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Our Typical Cape Cod Itinerary: 1 Week in the Summer

Since starting to visit the Cape years ago, we've kept much of our week-long itinerary the same. When I first took Josh to the Cape after moving back to New York, he just fell in love with it like I did when I was a kid, and we created so many great memories during our first trip together. So we continue to repeat a lot of the same things each year.

While we've seen and done a lot that the area has to offer, we've also started to simplify our week-long stays a lot more to allow as much beach and relaxation time as possible. The first few years we visited, we would always pack in quite a bit because we wanted to do all the things. Now that we've done a lot of those things, we see this trip as a way to really unwind, relax and move at a slower pace since a lot of our other trips and adventures keep up pretty active.

So, if you're looking to see how we plan our week-long stays, sit back and relax, because I'm going to share it all. And keep in mind that there's so much more to do in this beautiful area, this is just how we choose to spend our week based on how often we visit and our preferences.

July & August are peak hydrangea season, and you'll see masses of them in the Cape. 

Of course, everything in the Northeast is weather-dependant. It could rain at any moment, and while we've typically had pretty good luck with weather because we tend to visit in July, we've also experienced rain. So, we always have back-up plans for days when we can't get to the beach or be outside. Keep in mind that our days could end up changing if we get rained out, but I did include one day in this itinerary as our rain day.

We've stayed at the same cottage for years now because the price is right, they allow dogs (for a small extra fee) and the location is amazing. I'm not going to link it because selfishly, we both kind of want to make sure it's available every year when we want to visit (although, it does book up fast and we usually make our reservation 1 year in advance). We also want to protect our privacy. What I will say is, it's in Dennis Port and walking distance to an ocean beach, restaurants and Sundae School ice cream. It's very, very small, and more than 2 people would be really cramped, but it's perfect for us because we're all about location.

We usually go the same week in July for my birthday, because what better place is there for this ocean-loving Cancerean to be for a birthday celebration? We've been during the off-season as well, and don't have a strong preference for either because there are good and bad for both times.

Our rental is Saturday-Saturday, as about 98% of the rentals are in the Cape. In year's past, we'd often take the Friday before our first Cape night off work as well, and get up super early to drive to Boston, and stay the night there to break up the drive. It's a really great way to kick off your trip if you've got the extra PTO at work. We've stopped doing this in recent years because we've been going to Boston more for separate long weekend trips since we enjoy it so much. But, if you're driving, it's definitely worth considering since Boston is only about 1.5 hours from the Cape. This will also allow you to get an early start on Saturday morning.

I feel I must warn you, each night, we end our day with an ice cream cone. Yes, I said it. Us two fully grown adults get an ice cream cone every single night on vacation. And we have zero regrets. It's one week out of the year, so we go all in. And there's some really great ice cream to be had in this area.

I'm going to prepare you now. Traffic getting into the Cape, especially on weekends, is very unpleasant and gets extremely backed up. It'll be the worst part of your trip (but at least you'll get it over with in the beginning!). For the most part, you have to cross the Bourne Bridge, as it's what connects the Cape with the rest of Massachusettes. There are some alternative ways to get around it, but we've found them to be so much more lengthly, that it's almost just as easy to sit in the traffic. If you can get to the bridge before 9a, you'll be in a much better position and the traffic after then will get increasingly worse. Another reason a night's stay in Boston the day before (to get an early start) is a good idea.

If you arrive on the Cape way before check-in, like we do, we plan to run all our errands before heading to our cottage so we can get everything we need right off the bat and just enjoy the rest of our vacation once we check into the cottage.

I know it sounds weird, but Luke's is our first stop. And it's a liquor store. We stop for a few bottles of wine and some beers so we're set for the week. Luke's is our favorite place to go because their prices are good, their selection is great and they have a few locations around the areas we stay.

We've started to make it a habit to stop in Orleans and have lunch at Nauset Grill if the weather is nice. Since we have Emma with us, we obviously can't bring her in anywhere with us to eat, and Nauset Grill provides picnic tables outside. Their food is also really, really good. I usually go for the fish tacos and fried pickles, and they have quite a few veggie options for Josh.
Update July 2021: This restaurant has sadly closed. I don't have a strong recommendation for an alternative place in Orleans just yet (but working on it!). 

Stock up on a few books
After lunch, we'll head over to Main Street Books in Orleans to grab a few beach reads for the week. We love supporting local bookstores when we travel, and we especially love this one for their really lovely selection and even lovelier owner. She even recognizes us each year and often throws in an extra punch or two on our punch card.
Update July 2021: This book store was sold to a new owner a year or two ago, but they have kept everything else the same. It's now called Sea Howl Bookshop. I'm not sure if they still use a punch card, but the inside, as well as selection, is still pretty great. 

Grocery Stock Up
We always eat all our dinners out, but we do stop at Star Market in Harwich for things to make breakfasts at home and picnic lunches to bring to the beach. This market in particular is really nice and has everything you need.

Cottage Check-In
By now, our cottage is ready for check-in and we take a couple of hours to get settled. It's common for rentals to not provide bed linens and bathroom towels (although that's not always the case), so we'll get our bed made, put away our groceries and get our bathroom situated for the week. It sounds like a pain, but it's actually a ritual we've grown to enjoy because it means our vacation is finally here!

On our first night, we always go to The Skipper Chowder House in Yarmouth for dinner. Josh loves their nachos, and their clam chowder is the best I've ever had on the Cape (even better than the popular Lobster Pot in Provincetown). They also have a great fish 'n chips dinner and a veggie seafood pasta. It's right across the street from a small town beach, and has an upper dining room where you can see the water (not the most amazing view, but it's still a water view nonetheless). After dinner, we usually head over to the beach and walk on the water for a bit. It is very, very small, but it's an ocean beach and we can still smell the salty air. They also have benches overlooking the water. 
Update July 2021: The Skipper has pared down their menu as a result of COVID, and no longer serves nachos or anything else vegetarian on their main menu. We always call ahead of time, and they've always been more than willing to make Josh a vegetarian pasta dish. 

Inside The Skipper Chowder House.

Cheers! to our first night of vacation!

The chowder at The Skipper.

Fish 'n chips at The Skipper.

Scrod Zingarella at The Skipper.

Ice Cream
We grab a cone from Cape Cod Creamery in Yarmouth since we're already in the area, and it's so good. They have colorful yellow and blue Adirondack chairs lined up outside and they offer some nice flavors as well (I usually go for the Sandy Neck Snickers).

Cape Cod Salt Water Taffy
We don't do this every year, but again, since we're in the area, if we feel like swinging by for a few pieces of my personal favorite salt water taffy, we stop by the open-air Cape Cod Salt Water Taffy store. It looks just like a food stand, but they have endless flavors to choose from, and they're very reasonably priced.

Bass Hole Boardwalk
If it's a clear day, we'll end our first day at Bass Hole Boardwalk for an amazing view of the sun going down. The beautiful marsh lit up by glowing sunlight as it sets over the boardwalk is just such a beautiful sight to see. Tip: bring bug repellant with you, as the mosquitos and such can be a bit of a pain, and you don't want them to ruin your beautiful sunset moment.

Jog to the beach
I'll admit, I love a moody, foggy New England morning, and you get a lot of 'em on the Cape. We both like taking a jog (or for me, sometimes it's more of a brisk walk) to the beach each morning to burn off our ice cream cones from the night before and take in more salty air to jump start our day.

We love visiting Chatham because it has some of the best shopping in the area right on the main road, a cute little park and beautiful scenery. We spend the afternoon shopping, wandering the streets and going out for lunch. 
Tip: Parking in Chatham can be kind of crazy, so we suggest getting there between 10-11a, and then just park in the first spot you can find as you start to see the shops. It's not worth it to keep driving around looking for the best spot. 

Shopping housewares at Chatham Home is always so inspiring. 

We usually go to lunch at The Squire, which is a cute little tavern. They have a good lobster roll and fish sandwich. And since starting to take Emma with us, we'll now do a takeout order and bring our food to the park across the street for a picnic. After lunch, we stop at Buffy's Ice Cream. It's expensive for the portions you get, but man, it's so tasty! My go-to here is mint chip.
Update July 2021: Buffy's has sadly closed. We could not find another place right in Chatham's downtown that serves homemade ice cream. 

Mint chip cone from Buffy's in Chatham.

Grab a Pie
On our way out of Chatham, we sometimes stop at Marion's Pie Shop to pick up a pie for the week. We will usually place an order a few days prior for a cherry pie and it's such a fun treat to enjoy throughout the week. It's outside of the main street, though, so plan to go before or after parking your car in town.

In the late afternoon this day, we don't make plans, and will either take a nap, walk to the beach with our books or go for a quick dip or hang out on the deck at our cottage with some wine before heading to dinner.

Summer Shanty in Dennis Port is overlooking the marina and is really relaxing with great seafood. I love their fried clams, chowder and lobster roll. 

Ice Cream
Yes, our second cone of the day! We always walk from our cottage to the Dennis Port Sundae School, and Josh always gets the Shark's Tooth on his first visit (black raspberry ice cream with white chocolate chips). You have to say it like Shark Bait, though - Shark's Tooth, who-ha-ha!

Morning Jog to the Beach

Beach Day at the National Seashore
Our favorites at the National Seashore are Nauset and Coast Guard. We pack up our cooler with a perfect beach day lunch and spend the entire morning and afternoon here. Be sure to have cash on you for parking at the National Seashore beaches. They're usually between $15-25 for the day and are often cash only.
Update July 2021: As a result of COVID, the National Seashore is now preferring card payment at the gate. 

Coast Guard Beach.

Ember in Harwich Port. Really great coal-fired pizza, and we love their grilled peach salad. Starting around 7p every night, they light the fire pit outside which makes for a great atmosphere.
Update July 2021: We've officially crossed Ember off our favorite restaurant list. The past two years or so, it has started to go downhill, and this year, the quality of the pizza was terrible at best. Their peach salad is still awesome, but the pizza is just no longer good. We've found that it's increased so much in popularity that wait times for a table here exceed two hours or more at peak times, and I think they just can't keep up with it. George's Pizza down the street serves up great Greek-style pizza, and we recommend bringing that down to Bank Street Beach for a picnic, or taking it back to your hotel/rental. Our new favorite restaurant in Harwich Port is Mad Minnow. 

Grilled peach salad from Ember in Harwich Port.

Pizza at Ember in Harwich Port.

Ice Cream
Right next door from Ember is the Harwich Port Sundae School.

Walk on Bank Street Beach
Bank Street Beach is a short walk from Sundae School, and we'll take our cones to the beach, and wait until the sun goes down.

Nantucket Day Trip
We pretty much always take Freedom Cruises from Harwich Port because it's close to where we stay. It's a fast ferry and parking for day-trippers is free at the Freedom Cruises terminal. They also allow dogs on-board. 

See our Nantucket day trip itinerary here.

Freedom Cruises ferry from Harwich Port to Nantucket.

Since our ferry is in Harwich Port, we usually stop at one of our favorite restaurants, Mad Minnow, after docking. It gets super busy at night and there's always a very long wait during peak hours, but the food is worth it, I swear. Their filet-o-fish sandwich is my favorite fried seafood thing - ever. 

Ice Cream
Schoolhouse Ice Cream in Harwich Port. Known for their huge portions, so do yourself a favor and get the small size. Also, their ice cream is really good!

Morning Jog to the Beach

Beach Day
Beach day again! Let's say this is my birthday. I always want to spend the day at the beach on my birthday. We don't pack anything fancy in our cooler, and it's not any different than a normal beach day, but that's how I like it. 

For dinner on my birthday, we always go to the Ocean House in Dennis Port, and we can walk here from our cottage (but, they also offer free valet parking for anyone who drives there). The views are incredible since it's right on the water, and the food is delicious. It's also a bit fancier so this is the one night during our whole trip we dress up and have a proper date night. They have an outdoor bar next door that is also overlooking the ocean, and it's a more casual atmosphere, tables for ordering small plates of food and a full bar menu.

Seafood bruschetta at Ocean House.

Ice Cream
Sundae School in Dennis Port (yep, prefer this over dessert at Ocean House!).

Morning Jog to the Beach

Beach Day or Provincetown/Rain Day
If the weather stays nice, we'll do another beach day, but let's say this day it rains. We'll go to the movies or Provincetown. If it's off and on rain, or light sprinkles, Provincetown is actually really doable. While a lot of what is fun about Provincetown is outdoors, grab an umbrella and go for it. We've done it during light rain and it was still really enjoyable because we were going in and out of shops, ducking into restaurants for drinks and heading out to wander the marina when the rain stops for a bit.

You can't tell, but it was sprinkling this day when we visited Ptown.

Truro Vineyards
Before or after Ptown, stop at Truro Vineyards. We only recently discovered it, but they have a great lawn area outside with picnic tables. And if it does rain, there is an indoor area as well as a covered patio in the back for wine tastings, so it's a great way to still kind of be outside during not-so-perfect weather. They also specialize in rum, and have a great outdoor bar with awesome mixed drinks that incorporate rum, which is perfect for hot summer (even rainy) days.

Highland Light in Truro
Even in light rain, the walk up to Highland Light isn't awful. It's a very short walk from the parking area, and it has nice views up and around the lighthouse. The first time we went, it was lightly raining off and on and we still enjoyed it.

Rain Plan
If it's a downpour and we really can't be outside, we go to the movies. We rarely go to the movies at home, so this is actually kind of a treat for us (which I know sounds so lame, but it's true). Movies only kill so much time, so we may take a nap, grab lunch indoors somewhere, just hang out in our cottage, or maybe go out for drinks. We also pack a few movies from home and will sometimes do a Back to the Future marathon if it's heavy rain all day (or at night). 

If we feel like staying in this night (because of rain), we may grab pizza from George's Pizza in Harwich Port and eat in if we were lucky enough to be able to get outside during the day. They have really great Greek-style pizza. But even if it's raining, we usually like to still try and eat out somewhere specializing in seafood. If we're up for going out, we'll head over to Original Seafood in Dennis if we feel like staying close to the cottage. It's a very unassuming seafood joint with killer food. I love their lobster roll. But, if the weather clears up and it turns out to be a nice evening, we'll venture over to Sesuit Harbor Cafe in Dennis for the best lobster roll in the Cape. All seating is outdoor picnic tables, though, so we only do it if it's a nice night. We'll also pack up a bottle of white to bring because it's BYOB.

Fish sandwich from Original Seafood.

Sesuit Harbor Cafe.

Lobster roll from Sesuit Harbor Cafe.

Ice Cream
Sundae School in Dennis Port.

Morning Jog to the Beach

Beach day
We usually make it a beach day, going somewhere in Dennis or Harwich Port.

Dinner and Beach Fire
We'll grab dinner at Moby Dick's or Mac's On The Pier (both in Wellfleet) and plan a beach fire for our last night. Most beaches that allow beach fires are in the Eastham/Wellfleet/Truro/Ptown areas, and you have to request your fire permit a few days in advance. It takes a bit of effort to coordinate because you want to pick a night with good weather, but it's definitely worth it.

Moby Dick's in Wellfleet.

Fried clams from Mac's on the Pier in Wellfleet.

The next morning, we clean our cottage and pack up our car to leave by checkout time, which is 10a. Sometimes, we stop in Sandwich on our way out for a quick stroll around town. Then we drive to Wegmans (the best grocery store to ever exist) in Natick, MA to cheer ourselves up about vacation being over (yes, we actually do that). 

There's so much more to do in the Cape than what I've listed above. Be sure to peruse all my upcoming posts to learn more about things to do during your visit if you're looking to explore more of this beautiful area.

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  1. This was a wonderful read! Thank you for taking the time to put this together. I hope you and Josh are doing well! I'm curious as to how your big renovation project is going. I'm sure you guys are ready to have your living rooms back in order by now. Also, I tried to subscribe to this new blog and it keeps telling me that this feed does not have subscriptions by email enabled. Just wanted to let you know in case you were unaware. :) Have a beautiful day!

  2. Hello Casey! Oh, thank you so much. I'm so glad you enjoyed it! Renovations are going well - they just move so slowly. Living rooms are both still completely torn apart (although we're in the process of putting floors back in, so small steps!). Oh gosh, I had no idea, and thank you for letting me know. I'll have to have Josh look into it for me. Thank you again so much for stopping by!

  3. Going to the cape for the first time this summer (having been inspired by your videos for years!) and this blog is so super helpful. I always thought that your vacation style was very similar to what I love in a vacation, so thank you so much for passing on your cape wisdom to us newbies! I cannot wait to relax and beach quarantine :)