From beautiful beaches to upscale boutiques, this coastal enclave has everything you want for a perfect weekend — or maybe a permanent move
If your ideal town includes upscale eats, coastal trails, and a touch of East Coast glam, look no further than Greenwich, Connecticut. Just a quick train ride from Manhattan, this Fairfield County favorite offers a getaway that’s equal parts luxe and low-key. Whether you’re scoping out the suburbs for your next big move or just need a break from the city, Greenwich delivers.
Stay: Private Harbor Views or Contemporary Luxury
There’s no shortage of great places to stay in Greenwich, but if you want the full experience, two hotels stand out.
First, there’s the Delamar Greenwich Harbor, set right on the water. This hotel radiates coastal sophistication — think spa treatments, marina views, and the kind of guest service that makes you feel like a regular on your first stay. It’s a quick walk to downtown and perfectly positioned for watching the yachts float by while sipping your morning coffee.
Prefer a more modern vibe? Book a room at J House, a chic boutique hotel with sleek, contemporary design and plenty of high-tech touches. From digital concierge tablets to mirror TVs, it’s upscale without being stuffy. The on-site restaurant and spa don’t hurt either. Either way, you’re waking up well-rested and ready to explore.
Explore: Coastal Beauty Meets Classic Charm
Greenwich has mastered the art of offering a lot without being totally overwhelming — perfect for exploring like a local. Nature lovers, families, and city expats scoping the scene will all find plenty to do.
Our recommendation? Start your day at Tod’s Point (also known as Delamar Greenwich Harbor), the local go-to for beach walks, scenic overlooks, and a little breathing room. Whether you want to stroll the sand, jog the trails, or just sit and read, this spot is pure relaxation. It’s especially stunning at sunrise and sunset, with views that rival any New England coastal town.
If you’re in town during summer weekends, head to Greenwich Polo Club to catch a match. This is a great place to mix and mingle — think picnic blankets, statement hats, and plenty of bubbly.
For more grounded adventures, check out the trails at Mianus River Park or Pomerance Park. Both offer serene, wooded hikes just minutes from the downtown core, perfect for working off a big brunch or giving the kids a chance to burn energy.
If the weather’s not cooperating, keep things indoors with a trip to the Bruce Museum, where art, science, and natural history intersect. Right next door is Bruce Park, a leafy green space with a great playground and plenty of room to roam.
Eat: Polished Plates and Welcoming Vibes
This town knows how to eat. But don’t let the posh exteriors fool you. Greenwich’s food scene is welcoming, eclectic, and filled with spots you’ll want to go back to.
For casual lunch or dinner with a creative twist, locals love The Cottage, a cozy, modern American bistro with beautifully plated dishes and a seasonal menu that never misses. If your tastes run toward global fusion, Hinoki, MŌLÌ, and Orienta are all standout picks for stylish nights out, offering everything from elevated sushi to French-Asian mashups.
Craving something classic with a splash of waterfront romance? L’Escale, located in the Delamar, serves up French Riviera vibes (and food) that feel like a vacation within your vacation.
Happy Monkey, a playful concept from Jean-Georges, brings big city flair to downtown Greenwich. With bold cocktails and Latin-inspired plates, it’s buzzy, fun, and exactly where you want to be on a Saturday night.
Over in Old Greenwich, Juju Cantina adds a Mexican twist to the lineup, while Sweet Pea’s Baking Company is your go-to for pastries, sandwiches, and seriously addictive pão de queijo, ideal for breakfast or a mid-afternoon bite on the go.
Caffeine lovers have their pick: Coffee for Good is a high-end café that doubles as a nonprofit training center for people with developmental disabilities. Or duck into Reading Room in Cos Cob for a cozy cup and a good book. Over on Greenwich Avenue, CFCF Coffee serves up house-roasted beans in a sleek space perfect for a quick espresso or a longer catch-up. And in Old Greenwich, Joe Studio Café is known for its flaky French pastries, locally roasted coffee, and homey vibe. It’s even expanding, with outdoor seating planned
Shop: World-Class Retail
No Greenwich town tour is complete without a stroll down Greenwich Avenue, the town’s famed shopping district. This is more than retail therapy. It’s an experience.
You’ll find luxury mainstays like Hermès, Rag & Bone, Veronica Beard, and Intermix alongside indie boutiques and design-forward home shops. The mix is just right: part Fifth Avenue, part beach town, part old-school Connecticut charm.
Window shopping or full-blown retail experience — either way, this is one of those downtowns that makes you feel like you belong, whether you’re visiting for the day or moving in next month.
Why Spend the Weekend in Greenwich?
Because it has everything. And then some.
Greenwich is one of those rare suburbs that checks all the boxes without feeling curated or overly planned. It’s coastal, cultured, and connected, with express trains that get you into Grand Central in under an hour. But it also has beaches and playgrounds, hiking trails and backyard barbecues, polo matches and top-rated preschools.
It’s no wonder so many New Yorkers put Greenwich at the top of their list when they start their suburban search. And once you spend a weekend here, it’s hard not to picture yourself staying for a lifetime.
Want help making that weekend visit a permanent move? Schedule your free initial strategy call.
