Island Hopping - Nantucket, Massachusetts

We will continue our island hopping trip with quite possibly my favorite island of them all and a place where I have spent many memorable family vacations -
 Nantucket, Massachusetts 
My all time favorite photo of my children taken on Nantucket in front of Brant Point Light, by Cary Hazelgove in 1994.
It will be next to impossible to do Nantucket justice in only one post. (My friend Linda from Calling it Home dedicated an entire month to it!). Volumes have been written in travel guides, photo books and even in some very good novels about all there is to see and do on Nantucket. 

Admittedly, I have not spent much time in Nantucket in a number of years and I understand it has changed quite a bit.  As our children got older, we began to travel more rather than vacationing in one place every summer. So rather than trying to share the most up to date "hot spots" with you or cover everything there is to see and do, I am going to share the classics - my favorite things about Nantucket that haven't changed in years and years and which make it all the more special.
Go to several of the breathtaking beaches - Jettie's for a wide sandy beach and calm waves, Miacomet for gorgeous dunes and quieter beaches, Madaket and Cisco for surfing, or off-road it to Great Point for solitude (and that is only a few of the many beaches around the island).
Rent bikes - it's a great way to get around with miles of bike trails all over the island.
Drive out to S'conset (short for Siasconset) and see the gorgeous rose covered cottages, beaches surrounded by high dunes and the imposing Sankaty Head lighthouse.
Stroll along the cobblestone streets downtown and along the wharves that line the harbor.
Visit the Whaling Museum for a history of whaling around Nantucket.
Charter a sailboat for a sunset sail.
Go on a whale watch (not for the faint of heart - we saw a ton of whales but I was SO seasick that day).
Take a picnic and watch the sunset over one of the west facing beaches.


I haven't kept up with the restaurant scene on Nantucket (and there definitely IS one) so my choices are the old school standbys...nothing fancy, just quintessential Nantucket. These are all places I wouldn't miss on a trip back...
Downyflake - The best doughnuts EVER and great breakfasts.
Nantucket Pharmacy Lunch Counter - How many old fashioned pharmacy soda fountains are there left around the country? Do not miss this flash from the past!
Brotherhood of the Thieves - Best burger on Nantucket in a historic location.
For a special night out try Galley Beach (at Cliffside Beach Club) to watch the sunset, Company of the Cauldron or American Seasons.
I have eaten at all these places years ago - the fact that they are still going strong says a lot. The current great reviews say even more.
Over the years, I have stayed at many different types of places on Nantucket ranging from a cottage over a wharf, a beachside inn, numerous rental houses all over the island, and the worst B&B experience I have ever had anywhere (hopefully that place is now gone - I have blocked the name from my memory and so I can't even warn you away).
Many families enjoy renting a home and staying on Nantucket for several weeks or even the entire summer. While this is an ideal option, there are many other places to stay on Nantucket.
To find a vacation rental, here is a list of various rental agents on Nantucket.
I highly recommend Nashaquisset, a community of vacation homes available for weekly rentals. This small neighborhood is not on the beach, but is walking distance to town and Surfside beach, has a pool and tennis courts and is priced reasonably in comparison to many other Nantucket rentals. The property management oversees the properties so you know exactly what you are getting when you rent - a clean, nicely furnished and maintained home and can call someone if you have a problem (something that is not a given when renting on Nantucket).
Cliffside Beach Club is my favorite place to stay for a shorter trip to Nantucket. It is right on the beach, near Jettie's, and an easy bike ride to town.
If you want to stay in S'conset, try The Summerhouse where you can rent quaint rose covered cottages by the night.
If you really want to get away from it all and want top drawer luxury, stay at The Wauwinet, ten miles outside of town. They offer water taxi service to doesn't get better than this!


I am not going to include shopping in every island I cover, but I couldn't NOT include it for Nantucket. I love shopping on Nantucket! Main Street and the side streets off of it have one great store after the next. Here are my favorites:
Murray's Toggery Shop - Preppy heaven - THE place to buy the famous Nantucket Reds.
Mitchell's Book Corner - There is nothing like spending a foggy afternoon picking out a great book at an independent book store like Mitchell's. They have a great selection of books featuring Nantucket.
Le Cherche Midi - A little bit of France on Nantucket - this boutique is enchanting.
Peter Beaton - Originally a hat seller, they now have accessories and clothing.
Eye of the Needle - GREAT clothing store.
Artists Association of Nantucket - A good jumping off point for discovering the art scene in Nantucket.
Claire Murray - hand hooked rugs and other gorgeous Nantucket inspired home accessories.
Nantucket Looms - originally a weaving studio, it now sells unique textiles and home goods.  
Oh,wow, just writing this is making me NEED to plan a trip to Nantucket as soon as possible!!
Next stop on our island hopping tour will be Chincoteague Island, Virginia and Hatteras Island, North Carolina...See you tomorrow!