First Time Visiting Nantucket?

If you’re planning your first trip to Nantucket, you may have already heard that it’s unlike anywhere else in New England. Cobblestone streets, beautiful beaches, world-class dining, and miles of bike paths make it truly unique and memorable.

But Nantucket is also an island, which means things work a little differently than they do on the mainland. Reservations fill quickly, transportation takes some planning, and the weather can change faster than many visitors expect.

Here’s how to avoid some of the most common first-time mistakes so you can spend less time stressing and more time enjoying your vacation.

One of the biggest surprises for first-time visitors is just how quickly ferry reservations book out, especially if you're bringing a car.

Summer vehicle reservations can sell out months in advance, particularly around holiday weekends. Even passenger tickets for the high-speed ferry are worth booking early if you're traveling during peak season and know your dates.

If you don't need a vehicle, consider leaving your car behind. Many visitors find they can easily get around by bike, shuttle, rideshare, or on foot depending on where they're staying. See our guide to whether or not you need a car on the island.

Pro Tip: Reserve your ferry before you finalize dinner plans or activities. Transportation should be the first thing you lock in.

Downtown Nantucket, or Town, is wonderfully walkable, but the island is much larger than many visitors realize. Hint: Nantucket is about 14 to 15 miles long and roughly 3.5 miles wide.

A walk from Town to Brant Point takes only a few minutes. A walk to Surfside Beach is closer to an hour. Madaket, Cisco, and Sconset are even farther.

Where you stay makes a big difference. If you plan to spend most of your vacation exploring beaches, restaurants, and shops, choosing the right neighborhood can save a lot of travel time. See our guide to choosing your perfect Nantucket neighborhood based on your vacation style.

Pro Tip: Before booking your rental, check how far it is from the places you'll visit most often.

Many visitors discover that bicycles become their favorite way to explore Nantucket.

The island has an extensive network of paved bike paths connecting Town with Surfside, Cisco, Madaket, Sconset, and many other popular destinations. Riding often ends up being faster than driving during prime weeks of summer, and you never have to worry about finding a parking space at the beach.

If biking is part of your vacation plans, reserve rentals ahead of time during peak season. See the sidebar for information on our agent’s favorite island bike rental.

Pro Tip: Bring a small backpack for water, sunscreen, and a light sweater. You'll likely spend more time riding than you expect.

Yes, it's summer. But Nantucket's weather has a habit of changing throughout the day.

Morning fog, ocean breezes, and cool evenings often catch first-time visitors off guard. Even in July and August, you'll be glad you packed a sweatshirt or light jacket for dinner, sunset walks, or a ferry ride home.

Comfortable shoes are another must. Much of Nantucket’s downtown is made up of historic cobblestone streets that aren’t ideal for high heels or brand-new sandals.

Pro Tip: Pack layers instead of relying on the forecast. You'll probably use them.

Some of Nantucket’s most popular restaurants book well in advance during the summer.

Restaurants like Galley Beach, Cru, Lola 41, Straight Wharf Restaurant, and Nautilus often fill up weeks (or even months) before busy weekends.

If you know you’ll be celebrating a birthday, anniversary, or simply want dinner with a harbor view, make reservations as soon as your travel dates are confirmed.

Pro Tip: Book your restaurant reservations shortly after you reserve your accommodations. See our guide to booking reservations at some of the most sought-after and exclusive restaurants.

Uber and Lyft both operate on Nantucket, but availability isn’t the same as it is in larger cities.

During busy weekends, after dinner, or following major events, wait times can be longer than expected.

Many visitors combine walking, biking, the NRTA Wave shuttle, and occasional rideshares throughout their stay.

Pro Tip: Download the NRTA Wave shuttle app before your trip. It’s an easy and affordable way to explore the island.

The best homes are often reserved well before summer begins.

Whether you’re looking for a waterfront estate, a family-friendly home near Surfside, or a walkable property close to Town, booking earlier gives you more choices and often better value.

If your travel dates are flexible, your William Raveis agent can also help identify weeks when availability is strongest.

Pro Tip: Working with a local real estate company gives you access to firsthand knowledge of neighborhoods, amenities, and homes that best fit your vacation.

Do I need a car on Nantucket?

Not necessarily. Many visitors spend the week walking, biking, taking the shuttle, and using rideshares. It depends on where you’re staying and what you’d like to do.

When should I book my ferry?

As early as possible, especially if you're bringing a vehicle during the summer season.

What’s the biggest packing mistake?

Assuming every day will be hot. Bring layers for cool mornings, breezy afternoons, and evenings by the water.

How early should I reserve restaurants?

Popular restaurants can fill several weeks in advance during July and August, so reserve as soon as your travel plans are set.