The Insider's Guide: How To Prepare for a Grey Lady Spring

There’s a specific kind of magic that settles over Nantucket in the early spring. While we’re still several months away from high season, this time of year offers a unique opportunity to explore the island with an uninterrupted perspective. 

Whether it’s your first time to Nantucket or your 50th return visit, consider this your guide to on-island adventures this spring. 

Settle into spring solitude 

These early spring months are for those who prefer quiet New England days over the buzz of peak season crowds. Through April and May, you have the freedom to explore wide-open beaches, hidden trails, and highly acclaimed restaurants without bumping elbows with other island visitors. 

Plan your trip:

Behind the quiet exterior of the island, there’s a low hum of activity happening come spring. Whether you’re looking to be active, relax by the water, or food crawl your way through Town, here are some can’t-miss spots.

For those looking to exercise: 

• Take a walk along Steps Beach. This time of year offers some of the clearest views of the sandbars. 

• Grab a coffee from Handlebar Cafe. and explore all the wonderful shops along Main Street. Between the cobblestones and the shopping bags, you’ll definitely get your steps in — after all, shopping is cardio. 

• Bike the Milestone Road Path. Rent a bike in Town and head toward Siasconset. The air is crisp, the path is flat, and the spring hydrangeas are just starting to bloom. 

  
  

For those looking to unwind: 

• Book a massage at Lavender Farm Wellness. Located mid-island, this is the go-to spot for a "Best of Nantucket" massage. In the spring, it’s much easier to snag a last-minute appointment than in July.

• Visit the Whaling Museum. Spend a quiet morning getting lost in the island’s history. The rooftop deck offers a panoramic view of the harbor that’s incredibly peaceful before the summer crowds arrive.

• Pack a picnic for Madaket Beach. Grab a blanket and head to Madaket to watch the tides roll in. In the spring, you’ll often have the most famous sunset spot on the island nearly to yourself.

  
  

For those with an appetite: 

• Enjoy a fresh catch at Cru. Spring marks the reopening of many waterfront favorites. Grab a seat by the window for some world-class oysters and a view of the island’s returning fleet.

• Sample the spring menu at Proprietors. Their small plates are perfect for a "food crawl" style dinner where you can taste the best of the island’s seasonal produce and local seafood. They open back up for the season on April 16th! 

• Head out to Cisco Brewers. While it’s known for the lively atmosphere, a spring afternoon at the brewery is the perfect time to grab a flight and a lobster roll while enjoying live music in the sunshine. 

  
  

Experience spring the best way we know how 

For us at Nantucket by Water, spring is about intentionality. We're spending these next few weeks finalizing every detail of our 2026 season, from custom itineraries to the local pairings we offer on board.

Instead of waiting for the rest of the island to completely thaw, now is the time to see the Grey Lady “wake up” from her winter rest! Some of the best views can only be seen by boat, so pack your layers, book your trip, and plan your charter. 

We can’t wait to see you out on the water!