Short answer: the Nantucket off-season is the best marketing window of the year because your customers are planning while you finally have time. Build an email list from every guest and customer, send them something useful in the winter, refresh your website and photos, and publish content that answers the questions summer planners are asking in February. Businesses that do this fill their calendars before Daffodil weekend. Businesses that go dark from December to May start every season from zero.

Email is your winter storefront

Your shop may be shuttered, but your email list is open all year. It is the only marketing channel you own outright, and it is the one most island businesses neglect.

Build it in season. Every reservation, booking, order, and gallery sale is a chance to collect an email. A simple line, "Can I send you next year's dates?", works better than any pop-up.

Send in the off-season. Two or three emails between December and April is plenty.

  • December. A thank-you for the season and a gift card or holiday offer. Stroll weekend shoppers respond to this.
  • February. Next season's dates, what is new, and an early booking incentive for rentals, charters, and events.
  • April. A reopening note timed to Daffodil, with photos of the place coming back to life.

Rental owners have the strongest version of this. One email in October with next summer's calendar and a note about booking direct fills the best weeks with repeat guests. See direct bookings for Nantucket rentals.

Refresh the website

Winter is website season. The full timeline is in its own post, but the short version:

  • Fix what broke over the summer. Wrong hours, dead links, a contact form nobody checked.
  • Replace stock or tired photos with real ones. Shoot in December while the place is decorated, or in the shoulder season light.
  • Update prices, menus, and services for next year, and say "2027 season" so visitors know it is current.
  • Make sure Google has you marked temporarily closed rather than permanently closed. My seasonal Google Business Profile guide walks through it.

Content to publish

Off-island planners are searching in the winter, and the businesses with answers get the bookings. One or two useful pages published in January can bring visitors for years.

Ideas that work on Nantucket:

  • A guide to your part of the island for first-time visitors. Where to park, where to eat nearby, what to bring.
  • A "planning your Nantucket wedding weekend" page if you cater, host, photograph, or transport.
  • A seasonal calendar: Daffodil, Figawi, Fourth of July, the August peak, Stroll, with what your business offers around each.
  • An honest FAQ answering the questions you get on the phone every week.

Write like you talk. Specific and local beats polished and generic. The local SEO playbook covers how to make these pages findable.

Pre-season booking pushes

For businesses that take reservations, the winter push is where the season is made.

  • Charters and tours. Open next season's calendar in February and email past guests first. Figawi weekend and July fill early.
  • Rentals. Repeat guests get first refusal in October, then the list, then the platforms.
  • Event venues and caterers. Wedding and corporate planners book Nantucket a year out. Your site and Google profile need next year's availability by January.
  • Restaurants. Private event inquiries for rehearsal dinners and summer parties start in March. Have the page ready.

Stroll retargeting

Stroll weekend, the first weekend of December, brings tens of thousands of visitors for a few days. Every one of them is a potential summer customer.

  • Collect emails at the register with a simple incentive.
  • Post the weekend on social media and tag the Chamber and the island's publications.
  • Follow up in January with something worth opening.

A retail shop that turns Stroll shoppers into an email list has a summer customer base before the ferries start running full.

What to skip

Paid advertising in the deep off-season for a business that is closed. Daily social posting to an audience that is not on the island. Expensive holiday campaigns without an email list to send them to. Off-season marketing is about setting up the summer, not filling February.

Getting help

If you want your website, photography, and Google presence sorted before next season, this is the time to start, and it is what I do for island businesses every winter. Get in touch and tell me what next summer needs to look like.