Planning a trip to Nantucket in 2025? This iconic little island offers the perfect blend of history, outdoor adventures, incredible dining, and stunning natural beauty. To help you make the most of your stay, we’ve crafted the ultimate travel itinerary that ensures you’ll experience the best of Nantucket.

Explore the Must-See Landmarks

Nantucket’s rich history and unique character make it a must-visit destination for exploring its iconic landmarks. Start with Brant Point Lighthouse, one of the oldest lighthouses in the country, offering picturesque views of the harbor. Its proximity to Town and stunning harbor views make it a perfect spot for morning strolls, photo ops, or catching one of those iconic Nantucket sunsets.

The Nantucket Whaling Museum is another coined spot, where it’s easy to surround yourself with the island’s maritime history. The rooftop of the museum is a great place to take in panoramic views of Downtown and the Harbor!

Head to Sankaty Head Lighthouse on the southeastern tip for a peaceful escape and sweeping ocean views. Feeling adventurous? Drive out to Great Point Lighthouse, located at the northernmost tip of the island. But heads up—it can be quite the drive over sandy roads, so plan ahead and pack yourself some lunch. Grab a picnic lunch from local favorites like Claudette’s Sandwich Shop, Fresh, or Something Natural, and enjoy the lunch with a remote, incredible view.

 

Get Outside and Explore Nature

For those who love the outdoors, Nantucket offers endless opportunities for adventure. Rent a bike from Young’s Bicycle Shop or Cook’s Cycles and take on scenic trails like Polpis Road, which winds through salt marshes and woodlands.

If you’re a beach lover, Cisco Beach is a great destination for biking, surfing, or relaxing by the water. For a unique perspective of the island, take to the water with Endeavor Sailing for an intimate tour of the island’s coastline, or rent a kayak or paddleboard from Sea Nantucket to explore at your own pace!

Don’t miss out on the charm of Sconset Village, which is easily one of the most picturesque places on the island. Here, we recommend walking the Sconset Bluff Walk, a winding trail along the water, through backyards, and rose-covered cottages.

 

Indulge in Dining and Shopping

Downtown Nantucket’s culinary scene is as enticing as its landscapes and is also home to some of the best boutique shopping experiences! Begin your day with fresh coffee and pastries at The Handlebar Café, a local favorite. For lunch, enjoy waterfront dining at Straight Wharf Fish, known for its fresh lobster rolls and harbor views.

Spend your afternoon shopping on and around Main Street, where you’ll find unique treasures at Mitchell’s Book Corner and staple island apparel at The Sunken Ship. Finish your day with an upscale dinner at The Galley, known for its fresh seafood, New England classics, and spectacular sunsets.

 

Attend Nantucket’s Events and Festivals

Add a special touch to your trip by timing your visit around one of Nantucket’s signature events. In May, the Nantucket Wine & Food Festival offers tastings, dinners, and seminars celebrating the island’s culinary culture. June brings the Nantucket Film Festival, showcasing independent films and filmmaker discussions. If you’re visiting in December, the highly anticipated Christmas Stroll Weekend transforms the island into a holiday wonderland, with festive storefronts, holiday shopping, and plenty of seasonal cheer to get you into the spirit.

Relax and Unwind by the Water

No trip to Nantucket is complete without some downtime on the island’s stunning beaches. Cisco Beach is a local and traveler favorite for both relaxation and action, offering excellent surfing conditions and plenty of space to stretch out and enjoy the ocean breeze. For a truly unforgettable evening, head to Madaket Beach on the island’s westernmost tip to watch Nantucket’s famous sunsets. (We’d recommend grabbing tacos and a margarita at Millie’s to watch a Madaket sunset with!)

 

Choose the Perfect Place to Stay

Where you stay on Nantucket during your visit can shape your entire experience! The rose-covered cottages of ’Sconset provide a quiet and peaceful retreat, perfect for those seeking relaxation and a taste of the island’s signature architecture. Staying in Town places you in the heart of the action, with easy access to shopping, dining, and landmarks like Brant Point Lighthouse. For a slower pace, consider Madaket, where you’ll find serene coastal vibes and some of the island’s best sunset views. Each area offers its own unique taste of Nantucket, ensuring there’s a perfect fit for every traveler. Contact us at Lee Real Estate to find the perfect rental home for your stay, no matter how long or short.

Nantucket in 2025 is a destination that effortlessly blends history, adventure, and relaxation. Whether you’re exploring lighthouses, strolling through villages, or savoring fresh seafood, every moment brings something memorable. Use this guide to craft an itinerary that suits your style, and get ready to experience the magic of Nantucket!