“Long Island’s Best Daycations: One Town at a Time”

Greenport: “Where every street leads to the water, every shop has a story, and every sunset feels like a celebration of summer.”

Summer has a way of slipping through our fingers. We spend June making plans, July checking off our calendars, and before we know it, August quietly reminds us that another beautiful Long Island summer is beginning to wind down. But there is still time to slow down, breathe in the salty air, watch another breathtaking sunset, and make a few more unforgettable memories.

My memories of my parents taking my children and me to visit charming towns throughout Long Island have lingered with me. My parents would pack up their car with drinks, snacks, and “just in case” items for all of us. My Dad would pick the town of the day and, off we would go, venturing out early and coming home late. No matter which town it was, we had a fabulous time. I now pass along those memories. I am doing the very same thing with my children and my grandchildren and hope they will continue this family tradition. And those “just in case” items, well, I do that too. Sweatshirts in case someone gets cold. Band-aids in case someone gets a “boo-boo.” A change of clothes in case someone gets dirty. And always an extra pair of footwear in case someone steps in a puddle!

Greenport was one of my dad’s favorite towns to take us to. Now, it has become one of my favorite family-day destinations too.

Over the next five weeks, I’m inviting you to join me on a series called “Long Island’s Best Daycations: One Town at a Time.” No passports. No airports. Just wonderful destinations that I want to recommend to you. Whether you go with family, friends, or sola, these towns are not to be missed. Each week, I’ll take you on a sunrise-to-sunset adventure through one of Long Island’s most charming towns, sharing exactly how I spend the day. Let’s begin in Greenport. It is a picturesque North Fork village where waterfront views, quaint shops, lavender fields, vineyards, incredible seafood, and unforgettable sunsets come together to create the perfect summer daycation.

8:30 a.m. – Start Your Day at Aldo’s Coffee Company

103-105 Front Street, Greenport

Every perfect day deserves a perfect beginning, and there’s no better place than Aldo’s Coffee Company, a historic European-style café that has been welcoming locals and visitors since 1987.

Known for its small-batch roasted organic coffee, handcrafted biscotti, homemade pastries, and warm community atmosphere, Aldo’s feels like the kind of neighborhood coffee shop where everyone knows each other. Step inside and you’ll be greeted by the aroma of freshly brewed espresso and the friendly buzz of morning conversation.

Order a cappuccino, latte, cold brew, or espresso along with one of their freshly baked pastries or famous biscotti. If the weather is nice, grab a seat outside and watch Greenport slowly wake up around you.

My Personal Tip: Arrive before 9:00 a.m. for easier parking and a quieter village before the rest of the day-trippers arrive.

9:15 a.m. – Explore Main Street & Front Street

Now that the caffeine has been absorbed, spend the next hour wandering Greenport’s charming downtown.

Browse unique boutiques, nautical home décor stores, art galleries, bookstores, jewelry shops, specialty food stores, clothing boutiques, and antique shops. Unlike many shopping districts filled with chain stores, Greenport has maintained its authentic small-town character. I always like to support local businesses.

As you stroll, you’ll discover colorful storefronts overflowing with flowers, welcoming benches, and friendly shop owners eager to share stories about their village. In fact, I learned from one business owner that Greenport was once one of the busiest whaling and shipbuilding ports on the East Coast. Today, the harbor still reflects its rich maritime heritage while embracing a relaxed coastal lifestyle.

Take a walk along the marina at Mitchell Park, where fishing boats, sailboats, yachts, and the Shelter Island Ferry create a constantly changing waterfront scene.

My Personal Tip: Put your phone away for a few minutes. Some of the best memories come from simply sitting on a bench overlooking the harbor and watching village life unfold.

10:15 a.m. – Lavender by the Bay

7540 Main Road (Route 25), East Marion

Just a ten-minute drive west is one of North Fork’s most photographed destinations. During bloom season, Lavender by the Bay becomes a sea of purple stretching across the countryside. Thousands of lavender plants exhale their soothing fragrance. Inhale deeply. The sense of smell triggers the strongest and most vivid memories. Walk the rows, take beautiful photographs, and enjoy one of the most peaceful places on Long Island. Before leaving, browse the charming farm shop featuring handcrafted soaps, candles, lotions, essential oils, sachets, dried bouquets, culinary lavender, local honey, and unique gifts.

My Personal Tip: Morning offers the softest lighting for photographs and is usually less crowded.

11:30 a.m. – Mitchell Park Antique Carousel

115 Front Street, Greenport

Head back to the village and step back in time aboard Greenport’s beautifully restored 1920 Parker Carousel. It is my very favorite type of ride. I feel like a kid again when I’m on it. I go on this carousel more than once each time I visit. It is listed on the National Register of Historic Places. This antique carousel has delighted families for generations, including mine. Hand-carved horses, vintage music, and its beautiful waterfront setting make it one of Greenport’s most treasured landmarks. Even if you don’t ride (please try though), watching children laugh while parents and grandparents smile from nearby benches reminds us that some traditions never grow old.

My Personal Tip: Ask someone to video you while you are on the carousel. It will be a priceless memory for years to come.

Noon – Lunch at Claudio’s Waterfront

111 Main Street, Greenport

Few restaurants are as iconic on Long Island as Claudio’s Waterfront. Serving guests since the late 1800s, Claudio’s has become synonymous with summer on the North Fork. Its huge outdoor deck overlooks one of the busiest marinas on the East End, making every meal part waterfront dining, part front-row seat to the boating world. Try to get a table as close to the railing as possible. This way you can enjoy the spectacular harbor views over lunch. I recommend ordering their famous lobster roll, fresh local oysters, baked clams, fish tacos, or the fresh catch of the day.

My Personal Tip: Act like a tourist and take that photo in front of the hanging shark.

1:30 p.m. – Learn to Shuck Oysters

Little Creek Oyster Farm & Market
37 Front Street, Greenport

Just a few steps away sits one of Greenport’s hidden gems. At Little Creek Oyster Farm & Market, you’ll discover why Peconic Bay oysters are prized by chefs throughout the country. Sit at a picnic table overlooking the water and let the friendly staff teach you how to shuck your own oysters harvested just offshore. Even if you’ve never held an oyster knife before, you’ll quickly find out why this has become one of Greenport’s most unique experiences. Don’t like oysters? No worries. The waterfront setting alone is worth the stop.

My Personal Tip: Just try one! Even first-time oyster eaters often become fans here because nothing tastes fresher than oysters harvested just minutes earlier.

3:00 p.m. – Kontokosta Winery

825 North Road, Greenport

Time to “unwine?” No visit to Greenport is complete without experiencing Kontokosta Winery. Unlike most North Fork vineyards, Kontokosta sits dramatically atop bluffs overlooking the Long Island Sound, offering breathtaking panoramic water views that stretch for miles.

Rather than enjoying a full tasting, I recommend ordering one glass of wine, or an artisanal soda if you’re driving, and simply soaking in the scenery. Walk out to the bluff overlooking the Sound, feel the cool breeze, and appreciate one of the most beautiful vistas anywhere on Long Island.

My Personal Tip: This may be the most peaceful stop of the day. Sit quietly for a few minutes, you’ll be glad you did.

4:30 p.m. – Latham Farms

4559 Sound Avenue, Riverhead

Before returning for dinner, enjoy a leisurely drive along scenic Sound Avenue and stop at Latham Farms, one of the North Fork’s beloved family-owned farm stands. Depending on the season, you’ll find sweet corn, peaches, tomatoes, berries, fresh flowers, homemade pies, jams, cider, local honey, and just-picked vegetables. It’s the perfect place to bring home a delicious reminder of your North Fork adventure.

My Personal Tip: Buy a pie! Their homemade pies make wonderful desserts if you’re having company over (or, just treat yourself, one slice at a time!).

6:30 p.m. – Sunset Dinner at The Halyard

58775 County Road 48, Greenport (Sound View Greenport)

Save the best view for last. Trust me on this.

Sitting high above the Long Island Sound, The Halyard offers one of the finest sunset dining experiences on Long Island. Arrive a little early and enjoy a pre-dinner stroll along the private beach before being seated. The restaurant’s floor-to-ceiling windows and outdoor terrace provide unobstructed views as the sun slowly sinks into the Sound, painting the sky in spectacular colors.

The menu features locally sourced seafood, seasonal produce, and North Fork wines, making every course a celebration of the region. This isn’t simply dinner. It’s the perfect ending to the perfect day.

My Personal Tip: Even on warm August evenings, bring a light sweater (one of those “just in case” items I referred to). The breeze off the Long Island Sound can be surprisingly cool, and you’ll want to stay outside until the very last glimpse of sunset.

8:30 p.m. – Greenport Creamery

160 Main Street, Greenport

No summer day is complete without ice cream. Stop by Greenport Creamery for one last sweet treat before heading home. Choose from homemade favorites and seasonal flavors, then take a nice walk along the marina beneath the stars.

As the lights dance across the harbor and the village begins to quiet for the evening, you’ll understand why so many people return to Greenport year after year, just like I do.

My Personal Tip: Walk all the way to the end of the docks before leaving. The nighttime reflections across the harbor make for a magical ending to an unforgettable day.

Sometimes we spend so much time dreaming about vacations that we overlook the incredible places waiting to be explored right here at home. Greenport reminds us that the perfect summer day isn’t measured by how far we travel, but by how deeply we experience the moments along the way. A wonderful cup of coffee. A stroll through a charming village. Fields of fragrant lavender. Fresh seafood by the harbor. A vineyard overlooking the Long Island Sound. And a sunset that makes you stop, smile, and simply be grateful.

So don’t let summer slip away.

Pick a day. Invite your spouse, a dear friend, your sister, or even treat yourself to a solo adventure. Then head to Greenport and discover why this charming seaside village captures the hearts of everyone who visits, including mine.

Next week, I’ll meet you at the easternmost tip of Long Island as my “Long Island’s Best Daycations: One Town at a Time” continues in beautiful Montauk.

What are your favorite daycations on Long Island? Send me an email at: andreapeponakis@gmail.com and let’