Cape Cod Travel Guide || Summer 2023

Cap Cod has been one of my bucket list travel destinations for years now— the preppy style, gorgeous scenery, and timeless aesthetics were flooding my Pinterest feed so much that I decided it was finally time to pay a visit. 

We spent four days exploring Cape Cod and I so wish we had longer. There was a lot less to do here than I expected which I was pleasantly surprised by. The more I travel the more I love a destination that allows for a little wandering. We shopped, ate, and drank our way through the cute towns of the Cape. Today I’m breaking down our full itinerary including local favorites, food, and more. 

Fore reference we visited the last week of June which is supposedly right before peak season. Everything was open and inviting, we just missed the summer crowds! Unfortunately, we also missed the good weather. It was still pretty brisk during our visit, not yet warm enough to enjoy a good beach day. I supposed that means I’ll just have to come back sometime soon! 

Anywho, onto the recommendations. 

Transportation Within The Cape 

Another thing I was very surprised by was just how big (and spread out) Cape Cod was. I ended up driving this trip and was so glad I did. Getting from one town to the next isn’t doable by foot and while you can always call an Uber, we saved a lot of money (and headaches) by having my car with us.

Parking was also free everywhere we went which was music to my ears—if you know me you know there’s nothing I hate more than having to deal with valet, haha. 

Of course, you also have the option to fly. The closest airport is Cape Cod Gateway Airport.  

Where To Stay

There’s nothing I love more than a cute little inn. The Gryfinch Inn is nestled quietly in Chatham, Massachusetts arguably the chicest side of Cape Cod. This property was newly renovated so we were one of its first visitors. We were greeted with the most New England esq decor—beautiful blue and white hues, patriotic touches, and of course huge blooming hydrangeas. 

How adorable are these rooms?! As I said, they are newly designed and full of modern elements. Everything from the cozy linens to new headboards, to coastal decor made this room so inviting. There were three of us on this trip so they placed us in a 2 Queen Bed rooms and between the spacious seating area and luggage rack we had plenty of space to spread out. 

How thoughtful was this welcome basket too!? I was greeted with Greyfinch merch, sweet Cape Cod momentos, and yummy gummy snacks! 

Here’s a sneak peek at the bathroom area. We stay in a lot of different hotels as we are full-time traveling right now and I will say, this was one of my favorites we’ve had in a long time. The shower was beautiful with gold accents and a large glass door. 

Our double sinks were outside of the toilet/shower area. There was tons of space to spread out which made getting ready in one spot so much easier. However, the mirror is what really sold me on this space—finally one as big as the wall so nobody’s fighting for room in the morning, lol. 

Greyfinch Inn also had an amazing outdoor patio + pool area. We had the whole place to ourselves one evening for a happy hour wine night. We snapped photos and hung out here for a bit. It wasn’t warm enough to go in but they’ve got the place stocked with outdoor games and pool floats for when the time comes! Truly the perfect place to stay if you’ve got the whole fam together and are looking to hang out. 

The staff were so accommodating and we had a seamless stay. I highly suggest looking into this property if you’re looking for a mellow stay on the Cape. For the best rates and current availability at the Greyfinch Inn, click here. 

Where To Eat 

New England is known for its fresh seafood, tasty lobster rolls, and blueberry lemonades. You should know me well enough by now to know we enjoyed all of the above during our stay on the Cape. I asked you for recommendations on Instagram and spent a few hours scouring Tik Tok for cute places to eat— I’m sharing my favorites down below. Per usual I’m linking the most up-to-date menus so you can browse beforehand and the directions to each spot so you can plan accordingly! 

Pain D’Avignon 

menu || directions

Wow, what a spot! I cannot begin to describe what an incredibly unique dining experience we had at Pain D’Avignon. This restaurant offers a large French selection with hints of New England flair. We stopped in just in time for lunch and started off with the creamy burrata and the open-face steak sandwich. Definitely a yummy option however it was the catch of the day— fresh halibut with coconut sticky rice and a mango cucumber salsa that blew me away. I’m not usually a fan of fish but this was so flaky and flavorful I just couldn’t resist.

The owner stopped by to chat with us and I was so moved by his story. This restaurant also offers order-at-the-counter sandwiches and fresh pastries, cooked daily right there. He brought us around back and we were able to see the hundreds of baked goods being prepared for the evening. They sell their products in local grocery stores, Whole Foods, and Trader Joe’s so even if you can’t experience the restaurant firsthand, you can still get a taste of fine dining! 

They are currently building a pizza spot right next door that is set to open within the next few months. Here they will serve traditional Naples, Italy-style pizzas with the freshest ingredients. I can’t wait to visit once it’s all done. I’ll be cheering this family business on for years to come. 

The Port 

menu || directions

This spot was recommended to me numerous times and it certainly did not disappoint. Our waiter happened to be a follower of mine which made the evening that much better. You get the best of both worlds with the spot—it’s known as a chic family dining spot that turns into the most popular going-out spot for 20-somethings in the evenings. They have three different bars with live music, outdoor seating, and tasty drinks. We came in for dinner and had the best experience! 

I started off with one of their specialty mojitos—they use freshly muddled fruit making them the lightest drink for the summertime! Jules and I shared the crab cake and fish tacos. The crab was excellent with a crispy exterior and an amazing corn and bean garnish. Our tacos had the freshest fish, marinated perfectly with lots of guacamole and pico. Sam tried their lobster roll and was in heaven. 

Highly suggest coming here, especially if you’re an oyster fan. They do $1 oysters from 3-5 pm every day! We were here for four hours chatting with the staff—we even walked out with matching Port hoodies. Love love love.  

Ember Coal Pizza 

menu || directions

While we were at The Port for dinner, we learned they had a second restaurant, Ember; so naturally we had to go for lunch the next day. I found these blueberry lemonades on every menu here in Cape Cod and got them every chance I could get. You can get them virgin or spiked with vodka and they are the yummiest, freshest cocktail ever. 

We ordered two different pizzas—chicken pesto and the  XXX with arugula on top. However, the waiter surprised us with the blueberry goat cheese and prosciutto. Now trust me, I know this sounds like quite an interesting combination but it was by far the best. Such a unique flavor combination that you’ll be thinking of for days to come. Their pizza is thin curly and wood-fired meaning it has a crispier exterior. You can fill up on so many slices this way. 

Fish 

menu || directions

Fish is the cutest seafood restaurant you ever did see! They have adorable coastal decor inside and a huge outdoor patio with a view of the water. They had a huge cocktail menu and everything, I mean everything right down to the fruity margaritas was a fan favorite amongst our crew, lol. 

They have every protein you could imagine available as tacos, quesadillas, bowls, and burritos, I went with their grilled shrimp tacos and they were amazing. The tacos come in threes and are stuffed so full— I definitely recommend sharing a few things instead. We had rice, beans, guacamole, and pineapple salsa to top everything off. So yummy! 

The Attic

menu || directions

We went to The Attic for dinner while we were in Martha’s Vineyard and I have to say, I was a little disappointed by my food. They are known for their wide variety of burgers with unique toppings—I decided to try the turkey burger with brie cheese, arugula, and a light jam. I wanted to love this but something about it was just off. 

The girls both ordered their Attic Salad and said It was one of the best salads they’ve ever had out so I can’t be so quick to judge, haha. The atmosphere here was really cool, you’re up high in an Attic and get a cute view of the coastal town that is Vineyard Haven!

Wild Goose Tavern

menu || directions

The Greyfinch Inn is affiliated with the Chatham Wayside Inn which is just a few minutes down the road. This hotel has a restaurant called Wild Goose that offers free breakfast every day. You can also dine as normal so we popped in for a mellow dinner. They have a huge outdoor patio area that’s right along the block so you get a front-row seat of all the Cahtahm action. They had live music too which was such a nice treat! 

I needed something light so I went for the crab cake. It had tons of crab meat in it but wasn’t as crispy as I like them. Super yummy corn and beans with it though. I also tried the lobster bisque as this was their soup of the day and is supposedly a Cape Cod essential. 

Exploring Chatham 

Cape Cod is made up of several different towns, which was news to me upon arrival. As I mentioned, we stayed in Chatham which is one of the most expensive towns on the cape. For that reason, it also has the best shopping. (Or do I just have expensive taste, haha?!). Anywho each of these towns is made up of all kinds of summer homes and adorable neighborhoods. There is a small strip in each of them that has different restaurants, bars, shopping, and local favorites. 

You must stop in all of the souvenir shops if you’re looking for a cozy crewneck or postcard. I picked up a few small kink knacks and then made my way over to the high-end boutiques for more shopping. They also have preppy-blogger favs like Lilu Pulitzer, The Black Dog, and more. 

I really liked it over here. There are several gorgeous churches, bookstores, and a few thrift/flee markets going on. The perfect way to spend a dreary afternoon. 

Exploring Harwich 

Harwich is the town over from Chatham. It’s a lot smaller with fewer stores but definitely worth checking out. If you don’t plan on eating/drinking, you don’t need more than 2 hours to see and do it all. it’s super cute over this way so I highly suggest taking a stroll through the different neighborhoods and even walking over to the beach. There are more private accesses down this way so in the midst of a dreary afternoon we were able to catch a few peaceful minutes by the water. 

Exploring Marthas Vineyard 

We were debating taking the ferry to either Nantucket or Martha’s Vineyard for the day and ultimately decided on Martha’s Vineyard because it was much cheaper and a lot closer. #20 roundtrip and 40 minutes later we were greeted by the cutest place ever. Martha’s Vineyard is made up of six different towns, each with their own unique flair. 

We arrived in Vineyard Haven which had several ice cream shops, restaurants, and a few stores however, Edgartown was where all of the best shopping and views were! I popped in and out of every store, spending hours browsing the pretty (expensive) dresses and amazing straw accessories. Some of my favorites include Sea Legs, XXX, and XXX. 

Your wallet will be hurting after an afternoon here but you’re sure to come home with a banging new wardrobe. There are several adorable neighborhoods full of the chicest, most expensive ones along the water. We made sure to walk through them all, soaking up the American beauty. Several presidents spend their summers here and I can totally see why. 

It’s important to note that Martha’s Vineyard is huge. You can either Uber from one town to the next or ride their public transportation. It’s $8 for a day pass and you can get on and off however many times you desire. It was fairly clean and we felt plenty safe so I have no complaints. Definitely a cheaper alternative!

Of all the places we visited during our New England road trip, I liked Martha’s Vineyard best. I would love to come back and stay in a hotel on the island at some point—as well as get on a boat and enjoy the ocean. Everyone was just so happy to be summering here that the energy was contagious. So photogenic and so much fun! 

WHAT TO WEAR/PACKING LIST

Not sure what to wear to Cape Cod? Don’t worry I’ve got you covered—sharing all seven outfits I wore during my trip in this blog post. Per usual I’m sharing links to everything so you can shop as well as directions to each photo location so that you can spice up your Instagram feed!

Things to add to your summer packing list:

• Linen Button-Up: It gets chilly here in the evening. I highly suggest bringing a lightweight linen button-up with you when going to dinner/out for the evening. Aerie has some of my favorites right now.
• Pair Of Jeans: This was one of those trips I was so glad I had a pair of jeans packed with me. As I said, it gets a little brisk in the evenings, especially by the water so I suggest throwing a pair into your bag.
• Claw Clip/Hat/Hair Ties: It was so humid and rainy during our stay that I just couldn’t wear my hair down. I definitely suggest bringing a claw clip, hat, or a hair tie to tame your mane.
• Coastal Grandmother Attire: Now’s the time to break out all of your coastal grandma pieces the Tik Tok convinced you you “needed”. Whether it be that seersucker button-up, the frilly blue dress, or the gorgeous florals, bring them all. I scored so many compliments on my outfits this trip, I couldn’t believe it. I must have fit the part, haha. 

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What a fun few days we had in the Cape! I have to say, this is less of a trip and more of a vacation. There are no landmarks you “have” to see or bucket list items that must be checked off but rather a place that I’d suggest for a large group of friends rekindling their longest fun. Rent a huge Airbnb, spend your days wandering the shops and soaking up the sun, and then head to town for dinner and drinks. 

It’s a slow, expensive lifestyle here and I understand now why so many people love spending their summers here. The close-knit community aspect really showed through and charmed me instantly. I hope to be back here someday frolicking the streets with my loves! Until then.

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