Salt Air and Scenic Charm: A Cape Cod Getaway to Dennis Port & Chatham
Cape Cod is one my absolute favorite places to vacation. There are so many great towns to choose from, incredible restaurants, scenic views, cute boutiques, you name it. I am lucky to live within driving distance to get down over the bridge without too much of a hassle. This trip took place last summer and I am crossing my fingers I get down again. I spent my time in Dennis Port and Chatham which are a close 20-minute drive from each other on the Southeast side of Cape Cod. I went down with my boyfriend Sean, and my mom and uncle even came down for a night! I cannot recommend these towns more, they are the perfect summer getaway.
Where We Stayed
Sean and I came across the cutest Airbnb cottage that is walking distance from the beach. It is a condo with 1 bedroom, 2 beds and 1 bathroom. Essentially a little studio. There are a queen size bed and a sofa that folds out into a bed if needed. The complex even has a beautiful in-ground pool if you prefer pools over the ocean. Sean and I loved that there was a little private patio where we could sit outside in the morning having breakfast and it was perfect for drying our beach towels and bathing suits! The kitchen featured a small range, refrigerator, microwave and coffee pot. Linens are included except for beach towels. The .10mile proximity to the beach and Sailing Cow restaurant was the best part. You can hear the ocean waves and walk home after a couple drinks which is safe and easy.
What We Ate & Drank
We were lucky enough to have a small kitchen to store snacks and food in so we could make breakfast in the morning and prepare beach sandwiches. However, we could not miss going to some of our favorites.
The Sailing Cow – Steps away from the cottage is a local favorite beachfront restaurant called The Sailing Cow. They serve breakfast, lunch, dinner, have a full bar, takeout window and a side Tiki bar during the day. Monday to Friday from 2:30-4:30pm they have great deals on food and drinks such as dollar wings and half priced oysters. All day every day they have $7.99 margaritas, fruit punch, blue Hawaiian and $4,00 Narragansett drafts. We have come for breakfast, lunch, dinner and been there late night when they close and it is always a good time with friendly staff. Their mudslides are great too!
The Ocean House Restaurant, Dennis Port – If you are looking for a special date night spot, this is one of the most sought-after restaurants on the entire Cape. They were named one of the 2023 Top 100 Restaurants in America by OpenTable, they are a multiyear “Best of Cape Cod” gold winner, and a 2023 Community Choice honoree by Cape Cod Times for Fine Dining, Waterfront Dining, and Most Romantic Restaurant. Sean and I have gone two years in a row and always have the best drinks and the best meal. We always make a reservation in advance and get to sit at their bar which provides an intimate experience. The bartenders are always charismatic and treat guests like royalty. We always end up sitting next to the nicest people and make great conversation. The way they prepare and display their drinks is out of this world and they always taste AMAZING. I got a bone-in pork chop dinner entree while Sean got an Asian-flare style dinner entree with shrimp, veggies, noodles and tempura. The flavors running through these dishes were bursting with every bite. For dessert, we split a build your own cookie sundae which featured all the fun toppings.
Captain Parker’s Pub – Shoutout to Sean’s family for introducing me to this place because they have THE BEST clam chowder I have ever had in my entire life. Nothing beats it or even comes close. It is insanely creamy, the flavor is to die for, you even get a little crunch of sand and that is how you know it’s fresh and good! Sean and I always make sure to stop here for dinner one night because you cannot come to the Cape and not get a bowl of the chowder here. It is a super fun pub style restaurant that has a massive menu with plenty of options for everyone.
Woolfie’s Bakery – We stopped here one day mid-morning after hearing they have the best homemade muffins. The second you walk inside it smells like a bakery from heaven! Sean got a couple different flavors such as blueberry and double chocolate chip. I asked for a gluten free bagel which unfortunately ended up being store bought Udi’s and frozen. Always make sure to ask what you are getting when it comes to dietary needs!
The Veranda, Chatham Bars Inn – My mom and I decided to have a girl’s day and stroll over to Chatham. I have always wanted to go to the Chatham Bars Inn and experience the steps up with their beautiful and bountiful hydrangeas. We got to sit outside under the veranda and there was a beautiful breeze. We started off with two cocktails that were to die for, and I cannot even remember the name of them but just look at this picture and you will know! Then, we split one of their brick oven pizzas which was so light and delicious.
The Beach Bar, Chatham Bars Inn – After lunch we decided to venture down the steps to their beachfront area. They have a private quarter-mile beach with a pristine boardwalk and the option to rent cabanas. There are plenty of beach lounge chairs and umbrellas for the taking. The restaurant is The Beach Bar Grill. We cozied up to the gazebo bar, and each had a mudslide. They top their mudslides with strawberries which were so sweet! Absolutely delicious.
Tips & Practical Info
Getting there: Driving to the Cape is the easiest option as long as you go during the off hours. Sunday mornings and afternoons are brutal but if you get up early enough to get down and you leave late enough you should be in the clear. You can take either the Bourne Bridge or the Sagamore Bridge depending on the area you are coming from. South Shore peeps will most likely take the Sagamore while everyone else would end up going on the Bourne Bridge.
Getting around: The Airbnb reservation comes with assigned parking right out front for one vehicle. We walked to and from the beach as well as the Sailing Cow restaurant, but we mostly drove ourselves places and took an Uber when necessary.
Best time to visit: The best time to visit the Cape is obviously during the summer but you can go down prior to Memorial Day and after Labor Day when the weather is beautiful. That way you beat the typical crowds during the popular months. The weather is just as nice in May and September!
What I’d do differently: I would get a bigger Airbnb only to have more people come with us because it is so fun!
Would I recommend it? 10000% always yes 10/10. I will boast about the Cape till the day I die.
Final Thoughts
Cape Cod is a dream of a location during the summer. The ocean surrounds you, the hydrangeas are everywhere in all different colors, the seafood is spectacular and the hidden gems are always memorable. I love going into all the adorable boutiques, especially The Fisherman’s Daughter in downtown Chatham. I feel exceptionally lucky to live so close that I can go down whenever I please. I am so thankful to have grown up coming here with my family and now I have even shared memories with Sean’s family. This will always be one of our favorite’s and I am crossing my fingers I get down there this year to have a proper lobster roll and a tasty mudslide. That ocean breeze is calling all our names; I can feel it. Book your trip now while you can!
