I have been on the island of Nantucket for the past two weeks, so with my return, I would like to share our first travel guide: Nantucket.

For a tiny island off the coast of Massachusetts, Nantucket is incredibly special. Nantucket has a profound image on the east coast with streets of beautiful houses, hydrangeas, shops, and beaches. Although it is typically a popular summer vacation spot, Nantucket has year-round beauty and activities. The best thing about the island is that it is a perfect getaway for everyone; whether it is a family vacation, a girls trip, or a romantic weekend, Nantucket is always magical and filled with things to do for all types of people. I have been there countless times (about 12!), so I would love to share recommendations to ensure a perfect trip for anybody who wishes to visit.

When to Go:

Nantucket is truly beautiful any time of year. But it goes without saying that summer is the most popular season for the island. Starting at Memorial Day weekend, summer residents and vacationers come flooding in, many staying until labor day weekend. The summer season in Nantucket is filled with life in all corners of the island between the beaches, restaurants, shops, and streets. Although it may get a bit crowded, the most popular and fun weeks of the summer are the 4th of July and the first week in August. May and September are the best months to avoid any crowds at all. However, just because the summer is so popular does not mean it is the only good time to head to Nantucket. Nantucket Daffodil Festival (April), Nantucket Wine Festival (May), Nantucket Film Festival (June), Nantucket Book Festival (June), Thanksgiving (November), and the Christmas Stroll (December) are all wonderful occasions to visit the island for. They draw visitors, but not necessarily crowds, and you can get a feel for the island’s spirit and charm.

Where to Stay:

White Elephant: The White Elephant is undoubtedly known as the best and most luxurious hotel in Nantucket. Positioned right outside of town, the White Elephant provides its guests with space and privacy from bustling downtown while still overlooking the harbor and Children’s Beach and having the opportunity to take a 5-minute walk to get to various shops and restaurants.

The Wauwinet: Nestled in a small neighborhood on the far side of the island in Wauwinet, the Wauwinet’s biggest draw is luxury in privacy. It prides itself on the resort’s blend of “historic charm and modern coastal elegance.” This describes the feel of the hotel well, making it especially perfect for a romantic getaway. Interestingly, the Wauwinet is the White Elephant’s sister property, giving similar amenities but with a more private, formal feel.

The Faraway: Only opening last year, this newcomer to Nantucket has drawn some buzz. One of many boutique hotels in downtown Nantucket, the Faraway stands out because of its modern yet classic design. It is also surrounded by downtown shops and restaurants, putting you in the middle of the island’s best.

Rent a House: There are so many opportunities to rent on Nantucket ranging from only a week to the whole summer. It is a popular option among visitors because it gives you much more space and the opportunity to live like a local. Just make sure to book far in advance and stay in touch with your realtor for updates.

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What to Do:

Beaches

Nantucket beaches are divided into three: north shore, south shore, and east shore. All Nantucket beaches have wonderful island charm and fun activities, but they are certainly different in many ways.

North Shore: Small waves, private, relaxing, close to town

Steps Beach: Between Dionis and Jetties beaches; access from Lincoln Circle. Although it has no lifeguard, no facilities, and very little parking, so it is not optimal for a whole beach day, this remains a favorite on the island. With gentle surf and views of ferries coming into the island, this is a great beach for night swimming, walks, and picnics. The steps going down to the beach are absolutely beautiful, giving lovely views of the waters, beach, and Jetties.

Jetties Beach: Easy walk or ride from town. Water is always calm and relaxing, perfect for swimming and often there is a sandbar. Although the surf is gentle, the beach is still lifeguarded, making it a great beach to come to with families, especially young kids. It is more exciting than Children’s Beach in town, but still fun and safe for children. Plus it has a ton of facilities, such as restrooms, the Sand Bar restaurant, biking and walking paths, and a playground.

Eel Point: Although this beach isn’t the best north shore beach to spend the day at, this beach allows cars on it, making it a great excursion. It has beautiful views of the sunset while driving in the dunes. If you want to stop and take a dip, Eel Point also has gentle waters at the 40th pole.

Monomoy Beach: Not necessarily considered a north shore beach, but Monomoy is close to town, just on the other side. It is very small, but is great for picnics at dinner and watching the sunset. It provides beautiful views of the town and plenty of colorful kayaks and boats on its shores. It is also never crowded, so my favorite thing to do is bring Millies here for sunset (often when Madaket is too crowded).

South Shore: Big waves, crowded, good family beaches

Madaket Beach: My favorite beach on the island. It is a lifeguarded beach with good waves, nestled on the far west end of the south shore. The waves crash right on the shore, making it great for body surfing and fun games. It is a great beach to come to during high season because it is very popular, but not as popular as beaches like Cisco, Surfside, and Nobadeer. It also is a short walk away to Millie’s Restaurant for Baja-style eats, Millie’s Market for snacks and ice cream, and Madaket Marine for views of the Madaket harbor.

Cisco Beach: Cisco is a great surfing beach, home to the Nantucket Surf School which offers boards and lessons to people of all skill levels. Since it is a popular surfing beach, that means it has great waves, even if you don’t choose to surf. The only downside of Cisco is that is does get crowded in the summer. That again doesn’t bother most people, but if it does, the beach is so expansive that if you go a little bit farther down, you can lay more privately with remaining access to the lifeguards, surf school, and bustling nature of the main beach.

Nobadeer Beach: Large beach with great waves. Nobadeer often gets very crowded in high season, but it is known as the charm of the beach. Many high-school and college kids come here to socialize and have fun, especially at night. Since you can drive your car onto Nobadeer, many bring Oath pizza, music, and snacks in their jeeps!

East Shore: Secluded, far from most of Nantucket, small waves

Great Point Beach: None of the East Shore beaches stand out to me except Great Point. Taking your car up to drive on Great Point Beach for the day is a must-do every trip to Nantucket. Although it is more of an activity for the day because of its seclusion in Wauwinet and the fact that you have to stop a few times to fix the air in your tires, it is well worth it. People can’t drive all the way to the lighthouse this summer because of bird nesting, but you can drive up to a certain point. Great Point Beach is beautiful and has gentle waves. I recommend bringing chairs and a cooler and spending the day. You might even see some seals or sharks!

Explore

Bartlett’s Farm: A family-owned farm on Nantucket, Bartlett Farms has Nantucket’s best produce. The famous Bartlett’s Farm tomatoes truly live up to their name. Visit their store to grab lunch or walk around their beautiful fields.

Young’s Bicycle Shop: Although you can get around the island in many ways (via car, bus, or foot), renting a bike is a great way to see the island. I especially recommend this if you are staying for a week or more. Keep in mind they won’t let you drive a jeep till you are 30+ (weird I know!)

Dreamland Drive-In: Dreamland has both a movie theater and a drive-in that islanders love. The classic drive-in offers a ton of movies every week, such as Mamma Mia, The Goonies, and Jaws. Check out their website to look at the showings, which change every day.

Samuel Owen Gallery: With locations in Greenwich, Nantucket, Boston, and Palm Beach, this gallery is filled with incredible, unique works of art.

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Where to Shop:

Luxury: The Lovely, Salt Boutique, Cattivo, Peter Beaton Hat Studio

Trendy: BRODenim, Stoke ACK

Iconic: Annie & The Tees, Nantucket Surf Club, 3 Girls & A Dog

Practical: Mitchell’s Book Corner, Nantucket Bookworks, Sunken Ship

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What to Eat:

Breakfast

Straight Wharf Restaurant: A local favorite for all meals, Straight Wharf’s breakfasts are totally underrated. Their Eggs Benedict and waffles are amazing!

Lemon Press: A trendy, hippie hot spot on the island, Lemon Press has a great brunch, especially their juices and acai bowls.

Lunch

The Beet: Expensive, but the best salads on the island. “Make your Own” with the chicken is to die for (trust me!!!!)

Something Natural: If you see the hibiscus flower plastered on water bottles, computers, and even jeeps, that is just a hint of Something Natural’s charm all over the island. This cute sandwich shop is an iconic emblem of the island. It has even expanded with a shop in Greenwich, CT. My favorite order is a smoked turkey sandwich with avocado and swiss on oatmeal bread. Delicious!

Walter’s Deli: Another great sandwich shop on the island right in the middle of town. You can find it right when you get off the ferry. Pair it with the Juice Bar’s ice cream, which is right next door!

Dinner

Galley Beach: Galley Beach is the place to dine during the summer, mainly because they offer excellent food right on the beach. It is the epitome of luxury dining on the island.

Brant Point Grill: Right inside the most luxurious hotel on the island, the White Elephant, is the Brant Point Grill with great island fare overlooking the harbor. It is very family friendly having children running around the grass and playing cornhole, yet also luxury dining.

The Chanticleer: This modern French restaurant is nestled in the streets of Sconset and is known as one of the most picturesque restaurants on the island. It has a beautiful garden with vines and lovely flowers.

Oath Pizza: Oath Pizza has various locations, but with their flagship in ACK, it is a must-try! Personal pizzas with fun flavors — my favorite is the Bella, but the Tuscan Sausage and Muffled Trushroom are also great.

Millie’s Restaurant: Another great causal restaurant down by Madaket Beach. Great island cuisine with Baja-style eats. Popular to bring to Madaket or other beaches to eat while watching the sunset.

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Treats

The Juice Bar: The Juice Bar is an emblem of Nantucket, drawing lines and lines of people all of the way across the street. I have to say, it is worth the hype. They make their own warm waffle cones with homemade, delicious flavors. My favorite flavors would have to be the Dirty Grasshopper and Blackberry. They also do a flavor of the day each day; one time I got “Seagull Poop” which was vanilla ice cream with fudge swirls, oreo, and marshmallows and was the best ice cream I’ve EVER had! If the Juice Bar gets too crowded, which it often does, especially after dinner, Jack and Charlie’s is a great alternative. Jack and Charlie’s doesn’t have the press or charm that the Juice Bar does, but it is right near the wharf, serves delicious ice cream, and is much more efficient.

The Nantucket Bake Shop: Great bakery for cakes, donuts, and all treats. Nantucket’s famous Downyflake Donuts often gets too crowded, so this is a great alternative for morning donuts.

Handlebar Cafe: A local favorite for coffee. Right on the far end of downtown.