Located just 2 hours south of Boston sits a popular vacation spot visited by over 5 million people each year- from everyday families to world-renowned celebrities. This haute location is a relaxing reprieve from the hustle and bustle of any city, making it a top destination to reset and relax.
Cape Cod is made up of four regions: upper cape, mid-cape, lower cape, and outer cape. It takes about 1 hour and 30 minutes to drive the whole cape, it isn’t very large, but there is so much to do!
Cape Cod truly is a small town. It is a peaceful landscape with bountiful forests, long winding roads, and authentic, seafood restaurants scattered about. During the offseason, locals go about their day and as it comes closer to summer, they begin prepping for ‘the season’. This is peak travel time, usually lasting between June-September, the time 65% of those 5+ million travelers visit and enjoy the Cape. While a fantastic summer destination, I visited during April which was the perfect time for an authentic tour of the area.
Trip overview:
3 Days in Cape Cod, and then off to Martha’s Vineyard
Day One:
Flight TPA → BOS
The trip began with a three hour flight from Tampa to Boston. After touchdown, we took the Blue Line bus to the rental car center and picked up our trusty transportation for the week.
Note: Renting a car is really the simplest way to navigate around Cape Cod, you’ll appreciate being able to stop and sightsee wherever you like!
We drove straight to our hotel that evening where we stayed four nights at Wequassett Resort and Golf Club.
Hotel: Wequassett Resort and Golf Club
Luxury resort in Harwich
This four-star resort is tucked away in the neighborhoods of Harwich, MA. It features luxury cottages, suites, and private homes perfect for any traveler. There are many amenities to keep you busy, but what really stands out are the views of the Pleasant Bay, surrounding the East side of the resort.
We stayed in Iris Cottage, located near the dining hub and central to most resort experiences including the gift shop, tennis and pickleball courts, swimming pools, children’s center, and check-in.
Dinner: Thoreau’s
Fun fact: Henry David Thoreau is an important historical figure to the area, having described the cape’s beauty and nature in his writings. You’ll see many references to his writings from restaurants to gift shops.
We warmed up by the fire in this cozy restaurant and ordered the Halibut with risotto, which was delicious. After a long day of travel and a cozy dinner by the fireplace, we headed off to bed.
Day Two:
One important note if you are from Florida and traveling to Cape Cod in May, you must bundle up! Although we had beautiful weather the whole time, it was unexpectedly cold and wet. Being near the water will always cool down an area, but the main reason is the chilly weather during the day. Each day had high cloud coverage and was slightly damp, so I suggest to bring a few layers to warm the core. For my more northern friends, feel free to have a laugh at us southerners.
Note: When is the best time to visit the Cape? As confirmed by many locals, May is one of the best times as it is before ‘the season’ begins, after the hydrangea festival on Nantucket, and is a relatively calm time in the area. There is little to no traffic and a better sense of what life is like on the Cape.
Breakfast: 28 Atlantic
Breakfast is served in the 28 Atlantic dining room. This five star restaurant, in the evening, features a 3 course prix fixe dinner, said to be fantastic and rated by Forbes as the only 5-star restaurant in Cape Cod. The breakfast is just as delicious, featuring curated options from traditional breakfasts to lobster benedict. This is all enjoyed in front of the floor to ceiling windows, overlooking the bay.
This morning however featured in-room dining, so we could leisurely wake up and get ready, all while enjoying the view from our cottage and planning the activities for the day. We decided to spend the day around the area and began by exploring the resort.
What first caught my eye was the extraordinary gardening. For such cold weather, I’d expect to see mostly dead plants, but that was quite the opposite with vibrant daffodils and massive tulips everywhere you look.
We checked out the gift shop and found high-quality, hand selected jewelry, clothing, and more. From washable cashmere coats and jackets, to hand painted art. Located near the children’s center and the tennis and pickleball courts, this resort is certainly a hub for families.
Exploring more of the resort, I found a private path below the central food hub and took that to find an expansive view of the Bay. Following that path, I saw a number of cottages which were very well maintained and of many varying sizes. There is an outdoor bar that celebrated it’s first open day of the early ‘season’, located by the pool and fire.
Downtown:
Near Harwich, is the popular town of Chatham. This is a must-visit spot on your travel itinerary! Main street features tons of small shops, cafes, trinket stops and more. Located in the elbow of the cape, there are scenic views surrounding the area and a famous lighthouse nearby.
Lunch: Public Cafe
With a 5 star review on Trip Advisor, we checked out a local spot for lunch. If you’re looking for a quick break from seafood or are interested in a unique atmosphere, definitely check out this spot! I can say from experience the Avocado Panini and Turkey Pesto paninis are delicious!
Next up was Nauset Lighthouse and our first stop on the Cape Cod National Seashore. Located a mile from Chatham, this is an easy walk or a quick drive! The area is guarded by a fence, but very easy to see the lighthouse and accompanying building. Sitting in front of the lighthouse is the shoreline where you can walk down and enjoy the beach.
Chatham Bars Inn: You can’t visit Chatham and not see the famous Chatham Bars Inn! Another luxury 5-star resort with family-friendly cottages, restaurants, and resort area, this hotel has been local since 1914. The grandiose feel of the hotel is evident simply by entering the main area and seeing the tall ceilings and marble floors. This hotel was a bit busier than Wequassett, but luxurious nonetheless.
We took a walk around the property, checking out the golf club and spa, and my favorite spot, the beach and accompanying private sailboat.
Harwich port: This charming town is located on the picturesque marina on Nantucket Sound. After exploring main street and stopping for ice cream at Schoolhouse, it was time to test a local recommendation for dinner.
Dinner: La Bella Vita
Visiting during the off season, this restaurant was still very busy- showing off what a local spot it is. I highly suggest trying the Arancini and sharing a pizza, these were two of my favorite menu items!
Day 3:
Waking up with breakfast on the water at 28 Atlantic was the perfect way to start our next full day of activities. We spent day three exploring the outer cape, specifically the N to S stretch.
Cape Cod National Seashore: The seashore stretches almost the entirety of the outer cape, so we began our tour previously in Chatham and continued stopping off at spots as we traveled North to Provincetown.
National Park Service: There are quite a few stops in Cape Cod that feature national park service areas, our first stop was the Salt Pond Visitor Center which features a museum with great history of the life and culture of the area over time as well as the deep whaling history. There is a gift shop, restrooms, and 3D map showing how the landscape of the cape has changed over time.
Lunch: Joe Coffee House
We stopped at Joe Coffeehouse for a quick snack and beverage and made our way down the street.
A popular spot to visit for lunch is the Lobster Pot- a Cape Cod classic!
Beaches and national parks to stop by: We took a drive through the surrounding Provincetown area and saw:
- Herring Cove Beach
- Province Lands Visitor Center
- Race Point Beach (great for whale watching!!)
- Dune Shacks Trail – an amazing and short 10 minute walk up a VERY steep hill. Although challenging to scale, the view at the top is worth it!
On the drive back to Wequassett, we stopped off at Truro lighthouse and stopped for dinner at a nearby restaurant.
Dinner: Moby Dick
A quintessential cape cod restaurant. Located on the side of the highway, this spot has great service with waiters from around the world. I suggest getting the Lobster bisque or fish and chips, both were flavorful and rich.
Day Four:
After a morning breakfast at 28 Atlantic, we headed to Woods Hole to take the Steamship Authority ferry to Martha’s Vineyard and continue the rest of our trip!
Note: I highly suggest booking your ferry in advance, they fill up quickly and become more expensive as you get closer to your date. It is also a good idea to get to your ferry port about an hour in advance to ensure a smooth experience!
The rest of the journey through Martha’s Vineyard is coming soon, with just as exciting an itinerary as Cape Cod!
