Cape Cod, MA
Growing up, my parents took my sister Adrian and me on family vacations every summer. We did everything from road tripping to the Grand Canyon and lounging on the beach in Cozumel, to gallivanting around London and driving the Road to Hana in Hawaii. I always looked forward to those weeklong escapes when we would explore a new place none of us had been to before and spend lots of quality time together.
As Adrian and I got older and busier, it became harder to find a week where everyone in the family could jet off at the same time. Now, my parents live in Dallas, Adrian lives in Brooklyn, and I live in Birmingham. It’s almost impossible for all of us to be in the same place at the same time anymore (we weren’t even all together last Christmas!), so I thought it was time we reinstated our annual family vacations. When Adrian suggested Cape Cod, we all jumped on board, packed our bags, and headed northeast to spend a week in Chatham, MA, over the Fourth of July – our family’s favorite holiday.
Getting to Chatham was a little trickier than we expected. Almost all of my research suggested flying into Boston, renting a car, and driving out to Cape Cod, so that’s exactly what we did. We all arrived in Boston on a Sunday around noon, piled into our Jeep, and headed to the Cape! After driving for about an hour and a half, we stopped in Barnstable for lunch at Mattakeese Wharf. We got our first taste of fresh seafood and Cape Cod potato chips while overlooking the water, and Mom bought her first of many souvenir t-shirts. After lunch, we drove for about another 30 minutes before arriving at Chatham Inn, our home for the next few days. We stayed in Room 11, which had a king bed, large bathroom, balcony patio, and a loft with two twin beds. It was the perfect space for a family of four!
We were all super excited to explore, so after dropping off our bags, we went on a walking tour of our neighborhood. I loved seeing all of the blooming flowers and shingled houses decked out for the Fourth of July. After learning that we were only a few blocks from the beach, Adrian was determined to find the closest access point, and once she did, we all took off our shoes to feel the sand on our toes and dip our feet into the water.
Our inn was located right at the end of the business district on Main Street, so we spent the rest of the evening looking at all of the shops and restaurants. For dinner, we headed to Chatham Squire, the town’s signature watering hole, where we shared fried calamari and the most delicious lobster ravioli while sipping on local beers.
The next morning, Adrian got up early and walked down to the beach for yoga at Chatham Lighthouse. During the summer, they have yoga class every single morning for just $10. Adrian said there were about 50 people there from all different towns on Cape Cod, and the class was simple enough for everyone to participate in, no matter their skill level.
We loved that our stay at the Chatham Inn came with breakfast included. It was so easy to pop downstairs and get a personalized breakfast meal every morning. There’s no stale buffet or make-your-own omelet station. Instead, you’re seated at a dining table with a waiter and full-scale menu. Some of our favorites were the crab cake benedict, three-egg omelet, and 359 egg sandwich.
After breakfast, we drove out to the Brewster General Store to take in some New England charm. This general store was the perfect mix of old and new. They sold everything from vintage games and old-school candy, to handy kitchen tools and Cape Cod t-shirts. We spent over an hour looking at all of the merchandise tucked into every nook and cranny in this two-story shop.
For lunch, we went to Sesuit Harbor Café, which is known for its colorful buoy-covered wall and no-fuss lobster rolls. After ordering at the counter, we grabbed a picnic table outside and enjoyed the view of Northshore Marina and Cape Cod Bay. Dad ordered the fried scallop plate, Mom got the Rueben sandwich, and Adrian and I split a lobster roll and French fries. With such mild summers in this part of the country, we took advantage of the weather by eating almost every meal outside.
Our big activity of the day was taking a sailing lesson at Ridgevale Beach from Chatham Sail. We hopped into a Sunfish with our instructor Eric and learned how to control the sails, change directions, and use the wind to move along in just two hours. It’s definitely a lot harder than it looks to get going without a motor, but once we got the hang of it, we had so much fun sailing around Monomoy Island, seeing the Chatham Lighthouse from the water, and looking for seals.
We went back to our inn to freshen up before going to dinner at Cape Sea Grille. This restaurant is slightly more upscale, but still has a laid-back, casual vibe. To start, we ordered a round of cocktails and split a grilled peach salad that was on special. The place was pretty busy, so it took a little while to get our main courses, but it was so worth it. Dad ordered the surf ‘n’ turf, Mom got the grilled salmon, Adrian ordered the duck breast, and I got the lobster, shrimp, and scallop pasta. Our dinner lasted well into the evening and was insanely delicious. On the way home, we stopped by Sundae School Ice Cream for a few scoops to polish off a great first day on Cape Cod.
Adrian requested at least one “beach day,” so Tuesday was the day! We loaded up our Jeep with beach chairs, towels, and an umbrella from our inn and drove north to Wellfleet. We set up our stuff in the sand in front of The Beachcomber, a casual bar and restaurant where Adrian and I got beers and margaritas, and spent the better part of the day reading books, looking for seals and whales, and walking up and down the beach.
Once we started getting hungry for dinner, we packed up and headed even further north to Provincetown. We ate an early dinner on the patio at Pepe’s Wharf, which had the cutest nautical décor and a perfect view of the evening tide coming in. After sitting in the sun all day, everything on the menu looked delicious and we didn’t hold back. We started with a round of drinks –Stella Artois for Dad, gin and tonic for Mom, Pimms Cup for Adrian, the Don Hugo for me – and their black truffle and parmesan flatbread. For dinner, Dad got the steamed lobster clambake, Mom got the scallops and Brussels sprouts, Adrian ordered the lobster ravioli, and I got the lobster lettuce wraps. Everything was SO fresh and yummy! This was one of our favorite meals of the entire trip.
After dinner, we walked down Commercial Street in Provincetown and looked at all of the shops, restaurants, and houses. Unlike our home base in Chatham, all of the houses in Provincetown are super close together and don’t have any front or back yards. It’s set up more like a downtown city, where you can get almost everywhere by bike or foot. We loved seeing how every little town we visited on Cape Cod was so different from the other. They’re each so charming in their own way.
On Wednesday, we woke up early and took the Freedom Ferry from Harwich Port to Nantucket. We spent the morning walking around Straight Wharf and Main Street before heading to Cru for an early lunch. Cru is famous for their lobster rolls, so we couldn’t help but order four of those and some rosé cocktails. By the time we left, the place was packed, so I definitely recommend getting there early or making a reservation.
After lunch, we explored further into downtown Nantucket and stopped into a few shops. Some of my absolute favorites were Peter Beaton Hat Studio, The Skinny Dip, Current Vintage, and 28 Centre Pointe, as well as a few of the classics like Murray’s Toggery Shop, Ralph Lauren, Lilly Pulitzer, and Vineyard Vines.
For a mid-afternoon snack, we grabbed scoops of ice cream from The Juice Bar. They have the most amazing flavors all of which are made in-house, and serve their ice cream in freshly-made, warm waffles cones. It’s so delicious, but you have to devour your cone pretty fast before it starts to melt!
In search of a change of scenery, we headed out to ‘Sconset to check out a quieter part of Nantucket. Compared to the bustling and crowded downtown area, ‘Sconset is way more low-key and feels like a quaint neighborhood where residents spend all summer on the beach. We walked down the Bluff Walk to look at all of the different houses, and stumbled upon the infamous rose-covered cottage in full bloom!
There aren’t really any shops to pop into in ‘Sconset, so we continued on to the Sankaty Lighthouse. When you think of New England lighthouses, this is what you think of! The Sankaty Lighthouse sits right on the edge of a rocky bluff with a big red stripe painted across the center. We read about its history and walked around the bluff before heading back to town to catch our ferry home.
Nantucket feels like its own separate world away from everything else. It’s small enough that you can drive across the island in under 30 minutes, but large enough that each town has its own sense of place. All (and I mean ALL!) of the houses are covered in gray shingles and everyone drives a Jeep. Some day, I would love to spend a whole summer on Nantucket.
Thursday was the Fourth of July and we were pretty excited because Chatham really goes all out for the holiday! The night before as we were walking back to our inn, Main Street was already lined for miles with lawn chairs where people were staking out their spots to watch the parade the next morning. Lucky for us, the parade route went right in front of Chatham Inn, so we got to watch the whole thing from our front patio. We loved seeing all of the vintage fire trucks, handmade floats, and high school marching bands!
After the parade, we headed to Stick ‘N’ Rudder for the most adventurous activity of our trip –an aero tour of Chatham in an open cockpit airplane! Dad was so excited for this and Mom was a little scared, but it felt just like driving on the highway in a convertible. We could only go two at a time, so the pilot took Dad and me up first and then came back for Mom and Adrian. We opted for the 15-minute ride and it was more than enough time to see different parts of Cape Cod and take lots of photos from the sky.
Since it was our last day in Chatham, we wanted to spend the rest of the day in town. We had lunch on the front patio at Wild Goose Tavern, where Dad and Adrian both ordered scallop rolls and Mom and I both got lobster and crab quesadillas. We spent the rest of the day shopping on Main Street, stocking up on t-shirts and postcards, and then walked down to the beach to enjoy the last few hours of sunshine in the sand.
I ran into my friend Hillary from college, who happened to be in town for the weekend, and we caught up for a while before Mom and I went on a walk on the beach. We walked all the way to Chatham Lighthouse and saw so many tiny starfish along the way. I started a collection, and at the end of our walk, we made a starfish and sand American flag to celebrate the Fourth of July!
For our last evening in Chatham, we had appetizers and wine for a light dinner at our inn. We felt so lucky to have gotten such perfect weather all week. We got to enjoy the sunshine in shorts during the day, and only had to throw on light sweaters in the evening when the sun went down.
Before packing up, we took one last walk down Main Street and stocked up on homemade chocolates from Chatham Candy Manor and one last scoop from Buffy’s Ice Cream. It was the sweetest way to wrap up our family vacation and got us all excited for many more to come.