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My Family Roadtrip to Cape Cod

The Perfect East Coast Getaway

Cape Cod was one of those places that always felt familiar, even though I had never been there. My mom, uncle, and my grandparents made family trips there when my mom was little and always spoke so fondly about their time there. I even had a Cape Cod t-shirt when I was young that I wore until it fell apart.

So, when the chance came up for a family trip there in honour of my Grandma's birthday, I may or may not have (but definitely did) invite myself along.

Here's where we went, what I loved most, and why it makes the perfect getaway from Eastern Canada.

Houses along the beach in Yarmouth, Cape Cod, Massachusetts


After driving from Ottawa, Canada to Brockton MA to spend the night, we started our journey to Cape Cod by heading to Plymouth.

Plymouth is a nice little seaside town packed with American history from the days of its first settlers. If you're into that part of North American history this will be right up your alley.

Here you can see Plymouth Rock, the landing point of the Mayflower Pilgrims who founded Plymouth Colony in 1620. You can also see a replica of the Mayflower itself, however, when we were there the ship was relocated for maintenance.

If you're heading to Cape Cod by car it's worth stopping in Plymouth to see the sites, stroll along the waterfront, and have a lovely seafood lunch (of course).

Boats on the harbour in Plymouth MA
Plymouth Rock, Plymouth MA
Enclosure housing Plymouth Rock, in Plymouth MA
Boats on the harbour in Plymouth MA

South Yarmouth

Cape Cod is a hook-shaped peninsula off the coast of Massachusetts dotted with small towns, roadside seafood restaurants, and sandy dunes and beaches. We stayed in South Yarmouth along the southern shore of Cape Cod.

This location put us kind of in the middle of everything we wanted to see. It was also cheaper than some of the other towns like Hyannis Port, Chatham, and Provincetown.

The Seaside Cottages in South Yarmouth was our home for the week. Our perfect little cottage had two bedrooms and a sofa bed to accommodate us all, and ample living, dining, and cooking space.

I would highly recommend staying here if you are looking for somewhere you can cook meals and be right on the water.

See more about The Seaside Cottages here! 

Seaside Cottages, South Yarmouth, Cape Cod, MA
Beachfront of the Seaside Cottages, South Yarmouth, Cape Cod, MA
Rocks on a beach in Yarmouth, Cape Cod, Massachusetts
Lobster Roll from seaside restaurant in Cape Cod

Hyannis Port

One of our excursions took us to Hyannis Port, a nearby town that was high on my Grandma's list of places to see. This was about a 20-minute drive from The Seaside Cottages and made for a perfect morning excursion.

Hyannis Port is deeply rooted in Kennedy family history. There is a private Kennedy Compound nearby and a Kennedy museum which commemorates the life and death of JFK.

Aside from the political and historical linkages, Hyannis Port is a cute little tourist town, featuring adorable shops selling saltwater taffy, jewelry stores, gift shops, and great restaurants. Hyannis Port is also the main port between Cape Cod and Nantucket Island.

We strolled up and down the main street shopping and eventually stopped at a pub for lunch.

It is definitely worth a morning or afternoon exploring this picturesque little town.

The JFK Museum in Hyannis Port MA
Cute shop in Hyannis Port, MA
Hyannis Port MA main street
Salt Water Taffy from Cape Cod


Eastham is home to Nauset Beach and Nauset Lighthouse, which is one of the iconic lighthouses of Cape Cod. It was rainy, grey, and WINDY the day we went here. As you'll guess based on the photos below, we spent the day bundled up and bracing ourselves against the gusts and whipping sand.

The Nauset beach Light as it is called was built in 1923 using the 1877 tower which was originally Chatham Light.

Nauset Lighthouse is one of those iconic places that comes to mind when you think of Cape Cod and is listed on the National Register of Historic Places. Definitely worth pulling on the highway to stop and see it.

Nauset Lighthouse, Cape Cod, MA
Nauset Beach, Cape Cod, MA
Nauset Beach, Cape Cod, MA
Nauset Beach, Cape Cod, MA


The Stony Brook Grist Mill was another one of the spots on my grandma's list. The town of Brewster is home to a historic grist mill, some ponds and trails. It's a beautiful spot to stop and explore.

The stream, the mill itself, and the surrounding grounds are magical and tranquil. I recommend packing a lunch and spending some time here just enjoying the scenery.

We had a rainy day when we visited, so we didn't linger too long in the cold damp weather. As it was the beginning of the season, the Mill was not running, nor was the museum open. Still a beautiful spot to see!

Find out more about the mill and Stony Brook here!

The Stony Brook Grist Mill, Cape Cod MA
The Stony Brook Grist Mill, Cape Cod MA
The Stony Brook Grist Mill, Cape Cod MA


Way up on the northern point of the Cape Cod peninsula you'll find Provincetown. This was by far my favourite excursion of all of our road trips throughout the week.

The town felt bright, vibrant, and alive compared to some of the more remote, sleepy towns we stopped in.

Provincetown is packed with mom and pop restaurants, seafood carts, candy shops, and adorable street after adorable street. Cyclists passed us as smiling groups of tourists meandered and milled around the town. It was a lovely place to spend the better part of the day.

The Pilgrim Monument is an excellent way to get panoramic views of the town and the coast. I didn't climb to the top, but my Grandma and Uncle did. They said the views were spectacular. The monument is actually modelled after a tower in Sienna, Tuscany which I climbed. So cool!

After our visit had come to an end, we finished the day watching the sun go down on Race Point Beach. The perfect way to end the day before driving back down to South Yarmouth.

Cabbot's Candy Shop in Provincetown Cape Cod.
Happy Camper in Provincetown Cape Cod.
Street Car in Provincetown MA
Race Point Beach, Cape Cod
Race Point Beach, Cape Cod

Things to Know Before You Go

When to Go

As I mentioned before, we were in Cape Cod in early June and we had some unseasonably chilly weather while we were there. No sunbathing for us!

Nonetheless, the sites and views were amazing and there were no crowds to compete with. On another trip to Cape Cod, I would recommend going later in June in the hopes of better weather. We also encountered some restaurants and historic sites that weren't open for the season yet. Again, going in late June, July, or August will mean more crowds, but it will also mean all sites and eateries are open for business.

Stuff Gets Moved Around

One thing you'll know if you go to Cape Cod with a few decades between trips is that things get moved around and aren't always where you left them.

Due to the erosion of the shores, damage to windmills, lighthouses etc. things get moved around. A LOT. We were on a bit of a scavenger hunt trying to find windmills that are no longer in the same places they were in the 60s. There were some other historical sites that had been altered slightly, with items relocated as well, as a result of the eroding shoreline.

Not like London where things are where you left them for the most part! Something to keep in mind if you're on a bit of a pilgrimage as we were.

Windmill in Cape Cod
The hesitant Adventurer on South Yarmouth Beach, Cape Cod

An Extra Special Trip

This trip was also extra special because it was shared with family. Having the chance to travel with my grandmother, uncle, and mom was amazing. We made so many memories, laughed, got lost together, and got that much closer as a result.

It was amazing to be a part of a trip with my grandmother where I could hear her stories from days gone by and be a part of her journey to revisit such a special place to our family.

After all, what good is travel if you're not sharing it with the people that matter most to you?

My family walking along the beach in South Yarmouth, Cape Cod
My amazing grandma in Plymouth, MA

Happy Exploring!

Cape Cod is truly charming and iconic. The lighthouses, windmills, seafood restaurants, and east coast hospitality were all above and beyond. The people were amazing! Friendly, warm, welcoming and made the trip extra special.

I would love to go back to Cape Cod a little later in the season when things are really bustling to see what it's like. I think Cape Cod is somewhere I will definitely be back to in the future.

If you're after east coast charm, quaint towns, great local food, and a family beach vacation, Cape Cod ticks all the boxes!