The Essential Nantucket Travel Guide: Tips for First-Time Visitors
Nantucket May Be Small, but It Rewards Thoughtful Planning. Here Are Drives & Detours Tips About Culture, the Weather, and Activities for Your Visit
Nantucket is beautiful but traveling isn’t always straightforward — Manvendra Singh / Unsplash
Nantucket is a place that feels almost unreal the first time you step off the ferry or plane. The island has a timeless charm that draws visitors back year after year to visit its cobblestone streets, historic whaling-era homes, windswept beaches, and picture-perfect lighthouses.
But while Nantucket Island may be small, traveling here isn’t always straightforward. Between the unpredictable weather, high-season crowds, and tricky logistics, it helps to have a few insider tips before you go.
Drives & Detours’ Nantucket travel guide pulls together advice from seasoned visitors, locals, and frequent travelers on Reddit and TripAdvisor forums.
Here’s what you should know to make the most of your trip, whether you’re planning your first weekend getaway or a longer summer escape.
The Best Time to Visit Nantucket
Visiting Nantucket in the off-season is best for a more relaxed trip — Keenan Shepard / Unsplash
When people think of Nantucket, they usually imagine high summer. The island hums with activity, beaches are packed, and restaurants are buzzing with energy during July and August.
This can be an amazing time to visit if you love a lively atmosphere and don’t mind paying peak-season prices. But many travelers swear by late spring and early fall for a more balanced experience.
May and June are wonderful if you don’t mind cooler temperatures. Flowers and gardens are in bloom, the island shakes off its winter quiet, and you can explore without feeling crowded.
You’ll need a sweater at night and may want a rain jacket for those foggy, drizzly days, but the trade-off is worth it. Restaurants and shops are opening for the season, and biking around town or walking to the beach is far easier without the summer traffic.
September is often called Nantucket’s sweet spot. The ocean has warmed up after summer, so you might still enjoy a swim, and the crowds thin out dramatically after Labor Day.
The weather is usually pleasant—warm during the day, crisp in the evenings—and you’ll find more availability at hotels, rentals, and restaurants. September is your month if you want a relaxed trip that still feels like summer.
Winter and early spring are the quietest times to visit, with many businesses closed. You’ll find cozy inns, stormy beach walks, and lower prices if you’re looking for solitude and don’t mind limited options.
For most first-time visitors, late spring, early fall, and summer are the best times for an introduction to the island.
What to Pack for Nantucket
The weather on Nantucket Island can turn quickly so bring a sweater or two — Benjamin R / Unsplash
Don’t make the rookie mistake of packing only shorts and sundresses, even if you’re visiting in July.
Nantucket weather can change quickly. Fog rolls in, ocean breezes pick up, and temperatures drop after the sun goes down. Locals always recommend packing in layers—lightweight sweaters, a windbreaker, and a pair of jeans.
A rain jacket is also handy, as summer storms can come and go. Comfortable shoes are a must. Cobblestone streets and sandy paths don’t mix well with flimsy sandals.
One of the best ways to see the island is on a bike, so bring sneakers or sturdy shoes if you fancy a ride. And don’t forget sunscreen and a hat—the sun reflects off the water and can be stronger than you think.
Where to Stay on Nantucket
Downtown Nantucket is the most convenient option, but may not be your best depending on your plans — Andrew Wolff / Unsplash
Choosing where to stay can make or break your trip. The island may be small, but location really matters.
Downtown Nantucket is the most convenient option, especially if it’s your first time. You’ll be within walking distance of shops, restaurants, and ferries if you stay near the harbor and Main Street, which means you can skip the hassle of a car. This area is also home to many of the island’s historic inns and boutique hotels, offering a quintessential Nantucket experience.
Brant Point is another great choice if you want to be close to town and near the beach. It’s a short walk or bike ride from Main Street, and you’ll get sweeping ocean views and quick access to Brant Point Lighthouse.
Further out areas, such as Tom Nevers, Madequecham, and Madaket, offer a quieter, more secluded vibe. These are great if you’re renting a house with family or friends and don’t mind driving or biking longer distances. The payoff is often incredible views and less-crowded beaches.
For families, The Nantucket Hotel & Resort is a perennial favorite. It offers kid-friendly amenities like a children’s program, pools, and family-sized suites. Many inns and rentals also cater to families, but this resort is a reliable, full-service option.
Book as early as possible if you’re traveling in peak summer. Vacation rentals and hotels often sell out months in advance. You’ll have more flexibility for trips in the spring and fall, but it’s still wise to secure lodging ahead of time.
Getting Around the Island
Reaching the further-flung beaches may require a car, but Nantucket is easy to navigate — Jack Cohen / Unsplash
One of the best bits of Nantucket is how walkable and bike-friendly the island is. You can easily get around without a car if you’re staying in or near town. Bike rentals are widely available, and many hotels provide complimentary shuttles to beaches.
That said, if your lodging is farther out—or if you want to explore remote beaches and lighthouses—a car can be useful. Keep in mind that parking downtown is limited, and rental cars can be expensive. Some visitors solve this by renting a Jeep or SUV for just a day or two to explore the farther corners of the island.
Public buses, called The Wave, also run around the island, offering an affordable way to get between town, beaches, and popular neighborhoods.
Dining and Reservations
The seafood on the island is, of course, excellent and there’s much more to choose from — Jim Petkiewicz / Unsplash
Nantucket has an impressive food scene for such a small island, ranging from upscale seafood restaurants to casual beach shacks.
The catch? In summer, everyone wants a table. Make reservations as far in advance as possible if you have your heart set on dining at hotspots like The Nautilus or The Proprietors.
It helps to plan ahead, even for casual meals. Many locals and seasoned visitors recommend making both lunch and dinner reservations, especially if you’re visiting on a weekend.
However, don’t overschedule. Some of the island’s best meals happen when you stumble into a tucked-away café or grab tacos at Millie’s after a beach day.
Things First-Timers Often Overlook
Don’t try to do doo much on Nantucket and remember that opening hours change every month — Autumn Hassett / Unsplash
Business Hours Change by Season: In May and September, some restaurants and shops may have limited hours. Always check ahead if you’re traveling off-peak
Plan one big activity per day: Trying to do it all—beaches, museums, biking, shopping—can be exhausting. Focus on one highlight a day and leave time for wandering
Cash for Tips: While most places take cards, having cash for tips (especially for bike rentals, shuttles, or small cafés) is handy
Local Etiquette: Nantucket is friendly and laid-back, but remember to respect private property near beaches, and keep in mind that many roads and paths are shared by bikers, walkers, and cars
Plan Well for a Trip to Nantucket, but Don’t Overthink It
Your first trip to Nantucket will feel like the beginning of a lifelong tradition — Keenan Shepard / Unsplash
Nantucket may be small, but it rewards thoughtful planning. Visit in May or September if you want fewer crowds, choose your lodging carefully to match your style of trip, and never underestimate the island’s fickle weather. Yes, you’ll probably need that sweater in July.
Don’t overthink it at the same time. Some of Nantucket’s best moments are the unplanned ones—watching a golden sunset in Madaket, stumbling across a local band at The Chicken Box, or savoring a lobster roll by the harbor.
With a little preparation and a spirit of adventure, your first trip to Nantucket will feel like the beginning of a lifelong tradition.
Discover Nantucket at Your Own Pace with Drives & Detours
Drives & Detours will share the rich cultural history of Nantucket Town and guide you to must-see sights across the island — Emmy Gaddy / Unsplash
Experience Nantucket on your terms with Drives & Detours’ self-guided tours. Designed to be flexible, informative, and fully accessible offline, these tours let you explore the island at a pace that suits you.
Purchase your tour online ahead of time or download the app and start your adventure whenever it works for you.
Each tour shares the rich cultural history of Nantucket Town and guides you to must-see sights and hidden treasures across the island.
With Drives & Detours, you won’t miss the little-known spots and local favorites that make Nantucket truly special.
