Cape Cod to Boston – The best itinerary in 4 Days

Cape Cod to Boston – The best itinerary in 4 Days

Cape Cod combined with Boston offers the perfect mix of city and beach break combined into one. This area of America known as ‘New England’ is wonderful as it combines American modernity with European architecture. A wonderful mix.

How to get there?

Several airlines fly direct from London to Boston including British Airways, Virgin Atlantic, Norwegian Airlines.

I wanted to discuss a bit more about Norwegian Airlines. I was initially attracted to flying with them due to their low prices, I paid 300 pounds for a return flight in September. After more thorough research, found that they fly with modern dreamliner and their cost point is much more attractive than traditional airlines. With that said, they are a low-cost carrier, therefore don’t expect a free dinner, although you can order and pay on your inflight entertainment screen which is always an exciting novelty at first. For the price, they are so worth it and means more money for you to spend on your trip – treat yourself to the extra lobster roll!

When you land, the great thing about Boston is that it is a compact city, a taxi ride to the centre will be 15 minutes at the most! We were staying in the North End, which is considered the little Italy of Boston which felt so quaint and traditional. Thank you to my friend Taylor for hosting us!

Now here is our itinerary which I felt gave the opportunity to see lots of Boston and Chatham in Cape Cod – feel free to use the recommendations below!

Day 1 – Boston

Morning: Breakfast at Boston Public Market as the best way to start your day of walking is with some good fuel! The market has a wide range of options from coffee bars, juicers, creperies. I decided to kick start my day with an all American bagel. Delicious. The market has seating outside which was perfect as the sun was shining. 

Late Morning/Afternoon: managed to pack in a lot today as it is a speedy trip. After breakfast walked along the ‘Freedom Trail’. This is a 2.5 mile walk around the city (which can be seen my red markings on the floor) which point out to different historical monuments. It is a great way to soak in all the cultural sights. We finished this off at the waterfront with Lobster rolls we got from Quincy Market. This market is more well known than the others since it is much older having opened since 1826. The architecture around the building is well worth checking out as well.

As you know with city breaks my step count always goes through the roof! The best way to see a city is by walking as you stumble across new  neighbourhoods and sights along the way. Did a few pit stops at some of my favourite shops that they don’t sell in England – I could talk for ages about the shopping and how to get the best deals!

Shopping time 

Early evening: We went to Night Shift Brewery in the early evening just before sunset. This place was magical! In the summer they have an outdoor section that is just next to the Charles river. Here you can watch runners along the esplanade and sailors on the river. Make sure you go a bit earlier as there is a line to get into the Brewery as it is a closed off area. Also, don’t forget your ID! This place seemed much nicer than the larger breweries such as Samuel Adams or Harpoon – it is always great to get recommendations from locals!

Charles river esplanade 

Evening: now it was time to see a Red Socks Baseball game, this is a must do! A quintessentially Boston activity, from the brewery it was a 25 minute walk, which was lovely in the evening summer air. The game started at 7pm, and it was the Red Socks against New York. As they are two rivalry cities it made it even more fun and the atmosphere was wild!

Fenway park

Day 2 – Boston and Drive to Chatham (Cape Cod)

Morning: In the morning we went to pick up the car for the drive down to the Cape,  as a car wasn’t needed in Boston during day 1. Traffic in Boston can get quite busy especially during rush hour so I would recommend public transport and by foot when exploring the city. We ordered a Mustang Convertible – when in Rome right!

It was quite funny, they didn’t actually have a Mustang, and the only cars available were huge 4x4s which were just too big for 2 people. In the end we took a different car temporarily as the Mustang was being returned in a couple of hours. The car rental company ended up bringing the Mustang where we were having lunch and did a car swap. Thank you Alamo for your incredible service!!

Sunset in Boston

Lunch: brunch/lunch was served at a cute cafe in South Boston called Publico. In the evening it also becomes a bar if you’re in the area and looking for somewhere to get drinks. I had poached eggs on a muffin with lobster. Trying to get as much Lobster as possible when in New England! 

Afternoon: around 3pm we drove from Boston to the Cape. Since the driving is on the other side of the road, wanted to get there before it got dark. It was a 2 hour drive, so we arrived around 5pm.

I chose Chatham as it is known for being a classic town, easy access to beaches and a lovely high street to walk along. Chatham Lighthouse is also famous being one of the few traditional lighthouses still in operation. After driving through the other towns, it confirmed my decision that Chatham was the sweetest looking place!

Chatham Lighthouse

Evening: Our first night in Chatham, after checking in to the hotel, decided to have a walk along the main high street and find a spot for dinner. We then decided to have dinner at a place 10 minutes drive from the high street.

This place was perfect and had the most amazing sunset! If you eat anywhere in Chatham, make sure you check out Chatham Bars Inn. It is a 5* hotel situated on the beach and a colonial style building. There is a beach club and also a terrace restaurant where we had dinner. Just before dinner we sat on the Cape style deck chairs whilst watching the sunset in pink and blue hues. The food is American style sharing places from flatbreads to lobster rolls.

Day 3 – Chatham (Cape Cod)

Morning: took a early morning drive to Chatham Pier. This is currently a working pier with a visitor platform to check out the views and watch the Fishermans in action. We came early to see fisherman unload their catch of the day which was an interesting sight.  

Beach chairs for two 🙂

Afterwards, drove down to the high street to pick up some breakfast at Chatham Cookware. This is a takeaway style place with a range of pastries, sandwiches, coffee and tea. Their spinach pastry was my favourite. They have benches outside on their porch, so we sat there and watched the world pass-by. 

I loved how open people are here to have a conversation. We had a chat on the porch with a man who is well known in the shark conservation arena and has been in a documentary with David Attenborough. Other sights included a group of older men who would come every day with their glamorous old school cars and coffee on the Porch with their friends. 

Late Morning. / Early Afternoon: drove up to Nauset Beach for some beach relaxation time. There is plenty of parking on this beach and a really long sandy strip for you to relax. Driving around the Cape is so easy as the main road follows closely to the coast line, and if you aren’t the driver it is great to watch the coast go by. 

Nauset Beach, Cape Cod

I wanted to let you know that sharks do travel around the Cape, especially if you are on the sea side. A good way to spot is if you see seals, this is a good indicator and hunting ground for sharks – definetly get out of the water if you see them. 

Evening: we picked up a picnic from the supermarket and headed down to Chatham Lighthouse Beach. The lighthouse is just behind the beach with a line of car taking spots that once parked faces directly to the beach and ocean. This was perfect as we managed to spend a couple of hours by the sea. As the sun was starting to set, we then headed back to the car. The car was a convertible which was perfect to just sit in the front seat, have our picnic and watch the sun set. The end to a perfect day!

Day 4 – Last day, back to Boston

This was out final day of the trip! We spent the morning driving around the Chatham area and taking in the sights one last time!

Around Cape Cod 

Lunch: after checking out of our accommodation we went back to Chatham Pier for a local lobster roll!! The pier has a takeout shop with a range of fresh and cooked seafood. We got lobster rolls that were cooked fresh from the catch of the day and ate on the pier. It was just delicious.

After lunch it was our drive back to Boston, we went a slightly longer way through a couple other Cape towns including Falmouth. This town also was pretty but in my mind Chatham was just my favourite! 

A town called Mashpee was on our drive back, such a fun name for a town! We had a break at a shopping area called “Mashpee Commoms” which was so cute with all sorts of fun shops. We stopped at the Vineyard Vines store here. It still had a bunch of sales on. This brand is so cute and reminds me of the fun, preppy, beach vibe of the cape. Definetly will have some nice pieces to take home with you! 

Late afternoon: arrived back in Boston. Had a quick bite in the North End part of Boston before heading on our flight home.

I absolutely loved this itinerary and felt it was a short trip yet still didn’t feel too rushed. However next time I will come for longer so I can have a few days to just lie on the beach and not do much!!

Check out my overview of trips in 2018 that I did.

Happy travels!

Eileen xoxo



  1. Teresa
    February 3, 2019 / 4:34 am

    Done so much in 4 days – great iternery ! Good insights ! Fantastic photos especially the “Beach chairs for two” photo!

    • eileen
      February 3, 2019 / 10:08 am

      Thanks so much! I highly recommend the trip 🙂 xx

Leave a Reply

Your email address will not be published. Required fields are marked *