15 Things to Do in Nantucket Off Season

Want to know the Top 15 Things to Do in Nantucket Off Season? Look no farther. In briefest of words, and in prettiest of pictures, see Nantucket in late October with this Two-day Travel with me Thursday Tips Edition!

 

1. Take to the Sea

2. Go Slow on the Slow Ferry or Fast on the Fast Ferry, but stand on the railing for the view

3. Sail, or take pictures of those who sail and wish you were sailing

4. Stay somewhere really nice on the water

(we stayed at the White Elephant and some of the fine amenities they offered included these little in-room chocolates, really good morning coffee and pastries (for free), courtesy bike rentals, umbrellas (for when it rained), the option for them to pack you a picnic or bring you breakfast in bed, super soft sheets, super soft towels, comfortable beds and we had a room with two view of the harbor from front and side facing windows. Sublime.)

5. Walk along the harbor

 

6. Stop and smell the still-blooming flowers

7. Look for fall color, everywhere.

8. find living history in every railing, home and cobbled street.

Did you know that Nantucket has the most still-standing pre-civil war era structures in one place in the US? Fun fact.

 

9. Go inside some of the historic hotels and take a peek around.

This staircase was inside the Jared Coffin House.

 

10. Enjoy the picture postcard views of the city-scape, seemingly unchanged since founding.

11. Go to the Whaling Museum.

It’s pretty packed with historical artifacts, a real-life whale skeleton, and thoroughly covers the history, rise, and fall, and rise again of Nantucket.

 

12. Bike to Siasconset

Read what Travel and Leisure has to say about it. Side note, there is a beautiful lighthouse Sankaty Head Light there (see below) but off season there is nothing else – no amenities, no stores or restaurants, and nothing in between Nantucket and ‘Sconset. Pack a lunch or go there and back quickly : ) Round trip, it’s about 20 miles on the bike.

 

13. Walk main street at night

After the stores are shut down (which is right before dusk in off-season) the streets become quieter and well worth a nighttime stroll.

 

14. Have a drink, or two.

Only about 40% of the restaurants and retailers on Nantucket stay open after Columbus Day Weekend, so you are narrowed in options but you will encounter more locals and the same great food in a less hurried pace. This martini was photographed at Lola 41 where we also had a delicious dinner. But careful, the cocktails are strong and too easy to drink.

15. Visit the Brantpoint Lighthouse

The lighthouse is easy to walk to from town, is stationed on a lovely little strip of beach that, on less cloudy days, would have had a phenomenal sunset, and you can photograph it from every angle (including from the ferry as you approach the island).