A 3-Day Itinerary For A Weekend Getaway On Nantucket
09/10/2025
A weekend trip to Nantucket offers an unforgettable escape. The island is known for its beautiful beaches, historic charm, and quaint streets lined with cedar-shingled homes. If you are looking to relax by the beach, explore nature trails, or discover the local culture, a vacation to Nantucket is the perfect way to unwind.
With this 3-day itinerary, you can enjoy the best the island has to offer while ensuring your weekend in Nantucket is packed with adventure and relaxation.
Day 1: Arrival and Introduction to Nantucket's Charm
Upon arrival on the island, make your way to the heart of Nantucket town, where cobblestone streets, picturesque homes, and vibrant local businesses await. If you arrive in the evening, check into one of the cozy accommodations offered by Great Point Properties.
If you’re staying in the historic town or a serene rental near the beach, you’ll find a welcoming atmosphere and comfortable retreat after a day of travel. You can always check out the Nantucket guide to discover more about accommodations and local tips.
Once you've settled in, head out for your first Nantucket experience. A great start to your visit is the iconic Jetties Beach. It is a popular spot where locals and tourists alike gather for beachside relaxation and evening entertainment.
The Sandbar, a vibrant spot near the beach, is the ideal place to enjoy a drink as the sun sets. Try the classic island drink, the Painkiller, while listening to live music and soaking in the relaxed island vibe. This is the perfect way to ease into your weekend trip to Nantucket.
Day 2: Explore the Island’s Scenic Beauty and Beaches
Start your day early with a visit to Sconset, a scenic village with an authentic Nantucket charm. A leisurely bike ride from Nantucket town, Sconset is home to quiet streets, blooming gardens, and the breathtaking Sconset Bluff Walk, which offers panoramic views of the ocean and the village's beautiful cottages. The walk is around two miles and is an ideal activity for a peaceful morning.
If you’re feeling adventurous, you can head to Sankaty Lighthouse, located just a short distance from Sconset. The lighthouse stands tall over the bluffs and offers a perfect spot for a photo-op, with sweeping views of the Atlantic Ocean. You can also explore Great Point Properties’ extensive real estate options around this area for those interested in purchasing a piece of Nantucket paradise.
After your morning exploration, grab a bite at one of the local cafes or picnic spots. Nantucket has a vibrant food scene, and you'll find fresh, local fare served throughout the island. If you're in the mood for seafood, sandwiches, or pastries, there's something for everyone.
For an afternoon of local flavor, head to Cisco Brewers, one of Nantucket's most popular breweries. Here, you can enjoy live music, sample local craft beers, and sample bites from food trucks that line the parking lot. It’s the perfect place to unwind after a day at the beach.
In the evening, a sunset sail is a fantastic way to cap off your day. The Endeavor, a classic Nantucket sailing vessel, offers evening cruises that allow you to take in the stunning views of the coastline as the sun dips below the horizon. If you’re not able to book the sunset sail, there are plenty of other options for scenic boat rides that offer the same breathtaking views.
Day 3: A Day of Culture and Relaxation
On your final day in Nantucket, take a leisurely morning stroll to Brant Point Lighthouse. This lighthouse is one of the most iconic spots on the island and offers a picturesque view of the harbor. It's a peaceful start to your last day and a perfect place to snap a few photos.
After your morning visit, head to Or, The Whale for brunch. Known for its beautiful patio and delicious menu, it’s a fantastic place to enjoy the island’s laid-back atmosphere and good food. You can enjoy fresh seafood, hearty breakfast options, and, of course, coffee, to fuel your day.
Once you’re recharged, spend some time at the Nantucket Whaling Museum, a must-see for history lovers. Nantucket played a significant role in whaling history, and the museum offers an in-depth look at the island’s past. The museum’s exhibits and historical artifacts give a fascinating glimpse into Nantucket’s maritime heritage.
For those interested in shopping, Nantucket has a mix of upscale boutiques and local shops. If you’re looking for a souvenir, stop by Murray’s Toggery Shop, known for its famous Nantucket Red clothing line. It’s also a great place to pick up casual attire, perfect for a day of sightseeing.
Exploring Nantucket’s History and Shopping
After exploring the Nantucket Whaling Museum, take some time to wander through the charming streets of Nantucket Town. The town is lined with boutiques, art galleries, and unique shops offering everything from handcrafted jewelry to locally made goods. If you’re looking for a keepsake or just browsing, Nantucket’s shopping scene is one of the best on the East Coast.
For a true taste of island life, stop by the Nantucket Historical Association’s museum shops, where you can find books on local history, vintage maps, and antique-style home decor. This is the perfect way to bring a piece of Nantucket back home with you.
Lunch and Scenic Views at Cru Nantucket
After your shopping spree, it’s time for a delicious lunch. Head to Cru Nantucket, a well-loved spot known for its waterfront location and mouthwatering seafood. Positioned right at the end of Straight Wharf, the restaurant offers stunning views of the harbor and the boats coming in and out.
Dining here is an experience in itself, with fresh oysters, lobster rolls, and even spaghettini with littleneck clams – true local specialties. The setting is casual but sophisticated, with an inviting atmosphere that feels both intimate and lively. Dining here is the perfect way to celebrate your final day in Nantucket.
A Quiet Afternoon at Steps Beach
After lunch, take a short walk or drive to Steps Beach, located just 20 minutes from the center of town. This serene spot is quieter compared to the more bustling Surfside Beach, making it an excellent place to relax and reflect on your weekend in Nantucket. Spend your last afternoon here taking a walk along the shore, wading into the calm water, or simply relaxing on the beach and soaking in the last moments of your getaway.
If you’re a fan of photography or nature, this is also a great place to capture the beauty of Nantucket’s coastline. The stillness and natural beauty of Steps Beach offer perfect photo opportunities for capturing the magic of the island.
Wrapping Up Your Weekend: A Final Evening in Nantucket
As the afternoon winds down, prepare for one last special evening in Nantucket. Head to Dune, a renowned New American restaurant that combines Southern and Southeast Asian influences. With a cozy atmosphere and a diverse menu, it’s a great spot for a memorable dinner.
Some of the best dishes on the menu include shrimp tostada and tomato and watermelon salad with feta. The restaurant offers a more affordable dining experience compared to some other high-end options, yet the quality of food and ambiance remains exceptional.
After dinner, you can continue to embrace the relaxed Nantucket vibe. Head to one of the island’s intimate spots for an after-dinner drink or take a quiet walk around town. If you're in the mood for a little nightlife, Nantucket offers options such as The Chicken Box, a local watering hole, or The Gaslight, a lively spot to enjoy cocktails and good company.
Final Morning: A Peaceful Departure from Nantucket
On your final morning, take a last stroll around town and enjoy the peaceful atmosphere before heading to the ferry. If you’re departing by ferry or plane, a final walk around Nantucket Town is a great way to soak in the island’s charm one last time. Stop by the iconic Brant Point Lighthouse if you haven’t yet, or just enjoy the calm beauty of the harbor.
If you’re not in a rush, consider grabbing a light breakfast or brunch at one of the local cafes. Young’s Bicycle Shop often serves coffee and breakfast pastries, or you could enjoy a leisurely meal at Or, The Whale if you didn’t manage to dine there the previous day.
You’ll be able to enjoy one last moment of peace before heading off the island, knowing that Nantucket’s charm will stay with you long after you’ve left.
Great Point Properties: Your Ideal Getaway Partner
As you plan your next weekend trip to Nantucket, keep in mind that Great Point Properties offers a range of vacation rentals that perfectly suit your needs. We are deeply rooted in the Nantucket community and offer unique accommodations that cater to all types of travelers. We also offer helpful resources for getting around Nantucket Island.
If you're looking for a peaceful retreat or a lively townhouse in the heart of the island, we can help you find the perfect spot to stay during your getaway. Explore more about our listings and properties on our Nantucket directory and start planning your next adventure today.