1. Community: Yes, we have been named by National Geographic as the #1 Island in the World, but Nantucket is not just a pretty face! We have sophisticated restaurants, shopping, arts, theatre, music, and water sports that attract people with the most discerning of tastes. Couple those things with a vibrant and diverse community full of “Washashores and Locals,” and you have one of the best sanctuaries for quality living in the world!
2. Best Beaches: With more than 80 miles of beach surrounding the island, the best beaches change every day based on the weather. I always check the wind, and then make my pick based on where I think the water is the best.
"On a clear night, sunsets are attended by many and there is applause when the sun hits the water."
A Beach for Every Occasion:
Seclusion and calm: Dionis, Washing Pond, Steps Beach, Coatue
Seclusion with Waves: Sheeps Pond Beach, Smiths Point, Great Point
Surf: Cisco, Nobadeer, Madaket,
Family: Jetties for small kids, Surfside for kids that like waves
Overall Best: Fisherman’s Beach in Surfside, Fat Ladies in Miacomet, Madequecham
3. Hot new restaurants: The hottest, most anticipated new opening for 2017 is the Club Car. (A restaurant that is as small on the inside as it looks on the outside. It looks exactly like that fancy dining car that Johnny Cash was singing about in Folsom Prison.) This more traditional island favorite will be undergoing a major overhaul this winter. By next spring it will return with a fresh new look, taste, and feel. I can’t wait!
4. Boat Rental: If you are a member of Barton and Grey, then you can enjoy the water in style on one of their several Hinckleys. If not, contact Nantucket Mermaids for a family adventure lead by a knowledgeable captain. For the more experienced, get in touch with Island Boat Rental. The world is your ocean!
5. Fishing Charters: For the large group that wants a captain that knows where to catch any species in our waters on any given day contact Absolute Sportfishing. For smaller groups, Topspin, or the Althea K are always a great bet.
"For kids, try the Critter Cruise, they sail through the harbor and pick up lobsters, crabs and conch for the kids to touch and feel."
6. Best romantic dinner date: Clambake to go from Sayles Seafood, a bottle of wine, a blanket, and a seat on the beach to enjoy the sunset anywhere on the north shore. Just remember to leave the beach as clean as you found it!
7. Best Sunset spots: If you want an elegant spot to sip rosé with your feet in the sand while the sunsets over the water, the Galley is the only place to be. If you can’t get a reservation, just walk in for drinks and see if some beach couches open up. For a more casual, and second story sunset view of the Atlantic, Nantucket Sound, and our neighboring island, Tuckernuck, Millies (with the best quesadillas on the island) is your choice.
8. Best rainy day museums: Learn about the hundreds of shipwrecks off Nantucket at the Lifesaving Museum including the cruise ship Andrea Doria and MV Stockholm collision in 1956 (Nantucket fog was to blame for that.). Other great museums like the Whaling Museum are available through the Nantucket Historical Association. For the budding scientists out there, the Maria Mitchell Aquarium run by the Maria Mitchell Association has dozens of programs for all ages.
9. You will find the best “Off the Beaten Path” view of the island with Peter Brace from Nantucket Walkabout. When not teaching students on the Natural History of Nantucket, he offers guided tours of the island to find the hidden gems that even most “locals” can’t find.
10. Surfing Cisco Beach with Gary Kohner. Gary is not just the best instructor on the island, he also has a truckload of equipment for those who just want to rent traditional surf gear, or stand up paddle gear.
11. Kite Surfing is not only the fastest, but one of the fastest growing sports on the island. To check it out yourself, contact Jake and Jon at Next Level Watersports. Polpis Point in the harbor is one of the best launching spots you’ll find anywhere.
12. Spending the day at Great Point is great to just get away, have a picnic, do some fishing, or watch the seals (don’t get too close!). This 7 mile peninsula is only accessed by four wheel drive, but Affordable Rentals can set you up with the perfect vehicle to make the trek.
13. Best Breakfast in town: Black Eyed Susans – Make sure to try the Jarlsberg Cheese Pancakes and Huevos Rancheros! There will be a wait, so get there early. Best Breakfast out of town: Island Kitchen – Eat inside or out, have the Panko Breaded Eggs Benedict, or one of the great daily specials
14. Best Drunk Food: Stubby’s, but don’t just take my word for it. They were named the Best Drunk Food In Massachusetts!
15. Best daytime live music and drinks: Cisco Brewery/Triple 8 Distillery/Nantucket Vineyards Winery serves up locally made libations with live music everyday paired with some of our best local food trucks and raw bar. This place is both dog and kid friendly, but you may want to bring them all leashes. While you are there, have a glass of one of their many award winning products.
16. Favorite Summer Fundraisers: Nantucket Cottage Hospital hosts the Boston Pops on Nantucket with a new special guest every year. The Summer Groove to benefit the Boys and Girls Club of Nantucket is always a heartfelt blast.
17. A perfect Nantucket Day: Coffee at the Handlebar Café, breakfast sandwiches from Provisions, bagged lunch to take fishing with Boomie from Fresh, some music and a drink at the “Brewery,” sunset on the beach, dinner, then music at either an event, or the Chicken Box that night.
18. Best Holiday on Nantucket: Independence Day. Activities begin in the morning with a traditional reading of the Declaration of Independence at the Meeting House, followed by the parade, pie-eating contest, and water fight put on by the Nantucket Fire Department.
19. Best off-season weekend: Christmas Stroll. This weekend brings crowds of our part time residents and regular visitors to enjoy one last hurrah before winter. Restaurants re-open, the shops are packed full of gifts, and volunteers fill the streets caroling in colonial outfits to spread the holiday cheer.
20. Nantucket’s best kept secret: September! This often over-looked month is the best time to take advantage of less traffic, warm water, nice weather, and beautiful sunsets. The fishing is great, the shops begin to offer discounts, and prime season rates begin to decline. While everyone else is in school, this is the best time of year for Nantucket.