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.

Benefits

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!

Highlights

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.

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!

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

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!

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!

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!

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!

Benefits

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!

Highlights

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.

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!

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!

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!

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!

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!

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