The Ultimate Cape Cod Itinerary

Cape Cod has always been a dream destination for me thanks to the books I read during my teenage years which were based out of this region. While I grew up 7000 miles away dreaming of its numerous beaches, lighthouses, islands and villages, little did I know that I would be able to visit Cape Cod numerous times later in my life. What made it even more fascinating was that many authors made Cape Cod home, deriving inspiration for their books and stories.

While you could break this itinerary down for multiple visits the way I did, doing it all together at once is a great opportunity for those coming from outside the New England region.

Comprising of 15 towns and 3 islands, Cape Cod is a popular summer destination. It is divided into 4 sections – Upper Cape, Mid Cape, Lower Cape and Outer Cape.
Here is what this itinerary covers: Falmouth (Upper Cape) -> Martha’s Vineyard Island -> Hyannis/Barnstable (Mid Cape) -> Nantucket Island -> Provincetown (Outer Cape). If you have additional time, do make time for the quaint village of Chatham (Lower Cape) before heading to Provincetown.

While Cape Cod can get expensive, we did it on a budget by renting AirBnB wherever possible. The beach houses are usually affordable for bigger groups but you may find some good options if booked in advance. We also took day trip ferries to Martha’s Vineyard Island and Nantucket Island as accommodation on those islands is pretty expensive. While you can take your car on the ferries to the islands, it might not be worth it for just a day trip. However, you can rent bikes/mopeds/cars and take public buses to explore them. To balance things out, we rented mopeds on Martha’s Vineyard and used public transport in Nantucket. Bikes are a great way as well, but considering how big these islands are, you won’t be able to cover much ground in a single day.

I hope you love the Cape as much as we did and have a great time vacationing in this part of New England!

Day 1 – Falmouth

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We drove from Boston to Falmouth (72 miles) which was our first stop beginning the vacation on Cape Cod. You will want to book your accomodation for 2 nights in this town. We will be back the second night returning from our day trip to Martha’s Vineyard.

Start your day early by spending some time at Old Silver Beach. It’s a popular summer beach, great for swimming and spending time in the sun. There is a section of the beach limited to it’s residents and hotel guests. The Sea Crest Beach Hotel has changing rooms, a pool and volley ball net in case you prefer to stay at a waterfront property. There was a lot of seaweed when we visited but apart from that, the beach was clean and sandy.

After a hearty breakfast, get ready for a hike to The Knob and appreciate the panoramic views of Buzzards Bay and Quissett Harbor. It’s a little peninsula (12 acres) with hiking trails, small beaches (on both sides) and scenic views. The shape of the peninsula towards the end is very unique, and it offers great sunset views if you can manage to be there around that time.
Next we headed to the Nobska Lighthouse. Located on a bluff at the southwestern tip of Cape Cod, it is situated at the entrance to Woods Hole Harbor. This lighthouse will always have a special place in my heart as it was the first lighthouse I ever visited. It literally took my breath away.

Finally, we went to the Main Street in Falmouth downtown to grab a bite. The street, with plenty of shops and boutiques, is a great place for people watching. Take a stroll along the street and dine at one of the many restaurants. The town also has trolley tours in case you want to know more about it’s history from the comfort of a covered coach.

Day 2 – Martha’s Vineyard

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We started early on Day 2 as we had a 9 AM ferry departing for Martha’s Vineyard. You could walk to the ferry terminal in Wood’s Hole or book a full day parking at the terminal. Alternatively, you can also book a cab if that’s more convenient for you. We reached the terminal 45 minutes before departure. The ferry was comfortable, with both indoor and outdoor seating. You have an option to choose from high speed ferry or the regular one which is a little cheaper. We went for the high speed ferry to save time and get more time on the island.

After our arrival at Oak Bluffs, we rented some nice colorful mopeds and set off on our journey to explore this gorgeous island. The idea was to ride all the way to Edgartown in the east and then Aquinnah which is on the other side of the island.

Our first stop was the Gingerbread Cottage Village only a few miles away from the terminal. This fairy tale village looks as beautiful in reality as it does in its pictures. Originally created in the 19th century as Methodist campgrounds, these 300 colorful Victorian cottages are right out of a storybook. We are not allowed to ride the mopeds all the way, so park them at the entrance and walk into the village.

Next, we headed to Jaws Bridge in Edgartown, my personal favorite on the island. The bridge has been named after the 1975 movie ‘Jaws’ which was filmed at this location and around the town. People love to jump from this bridge during summers and dive into the water below. It is a lovely sight, even if you are not into jumping off the bridges! We stopped for lunch on our way to the Edgartown Lighthouse. The lighthouse is located close to harbor offering a stunning background for photo ops. It was beautiful and every bit worth the trip to this side of the island.

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It was time to get on our mopeds and ride to the other corner of the island, Aquinnah. It took a good 40 minutes on the moped at the speed of 35 MPH. The weather was perfect and we relished the last few days of summer. We even spotted a recital practice on our way while departing the town! Aquinnah Cliffs Overlook has the most dramatic views on Martha’s Vineyard. Since we mostly come across flat beaches on the east coast, the lower beach was dreamlike offering views of the cliff up close. There is also a lighthouse called Gay Head Light on premises. It can be viewed from the Aquinnah Cliffs Overlook lookout and forms a post card perfect view together with the cliffs in one frame.

Head to the Aquinnah Shop Restaurant, grab a table at outdoor deck and enjoy a beer with spectacular views of the ocean. This was easily one of the best restaurant views I have had in my life. I wish we could have stayed for sunset but unfortunately had to catch the evening ferry back to Falmouth.
We returned to Oaks Bluff and had an hour left to spend on the island. The area around the ferry terminal is full of life. Bars, restaurants, shops, yachts.. it is lovely in every direction. We had an ice cream from Mad Martha’s and strolled around. We didn’t realize that we would be on our return ferry during sunset which was a bonus!

Called it an early night after getting back, as we were headed to our next stop Hyannis tomorrow.

Day 3 – Hyannis

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We left Falmouth next day and drove to Hyannis which is only 25 miles away. Hyannis is a bustling town right in the center of Cape and is considered an excellent base to explore the surrounding towns. We took a detour to grab lunch at Fisherman’s View in Sandwich, MA. We love dining with a view and the food pictures on Yelp were drool worthy to say the least. We booked a table at the patio in advance and enjoyed delish seafood including lobster rolls, sushi, fried calamari and crab cakes! After checking in to our AirBnB in Hyannis, we got ready for our Stand Up Paddle Boarding lesson booked with ‘Stand Up & Paddle Cape Cod’. The accommodation came with a beach pass which helped us save on parking throughout our stay. The location for the lesson is finalized the morning of the activity, based on the weather. Plus, they guarantee that it would be 20 minutes from your accommodation which is quite convenient. Amy was a great coach and patiently helped us learn the activity. Towards the end, most of us were paddle boarding without effort and loving the sport to no end.

Next we left for Dowses beach, a residential beach lesser crowded than other public beaches. If you prefer a bigger beach, go for the Craigville beach which is another great option in the neighborhood. The AirBnB had beach chairs available for our use and they came in handy during our beach visit. We stayed for the sunset, our first experience ever. It was beautiful with the sky gradually changing colors and water glistening in many hues. It was time to head home, take a shower and leave for dinner at Tumi Ceviche Bar & Ristorante. This Peruvian & Italian fine dine restaurant is located at Main Street in Hyannis. The food was excellent – their Lamb Osso Bucco, a Peruvian dish, is one of my favorites till date. The street is full of bars, boutiques, cafes and shops, great for people watching and strolling around the town center. It was an eventful day and it was time to get some good sleep before leaving for Nantucket the morning after.

Day 4 – Nantucket

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Next morning, we took a ferry to Nantucket from Hyannis terminal. We booked parking with Hy-line cruises and they had a shuttle from the parking lot to our departure terminal. If you choose to park with them, plan to reach there 45 minutes before departure. There was a cafe on premises, we picked up some coffee and muffins and boarded the high speed ferry to Nantucket.
Travelers often draw a parallel between Martha’s Vineyard and Nantucket. Both islands are like cousins, similar in some ways yet different! Nantucket is smaller but farther out into the sea. While Martha’s Vineyard is colorful and casual, Nantucket is more polished and known for it’s classic gray cottages. Both of the islands were a beautiful experience on their own.

We began our journey by walking to Brant Point Lighthouse. Located at the entrance to the Nantucket harbor, it is the second oldest lighthouse in America. Originally erected to protect from shipwrecks caused by shoals around the island, this lighthouse is now a part of The National Register of Historic Places.
Next, we had a hearty lunch at the Charlie Noble. The food was scrumptious and I had the best crab cakes ever!

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After lunch, we took a bus to the village of Siasconset where we were welcomed by lovely luxurious cottages. We grabbing a quick coffee and started the Sconset Bluff Walk also known as Cliff Walk. It cuts through the village of Siasconset with lavish cottages and summer homes along the bluff on one side and ocean on the other side. It is the most scenic hike on the island with a dreamlike setting unlike ever seen before. These are some of the most expensive and beautiful properties on the island, some of them even owned by celebrities.
The walk took us to Sankaty Head Lighthouse. The name ‘Sankaty’ is derived from a Wampanoag word meaning ‘highland’. Fun Fact: Back in the day, the bluffs were used as a lookout for whales by some of the early European settlers heading for longer expeditions.

It was time to head back to Downtown Historic District from where we would board our ferry back to Hyannis. We did however have an hour to explore the Straight Wharf Marina and Old South Wharf. They were lined with luxurious yachts and cute little stores. There were plenty of restaurants, cafes, shops and boutiques in town. The hustle and bustle of main town was a lively contrast to the quieter Siasconset village.

We lucked out again by witnessing sunset from our ferry back to Hyannis. Perfect end to another beautiful day!

Day 5 – Provincetown

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Next morning, we drove to Provincetown (50 miles), also known as Ptown which is located at the tip of Cape Cod. First thing that stood out for me was how we couldn’t spot any chain restaurants and cafes unlike other towns in Cape Cod. It was a delightful change not coming across a Dunkin Donut, Starbucks or McDonalds at every corner. Instead the town was lined only with locally owned joints which was a pleasant surprise.

We started exploring the town by strolling the Commercial street. After grabbing a coffee from the Wired Puppy, we walked around the historic district before heading to the Pilgrims monument. The town was full of life with LGBTQ flags all around. This town was one of the earliest ones to have accepted homosexuality and celebrated it. Home to a number of LGBTQ festivals and events, people take pride in their culture and beliefs which is so empowering.

Our next stop was the Race Point beach, one of the most beautiful beaches I have ever visited. If you get time , do visit the 5.25 mile long biking and walking trail known as Cape Cod Provincelands Trail. After getting back late in the evening, we changed and went for dinner to The Canteen near Commercial street. It had a lovely outdoor seating and amazing food. Surprisingly, the shops and almost entire street was lit and open late into the night unlike any other town in New England. It almost looked festive and everyone around was having great fun!

It was the perfect last night in Cape Cod. We returned to Boston the next day, with fond memories and greater love for the Cape!