How to Plan the Perfect Nantucket Day on the Water

Nantucket is one of those rare places that’s genuinely hard to describe to someone who hasn’t been. The light is different here. The pace is different. And nowhere is that more true than on the harbor, where the cobblestone streets give way to open water and the whole island seems to exhale.

Whether you’re planning a full day of island adventures or simply trying to make the most of your time in Nantucket, getting out on the water should be at the top of your list. Here’s how to build the perfect day, anchored by a cruise (or two) aboard Chugalugatug with Nantucket Tug Company.

Start Your Morning Right: The Midday Harbor Cruise

There’s something almost meditative about Nantucket Harbor in the morning. The tour boats haven’t fully revved up yet, the fishing boats are heading out, and the light is clear and clean in a way it won’t be by midday.

The Nantucket Midday Harbor Cruise with Nantucket Tug Company is the ideal way to kick off a day on the island. Whether you’re sipping coffee, sharing a bottle of champagne, or just snapping photos of the waterfront as it glides past, this cruise sets the tone for everything that follows.

The iconic tugboat Chugalugatug — a 1980 Crosby Tug with a history as rich as the island itself — carries up to six passengers in close-knit comfort. It’s not a party barge. It’s an intimate experience, the kind you’ll still be talking about at dinner.

After the Cruise: Making the Most of Nantucket

Once you’re back on dry land with a clear head and a fresh perspective on the island, Nantucket opens up beautifully. A few ideas to fill your afternoon:

Explore the Town

Nantucket’s downtown is compact and walkable, lined with boutiques, galleries, and some of the best restaurants in New England. After a morning on the water, stroll the cobblestoned Main Street and pop into whatever catches your eye.

Rent Bikes or Hit the Beaches

Nantucket’s bike paths are legendary. Rent a cruiser and pedal out to Surfside or Cisco Beach for an afternoon in the sun. If you’re with kids, the calmer waters at Children’s Beach are right near Town Dock — convenient if you’re looping back for your evening cruise.

Eat Well

From chowder shacks to fine dining, Nantucket has a food scene that punches well above its size. The island has a strong local food culture, and Nantucket Tug Company can recommend  provisions from their favorite island purveyors to enjoy on board — charcuterie, snacks, & drinks. 

End the Day with a Sunset Cruise

Here’s the move that takes a great Nantucket day and makes it a perfect one: book the Sunset Harbor Cruise and let Chugalugatug carry you into the evening.

The timing is designed for golden hour — that magical window when the sky turns from blue to amber to rose and the harbor looks like it was lit by a film crew. Bring a charcuterie board. Open a bottle of something cold. Watch the island you’ve spent the day exploring slowly glow from the water.

The sunset cruise is the perfect aperitivo hour before heading to dinner. You’ll be in the best mood of your trip by the time you step back onto the dock.

Tips for Planning Your Day

Book Early

Nantucket Tug Company limits each cruise to six passengers, which means spots go quickly — especially during peak summer weeks in July and August. Book both the midday and sunset cruise at the same time if you’re planning a full day on the water.

Plan Your Parking

Town Dock has a parking lot directly across the street. The front rows are reserved for permit holders, but there’s free public parking toward the back. Give yourself an extra 15 minutes to find a spot, especially on busy summer weekends. Arriving early also gives you time to explore the dock area before you board.

Dress for the Water

Even in peak summer, the harbor can be breezy. Pack a light jacket, especially for the evening cruise. Sunscreen, sunglasses, and comfortable shoes round out the list. Bring your camera — you’ll want it.

Take Advantage of BYOB

Both the midday and sunset cruises are fully BYOB. Pack what you love, or let Nantucket Tug Company handle the provisions. Either way, make sure everything is packed securely to avoid spills on the water.

A Note on the Boat

Chugalugatug isn’t just a vessel — she’s a conversation starter. Built in 1980 at the Crosby Tug yard in Massachusetts, she spent 45 years on a lake outside Chicago before being rescued, restored, and brought to Nantucket by Matthew and Erika, the founders of Nantucket Tug Company. There’s a warmth to this boat that you don’t find on bigger, newer vessels. She feels cared for, because she is.

Nantucket Tug Company was founded on a simple idea: that the best things in life happen on the water, with the people you love, with good food and something cold to drink. A full day on the water in Nantucket is the perfect expression of that idea.

Book your Nantucket harbor cruise at nantuckettugcompany.com — morning, sunset, or both.