Situated off the Massachusetts coast, Nantucket beckons with its storied past, sandy shores, and enchanting landscapes, making it an idyllic retreat from the everyday hustle. Whether you're a seasoned Nantucket lover or a first-time explorer, our handcrafted itinerary will lead you through the island's hidden treasures, local delights, and unforgettable experiences that will leave you yearning for more. So, pack your bags with a spirit of adventure, let the ocean breeze guide your way, and allow us to be your trusted travel companion on this Nantucket Weekend Itinerary.

Nantucket Weekend Itinerary: Day 1

Morning: Arrive on the Island 

If you arrive by either ferry, you’ll be dropped off in downtown Nantucket. Checked luggage can be picked up in the blue trolleys on the streetside near the boats, and off you go! The whole process is rather quick and easy. Depending on the location of where you stay and how much luggage you have, you can either walk or take an Uber or Lyft to your destination.

Part of Nantucket’s quintessential charm is the winding and uneven cobblestone streets in its downtown area. If you’re hauling several large suitcases up hills and on people-packed sidewalks, it’s not so charming. With a weekend bag or carry-on roller, you’ll be fine to walk to most hotels. Be sure to check with your accommodations, as they may offer complimentary transportation.

Most hotels in Nantucket offer a 3 PM check-in time and will hold your bags while you explore before then. We packed an easy-to-reach change of clothes in a day bag to hit the ground running once we dropped off the other suitcases.

We also traveled here with our dog, Luna! Nantucket is one of the most dog-friendly islands in New England and also the United States. We found out at the last minute that Life House Hotels, unfortunately, does not offer accommodations for furry friends, so we gave Luna a little staycation with a highly-rated local dog sitter, Scott and Shayla. We found them on the Rover App.

Rent a Bike on Nantucket

Nantucket is small in terms of land mass and is notorious for limited vehicle parking. Simply put, renting a bike is the best way to get around the island. The hotel we were staying at, Blue Iris, offered a fleet of complimentary blue bicycles with spacious baskets. If you’re visiting during high season on a weekend (any time between Memorial Day to Labor Day), secure a bike early in the day before they are all gone. If your hotel does not offer bikes, be sure to check out local outfits like Young’s Bicycle Shop, Nantucket Bike Shop, or Easy Rider Bicycle Rentals.

Youngs Bicycle Shop | 6 Broad St, Nantucket, MA 02554
Nantucket Bike Shop | 10 Broad St, Nantucket, MA 02554
Easy Rider Bicycle Rentals | 65 Surfside Rd, Nantucket, MA 02554

Pick Up Provisions for the Day

Located in the heart of downtown Nantucket is a cozy bakery and provisions shop known for artisan bread and sandwiches. Toss a simple breakfast sandwich from Born and Bread into your bicycle basket and hit the road to the beach. If you’re a wine lover like us, no day is complete without a little vino. Stop by Epernay Wine & Spirits or Brix and grab a bottle or two for the day.

Born and Bread | 35 Centre Street, Nantucket, MA 02554
Epernay Wine & Spirits | 1 N Beach St, Nantucket, MA 02554

Head to Brant Point Lighthouse

In our opinion, the best way to experience Nantucket is to get lost in the small neighborhoods on the way to your destination. Stop and admire the houses, smell the roses and hydrangeas, and soak in the salty sea air as you head to the historic Brant Point Lighthouse.

Located on the northern coast of Nantucket, Brant Point is the second oldest lighthouse in the United States, with history dating back to the early 18th century.

The first Brant Point Light was constructed in 1746 as a wooden tower with a single lantern, serving as a guide for ships entering Nantucket Harbor. However, due to its vulnerable structure and deteriorating condition, it was eventually replaced in 1758 by a more substantial stone tower. Over the years, the lighthouse underwent several renovations and improvements to enhance its effectiveness. In 1856, the original stone tower was replaced with a taller, more modern cast-iron tower, standing at 26 feet. Additionally, a distinctive fifth-order Fresnel lens was installed to increase the light's visibility.

Throughout its existence, Brant Point Light played a crucial role in maritime navigation, guiding countless ships safely into Nantucket Harbor. Its location at the entrance of the harbor made it a vital beacon for sailors and contributed to the island's reputation as a significant whaling port. As technology advanced, the lighthouse was automated in 1965, ending the era of resident lighthouse keepers. Today, Brant Point Light stands as an iconic symbol of Nantucket's maritime history.

A local also recommended checking out the Jethro Coffin House, also known as “Oldest House”, which is located close to Brant Point Lighthouse. Dating back to 1686, this venerable saltbox home proudly holds the title of Nantucket's oldest-standing house. Stepping through its doorways is like taking a journey back in time, offering visitors a glimpse into early colonial life on the island.

Brant Point Lighthouse | Easton St, Nantucket, MA 02554
Jethro Coffin House | 16 Sunset Hill Ln, Nantucket, MA 02554

Steps Beach and Galley Beach

Steps Beach is a beautiful beach on the north side of the island, infamous for watching pink-hued New England sunsets. Grey weather-worn homes overlook quiet bluffs on Nantucket’s coast, dotted with sunkissed people swimming, reading, and catching warm summer rays.

Neighboring Steps Beach is Galley’s Beach, which is less than a 5-minute walk down the shoreline, famous for beachside dining during sunset. Come dressed to impress if you’re coming for dinner reservations, otherwise stop here for a happy hour drink and appetizers like we did. While the restaurant would have seated us in the dining section, we definitely would have felt underdressed (and shoeless!). They have two different menus — the lounge one is pretty limited food-wise. Enjoy the sunset but be sure to leave with enough sunlight to get home safely if biking or walking back. 

After the sun sets, use the time to check into your hotel and enjoy a fresh shower.

Galley Beach | 54 Jefferson Ave, Nantucket, MA 02554

Drinks and Lobster Rolls at CRU

CRU is an infamous dining destination in Nantucket, known for mouth-watering drinks and surprise: fresh, locally-caught seafood. Martinis, champagne, New England oysters, and succulent warm lobster rolls reign supreme in their menu. While eating CRU is undeniably a treat in terms of upscale ambiance and superb food quality, don’t be surprised by the $50 Lobster Rolls on the menu. Wondering if the rolls were worth it? Absolutely.  

CRU | 1 Straight Wharf, Nantucket, MA 02554

Late-Night Music at Chicken Box

A local bartender recommended we check out Chicken Box for late-night music. It’s a legendary institution that blends the spirit of a lively pub with the laid-back island energy, frequented by locals. If you had light bites at CRU, you can find mouthwatering chicken wings, crispy fries, and a variety of delicious comfort foods at Chicken Box.  offers a taste of true Nantucket flavor. Live music adds to the vibrant atmosphere, making it the perfect spot to unwind, dance, and enjoy some fantastic tunes. Mondays are industry night.

The Gaslight is also a popular late-night spot among locals, with live music all weekend as well.

Chicken Box | 16 Dave St, Nantucket, MA 02554
The Gaslight | 3 N Union St, Nantucket, MA 02554

Nantucket Weekend Itinerary: Day 2 

Now that you’re acquainted with the island and have seen the popular spots, it’s time to venture off to the lesser frequented areas. Depending on how late you stayed out at the Chicken Box or Gaslight, chances are you may be waking up in time for lunch! This was our favorite day on Nantucket, and we can’t wait to come back to visit the more rural parts of the island.

Pick up Lunch at Sayles Seafood Market

If you are going to go to one place to eat seafood in Nantucket, make it to Sayles. Sayles Seafood is a complete fish market with ready-to-eat dishes ranging from freshly steamed lobsters, fried fish, clam chowder, and clambakes for takeout. Sayles has a great porch with a few tables to eat outside, otherwise, take these for a beachside picnic. Insider tip: get the lobster salad roll! It makes for a refreshing lunch before heading out in the sun.

Sayles Seafood | 99 Washington St Ext, Nantucket, MA 02554

Head to Nantucket’s Southern Beaches

From Sayles, head to Miacomet Beach or Cisco Beach by bike, which are some of the best-kept secrets on the island. These south shore beaches offer fewer crowds and fun waves. 
Cisco Beach, which is home to some of the best waves on Nantucket, and, notably, is one of the best surfing spots on the island. The beach is fairly accessible in season, with a sizeable dirt parking lot and bike and pedestrian access via the Hummock Pond bike path. There is a steep dropoff from the parking area to the beach, and a seasonal ramp provides access to the beach.

Miacomet Beach is located at the end of Miacomet Road, and there are no lifeguards. You can also find Ladies Beach, a remote stretch of sand at the end of Bartlett Road that cannot be accessed by vehicles. Miacomet is the only established nude beach on Nantucket, drawing small crowds of nudists for at least several decades. As of December 2022, it is legal for women to sunbathe topless on any Nantucket beach.

Be sure to also check out Miacomet Pond, which is great for fishing and relaxing. It's a large freshwater pond in the middle of the Miacomet Loop, and good for young children.

Have Beers at Cisco Brewery

After wrapping up a successful afternoon at the beach, head to Cisco Brewery on the way back to town. The brewery, winery, and distillery are all housed on the same premises. With ample outdoor seating, including picnic tables and spacious lawns, guests enjoy a more relaxed side of Nantucket, sipping on locally crafted beers, listening to live music, and enjoying local food truck options. And, in the spirit of Nantucket — there are freshly shucked oysters.

Keep in mind that Cisco dies down very quickly around sunset, and isn’t open on the weekends. We caught the tail end of the live music, but it quickly cleared out with enough time to get back to the hotel on the bike before dusk.

Freshen Up and Have Dinner

We heard great things about Proprietors Bar and Table. The restaurant blends international flavors with locally sourced ingredients, with most dishes echoes the island’s eclectic whaling history. This menu is structured to encourage guests to experience a number of shared-plates and runs from smaller dishes to entrée-sized portions. The entire menu is designed to be enjoyed family-style and offers many vegetarian choices.

Proprietors Bar and Table | 9 India St, Nantucket, MA 02554

If you’re looking for a nightcap with drinks, head to The Brotherhood of Thieves, an 1840’s former whaling bar. Brotherhood is a family-friendly pub with hearty snacks, craft beers, a patio, and a cozy fireside. Closes 1 AM.

Nantucket Weekend Itinerary: Day 3 

If you can swing a long weekend in Nantucket, this is your sign. For us, this was a Monday where we worked remotely from Blue Iris’ courtyard and explored around town on our lunch break and before heading out on the last Hy-Line ferry of the night. 

Lunch (or Brunch) at Lemon Press

Lemon Press, a bright, brick-lined cafe in the heart of downtown Historic Nantucket, complete with outdoor tables offering eclectic eats, smoothies & creative cocktails. The menu is inspired by the owner’s Persian heritage and upbringing. We had the Avocado Toast, Veganwich, and Kami’s Bowl — and all were to die for. Highly recommend it.

Lemon Press | 41 Main St, Nantucket, MA 02554

Shop Downtown Nantucket

There are so many options for shopping in downtown Nantucket. You’ll find quintessential East Coast fashion boutiques, homeware stores, and even upscale retailers for your furry friends. Meander down the cobblestone streets and breeze in and out of countless storefronts. Be sure to stop by Juice Bar for the best ice cream on the island.

Conclusion

As the sun dips below the horizon, we reluctantly bid farewell to this captivating Nantucket weekend getaway. From the charming Brant Point Light to the peaceful shores of Miacomet Beach, our hearts are brimming with treasured memories.

Strolling through the cobblestone streets, savoring every fresh seafood bite, and embracing the island's laid-back vibe, we've crafted unforgettable moments etched in our souls.

Nantucket's timeless allure, friendly locals, and diverse attractions have won us over completely. Whether you're a history buff, a beach enthusiast, or simply seeking solace, Nantucket caters to every traveler's desires.

As we sail back to the mainland, we carry Nantucket's spirit with us – its rich maritime heritage, breathtaking landscapes, and warm community. Until we return, we'll cherish the essence of Nantucket, knowing that more incredible experiences await.

Thank you for sharing this Nantucket journey with us. We hope our itinerary has sparked a desire to explore, discover, and embrace the magic of Nantucket for yourself. Until our paths cross again in this coastal haven, safe travels, and may your adventures be filled with wonder and joy!

Planning your first trip to Nantucket? Check out our Getaway Guide to Nantucket with insider tips and intel for planning your trip to this exclusive New England destination.

This post may be sponsored or contain affiliate links, which means I receive a small commission, at no cost to you, if you make a purchase through a link.