49th Annual Nantucket Holiday Stroll Weekend

49th Annual Nantucket Holiday Stroll Weekend 

Friday, December 1 through Sunday, December 3, 2023

NANTUCKET, MASSACHUSETTS (Holiday 2023) – Celebrate the 49^th annual Nantucket Stroll Weekend from Friday, December 1 through Sunday, December 3, 2023. Santa arrives Saturday via his nautical “sleigh” at noon. Enjoy all the holiday activities, including strolling carolers in Victorian garb, Magical Talking Tree, craft shows, European-style Christmas Marketplace and more.

Nantucket's unique shops and restaurants will celebrate Stroll Weekend with special sales, promotions, and holiday cheer. For a listing of shops, restaurants, and accommodations, visit ShopNantucketIsland.com.

Stroll Weekend highlights include:

Anna P. Jay

14 Federal Street

Visit a special jewelry trunk show at Anna P. Jay with Devon Woodhill Fine Jewelry and a personal appearance from the designer herself, Melissa, on Saturday, December 2^nd during Stroll.

bar Yoshi and O Bar

21 Old South Wharf

bar Yoshi and O Bar will be open for Nantucket’s annual Christmas Stroll Thursday through Sunday from noon to 10:00 p.m. (kitchen hours) and noon to 1:00 a.m. (bar hours). During the event, bar Yoshi will have its popular outdoor bar open serving oysters, bloody mary’s, margaritas, and mimosas. Special for Stroll, a $25 bloody mary will come with shrimp, bacon, olives, celery, jalapeño, and lemon/lime. For more information or reservations, visit bar-yoshi.com.

Bodega

2 Candle Street

Featuring four themed trees with seasonal ornaments including a nautical tree, animal tree, mystical forest tree and a naughty tree. Shop for stocking stuffers and gifts for everyone on your holiday shopping list. Enjoy holiday libations all weekend long.

Cattivo

20 Centre Street

Save 25% off all clothing including sale for savings of up to 75% off. Additional highlights include $20 merchandise bins freshly stocked, along with a photo booth and holiday sips and sweets!

Centre Pointe

22 Centre Street

Stroll 'secco being poured all weekend. Enjoy 30% off the entire store including Cartolina (except for holiday and fine jewelry). Other sale items available up to 70% off. Spend over $200 and receive a FREE Gray Malin Surfboard Beach Tote (retail value of $90).

Charleston Shoe Company

4 South Water Street

Shop the Stroll Weekend sale and save up to 15% off shoes. Select sale shoe styles $50. Shoppers can enter for their chance to win a $150 certificate to be used toward a pair of shoes. Light refreshments will be served.

Freedman’s of Nantucket

14 Centre Street

Save up to 40% off entire store.

G.S. Hill Gallery/Nantucket Pearl Company

40 Straight Wharf

Save 20% off all pearl earrings. Visit G.S. Hill Gallery on Saturday of Stroll Weekend to enter their annual free raffle drawing. Tickets are free to shoppers. No purchase required.

Jewelers Gallery

21 Centre Street

Virginia Salem of ANTIQUES ROADSHOW is showing her antique and estate jewelry at Jewelers Gallery during Stroll Weekend. Visit this collection of carefully curated jewelry pieces.

Lola 41

15 South Beach Street

Special Stroll operating hours with lunch additions and regular dinner menu available (sushi bar and bar open all day). Regular dinner service all weekend starting at 5:00 p.m.

Nantucket Boat Basin Authentic Shop

33 Straight Wharf

Save up to 50% off select merchandise (Stroll items excluded). Shop for special Stroll merchandise all weekend long including the original Nantucket Stroll Scarf, created 18 years ago by Nantucket Boat Basin Authentic Shop. Get one before they are gone!

Nantucket Peddler

37 Straight Wharf

Featuring a wide selection of new Stroll merchandise including long sleeve tee shirts for men and women, sweatshirts, sweaters and the Peddler’s original holiday scarves and hats. Storewide savings on tees and sweatshirts at 25-50% off.

O&CO. Nantucket

The Courtyard at 16 Straight Wharf

Featuring Stroll hats and scarves, as well as holiday inspired luxury soaps, lotions, candles, and ornaments. Select sale crew sweatshirts, starting at $29.99, and select hoodies, starting at $39.99. 

Olivela

25 Centre Street

Offering festive drinks and free beauty samples during Stroll Weekend.

Serenella

9B South Beach Street

Custom embroidery on any Leret Leret purchase through December 3, 2023. 

Slip 14

14 Old South Wharf

Serving lunch from 11:30 a.m. to 3:00 p.m. and dinner from 5:30 p.m. to 9:30 p.m. during Stroll Weekend. The special Stroll dinner menu features a two-course price fixed menu with Slip 14 classics as well as featured seasonal and local dishes. The bar will also be offering holiday twists on favorite and classic drinks.

Summer Shades

The Courtyard at 16 Straight Wharf

Indulge with Sweet Sips featuring the Sugar Cookie Martini while shopping with sunglasses at 20%-60% off, and select styles featured at $99. Enter the Ray Ban Raffle where 2 lucky winners will receive a Ray Ban backpack and pair of aviator sunglasses. Maui Jim gift with purchase (choice of reusable tote, sunglasses retainer, or hat). Also, Chanel gift with purchase, limited-edition cleaning cloth. New this season: Aprés Beach scented candles and room spray.

Straight Wharf Restaurant

6 Harbor Square

Open for lunch and dinner Stroll Weekend with seating available at the heated bar and front patio (weather permitting). Enjoy a preview menu from sister restaurant Straight Wharf Fish, serving clam shack staples including lobster rolls, fish sandwiches, chowder, fried clams, and more. Stroll Straight Wharf Restaurant  t-shirts and hats available for purchase. 

NIR Retail

NIR Retail, a New England Development company, leases 100 of Nantucket’s premier retail locations found on Nantucket’s most popular shopping streets: Main, Centre, Federal, South Beach and South Water, and on Old South Wharf and Straight Wharf. Shops and galleries include Veronica Beard, Olivela, Southern Tide Nantucket, Skinny Dip Nantucket, Cavalier Ebanks Gallery, Brown Basket Gallery, Style Paris, vineyard vines Nantucket, and Vis-à-vis. Favorite Island restaurants include CRU, Lola 41, Ventuno, The Nantucket Tap Room, The Gaslight Nantucket and more. Located off the coast of Massachusetts, Nantucket has welcomed generations of visitors and residents. Its world-class shops, restaurants, hotels, and seaside beauty have made Nantucket one of the most popular resort destinations for vacationers from around the globe. Visit ShopNantucketIsland.com for a full listing of galleries, shops and restaurants.

New England Development 

For over 40 years, New England Development has taken a creative, entrepreneurial approach to real estate development and management, delivering, and sustaining successful projects across a wide range of property types. The company’s national portfolio includes mixed-use developments that combine retail, residential, office, lab and hotel use, outlet centers, high-end and street-front retail, airport retail, hotels, golf courses, restaurants, and marinas. New England Development’s diverse portfolio includes CambridgeSide in Cambridge, MA, Chestnut Hill Square in Chestnut Hill, MA, Outlets of Des Moines in Altoona, Iowa, Clarksburg Premium Outlets in Clarksburg, Maryland, Newburyport Development and Marinas, Nantucket Island Retail and The White Elephant Resorts, among others. For more information, visit NEDevelopment.com.

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