We recently visited Cape Cod and Nantucket and it was such a fun trip. If you’re planning a trip to Cape Cod or Nantucket, be sure to add some of these great local restaurants and must-dos to your list. 

Day One

After arriving in Boston, we drove down to Plymouth for dinner at Tavern On the Wharf. There were tons of people in the area for a fireworks show! After dinner, we checked out a Massachusetts must-see: Plymouth Rock.

Then we hopped back in the car and continued to Falmouth, located just over the bridge on Cape Cod. We were staying at the cutest little bed and breakfast, Inn On The Sound. Our patio even had a view of Martha’s Vineyard!  

Day Two

We woke up early and took the ferry from Cape Cod to Nantucket. We rented bikes from Young’s Bike shop then set out to explore the island. While waiting for a table at Nantucket Tavern, we hung out at the Gazebo, one of the most popular bars on the island; you have to try the mudslide; it’s world-renowned for a reason! After lunch, we walked along the pier and saw some pretty incredible Yachts. 

If it is your first time on Nantucket, you have to visit The Whaling Museum. Three stories of history with a rooftop patio view that has incredible views of downtown Nantucket. We then rode the bike only a mile down to Steps Beach. Ralph may or may not have fallen asleep while I enjoyed the view.

Just a short walk from Steps is Galley Beach, a fantastic restaurant located right on the beach. Pro-tip, they’re closed on Tuesdays, so be sure to plan. We will be stopping by for lunch or dinner next time we visit.

Once you’re done exploring downtown, head to Cisco Brewery, we rode the 3 miles on our bikes, but they also have a free shuttle bus that will pick you up right downtown. Cisco is a great place to relax and enjoy the afternoon; they have tons of local beer, cocktails, and Nantucket Winery also does wine tastings on site. There is always live music, food trucks, and lots of people watching! 

An Evening On Nantucket

After a few drinks, we rode back downtown to return our bikes and walk around. We stopped into B-ACK Yard BBQ for some shrimp and wings. One thing for certain, everyone eats ice cream on Nantucket. We’ve never seen so many ice cream shops, lol! So, of course, we indulged.

We stopped at Jack and Charlie’s, which is located right by the ferry and is amazing! I had cow tracks on a chocolate waffle cone and Ralph chocolate peanut butter. But if you have time to wait in line, you should check out The Juice Bar; everyone raves that this is the best ice cream on the island. 

As we stood in line for our 8:45 ferry, we were informed it had been canceled! We quickly made our online reservation with another company for the last ferry off the island at 9:20 pm. New England weather is unpredictable, so be prepared to think on your feet and make some last-minute changes.

While we were waiting to see if the later ferry would stay on the schedule, I booked a last-minute B&B just in case! Ralph was teasing me about sleeping on the streets. Can you imagine? We would definitely end up on the infamous Instagram account Chadtucket, lol. We made it back just in time to get our rental car before the gates were locked and headed back to Cape Cod and Inn on the Sound.

Day Three

We got up and hit the road early to meet Captain Rick with Sweet Yacht Charters at the Wequassett Inn in Chatham. Chatham is about a 45-minute ride from Falmouth, depending on traffic. Captain Patrick and Gillian were incredible hosts. We cruised in a stylish Hinckley yacht, explored the harbor, and were up close and personal to the many seals.

We cruised through Pleasant Bay outside of the harbor and observed its true beauty, including hidden coves, beaches, and tiny white-sand islands. Then, we docked at Chatham Bars Inn for lunch, where the lobster nachos were too much but too good all in the same.

From there, we set out to explore the lighthouses in the area, beached, and walked across where the Atlantic waters were FREEZING. It’s crazy how much warmer the water is in Pleasant Bay.  Overall we had a fabulous day, and I highly recommend booking Sweet Yacht Charters for your on-the-water adventure. 

Before heading back to Falmouth, we made one more stop at the Wequassett for oysters and drinks.

Back at Falmouth, we ate dinner at the new Shipwrecked, formerly British Beer Company. Ralph had salmon, and I had scallops that literally melted in your mouth. 

Day Four, Our Last Day In Cape Cod

On our last day in Cape Cod, we made the hour and a half drive back to Boston. At Logan Airport, we stopped at Legal Seafood, one of our favorite traditions, before boarding our flight. Then home to meet the whole family for a weekend together!  

I’ve got some great pics to share and have already done two reels on insta. I will be making one more. Follow me at @mauriadillard for mo