Exploring Nantucket by Land and by Sea

Updated July 21, 2020.

It’s Motivation Monday! If you’ve been following along on Facebook and Instagram, you know I spent a few days in Nantucket last week. It was my first time there, and I wanted to cover as much ground as possible, so I booked a couple of tours and got excited to explore the island both by land and by sea!

By Land

First up, a bike tour with Nantucket Bike Tours! My flight landed on Nantucket at 10:06am, so I taxied over to the bike shop and met Cole for my private tour. We had the best time, and it was the perfect way to start my trip.

Meet the Bicycle Lucretia!


Not only did this get me moving after my super early wake-up time and flights, it gave me a lay of the land so I knew what I wanted to go back to and what I could probably say I’d already seen. It’s the easiest way to get around the narrow roads, and the highest point on the island is only 95 feet above sea level, so there aren’t too many daunting hills!


Cole took me all over the place! I told him I’m a history-loving travel blogger, and he made sure to show me all the best places that even locals sometimes don’t know about! This is the site of a lily pond where the whaling ships once came for repairs. One day a little girl named Love Paddack was playing by the pond, digging trenches with a shell. The next day, in an unfortunate coincidence, the pond was gone. It wasn’t her fault the water all ran out, but as a little girl, she sure thought it was. She never told anyone until she lay on her deathbed decades later and confessed.

Raised boardwalk through a former whaling dock station.

Aren’t these shells pretty? We came across hundreds of them at the Brant Point Light House! So pretty, in fact, that they were once used as currency by the Native Wampum people!

Shells: ancient Wampum currency

And speaking of Brant Point Light House, I got a rare shot of it with no people!

Brant Point Light House
IMG_6996 2
Operating since 1746–second oldest in the USA!

He also showed me to the beautiful Steps Beach, somewhere between Tommy Hilfiger’s house and the most beautiful hydrangeas I’ve ever seen. Nantucket is much more diverse than I thought!

No secret why they call it Steps Beach. 

And what’s more charming than riding around adorable Nantucket’s historic homes? This one is a favorite! This was our last stop before pedaling back to the bike shop. He saved the best for last. Look at those climbing roses! That pink door! The lattice!

The cutest house on Nantucket!

My bike tour was fantastic! I hadn’t ridden a bike in probably 4 years, but I picked it right back up–just like riding a bike!

IMG_7041 2
Finished up a fun tour!

By Sea

I headed down to Straight Wharf in the afternoon for my sailing tour with Endeavor Sailing! Captain Jim built this sailing ship himself 40 years ago, and he and his son James have been giving tours for years!

The Endeavor


This is a beautiful way to see the island from a unique–and historic–perspective. Since this was a whaling island for over 150 years, this is the view those whalers looked forward to after three to five years at sea. Captain Jim is happy to chat and give you the history of both the island and his boat!


Off we go! This is what I think of when I think of sailing in New England! We made our way through the harbor and out to sea, avoiding sandbars and other underwater obstacles easily.

Off we go!

If you want, you can help raise the sails! Captain Jim and James can certainly take care of it themselves, but you’re welcome to help if you want the experience!

These gentlemen hoisted our sails and got us on our way!
Sails up!

And he’ll even let you steer! There were two other bloggers on the boat tour, and they were taking much better pictures than I was. Give @jenniferlake a follow on Instagram and check out her blog, Style Charade!

Jenn Lake of Style Charade shoed us how it’s done in style!

We also learned a little about how dangerous it still is getting into Nantucket Harbor. Ships still have to be very careful of the shoals (sandbars) and rocks. Captain Jim said it’s pretty embarrassing when the big ones run up onto a huge rock that blocks the way! We saw some beautiful ships waiting for high tide to avoid the rocks!

There’s a big one hanging out on the water.

We sailed out of the harbor and back in, catching lovely views of the shoreline, including Brant Point Light House. Actually, I learned on my bike tour that this is no longer a true light house, but a fog warning system instead! Nantucket is sometimes called “The Gray Lady” due to the heavy, thick fog that covers the island many mornings. This light house sends out a laser signal to another laser across the entrance to the bay, and when the fog gets too thick for the lasers to “see” each other, Brant Point Light House sounds a fog horn to alert the ships!

Brant Point Light House from the sea!

So which do you think you’d prefer? Nantucket by land, by sea, or both? This is just a taste of Nantucket, but I hope to go back to visit again with my sweetheart soon!

Want more? Check out my United States Page!

Love this post? Pin it for later!

7 responses to “Exploring Nantucket by Land and by Sea”

  1. […] 1 Scoop Cake Batter + 1 Scoop Cookies n Cream in a Waffle Bowl from the Juice Bar Sea Salt and Caramel Ice Cream Sundae with Hot Fudge and Marshmallows from Jack and Charlie’sAre you ready for your own culinary adventure through New England’s favorite summer destination? Check out Exploring Nantucket by Land and by Sea! […]

  2. […] Private Bike Tour This was the best way to start my quick trip! Cole at Nantucket Bike Tours was a phenomenal guide. […]

  3. […] I knew when I landed, I’d have time to drop my stuff off at the hotel, then go right for a two-hour bike tour! Later that afternoon, I scheduled a sailing cruise around the island, and I didn’t want to […]

  4. […] historic walking tours, ghost tours, sailing tours, fishing tours, and my personal favorite–bike tours! Use Trip Advisor to find the best […]

  5. […] I didn’t think I’d look nice enough! But it is one of my favorite trips to date. Take a sailing tour, ride bikes all over the island, and check out all the incredible hotels and restaurants they have to offer on […]

  6. […] reading: Nantucket by Land and By Sea,Biking Block Island, and Running […]

  7. […] reading: Nantucket by Land and By Sea,Biking Block Island, and Running […]

Leave a Reply

Verified by ExactMetrics