch if possible.


We recommend dining at Skippers Restaurant and Chowder House in South Yarmouth, across from Parkers River Beach. Sample their award-winning “chowdah” and some amazing fried, grilled, or baked fish dishes, lobster rolls, and a raw bar. No matter what you choose, you can always count on it being fresh. It’s walk-in only. So, put your name on their list and take a short stroll along the beach while you wait. You may want to continue that stroll after lunch and feel the sun on your face and the wind in your hair.

Check-in to the Captain Farris House

We welcome guests beginning at 3:00 pm. Ease into your Cape Cod vacation by relaxing in the garden or in the comfort of your luxurious room. Take a seat on the front porch with a complimentary cup of tea and a freshly baked sweet treat.

Dinner Options

We like to plan dinner around the sunset. Nearby options include the Old Yarmouth Inn, Chapin’s Bayside, or the Encore Bistro and Bar. Any of these lovely restaurants put you in a great position to catch the sunset at either Grey’s Beach in Yarmouthport or Mayflower Beach in Dennis before or after dinner.

Live Entertainment

After dinner, you may be in the mood to linger a little longer with a nightcap at a local pub or bar. Depending upon your mood, you can catch some live entertainment at O’Shea’s Olde Inne in West Dennis or The Loft in West Yarmouth. Either nightspot will put the finishing touches on your day.

Day 2


Start your day with breakfast at the inn. Served in two elegant sun-filled dining rooms, breakfast is an event. The menu alternates daily between sweet and savory entrees, always freshly prepared and locally sourced. Hot tea, coffee, fresh fruit, and fruit juices accompany your dish.

Visit Chatham

We highly recommend starting your tour of Cape Cod by taking a leisurely drive to Chatham, one of the prettiest towns you’ll ever see. Main Street is lined with unique and unusual shops to peruse if you’re in the mood for a little retail therapy. Later, stop at Lighthouse Beach, across from the Chatham Lighthouse, for a beach walk or dip in the ocean. Then proceed to the Chatham Fish Pier for an auditory and olfactory adventure. Take the stairs to the viewing platform for the best view. At high tide, you can watch fishermen unload their daily catch and marvel at the seals and seagulls that come in hopes of catching a wayward morsel.

Cape Cod National Seashore

From Chatham, follow Route 28 to Route 6 down the length of the arm of Cape Cod and stop in at the Salt Pond Visitor Center. Here you’ll find everything you need to know about the Cape Cod National Seashore. It’s a great spot to get oriented for all the marvelous things to see and do in this magnificent national park. Follow Doane Road to Coast Guard Beach, one of the Cape’s most beautiful beaches. Link up with Ocean View Drive for a scenic jaunt atop the dunes and above the wild Atlantic waves.

Highland Lighthouse

Continue your journey through the lower Cape, stopping at Highland Light in Truro. One of only 16 remaining lighthouses on the Cape, it’s one of the few you may be able to climb in season for a spectacular view from the top.


Provincetown forms the fist of the Cape at the end of its long arm. Commercial Street is the busy central heart of town, with visitors and locals strolling the street window shopping, and stopping for treats at the many restaurants. It’s best to park on a side street and walk over to Commercial Street. The Lobster Pot is one of our favorite watering holes, with a lovely seaside location and fabulous seafood. In town, you can climb the Pilgrim Monument for another spectacular view of Cape Cod Bay and the Atlantic Ocean, as well as the dunes of the Provincelands. But if you really want to get up close and personal with the protected sand dunes, take one of Art’s Dune Tours. Seated in a comfortable SUV, you’ll motor through the dunes while learning a little bit about the history and ecology of the area.

Truro Vineyard

On your way back to the inn, stop by Truro Vineyards for a wine tasting and tour. Family-owned and operated, this stunning vineyard sits between Cape Cod Bay and the Atlantic Ocean. Offering a variety of red and white wines, plus their exclusive Lighthouse wine series, it’s a refreshing stop on your trip back to the inn.

Dinner with a View

On the final evening of your 36-hour itinerary on Cape Cod, it’s time to indulge in a fine dining experience with a view of the ocean. Sitting literally above Nantucket Sound, the Ocean House in Dennis Port is a sought-after spot for waterfront dining. Another delightful dining option is the Rooftop at the Pelham House Resort, also in Dennis Port. Both restaurants offer fresh and inventive entrees and amazing craft cocktails.

Say Goodnight, Gracie

Return to your cozy room at the inn for another relaxing evening, knowing that breakfast will be ready and waiting for you in the morning. We’re sure that although short, this will be a sweet adventure. Check availability today to plan your getaway.

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