The Best 5 Day Itinerary for your Cape Cod Getaway

A path through the dunes to Race Point Beach, on Cape Cod near Provience Town MA. Sunset over the water

Did you know that Cape Cod is a 65-mile-long peninsula that extends east from the mainland and curls north, like an open arm? There are 15 beautiful coastal towns with quaint downtowns, dune-lined beaches, and rich history. The Islands of Martha’s Vineyard and Nantucket are situated off the Cape coast, making them ideal for day trips.

If you are coming from Boston, we recommend renting a car and driving south to Cape Cod. Make a stop in Plymouth, home of the famous Plymouth Rock, Plimouth Plantation, and the Mayflower. Further south, stop for a quick lunch in Sandwich. Walk along the quaint, oak-lined Main Street, tour the Heritage Museum and Gardens, and finish with a stop at the Sandwich boardwalk. For more fun things to do in Sandwich, visit our blog: “Best things to do in Sandwich this fall”.

When you arrive in Chatham, check into your chosen guest room and unwind a bit before heading out to explore the area.  You can choose from a full check-in where we will show you around, give you tips on how to make the most of your stay, and book all of your day trips and dinner reservations. If you prefer a contactless check-in, simply follow the instructions that we’ve sent to you prior to arrival to find your room. Our digital guestbook is available to all of our guests for free and it’s the best Cape Cod Vacation Guide.

Day 1: Explore Chatham

After a night of good rest and a delicious homemade breakfast, take a stroll through downtown Chatham. The downtown area consists of many unique shops, galleries, restaurants, and opportunities for sightseeing. Take the 1.2-mile walk to the famous Chatham Lighthouse, see the breathtaking overlook, and take a walk on the soft sand beach. On the way back take Bridge Street and walk over the new wooden bridge overlooking Stage Harbor and Mill Pond. Make a right on Stage Harbor Rd. and walk to Oyster Pond beach and back to the Inn. In the afternoon head to the Fish Pier for lunch. Try the Cape’s famous Clam Chowder, Fish and Chips, or yummy lobster roll. If you are in a mood for adventure, take a Seal Tour; booking it in advance is required. The newly renovated observation deck at the Fish Pier offers sweeping views of Chatham Harbor. This is the best place to watch fishermen come in with their daily catch and see seals swimming around waiting for a little treat. After a fun day of exploring the town enjoy your favorite beverage on our cozy deck before you head out for a fun night on the town. Choose from many restaurants within walking distance from the Inn – make sure you visit our favorites Impudent Oyster, Bistro on Main, and Del Mar! For more restaurants in town visit our “Best Restaurants in Chatham” blog.

Day 2: Explore the Cape Cod National Seashore

Explore the Cape Cod National Seashore, a gorgeous 30 miles stretch of beaches and wetlands from Chatham to Provincetown. We highly recommend stopping at the Salt Pond Visitor Center for some interesting information about the area, free movies, and extra tips. You can take one of the walking trails and walk to Coast Guard Beach, you can rent bikes and take the bike trail to Wellfleet, or you can just relax on one of the nearby beaches. Coast Guard Beach is always on the list of top 10 Beaches in the U.S. and Nauset Light Beach is also very popular. You might recognize it from the Cape Cod potato chips bags. If you are craving delicious seafood and flavorful shellfish stay in the area and dine in  Wellfleet. Famous for the best oysters in the country this touristy town offers so many amazing outdoor dining options. Try Mac’s on the Pier, the Book Store, and The Pearl restaurant.  

Day 3: Day trip to Provincetown

Provincetown is a short hour drive from Chatham and draws nearly 60,000 annual visitors a year with its scenic beaches, art colonies, galleries, nightly entertainment, and quirky shops. Start with the famous Commercial Street and stretch your legs, grab an ice cream cone, and people watch. Climb the Pilgrim Monument and Museum to see some spectacular views of the area. Walk down to the harbor and go on a Whale Watching excursion. This is an extraordinary experience like no other and Provincetown is one of the best places in the U.S. to see these majestic creatures. Whale Watching Season runs from April-October and we highly recommend booking it in advance. On your way back to Chatham, stop at Truro Vineyards, a great outdoor spot for wine tasting, light dinner, and live music entertainment.

Day 4: Island Excursion

Martha’s Vineyards and Nantucket are easily accessible from Chatham. Ferries are available from both Harwich, Hyannis, and Woods Hole and take no more than an hour to reach the islands. Make sure you catch one of the earliest departures so you have plenty of time to enjoy all the incredible activities and attractions. Both islands are unique and there are plenty of activities to do. Nantucket is closer to Chatham and the smaller of the two islands. Once on the island, we recommend strolling the cobblestone streets, window shop, and grab a seafood lunch on the water. Visit the Whaling Museum and the observation deck, take a guided tour of the island, or simply rent bikes and explore on your own. Martha’s Vineyard is bigger and offers even more things to do. Ride the oldest carousel in the U.S., visit an alpaca farm, stroll in a gingerbread house village, and grab a bite to eat at the famous Black Dog Tavern. The possibilities are endless. For more information about the islands visit our best of Martha’s Vineyard and Nantucket blogs.

Day 5: Day at the Beach

The last day of your Cape Cod vacation calls for a relaxing beach day. Take advantage of the many beaches within a short drive or walk from the Inn. (visit our “Best Chatham Beaches” blog to find out more). Rent kayaks and explore Chatham’s beautiful seashore. Grab our complimentary beach chairs, umbrellas, and towels and head to the popular Hardings Beach. Hike on Monomoy Island and explore the natural wildlife while enjoying the summer breeze. On the way back from the beach, stop at Buffy’s for the best ice-cream cone around. After a day at the beach, the perfect way to end your vacation is to watch one of the Cape’s famous sunsets. The best place to go is Rock Harbor in Orleans. Let us pack you a picnic basket with all your sunset essentials so you can just enjoy and take it all in.

There is no place like Cape Cod, there are many adventures to be had, rays of sun to be soaked in, restaurants to be dined in, and day trips to be taken. No matter how you decide to spend your time on the Cape, there is something for everyone. Treat your loved one and yourself to a well-deserved romantic escape to Cape Cod. Do not forget to browse our many Specials & Packages and in-room add on’s to make this trip even more special. Check the availability today and book your stay at The Old Harbor Inn.

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