Daydream Destination – Nantucket

steps beach nantucket

It is hard not to fall in love with the charming New England island of Nantucket with it’s unspoiled beaches, quaint downtown with cobblestone streets lined with small boutiques and restaurants, stately historic homes and gray shingled cottages surrounded by beautiful blue hydrangeas and pink roses.

rose covered cottage Sconset Nantucket
Rose Covered Cottage, Village Of Sconset, Nantucket Island

Summers used to be about getaways to dream vacation spots but while travel plans have been put on hold, it doesn’t stop us from daydreaming. Take a virtual trip back to Nantucket with me and enjoy the charm of this 48 square mile island located 30 miles off the coast of Cape Cod. Just 14 miles long and 3.5 miles wide, it is known for having some of the best unspoiled beaches in the world.

Sankaty Head Lighthouse
Sankaty Head Lighthouse On Nantucket

Thanks to strict development and preservation laws, Nantucket is where people come to relax and enjoy its endearing New England atmosphere. I believe you will fall in love, as I did, with it’s historic downtown and harbor. Cobbleston streets are lined with high end boutique shops and galleries, good restaurants, stately historic ship captain’s homes and weathered gray cedar shingled cottages surrounded by beautiful hydrangeas and roses in the summer.

old south wharf
Old South Wharf, Nantucket

Many of the island’s buildings date back over a hundred years to when Nantucket was a hub for the whaling industry. Did you know that during the late 18th and early 19th century its whaling port made the island one of the wealthiest communities in America. Brick mansions and grand homes clad in white clapboard, many with widow’s walks perched high on their rooftops, were built for the wealthy sea captains who prospered during the bygone era of whaling.

To really appreciate Nantucket, you should walk its lovely tree lined streets and explore the island on its endless bicycling paths. You will then understand why this picturesque island has attracted artists, writers and thousands of summer visitors for decades.

Nantucket Painter Illya Kagan Painting “The Three Bricks"
Nantucket Painter Illya Kagan Painting “The Three Bricks”

Like most islands, Nantucket is a pricey destination so many of its visitors are day trippers who come over on the fast ferry which takes about an hour to reach the island. A lot of people choose to fly into Nantucket Airport on one of the direct flights from Boston, New York or Washington, D.C. My husband and I usually fly out of Hyannis on one of the small regional Cape Air planes. I’ve sometimes sat in the front seat next to the pilot for an incredibly scenic flight.

We are fortunate to always stay with good friends that have a home on a cliff road right above the town. If you would like to see a tour of their beautifully decorated home, just click here.

If you do plan to stay on the island, there is a large choice of accommodations choose from. You will find B&Bs, captain’s homes that have been turned into small boutiques hotels, luxurious resort properties with unrivaled amenities, as well as homes of all sizes available for rent. One thing to remember is that during the summer the vacation island’s population goes from about 10,000 permanent residents to more than 60,000 that includes seasonal home owners, renters and tourists. The town will be bustling with crowds and restaurant tables can be filled to capacity.

the white elephant
The White Elephant, One Of Nantucket’s Best Hotels

With that in mind, you must make your reservations to stay on Nantucket as early as possible as it is one of the most sought after summer vacation spots on the East Coast of the U.S. After August, it is much quieter and easier to secure lodging. However, some businesses and restaurants are seasonal so you need to keep that in mind when planning a stay.

There is no shortage of dining on Nantucket. It varies from casual laid back sandwich shops and takeout to fine dining restaurants on par with major cities famous for their fresh lobsters, seafood and other specialties.

Something Natural is a local sandwich institution on the outskirts of town, where you can eat one of their huge sandwiches and a chocolate chip cookie at one of their picnic tables or brown bag it for a picnic on the beach. Another option is to head out to Claudette’s in Sconset for one of their famous cold meatloaf sandwiches then stroll along The Bluff Walk. The Juice Bar, near the whaling museum is known for their dozens of flavors of homemade ice cream to choose from served in a fresh waffle cone. Don’t worry, the long lines move fast.

If you want to have a chilled glass of rosé and a fully packed lobster roll overlooking the water and yachts, Cru is an upscale oyster bar right on the Boat Basin at the end of the Straight Wharf. The hip restaurant is the “must go” place to see and be seen. For something  casual with a laidback but packed atmosphere, take the free shuttle out to the casual Cisco Brewers for award winning beer as well as cocktails and wine. Order something to eat from the various food trucks to enjoy while listening to live afternoon music.

For a classic French Bistro meal head to Languedoc, if Asian is more to your liking make a reservation at The Pearl or Nautilus and for Italian try Ventuno, which is Italian for the number 21. It is the former home of the 21 Federal Restaurant which was one of our favorites. I would say that Ventuno is now our new favorite for dining on the island, our food was delicious . Be sure to order the fried castelvetrano olives stuffed with pork sausage for the table. 

Put Nantucket on your bucket list and when we can once again travel, consider a trip to this idyllic picture postcard island. Walk everywhere, eat a lobster roll, go to the beach, see historical lighthouses, and visit a museum. I know that if you ever get a chance to visit picturesque Nantucket, you will want to return to enjoy the natural beauty of the pristine beaches, windblown sand dunes and bluffs, its moors and cranberry bogs. In town, the cobbled streets, gray shingled cottages covered in roses, seafood fresh from the waters surrounding the island, and if you are observant, spotting one of the rich and famous celebrities that frequent the island, will all make for a memorable vacation.

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I travel the back roads of the world, sharing great food and interesting places and enjoyable pastimes.

54 thoughts on “Daydream Destination – Nantucket

  1. I used to travel to Boston and NYC regularly and always wanted to visit Nantucket and Martha’s Vineyard but never made it. I know I’d love it, but probably beyond my budget these days. Thanks for a lovely tour.

  2. How beautiful and what fabulous food – I’d love to try the fried castelvetrano olives stuffed with pork sausage!
    Nantucket always makes me think of the Mountain song – Nantucket Sleighride.

  3. This brings back lovely memories of a day in Nantucket a few years ago. (They had a great thrift shop, as you can imagine!) I could spend FAR more time here. Your photos, as always, are lovely and so are your recommendations. What I wouldn’t do for a lobster roll right now!

  4. Many years ago after serving as best man in his brother’s wedding in New Bedford, MA, my husband, his family & I stayed in a weather beaten – no roses – cottage on the beach in Madaket on Nantucket for a wonderful holiday. We walked the beach & dunes & I painted several watercolors with my travel sketch pad & paints. My mother-in-law helped me sell a small satchel full of my paintings I’d brought along in a small gallery in town. We visited the whaling museum, toured several historic homes, & ate delicious lobster rolls & other island specialties. I particularly remember those beautiful houses, & the stately old elms shading them & the cobblestoned streets. We traveled back to the mainland & our busy lives by same ferry that brought us out to that beautiful summer island. My Mother-in-law suffered seasickness both going out & coming back. She was a terrific “shill” – as she called it – for my artwork, but not much for sea-faring. I’ve never returned but I’ve never forgotten special Nantucket. Thank you for refreshing my lovely memories.

  5. I’ve never been to Nantucket, and after seeing your pictures, I really want to go! Terrific photos and post — thanks so much.

  6. Karen, we rented a home on Nantucket for Thanksgiving week last year and absolutely loved it. Lots of businesses were open and the Christmas tree lighting ceremony was beautiful. Of course, water activities were off the table, but sight-seeing, cocktail hour and dining were still first-rate. I loved the homes at Sconset and imagined them with roses in bloom and the views from the lighthouses were just perfect. One day we will go back in the summer. Thanks for the pictorial of what to expect.

  7. My son and family have just got back from a lovely week in Nantucket. We first went there with them about ten years ago and I rode a bicycle for the first time since I was sixteen; thirty miles to the coast and back. I was very proud of myself. Your photos are really gorgeous as always, Karen. They took me right back there. 🙂

  8. Oh how much sadder current life would brr if we could not ‘do’ things virtually ! Much to my delight have been to a Covent Garden opera, a Tokyo ‘new’ symphony performance and a ‘bucket list’ Vietnamese food tour all within the last week ! And Australian media, Instagram et al have been so rich in fascinating interviews ! All safe and informative 🙂 !!! Have never been to New England to my large regret ! Was always somehow ‘stuck’ in the Big Apple and surrounds during my many trips to the East Coast. It looks absolutely lovely in all its aspects . . . food being a very important issue . . . thank you for allowing us to travel and smell the roses with you . . .

  9. We have never been but it was so nice to travel there via the photos from your blog. This sounds like the perfect getaway. Needs to get on the bucket list. Sooner or later travel will open up again… Stay well and take care

  10. Karen yoiu are very naughty posting an article like this on a Monday morning! Well, you didn’t post it on a Monday but I did not get around to reading until just now (Monday). I got up full of good intentions to be brave and proactive and do ‘stuff’ that I have been putting off for days and days (tidying, sorting, and boring) and now I am just not in the mood any more – all your fault for making me dream of visiting Nantucket and wanting to spend the rest of the day just day-dreaming about travelling, ha ha. I have been to Martha’s Vineyard and fell in love. And had a fabulous lobster roll AND oysters, sigh. Re the stuffed olives … I am wondering whether they are a take on the famous stuffed olives from the Marche called “olive ascolane” (olives from Ascoli, a beautiful town in the Marche and renowned for its huge olives) ? I adore them but have never attempted to make them at home. Here is a recipe for the Castelvetrano ones: https://www.saveur.com/article/recipes/fried-stuffed-castelvetrano-olives/
    Very finicky to make but delicious I am sure!
    Thank you for this virtual trip to Nantucket and have a good week !

  11. Thank you for this virtual holiday – much needed right now. Amazing how much money there was in whaling and you are lucky to have friends to stay with. I have not flown in the cockpit of a plane for ages – it is such a treat 🙂

  12. Thank you for that daydream, Karen 🙂 . Cape Cod has been on my US places to visit list and I’ve just added Nantucket after reading your post. I’ve seen a documentary about it once but it has not been on my mind since then. Hopefully on my next trip over I’ll be able to make that daydream come true.

  13. Oh what a lovely paradise! There’s just something about New England’s charm… ahhhhh how I would love to return.
    Your friends home was stunning. We would all get along well as we enjoy antiquing and treasure hunting!
    Thank you for taking us on a trip… we can all definitely dream of!
    Enjoy your week my friend!

  14. Years ago we visited the east coast but sadly didn’t manage to get to Nantucket. We did a little tour of Marthas Vineyard which was wonderful. I sure hope we can travel to the US again in the future.

  15. Ok, you’ve convinced me! We’re always looking for fun places for our next vacation, and to be honest I’d never really looked at Nantucket. However, the photos and glowing review certainly caught my attention! Everything is virtual these days, but I appreciate the chance to jet away to Nantucket over my mug of coffee this morning. Also, I can’t stop thinking about fried castelvetrano olives. 🙂

  16. this looks like a glorious place to be! how wonderful to have friends there to stay with. i always remember that limerick – there once was a man in nantucket etc…

  17. I love this Island!! And would love to get there sometime. You did a wonderful job describing the beauty and charm of Nantucket. Lovely…..

  18. This looks like such a beautiful place to visit! I don’t know how I would ever leave. The painter is very talented. His painting looks just like a photograph!

  19. Such a beautiful island to relax and enjoy the charming place and good food. I love the photo of the painter, wonderful angle you took. 🙂

  20. 💗 Paradise! 💗 I usually go to Nantucket in September when the last tourist leaves on the ferry! I have returned 3 times now. Love to go back one more time. Fond memories! Thank you for the super pictures! 💗 Beautiful! 💗

  21. Thank you Karen, for taking us on some joy-filled armchair travel. I have told many of my friends about your post previously in which you suggested that we need to continue to plan our travel adventures . . . because that really is part of the fun. I took your advice and began our search for the NW and sure enough, as Americans are banned from more international destinations, lodging is filling up fast for next summer! I’m teach at a university so we are big planners for summer journeys. My husband is a northeasterner (whereas I am a Midwesterner and Westerner)… and I enjoyed this post simply because I am such a novice at the region. I’ve now added this to my summer escape from Southern heat in S.C.’ bucket list. Stay safe my dear.
    Roz

  22. Lovely photos and descriptions, as ever. I have always wanted to go but have only made it to Martha’s Vineyard, a very difference experience, I am sure.

    My family was all supposed to be there next month for a wedding… alas, we all know that isn’t happening. hey are rescheduling for next year so let’s keep our fingers crossed.

  23. Would you believe I’ve only been in the waters of Nantucket, and not Nantucket, itself? These photos show exactly the charm I’ve missed. Gotta put this on my list of to-go places once the pandemic is over.

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