Perfect 3 Day Itinerary for Cape Cod, Massachusetts

June 2024

Perfect 3 Day Itinerary for Cape Cod, Massachusetts

One area that Kevin has had on his travel list for many years is Cape Cod, Massachusetts and we finally had the opportunity to explore this area. The hook-shaped peninsula is iconic for many reasons – the gorgeous beaches, the elegant coastal cottage homes, and the diversity of the 15 towns plus two islands that make up Cape Cod – there is so much to see and do. From relaxing beach vacations, to jamming local bands, to miles of conserved wildlife sanctuaries, to exciting aquatic activities, and tons of seafood – the trip can really be whatever you are craving out of your vacation.

Know Before You Go 

Cape Cod is primarily a seasonal destination and while some towns are active all year round, for vacation you are going to want to travel between Memorial Day and Labor Day when everything is open and you can take advantage of everything Cape Cod has to offer. With 15 towns to explore, you will have to make some decisions for a shorter trip on what to focus on. There are four regions to Cape Cod and two islands:

• Upper Cape: Bourne, Falmouth, Sandwich & Mashpee

• Mid Cape: Barnstable, Yarmouth & Dennis

• Lower Cape: Harwich, Brewster, Chatham & Orleans

• Outer Cape: Eastham, Wellfleet, Truro & Provincetown

• Islands: Martha’s Vineyard & Nantucket

You can focus your itinerary on one region, or even focus on just one town like Provincetown or spend ample time at the beach instead. You can also mix and match like we did. We had three days of our trip, so we opted to do a day in the Outer Cape, and day in the Lower Cape, and a day on one of the islands. Since we were doing a day in each area, we were certainly far from experiencing everything that region has to offer, it was more of a sampling. Just know that if you are exploring more of Cape Cod, that it is an hour drive from one side to another so you will want to avoid being in the car the long periods of time on your vacation. How you structure your trip will dictate the rest of the decisions you make for completing your trip planning. 

Where to Stay

Where to stay is going to depend on the itinerary you build. If you plan on staying in one spot for a long weekend, that makes this decision very easy. If you are exploring more of Cape Cod, you will want to position yourself in the middle of your destinations. For our trip to the Lower and Outer Cape, we knew we would go as far north as Provincetown and as far south as Chatham which is an hour drive between the two. So, to give us a half hour drive to each, we picked an Airbnb in Wellfleet which ended up working so well for our trip. And even if we added beach time, this spot was less than ten minutes from the closest beach. If you are following a similar trip itinerary to what we did, Wellfleet is a great spot to base yourself.  If you opt for a trip to the Upper and Mid Cape, then consider centralizing yourself near Barnstable. 

How to Get Around

An hour to drive from the start of Upper Cape to the tip of Outer Cape so there is a lot to cover. You will most likely want a car to get around if you want to explore. This gives you the most flexibility to fill up the itinerary with a variety of things. Once you are there, bikes are very popular and bike trails can be found all over. I even think this would be a great spot to rent a scooter to bop around. If you do not have a car, it is best to travel through Boston and take the ferry to Provincetown and plan your trip around there. 

What is There To Do

There is so much to do for your Cape Cod vacation. Generally, you will find similar activities in any region you decide to visit. 

• Wildlife Sanctuaries – There are multiple areas of trails and walking paths with opportunities to see birds. And even along the coast, you may catch dolphins or seals – and on the rare occasion, a shark.
• Bike trails – Being outdoors in the summertime is supreme and Cape Cod is full of dedicated bike trails and lanes that make getting around towns very easy.
• Cape Cod National Seashore – Beaches can be found all along the peninsula and they are all enjoyable with varying amenities. Just do some research ahead of time for parking and entrance fees where applicable. 
• Fifteen Towns to choose from – This is certainly one of the best parts of exploring Cape Cod is getting to explore all the different towns. The main street vibes are all different depending on where you visit, and you get to experience the shops. 
• Minigolf – Minigolf can be found throughout the Cape Cod area and makes for a fun evening activity. Most even include a spot for food and ice cream to extend
• Lighthouses – Along the entire coastline are lighthouses that serve both historical and practical purposes. It is easy to arrange a route up the coast that hits many of these structures that give a great view along the shore line.

Here are some great things in these regions to look out for: 

Upper Cape: Bourne, Falmouth, Sandwich & Mashpee

• Sandwich: Tree House Brewing, Sandwich Boardwalk,
• Falmouth: Shining Sea Bikeway, Highfield Hall & Gardens, The Knob, Nobska Lighthouse, Woods Hole Oceanographic Institution Ocean Science Discovery Center, Marine Biological Laboratory

Lower Cape: Harwich, Brewster, Chatham & Orleans

• Orleans: Skaket Beach, Cape Escape Adventure Golf, Bird Watchers’ General Store
• Chatham: Jacknife Beach, Chatham Pier Fish Market, Chatham Lighthouse and Beach, Godfrey Windmill, Main Street, Monomoy National Wildlife Refuge

Outer Cape: Eastham, Wellfleet, Truro & Provincetown

• Provincetown: Commercial Street Dune Shacks Trail, Race Point Beach (perfect for sunset!), Pilgrim Monument and Provincetown Museum, Peregrine Theatre Ensemble
• Wellfleet: Mayo Beach, Herridge Books, Atlantic White Cedar Swamp Trail, Marconi Beach and Wireless Station, Mass Audubon Wellfleet Bay Wildlife Sanctuary, Wellfleet Cinemas and Flea Market, Nauset Lighthouse

Islands: Martha’s Vineyard & Nantucket

• Martha’s Vineyard: Aquinnah Cliffs Overlook, Gay Head Light, Oaks Bluff, Vineyard Haven
• Nantucket: Madaket Beach, Steps Beach, Brant Point Lighthouse, Broad Street and surrounding downtown area, Sankaty Head Lighthouse, ‘Sconset Bluff Walk and beach
• Notes on Martha’s Vineyard and Nantucket: I evaluated both islands and knew we only had room for one during our trip and I ultimately picked Nantucket as seemed better for a day trip and we did not need a car to get around and see all the sights. 

Where to Eat 

Cape Cod is home of seafood and it will be hard to go wrong. We certainly did not get the opportunity to explore to explore the countless dining options that are available but based on the major areas, here are some places we had on our list.

 Upper Cape: Bourne, Falmouth, Sandwich & Mashpee

• Sandwich: Bob O’Malley’s Whaleback Restaurant, Twin Acres Ice Cream, Ice Cream Sandwich, Cafe Chew, the Shipwreck Ice Cream, Fishermen’s View Seafood, Superior Lobster & Seafood, Seafood Sam’s, Beth’s Cafe
• Falmouth: Pie in the Sky Cafe, Glass Onion, Anjeo Mexican Bsitro, Quahog Republic, Falmouth Fish Market

Lower Cape: Harwich, Brewster, Chatham & Orleans

• Orleans: How Chocolate Sparrow, Mahoney’s Atlantic Grill, Sunbird, Ice Cream Cafe, Cooke’s Seafood, Sir Cricket’s Fish & Chips, Smitty’s Ice Cream, twenty-eight atlanic
• Chatham: Hangar B Eatery, Buffy’s Ice Cream, Chatham Squire, Impudent Oyster, Aplaya Tiki Bar, Snowy Owl Coffee, Bluefins Sushi

Outer Cape: Eastham, Wellfleet, Truro & Provincetown

• Provincetown: Liz’s Cafe, Ocean 193, The Canteen, The Lobster Pot, Tin Pin Alley, Portuguese Bakery, Provincetown Brewing Company, Far Land Provisions, 361 Coffee, Ciro and Sal’s
• Eastham: Arnold’s Lobster & Clam Bar, Beanstock Coffee Roasters, Friendly Fisherman, Hole in One Donut
• Wellfleet: Harrigan’s Cafe, Hog Island Beer Yard, Bagel Hound, Lobster & Chowder House, PB Boulangerie Bistro, Blue Willow Bakery, Beachcomber, The Wicked Oyster, Mac’s Seafood, Bookstore, Ceraldi, Gelato Joy, Moby Dick’s Restaurant
• Truro: Blackfish, Box Lunch, Savory & the Sweet Escape, Chequessett Chocolate, Montano’s Restaurant

Islands: Martha’s Vineyard & Nantucket

• Nantucket: Handle Bar Cafe, Lemon Press, Or the Whale, The Corner Table, Walter’s Deli, The Charlie Noble, Misogi Noodle Bar, The Nautilus, B-ACK Yard BBQ, Sayle’s Seafood, Island Kitchen & Ice Cream, Cisco Brewers, Claudette’s Sandwich Shop, Millie’s

Perfect Itinerary 

This itinerary works very well as a stand alone trip or as part of a longer trip – you could even extend into Boston. There is so much to see so if you have more time to explore, I highly recommend it! You can mix and match days or double up in activities you really want to do. Or you can simplify your long weekend by staying put in one spot. 

If you are up for exploring and have three full days, I would recommend either doing Upper and Mid Cape as a pair or Outer and Lower Cape. Then you can centralize yourself in the middle of those areas to optimize driving time. If you want to have a more relaxing summer vacation, focus on one region or even one town to optimize the beach time.

	Option 1: Outer and Lower Cape	Option 2: Mid and Upper Cape
Day 0	Arrive in Cape Cod in the evening	Arrive in Cape Cod in the evening
Day 1	Outer Cape – Morning: Eastham – Afternoon: Wellfleet – Evening: Provincetown	Upper Cape – Morning: Falmouth – Evening: Sandwich
Day 2	Day trip to Island – Nantucket	Day trip to Island – Nantucket
Day 3	Lower Cape – Morning: Chatham – Evening: Orleans	Mid Cape  – Morning: Dennis – Evening: Yarmouth
	Departure	Departure

	Option 1: Outer and Lower Cape	Details
Day 0	Arrive in Cape Cod in the evening	Arrive in Cape Cod in the evening
Day 1	Outer Cape – Morning: Eastham – Afternoon: Wellfleet – Evening: Provincetown	Nauset Lighthouse and Beach, Mass Audubon Wellfleet Bay Wildlife Sanctuary, Mayo Beach, Downtown Wellfleet Dunes, Downtown Provincetown, sunset at Race Point Beach
Day 2	Day trip to Island – Nantucket	Day trip to Island – Nantucket – Morning: Ferry, Rent bikes to ‘Sconset – Afternoon: Downtown ACK – Evening: Ferry
Day 3	Lower Cape – Morning: Chatham – Afternoon: Orleans	Downtown Chatham, Chatham Pier Fish Market, Chatham Lighthouse Downtown Orleans
	Departure	Departure

Read all blog posts for Cape Cod here!

See our complete itinerary here!

For more Perfect Itineraries and Travel Inspiration – here!