Guide to 5 perfect days in Cape Cod

With summer just ahead of us, I know some of my fellow New Yorkers are planning out thier vacations. If you're looking for the perfect place to go that is driving distance but also has beautiful ocean beaches, you should definitely look into visiting CAPE COD!

For our 1st anniversary on September 7th, 2020, we planned on doing something big- especially since we didn't exactly go on a honeymoon. With the pandemic, we decided not to travel too far and opted to find somewhere close that we could drive to but still be on the water. Cape Cod was our choice and it did not disappoint! We wouldn't have chosen Cape Cod if it weren't for travel restrictions and I can honestly say I'm so thankful for this. It was like fate. Every single day we spent there was sunny and warm, and we filled our days with just enough adventure and relaxation. There's so much you can do on the Cape, but I'll write mostly about what we did, with a list of things I wish we got to do/will make sure to do next time. Enjoy!

WHERE WE STAYED:

We went to Cape Cod on Labor Day weekend, so a lot of places were booked by the time we looked. We ended up finding the sweetest bed & breakfast, the Queen Anne Inn. The inn keeper was so friendly and sweet, asking us everyday how we were and what we were doing for the day! She knew us by name, and even learned what we liked to eat and drink! It really felt like coming home after a long day. One of the nicest parts of our stay was the gormet full american breakfast that came with our room everyday! You could choose to get your breakfast delivered to your room, or choose to sit in their beautiful sun room, dining area, or even outside in the garden. Each night when we arrived back, the inn keeper would also serve us our wine where ever we chose to sit that night. One night, we met some new friends right on the front porch of the inn sitting by the fire. It was overall just a very homey, relaxing place to stay.

If you want to splurge on a place to stay, check out Chatham Bars Inn or the Wequassett Resort and Golf Club. We tried to get into Chatham Bars Inn for our anniversary dinner, but again, it was Labor Day weekend and it was fully booked. We ended up eating at the Wequassett and it was BREATHTAKING!!!

There are also so many cute Airbnbs to rent!

WHERE WE ATE:

BREAKFAST:

Captain's Table

Marion's Pie Shop

LUNCH & DINNER:

Bistro on Main (Chatham)

Beachcomber (Wellfleet)

Chatham Pier Fish Market (Chatham)

Wild Goose Tavern (Chatham)

The Summer House (Nantucket)

The Pelham House (Dennis Port)

Ember Coal Fired Pizza & Wings (Harwich Port)

Outer Bar & Grille at the Wequassett (Chatham)

5 PERFECT DAYS IN CAPE COD

(FULL ITINERARY)

Do you like to create a written itinerary for every day when you travel, or do you like to go with the flow? If you're like me and need an itinerary not only for your sanity, but also to plan outfits, save your time- I did it for you below! ☺️

Day 1:

After we checked in, we had a few hours to spare so we decided to walk to downtown Chatham to kick off our trip with drinks and soup at the Bistro on Main. I mean what's a trip to Cape Cod without New England Clam Chower? Afterwards, we drove up to Wellfleet (about a 40 minute drive) to have dinner with close family that live in Massachusetts. We ate at the Beachcomber and it was great! What was even better than the food, was the view! We walked over to the ocean after dinner and watched the waves crash for bit. I would love to plan a trip back to the Cape just to explore this area more. It was stunning!

(pictured above: soup from Bistro on Main)

(pictured: us on the beach in Wellfleet)

Day 2:

The next morning, we enjoyed our breakfast in the sunroom at our Inn. Then, we picked up our paddleboard & kayak from the Cape Cod Beach Chair Company at 10am. I made arrangements for this before the trip, so it was seamless and easy! They helped us load them onto our truck and we were free to use them wherever we pleased until 5pm. We took them to Oyster Pond first, which was right down the road from where we were staying. We paddled for a couple hours here and decided we wanted to be near or on the ocean. We ended up parking the truck on a random side road off of Old Harbor Road (see below), where we saw a bunch of other people parked and using the beach.

We stopped to ask a few people how they parked and they said no one has bothered them and that they had been there for hours. I'm not sure what the rules are for this road usually, so hopefully it works out for you just as good as it did for us. There are a lot of signs around the Cape to beware of sharks, so I was a little skeptical to paddle out too far. We paddled literally right along the Catham Harbor shore as close to the beach as possible. Along the way, we saw seals in the distance (a huge sign sharks may be near so you can only imagine how much I was freaking out). We stayed close to the beach, but the seals were out to play! They swam all around us, and even got close enough to my board to make Lucas scared they were going to flip me over. It was amazing but also a little scary to me so we decided to move on to the Chatham Pier Fish Market for lunch. We left our paddleboard and kayak on the beach and walked over to the market (DISCLAIMER: I think was private property, lol- good thing I'm not some big time blogger and could get in trouble for this please don't tell on me). Take chances at your own risk, people. This place was so cool because not only to you get an authentic, fresh Cape Cod lobster roll, but you can eat it with a view of the fishermen in action! This is when we realized why there were so many seals- because the fishermen were tossing in their unwanted catch to feed them! There were so many seals swimming, eating, and playing around. Overall, this day turned out way better than we imagined, even for Lucas who hates strenuous activity. 🤣 It was mostly unplanned, and a bit unorganized, but it turned out perfect!

The night after paddleboarding, we showered and got dressed to go back to downtown Chatham to take our time shopping and getting dinner. Side note- we LOVED how our Bed & Breakfast was walking distance to town. We ate at the Wild Goose Tavern. I recommend stopping in or calling to get your reservation before shopping. We did this and it was a great way to enjoy our 2 hour wait.

(pictured above: one of the cute shops in Chatham)

Day 3:

Nantucket day! We booked a ferry in advance through Hy-Line Cruises that left at 8:30am. The drive to the port was about 45 mins from where we stayed, so we had to get up early to make it. A staple in Chatham, that was recommended to us by our Uncle Kevin who grew up in MA, is Marion's Pie Shop. We ended up stopping on the way to our ferry to Nantucket as it was right along the way! If you run out of time to do this, there is food and beverages on the ferry itself. We arrived to Nantucket at 9:30am and picked up our bike rentals at 10am from Young's Bicycle Shop. It was $70 for 2 pedal bikes, from 10am to 5pm. Honestly, I wish we spent the extra money and rented motorized ones. (A must do if you want to see the whole island in a day.) This was another thing I booked ahead to save time and effort. We decided to ride our bikes to Siaconset. It was a long, straight bike path along the road, that took a litte less than an hour. There was really no place to stop for water, so plan ahead and bring some. Once we arrived we stopped at a local market to grab waters and snacks, then headed to 'Sconset Bluff Walk, a footpath that takes you through the backyards of waterfront mansions! You have the sea on one side of you, and gorgeous homes on the other side. It's difficult to choose which way to look! It was a bit hard to find, but we just asked locals that were walking for help. I do not reccomend walking your bikes through this. We did and regretted it. On the plus side I did get this cute photo below with my bike on the path. 😆 I would lock them up somewhere ahead of time to fully enjoy the walk.

After our walk, we came across the cutest place for lunch that you could eat RIGHT ON THE SAND! It's called The Summer House. You can also stay here, which is officially on my bucket list!

After lunch, we decided head back to the other side of the island and visit Cisco Brewers. This is definitely a MUST, especially if you like beer. Even if you don't, the "vibes are immaculate" or whatever the kids say these days. They have food trucks to eat at, live music, and the best atmosphere you could ask for. Once we arrived here, we had already biked 16+ miles! Pretty much as soon as we ate and had drinks, we started to relax and did not want to ride our bikes back to town. Lucky for us, we weren't the first ones to feel this way, and Young's Bike Shop was prepared. There was a drop box for your bike keys so you could leave it, locked up of course, for them to pick up. We took an Uber back to town and still had time to enjoy Nantucket and explore while making our way to our ferry ride home. We even caught a sunset on the docks while waiting!

Day 4:

Day 4 was also Sunday, and the day after we made friends on the front porch and had a little extra to drink lol. We decided to have a beach day and relax! We went to Chatham Lighthouse Beach. Parking here was tough, so try to arrive early to get a good spot. We spent the afternoon in the sun, reading our books and having a few beers.

After our beach day, we headed back to get ready to go watch the sunset in Yarmouth Port at the Bass Hole Boardwalk. This was so precious, I loved it so much.After sunset, we headed to dinner in Dennis Port at the Pelham House. This place is STUNNING. We arrived an hour before our reseration and had drinks outside by the fire that overlooks the ocean. When we were called for our table, we went to the top floor that was enclosed with glass to also provide views of the ocean. Not only were the views stunning, but the food was 10/10. On the way home from dinner, we stopped to Ember Coal Fired Pizza & Wings for a night cap by the fire bar. We did not regret this decision! This was also such a fun vibe.

(pictured: seafood at the Pelham House)

Day 5:

On our last full day, and our anniversary, we rented a boat to enjoy. This was Lucas' #1 request, so it was worth the splurge. We took the boat down the coast to Bass River, and found a place to have lunch that was right at the marina, called the Summer Shanty. After napping in the sun and fishing, we went back to our B&B to shower and get dressed up. The owner of the Queen Anne Inn was so nice to provide complimentary champagne for us to enjoy on our balcony to celebrate before taking off for dinner. This was the night we had dinner at the Wequassett. One word- phenominal. We were treated like royalty and the food was amazing. Highly recommend!

(pictured above: the outdoor space at the Wequassett and our dinner)

Day 6:

Check out day. We packed our things and then headed back to town one last time for breakfast and last minute shopping. Although breakfast came with our stay, we decided to eat at The Captain's Table this morning. It was one of my favorite breakfasts on the trip. If you have kids, you should definitely check out Ducks in the Window. You can customize any size duck you'd like for your little ones to take home as a souvenir, or let them choose themselves! Another Cape Cod original souvenir shop is the Black Dog. We grabbed some things for our dog, Fiji, here and also our daughter, Kinsley. After shopping we headed home to our babies.

Things on our Cape Cod bucket list:

Sailing

Truro Winery

Explore Wellfleet (and the Cape Cod National Seashore Park) area more

Provincetown

Marthas' Vineyard

I truly hope you enjoyed this travel guide and blog post! It was very special to me considering it was on this very trip that I decided I wanted to start my blog to help people find the best things to do and places to see on vacations like this! We got lucky a few times, but it honestly took weeks of planning and research for it all to come together. Hopefully this post helps you plan the perfect trip, too! Happy travels! 🧡🦭