Anniversary Sweet Escape: Nantucket, MA

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Mara Maund
Curated By

Mara Maund

  • Nantucket

  • Couples Travel

  • Weekend Getaways

  • Beaches

  • Food & Wine

  • Romantic

Advisor - Anniversary Sweet Escape: Nantucket, MA
Curator’s statement

Nantucket is such a charming destination with a welcoming atmosphere and incredibly friendly locals who make you feel right at home. Despite being a small island, it offers an amazing variety of fantastic restaurants, beautiful scenery, and so many unique places to explore. From the coastal views to the relaxed pace, every corner feels special. This sweet escape creates the perfect setting for an unforgettable anniversary trip, romantically quite perfect.

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Where to stay in Nantucket

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Things to do in Nantucket

Our biking adventure, heading to the Sconset Bluff Walk

Sconset Bluff Walk

This was one of my favorite spots on the island. It’s such a peaceful walk with incredible ocean views, beautiful wildflowers, and some of the most charming cottages you’ll ever see. It’s the perfect place to slow down, take in Nantucket’s beauty, and snap a few photos along the way.

Whaling Museum

If you’re looking for a break from the sun or want to learn more about the island, I definitely recommend stopping here. It gives you a great appreciation for Nantucket’s history and the story behind this special place.

Rent bikes

One of my favorite ways to explore Nantucket is by bike! We rode all the way to Siasconset (about 8 miles each way), and it ended up being one of the highlights of our trip. You’ll pass beautiful homes, quiet beaches, and so many scenic spots along the way. If biking isn’t your thing, rent a Jeep and spend the day exploring the island with the top down.

Shopping downtown

I could spend hours wandering through downtown Nantucket. The cobblestone streets, locally owned boutiques, and overflowing window boxes make every corner feel picture-perfect. Start with a coffee from Lemon Press, then take your time exploring—you never know what hidden gem you’ll find.

Cisco Brewers

This is a must-visit while you’re on the island! The atmosphere is so much fun, with live music, local food trucks, and great drinks. We loved grabbing a lobster roll and pairing it with the Wandering Haze Hazy IPA before spending the afternoon relaxing outside.

Golf at Miacomet Golf Club

We always try to experience a destination through its local golf course, and Miacomet didn’t disappoint. The course is beautiful, the coastal views are incredible, and it’s a fun way to spend a morning or afternoon if you enjoy golf.

Places to eat & drink in Nantucket

The delish bolognese from Queequeg’s

Island Kitchen

This is a must for breakfast, especially if you can enjoy it on the porch. The freshly squeezed mimosas, classic Eggs Benny, and homemade buttermilk pancakes are all worth it—you’ll thank me later. It’s the perfect spot for a clean, delicious start to the day in Nantucket.

Lemon Press

Need an afternoon boost? This is my go-to for coffee, fresh juices, and even a sweet treat like ice cream. It’s such a cozy place to recharge before heading back out to explore.

The Nautilus

If you want something a little different, this spot blends New England charm with Asian-inspired flavors in the best way. We started our trip here on night one, and it set the bar high for the rest of the week. The small plates are perfect for sharing and trying a little bit of everything.

Queequeg's

This is such a lovely choice for a romantic dinner with a fun bistro feel. I’d definitely try to grab a seat at the intimate bar and soak up the atmosphere. I still think about the mussels and the QQ Bolognese, and chatting with the bartender is a great way to get a few local tips.

Millie's

Head here after catching sunset at Madaket Beach. It’s relaxed, casual, and the food is so good, with beautiful views to match. The tacos are some of the freshest on the island.

Topper's

Located at the far end of the island and connected to The Wauwinet Hotel, Topper’s is a slightly more upscale option that feels perfect for a special night out. The views of the point make it even more memorable, and it was the perfect anniversary meal for us.

Need to know

Finally, the best part of Nantucket is the pace. It’s meant to feel slow, coastal, and unstructured. The best days usually mix a little golf, a beach stop, and a long dinner without rushing between them. Stop and admire each and every flower box!

Mara Maund

Travel Advisor

Mara Maund

Advisor - Mara Maund

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For more inspiration and insider recommendations, visit our Nantucket page.