Your Complete Nantucket Vacation Planning Guide

Nantucket is one of those rare places that lives up to every expectation. Cobblestone streets, grey-shingled cottages draped in roses, world-class seafood, and miles of pristine Atlantic shoreline — it's a destination that draws visitors back year after year. But like any special place, a little planning goes a long way toward making your trip truly memorable.

Whether it's your first time on the island or your tenth, this guide covers everything you need to know to make the most of your Nantucket vacation.

When to Visit

The Nantucket season runs from late May through mid-October, with each stretch of the summer offering its own distinct character.

Late May & June is the sweet spot for those who prefer a quieter island. The weather is mild, the beaches are uncrowded, and the hydrangeas are just beginning to bloom. Restaurants and shops are fully open, but you won't be fighting for a table or a parking spot.

July & August is peak season — and for good reason. The weather is warmest, the social calendar is packed, and the island buzzes with energy. Expect full beaches, lively evenings in town, and a festive atmosphere throughout. Book well in advance if you're visiting during this window.

September & early October is a local favorite. The summer crowds thin out, the water is still warm from months of sun, and the island takes on a golden, unhurried quality. Rates are often lower, and you'll find it easier to snag a reservation at the best restaurants.

Getting There

Most visitors arrive by ferry from Hyannis on Cape Cod. The Steamship Authority operates year-round service and is the only ferry that carries vehicles — essential if you're bringing bikes or prefer the flexibility of a car. The high-speed passenger ferry takes about an hour; the traditional ferry with vehicles runs about two and a quarter hours.

Hy-Line Cruises also offers high-speed passenger service from Hyannis, as well as seasonal service from Harwich Port and New Bedford.

Flying is another option. Nantucket Memorial Airport is served by several regional carriers with connections through Boston, New York, and other Northeast hubs. It's a convenient choice if you're coming from farther away.

Getting Around the Island

Once you're on Nantucket, you have several good options for getting around.

Bicycles are the island's unofficial mode of transport. A network of well-maintained bike paths connects the town to Surfside Beach, Madaket, Siasconset, and beyond. We have four bicycles for use in the shed on the property for tenants — please use the locks and text the property manager for the code. If you need additional rentals, they are available throughout town (Young's Bicycles, for example, will deliver to the house).

The NRTA Wave is Nantucket's public shuttle system, with routes covering most of the island's popular destinations. It's reliable and a great way to get to the beach without worrying about parking. The Surfside route is seasonal and currently free to ride — a convenient option right from the neighborhood.

Taxis and rideshares are readily available, particularly in town and near the ferry. For longer trips across the island, they're a convenient option.

Renting a car gives you maximum flexibility, especially if you want to explore the more remote beaches or carry gear. That said, parking in town can be challenging in peak season, so many visitors leave the car at the rental house and rely on bikes and shuttles for day-to-day exploring. Note that driving on any Nantucket beach requires a beach permit — plan ahead if that's on your list.

The property also has a Jeep that may be available to rent for tenants. If you're interested, reach out to the property manager for details and availability.

The Best Beaches

Nantucket has more than 80 miles of coastline, and the beaches vary considerably in character.

Surfside Beach is one of the island's most beloved stretches — a wide, south-facing Atlantic beach with reliable surf and a lively summertime atmosphere. At just 400 feet from the property, it's a simple 5-minute walk or a short bike ride — as easy a beach access as you'll find anywhere on the island.

Cisco Beach is another south shore favorite, popular with surfers and known for its strong waves and beautiful dunes. The nearby Cisco Brewers complex makes it a natural stop for an afternoon drink.

Madaket Beach sits at the western tip of the island and offers some of the most spectacular sunsets anywhere on the East Coast. Plan to arrive an hour before sunset and stay for the show.

Children's Beach and Jetties Beach are both located near town on the calmer harbor side — ideal for families with young children or anyone who prefers gentler water.

Siasconset (Sconset) on the eastern end of the island has a small, charming beach and is worth the trip for the village itself — a cluster of rose-covered cottages that feels like a step back in time.

Dining Highlights

Nantucket's restaurant scene punches well above its weight for an island of its size. A few standouts worth knowing:

The Proprietors is a local institution — creative cocktails, a thoughtful wine list, and a menu that changes with the seasons. Reserve well ahead in summer.

Cru sits right on the harbor and is the place for oysters and a sunset cocktail. The raw bar is exceptional.

Lola 41 offers a lively atmosphere and a menu that spans sushi, tacos, and wood-fired dishes — a reliable crowd-pleaser for groups with varied tastes.

Ventuno is the spot for a special occasion dinner — refined Italian cuisine in an elegant setting just off Main Street.

For a more casual meal, Millie's at Madaket serves excellent fish tacos and sandwiches with a laid-back beach vibe. And no trip is complete without a lobster roll from Sayle's Seafood or a stop at The Juice Bar for homemade ice cream.

Things to Do

Beyond the beach, Nantucket offers a surprising range of activities.

Explore downtown Nantucket — the cobblestone streets, historic architecture, and independent shops make for a genuinely enjoyable afternoon of wandering. The Nantucket Whaling Museum is one of the best small museums in New England and well worth a few hours.

Rent bikes and ride the paths — the Surfside Bike Path from town to Surfside Beach is a classic, and the path to Siasconset through the moors is one of the most scenic rides on the island.

Take a harbor cruise — several operators offer sunset sails and fishing charters. It's a lovely way to see the island from the water.

Visit the lighthouses — Brant Point Light near the ferry dock is iconic, and Great Point Light at the northern tip of the island is a rewarding destination for a four-wheel-drive excursion across the sand.

Attend a local event — Nantucket's event calendar is rich throughout the season. The Daffodil Festival in late April, the Nantucket Film Festival in June, and the Nantucket Wine & Food Festival in October are among the highlights.

What to Pack

Nantucket weather can be variable, even in midsummer. A few essentials:

• Layers — evenings can be cool even in July and August; a light jacket or fleece is always useful
• Sun protection — the island sun is strong; bring quality sunscreen, sunglasses, and a hat
• Bike-friendly footwear — comfortable shoes you can ride in make a big difference
• A reusable bag — Nantucket has banned single-use plastic bags, so bring your own for shopping and beach days
• Cash — some smaller vendors and farm stands are cash-only

A Few Local Tips

• Book early — the best restaurants fill up weeks in advance in peak season; make reservations before you arrive
• Respect the dunes — Nantucket's dunes are fragile ecosystems; always use the designated beach access paths
• The island runs on island time — embrace a slower pace; it's part of what makes Nantucket special
• Explore beyond the town — the moors, the eastern end, and the remote beaches reward those who venture off the main routes

Making the Most of Your Stay at 155 Surfside

Staying at 155 Surfside puts you in an ideal position to experience the best of the island. Surfside Beach is minutes away by bike, downtown Nantucket is an easy ride along the bike path, and the house itself is set up to make your stay as comfortable and effortless as possible.

If you have questions about the island — restaurant recommendations, activity ideas, or anything else — don't hesitate to reach out. Part of what makes a Nantucket vacation special is knowing where to go, and we're happy to share what we know.

Welcome to the island. We hope it becomes one of your favorite places on earth.