Cape Cod Vacation
Cape Life!
I had always heard great things about Cape Cod, Massachusetts. The adorable beach towns, delicious seafood restaurants, and it’s nautical New England style homes… it always seemed like a perfect summer vacation on paper. But despite only living a few hours away, I had surprisingly never visited myself. My parents and grandparents had made a few trips, but never dragged along the kids.
After a crazy year and limited travel for my family, we decided to plan a summer vacation. We explored a few different destinations within driving distance, but my top pick was Cape Cod. We wanted to go somewhere new where our family hadn’t been together before, and we wanted it to feel relaxing without being boring. After a little research we decided on spending a week in July on the Cape in Chatham, Massachusetts.
The trip didn’t go exactly as planned, but we had an amazing time spending a few days together as a family and discovering the Cape. We picked a week in the height of summer so that we could take advantage of great weather before hurricane season. Originally our plan was to spend most of the time at the beach and so we strategically picked a house near the water. We imagined happy days on the shore, and heading home in the late afternoon to enjoy an outdoor dinner at sunset.
As beach people this sounded like the most ideal vacation, so of course we were a little crushed when the weather forecast showed storms for most of the week. We prepared some rainy-day activities just in case.
Ultimately, we spent some time exploring the towns when there was rain coming in, and we got to see way more of the Cape than we would have from the beach! But we were so pleasantly surprised to have some sunny beach days too.
Ultimately by planning out the trip well we were able to make the most of our week on the Cape. I’m glad we had an opportunity to explore it together this summer, and I’m already excited about going back one day to do more of the things we loved!
Read more all about Cape Cod, and tips for planning your own vacation there below!
Getting to Cape Cod
From Westchester or the surrounding NYC area the best way to get to Cape Cod is by car. The trip took us about five hours and I didn’t find it to be bad at all, as long as you go early to beat the traffic! But I do think it’s worth spending a few days there to make the long travel worth it. Having a car to get around when you’re there is great too. Easy access!
Chatham, Cape Cod
Chatham was a perfect place for us to stay as a group of first timers. It’s a quintessential cape town known for its beautiful homes and gardens of hydrangeas everywhere. While it’s not right over the Sagamore Bridge that you cross into the cape, it is a central location to some of the larger towns and an equidistant drive to either Provincetown or Falmouth.
The town has so many great shops, bars, and restaurants which is why even after exploring other areas on the cape we continued coming back to Chatham. Our family agreed it was our favorite town in Cape Cod, and I’d suggest staying here if you are unsure on where to go!
Where we stayed specifically is South Chatham, and just a short distance into town or to the cute village of Harwich. In my opinion some of the greatest houses are in this area, and we spent a lot of time exploring it. Though I loved it for a family vacation, I think if visiting with friends it would be nice to be right in town without a need to drive anywhere.
We found a great house on VRBO for our family of six including Ryan. Even though there were a few options for home rentals we chose this one for a few reasons. First was location! We loved that it was in Chatham, in walking distance to the beach and a short drive to town. The home was spacious, dog friendly, and felt safe. We also liked that it had some outdoor space for entertaining, including a dining area and fire pit.
The management company we rented from helped make the check in and check out process extremely easy, and we had a great experience overall. My favorite bonus was that the home came with a few bicycles, which we got a ton of use out of!
The Beach
After a few days of clouds and rain the weather gods treated us to two glorious beach days towards the end of our vacation. Given they were limited we did not take them for granted! We got out early and made the most of them! I highly recommend Nauset Beach in East Orleans.
We had known Cape Cod had some shark sightings the past few years so we were a little nervous about the beach. But during our trip we didn’t have any run ins! We did however see some seals! Though the beach was a little rocky, the water was gorgeous. Refreshing on a warm day, and clear blue.
The second day of our trip we made an outing to Forest Beach on Cockle Cove, just a few blocks away from our rental home. We were excited to be so close to the water! But even though the view was pretty and the sun was shining, we came across some horse fly’s out on the bay. We ended up spending the other beach days on the Cape Cod National Seashore instead, which was a bit further but worth the drive!
Nothing but the deep blue sea…
Chatham Bars Inn
Our evening at Chatham Bars Inn was my favorite memory of the week. I’ve known about this resort on Cape Cod for a few years, as it’s become popular as both a travel destination and a wedding venue. I received several recommendations to explore it from people who frequent the Cape. I was really hoping to catch a beautiful happy hour sunset, so we waited all week to visit until the sun came out - on one of our last nights there. My experience at Chatham Bars Inn did not disappoint. Somehow it was even more wonderful than people described, and the views from the property were even more beautiful than in pictures. I guess nothing truly does this place justice, so you must go see it for yourself.
I worried we would have trouble getting a reservation at one of the restaurants, but we called to ask what our best options were, and the hotel suggested trying for a table at the more casual Beach House, which was a cute and coastally inspired outdoor restaurant. We figured we’ll explore the resort and try to find a space to have a drink and watch the sunset.
We also saw lots of people enjoying cocktails and views of the water from the scenic overlook and bar at Bayview Terrace. But when we got to Beach House we had no trouble getting a table! The vibe was perfect with good music, a buzzing bar, and a view of the pool and beach. It’s also right next to another restaurant that does a massive buffet and clam bake nightly, so we got to see what that was al about for next time.
The menu at Beach House was small but do not sleep on it!! We had the best calamari we’ve ever tasted, amongst a few other solid dishes to pick on! We ended up staying here for the whole night and skipped our actual dinner reservation in town. We watched the sun set over the water, and got to see a beautiful wedding taking place on the property. Such a gorgeous environment!
Our family felt an instant connection to the Chatham Bars Inn, as it reminded us of another favorite Northeast resort, The Sagamore at Lake George! Even though the hotel is a splurge, we talked about coming back for a long weekend stay with the intention of staying put in Chatham and enjoying everything the resort offers.
If you plan on visiting Cape Cod then I recommend stopping at Chatham Bars Inn late afternoon to enjoy a happy hour drink, watch the sun go down, and have a nice dinner. Be sure to make a dinner reservation at one of the hotel’s highly rated restaurants, like STARS or The Sacred Cod.
I can’t wait to go back!
Food in Chatham
One of the reasons we loved this area is because there were so many options of places to dine! I think objectively some of the best restaurants in all of Cape Cod are in this area. That’s one of the reasons that make it such a perfect beach town, and vacation destination.
Here are a few of the best places we visited during the week!
Mac’s Chatham Fish & Lobster
One of our favorite dinners was at Mac’s! It’s a casual spot off route 28 where you can either call and take food to go, or wait on line to order. If you order at the restaurant there are plenty of tables outdoor and inside to dine at. When your meal is ready someone will drop it off for you.
We received so many recommendations to go here, but knew it may be hard to get a table. We ended up going early on a cloudy evening and we were lucky to find the line wasn’t more than 15 minutes long! From what I’ve heard it could sometimes take an hour on a crowded night, but that the wait is worth it for fresh seafood.
My family all enjoyed lobster rolls, clam chowder, crab cakes and the like! But as I’m not a seafood lover I hoped there would be some other options. I was pleasantly surprised with the unique dishes they offered beyond seafood! I enjoyed blistered shishito peppers to start, and a chicken crunch bowl with pulled roasted chicken, sushi rice, spicy mayo, sweet soy, tempura flakes, and toasted sesame seeds. Delicious!
Chatham Squire
If you’re in Cape Cod, you have to visit the Squire ! It’s an institution in Chatham, serving a loyal clientele since 1968! The bar is covered floor to ceiling in knick knacks, retro things, funky license plates and funny signs. It’s a very casual and laidback atmosphere.
We spent an afternoon sipping mud slides and making friends at the bar while watching the Euro soccer final. It was so fun! Would be a great spot for drinks after dinner too.
Where to Go in Cape Cod
There are lots of great areas along the Cape! Because we spent seven days there we had an opportunity to visit other towns beyond Chatham including :
Harwich
Hyannis
Orleans
Provincetown
Brewster
Dennis
& Nantucket (check out my post at the bottom of this page!)
But that’s just what we covered! Popular areas also include Falmouth, Wellfleet, Woods Hole, Truro, Barnstable, Cotuit, and Yarmouth amongst others.
Now I’ll dive into a few of the towns I did visit!
Harwich
What a lovely little place! Our rental home in South Chatham was about equidistant to both Chatham and Harwich. I didn’t know too much about Harwich before arriving in Cape Cod, but I have to say this was one of my favorite towns we visited. On our first evening in the Cape we made a dinner reservation at a restaurant in Harwich called Cape Sea Grill
The restaurant was a little behind in reservations unfortunately so we had time to kill when we got there. We walked around town, stopping by some of the bars and shops, and even checked out the beautiful homes along the beach. After dinner we walked into town again for a drink before heading home. There were plenty of fun spots gathered with people watching the games on TV at bars like Hot Stove Saloon and The Port.
One morning that week Ryan and I rode bikes through the residential area and into town. We grabbed coffee and breakfast from Cape Roots Market, but Perks Coffee Shop and Beer Garden is another great spot for a morning cup of joe.
Another day we had lunch at little hidden gem on the water called Brax’s Landing. It doesn’t have a fancy website or a high rating but both my brother Alex & Ryan said this was their favorite lobster roll of the week. So don’t sleep on it!
Our last visit to Harwich was a trip to the best ice cream spot in town, Sundae School. There are many ice cream shops across Cape Cod, but this is known to be highly loved and rated. We waited on line and pondered our orders for about fifteen minutes, the menu is impressive with so many combinations and options to choose from.
Ultimately my sister and I both got what we thought was a mini banana split. But it was not mini at all.. it was the largest ice cream I’ve ever finished. It was unreal and totally lived up to the hype.
Hyannis
Our original purpose of visiting Hyannis was to possibly stop in town for dinner when we returned from the ferry from Nantucket. Since the biggest harbor on Cape Cod is in Hyannis, so it’s naturally become one of the larger towns in the area. This is where the ferries from Nantucket, Martha’s Vineyard and New York come in. But after a long day we were ready to head home and relax. But the town looked adorable and we made plans to return on our last night in Cape Cod for dinner and to shop through town.
Hyannis was put on the map when JFK and his family bought a vacation home there. The Kennedy’s loved Cape Cod, and there are many tributes to them throughout Hyannis including a proper John F Kennedy Hyannis Museum on Main Street. Though I didn’t get a chance to explore the beach or surrounding area much, we all loved the tons of shops and restaurants on Main Street. We popped into a variety of jewelry stores, clothing and home boutiques finding gifts to bring home.
Provincetown
My parents were really excited to take our family to Provincetown, as was I. My grandparents took a trip here together and we have a precious photo framed of them hugging on the beach. We were excited to see that spot we’ve almost memorized, with our own eyes.
Even though its at the furthest tip of the cape, we decided to drive out there on a cloudy morning and explore the town for ourselves like they had once done.
Now I need to interrupt this sweet story to say it’s also a beach town where many of my gay friends come to party in the summer, and after visiting I can see why - P Town is SO FUN.
It’s hard to describe how wonderful it was, but the best way to sum it up is that Provincetown is equal parts eclectic, charming, and wonderful. It’s a diverse community full of beautiful homes, restaurants with live music, cozy café’s, souvenir shops, beach clubs, boutiques and night clubs and bars. And it’s completely adorable!
We covered a lot of ground in in Provincetown, and we were happy to experience so much of it in our short time there! But whether you are vacationing here for a few days, or just passing through, be sure to explore Commercial Street. This is where most of the shops and restaurants are. While there are some stores that felt like a tourist trap, we sort of loved the whole vibe!
We took a picture with a “great white shark”, honored our heritage with a trip to the Portuguese bakery, and stopped in a few art gallery’s! We enjoyed a lovely lunch at Tin Pan Alley and had to bring home some delicious sweets.
I don’t know if I’ve ever been somewhere that had so much history, and was clearly historic, without feeling stuffy. I mean, there is a pilgrim monument and a place called Purgatory Dance Club within 500ft of each other and have to say I love that.
I’d love to come back and spend more time in Provincetown!
Before You Go!
Here is a list of a few more must-do activities in the Cape.. you can’t leave without trying out the following!
Playing a round of mini golf at Cape Escape Adventures in East Orleans!
We had a blast! I came in 2nd place behind my dad but before Ryan and Alex which I will never let down.
Eat fresh fish and wash the seals play at the Chatham Pier Fishmarket
The fisherman come in with the freshest catch! And the seals are so cute and sassy. Apparently this spot has some of the best CHOWDAH too!
Whale Watching! If you want to really experience life on the Cape, this is a great bucket list experience in New England. Hyannis Whale Watching which runs out of Barnstable was one of the recommended tours on the Cape.
Make sure to plan your visit during whale watching season!
And a few more places on the Cape to explore…
Pick something off this list and you won’t go wrong!
Hotels & Resorts
Wychmere Beach Club - Waterside resort in Harwich
Wequasset - 5 Star Luxury Resort & Golf Club in East Harwich
Ocean Edge - Resort & Golf Club in Brewster
Typical Cape Cod Restaurants
Beach Bars & Restaurants
The Beachcomber - Beach bar with live music in Wellfleet #thecomah
Sea Dog Brew Pub - Craft beer, trivia & they have a DOG OF THE MONTH!
Barley Neck - Outdoor lawn with live music
Wild Goose Tavern - Drinks on the porch or in the courtyard! Dinner too
Historic Cape Cod
Chatham Lighthouse
The Black Dog General Store - for shopping!
This trip to Cape Cod was planned in a pandemic, when we knew there would be no family Euro trip happening. But just like 2020, 2021 has made us hold the ones we love a little tighter! After losing our dog in May we really needed a trip like this to bring some joy.
I’m grateful for the happy memories we made there this summer, especially including Ryan in a proper family trip! I can picture us going back with our own kids one day. Cape Cod is a perfect summer vacation.
I hope this inspires you to add Cape Cod to your list too!
Xx Gab
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