Nantucket, Massachusets

• More about your oliver guide: Cynthia Pillsbury
• Trip type: Family, Group getaway, Beach
• Activity level: easy
• Ideal length of trip: 10 DAYS-TWO WEEKS (OR A SUMMER!)

to & from

• Depends on how long you are going… either way fly into NY/JFK and take Jet Blue or fly into Boston Logan Airport and rent a car and drive to Hyannis and take the car ferry (** which books in January/February for the summer).
• Rental cars are very expensive on island, so smart to rent a car on mainland and take car ferry over. Another option is to fly Cape Air from Boston, but be aware that the planes are small (8 seats) and delays are very common, especially getting OFF island, which equals missed connections if you are heading west.

Where to Stay

• Best to VRBO or work with a local real estate company to rent a house. The island doesn’t have a “bad” area. Quindnet and S’conset are great for a quieter escape (20 is Plenty!), Madaket has the best sunsets and Millie's, Miacomet & Cisco ares are close to waves, Cisco Brewery and Bartlett's Farm (best tomatoes and bacon broccoli slaw) and Town is charming, with a big perk being able to walk a few minutes for coffee and a morning bun in the am and into dinner (Brant Point also affords these same perks and houses usually have more outdoor space). Older kids will love the freedom to walk to pizza on the Wharf and Force 5 candy room at night.
• For the hotel enthusiast:
  • White Elephant is a high-end hotel, right in town that is super for families with harbor views.
  • 21 Broad is a great, modern take on the B&B that has an ample breakfast and is located in the heart of Nantucket Town (not ideal for families with more than 1 child or older kids).
  • Greydon House is a brand new (opened Fall 2016) high-end boutique hotel (18 rooms) that also offers a restaurant led by a Michelin star chef and a cozy, chic bar. Can't wait to check-out!
  • Another spot with a perfect location in town with water views is the Harborview Nantucket- gives you a great hybrid of a hotel and a fresh, new cottage--one to four bedrooms, complete with kitchens. This is unusual on Nantucket and worth checking-out.

Where to Eat and Drink

• Straight Wharf: Never disappoints with their blue fish pate and charming atmosphere and you can check-out the scene at the bar on your way out (and feel kinda old)...
• Ventuno: Clubby and cozy and Johnny B. makes a great cocktail....
• Madaket Millies’s: Best tacos for at least 30 miles… and margaritas. We usually go 2x/week because great for families… always a wait… and again always worth it!
• S’conset Cafe: Great fish, charming, BYOB, call ahead and make reservations for their two seatings.
• Club Car: Brand (new) take on Nantucket institution. Three foodie and Nantucket veterans, one I know personally (Yay Ty!) I have no doubt this will be a big hit with the old and new guard. Make a reservation (up to two weeks in advance).
• The Nautilus: Line up at noon and get your reservation --Asian take on delicious seafood, really interesting ingredient combo, nice addition to restaurant scene.
• The Proprietors: GREAT atmosphere, amazing food, love sitting upstairs and having a bird’s eye view of India Street.

What to Do

Weather rules the day…

• Sunny Day:
  • Beach, Beach and more beach… find a new beach to explore and make home each day. The beaches all have their own personality, waves, sand and views… talk to a local or summer local to find the beaches less traveled (avoid Jetties and Cisco if possible, unless you want lifeguards and/or surf lessons). You need a car to go to most beaches- and it’s worth it.
  • Fun to rent a boat (or better yet, have a friend with one) and go out to Coatue to swim and dive for clams.
  • BBQ and fish at Great Point – you need a beach pass, but worth it to drive out on the sand and stake your claim… just watch out for the sharks. Seriously.
• Rainy Day:
  • Hit the Whaling Museum: Sperm whale skeleton on view, film about the incredible history of Nantucket.
  • Life Saving Museum: Town gets crowded so head out on Polpis Road, nice escape.
  • Shop and Sip: Great lunches and shopping, tuck into Mitchell’s Book Store and get a summer read, have lunch at Cru (longer, table service, yacht gazing) or Provisions, delicious (gazpacho) soups and sandwiches in town.
  • If it's not pouring and cold I usually don't miss a day at the beach... even on a grey day, after all Grey Lady is Nantucket's nickname.
  • Cisco Brewery: Fun on a sunny or grey day, live music, food and local beverages. Most summer days they have food trucks.

inside scoop

• Nantucket gets crowded, so plan for crowds especially in July and early August. If you can swing Fall, that is when to go.
• Rent houses 3 months in advance and make dinner reservations at least two weeks in advance.
• If you are coming from the West Coast you need a week to get in the groove.
• Plan on being fogged in, then you won't be surprised when are are spending Sunday night on Nantucket.
• I love exploring Nantucket by bike. When I first lived on Nantucket in college it was my mode of transportation... now it's my favored mode of escape and exercise!

skip it

• Skip Cape Air- they have terrible customer service and I almost alway miss my connection if Cape Air is involved.