Named for the brightest constellation in the summer sky, Calissa occupies a peculiar position on Long Island’s South Fork — a restaurant that manages to be both unapologetically Greek and unmistakably Hamptons, channeling the whitewashed energy of a Cycladic island while remaining rooted in the agricultural rhythms of Water Mill. Since opening its doors in the summer of 2017, this Montauk Highway destination has evolved from an ambitious newcomer on a notoriously cursed restaurant site into one of the East End’s most enduring and celebrated dining establishments. For anyone who has spent twenty-five years behind a flat-top griddle on Long Island’s North Shore — as I have at The Heritage Diner in Mount Sinai — watching a restaurant defy the seasonal volatility of the Hamptons and operate year-round is something worth studying closely. Calissa does not merely survive. It thrives, and it does so by understanding something fundamental about hospitality that transcends geography: the table is where culture happens.
The Lineage of a Hospitality Empire
Calissa did not materialize from thin air. It carries the DNA of some of Manhattan’s most respected Mediterranean restaurants, and understanding that pedigree is essential to understanding why Calissa works. James Mallios, the managing partner and co-owner, is the driving force behind Civetta Hospitality, which operates Calissa alongside sister venues Amali on Manhattan’s Upper East Side, Bar Marseille in Rockaway Beach, and Juniper at The Vanderbilt in Nassau County (The East Hampton Star, 2017). Mallios himself is an unlikely restaurateur — a Queens-born attorney who practiced labor and employment law before trading depositions for reservations. His family roots in the restaurant business, however, run deep: a grandfather who was a dishwasher, uncles who worked as waiters, and a father’s family that ran a coffee shop in Hell’s Kitchen (The Wave, 2022).
Before launching Civetta in mid-2020, Mallios served as in-house counsel and managing partner for the hotels and restaurants of Kotsoni and Tzolis, the partnership responsible for legendary New York establishments including Periyali, Il Cantinori, and Bar Six (StarChefs). Periyali alone earned a two-fork Michelin Guide rating in 2014, with the Guide noting it had maintained both popularity and culinary standards for over two decades. That consistency — what the Greeks might call philotimo, or a devotion to doing right by others — is encoded in Calissa’s operations. Mallios is not building restaurants to flip them. He signed a long-term lease on the Water Mill property, a deliberate signal of permanence on a stretch of Montauk Highway that had cycled through Trata East and a succession of short-lived ventures before Calissa arrived (The East Hampton Star, 2017).
The ownership group is notably partially women-owned, with partners Kylie Monagan and Tanya Saxena, alongside Michael Van Kamp, bringing a nuanced energy to the operation that multiple reviewers have credited with shaping Calissa’s distinctively warm aesthetic (Hamptons.com, 2025). In the world of bespoke craftsmanship — whether stitching a Marcellino NY briefcase or building a restaurant team — the invisible hand of intentional collaboration is always the thing that elevates the final product.
Aegean Architecture Meets East End Sensibility
Walk through the entrance and you are met with rope-accented outdoor furniture, decorative evil-eye pillows shipped directly from Mykonos, and cozy bamboo ceilings suspended over baskets of lemons and lavender bouquets (Edible East End, 2017). The bar — half inside, half outdoors — runs the full length of the entryway into the dining room and the open kitchen, creating a flow that mirrors the spatial logic of a Greek island taverna where indoor and outdoor distinctions dissolve beneath the Mediterranean sun.
The restaurant can accommodate approximately 300 guests across its multiple spaces. Outdoors, the expansive Garden features a transparent tent with twinkling lights, while the covered Terrace overlooks a stage that has hosted everyone from Questlove to Ashanti. The open-air Meadow serves as a breathtaking canvas for weddings and large-scale events. Indoors, more intimate spaces include the Private Dining Room, the Lounge, the Bar, and the Main Dining Room — each designed with Mediterranean blue tones, light wood, and candlelight that creates what one reviewer described as a sensation of dining on a Greek island rather than sitting beside Montauk Highway.
But Calissa does not rest on a single season’s laurels. In an inspired move that speaks to the operational intelligence of a year-round establishment, the restaurant transforms into Calissa Chalet from November through March — an après-ski-inspired lounge concept featuring cheese fondue, chocolate fondue, mulled wine, spiked hot chocolate, and a Rakomelo Toddy that could warm even the most cynical February skeptic (Dan’s Papers, 2025). The Winter Feast menu, offered as a lavish family-style experience for groups of six or more, showcases branzino, prime rib, and roasted lamb. This seasonal reinvention is the kind of operational creativity that separates restaurants built for legacy from those built for a single summer.
The Mediterranean Table: A Philosophy of Abundance
Executive Chef Dominic Rice, who came to Calissa from the kitchens of Jean-Georges and Narcissa, has crafted a menu that functions as an ode to communal Aegean dining (Edible East End, 2017). The approach is rooted in simplicity of ingredients married to complexity of flavor — the same principle that governs great leather tanning or, for that matter, the perfect Heritage Diner breakfast: let quality sourcing do the work, and then get out of its way.
The mezze program alone justifies the drive. Santorini Fava with capers and onion, the spicy kafteri with roasted red peppers and feta, melitzana, and the Pikilia Platter — a grand tour of all six mezze items — arrive alongside warm pita that is, by multiple accounts, both plentiful and impeccable. The seafood carries the menu’s highest notes: salt-baked whole fish, lobster bucatini, a Canary Islands branzino of unusual size that serves two to three, grilled octopus, and daily preparations that reflect the catch and the season. Lamb chops, a New York strip with oregano fries and harissa ketchup, and classic Greek salads round out a menu designed for the long table and the shared plate.
The wine program, overseen by Monagan — who is both a partner and the restaurant’s in-house sommelier — has earned the Award of Excellence from Wine Spectator and carries what is reportedly the largest selection of rosé in the Hamptons. More significantly, Monagan has built a list that pushes boundaries while honoring tradition, incorporating obscure Greek island varietals alongside Burgundy, Bordeaux, and Provençal rosé. Cases of grapes nobody outside the Cyclades has heard of move through the cellar because the team has cultivated a clientele willing to explore (Wine & Spirits Magazine, 2022). Calissa’s cocktail program runs equally deep, with mixology-driven creations and the Espresso Martini “Affogato” earning particular praise during the Chalet season.
Where Music Meets Mykonos
Perhaps nothing distinguishes Calissa from the East End’s crowded restaurant landscape more than its commitment to live entertainment as an integrated element of the dining experience rather than an afterthought. The Calissa Sounds concert series, co-produced with BCL Entertainment, launched in the summer of 2021 with a performance by Wyclef Jean and has since hosted Questlove, Ashanti, Fat Joe, Rev Run x Ruckus, DJ Cassidy, Gorgon City, Bob Moses, Chromeo, Duke Dumont, and Armand Van Helden, among others (Social Life Magazine, 2021). Mallios invested nearly $100,000 in professional-grade lighting and sound equipment to build the infrastructure, and the results have been staggering — Questlove famously DJed for two hours when contracted for only one (Social Life Magazine, 2021).
Running parallel to Calissa Sounds, the Broadway Out East series — produced by Justin Smith, concertmaster of Dear Evan Hansen — has brought Tony nominees and Broadway headliners to the Water Mill stage, including Brandon Victor Dixon, Tituss Burgess, Clay Aiken, Jessica Vosk, Andrew Barth Feldman, and Teal Wicks (Dan’s Papers, 2021). The series is philanthropic at its core. Calissa Sounds has raised over $10,000 for local first-responder charities including the Southampton Volunteer Ambulance Corps, the Southampton STARR Aqua Center, and The Headstrong Foundation, which provides mental health care to veterans (Time Out New York, 2023). The tradition continues each summer with regular DJ sets on Friday and Saturday nights and the Gipsy Kings tribute act Cristo and Rafael, who have returned for seven consecutive seasons.
Most recently, Ja Rule hosted an event at Calissa celebrating the launch of his whiskey brand Amber & Opal, further cementing the restaurant’s status as the Hamptons’ crossroads of food, music, and cultural spectacle (Hamptons.com, 2025). The ownership group has also expanded its entrepreneurial reach beyond the restaurant itself, founding Charlie Fox Dispensary — a luxury cannabis boutique in Southampton — described by Hamptons.com as having the most elevated retail experience on the East End (Hamptons.com, 2026).
Weddings, Events, and the Art of Gathering
Calissa has established itself as one of Southampton’s premiere wedding and private event venues, offering private dining for groups ranging from ten to three hundred guests. The events team has catered functions at Hearst Castle, the James Beard House, and the Freedom Tower — a portfolio that speaks to a level of execution few Hamptons establishments can claim (OpenTable, 2026). The restaurant serves as the exclusive caterer for The Muses in Southampton and hosts both indoor celebrations and tented weddings on The Meadow at Calissa.
The Mom Club has partnered with Calissa for community-focused morning gatherings, and the restaurant regularly hosts branded pop-ups, including the Caravana shop from Tulum, farmer’s market collaborations with Cascun Farms, and themed food truck programming. Grey Goose has partnered with Calissa for US Open viewing parties, complete with the tournament’s signature Honey Deuce cocktail (Hamptons.com, 2021). From corporate retreats to engagement parties, farewell brunches to after-parties, the restaurant’s ability to scale and adapt its spaces reflects the operational philosophy of a team that understands hospitality as a living, evolving practice.
Civetta Hospitality’s restaurants have received recognition from President Barack Obama, The Ford Foundation, and the City of New York for their commitment to community, philanthropy, and sustainable business practices (Long Island Press, 2021). Mallios himself sits on the boards of the Hospitality Alliance, the New York City Hospitality Council, and the East Midtown Partnership BID, and has spoken at Columbia Law School, Hunter College, and the 92nd Street Y on labor issues facing the restaurant industry (Pullp).
The Year-Round Constellation
Operating year-round in the Hamptons remains a badge of honor that few restaurants earn, and Calissa wears it with quiet authority. Sunday brunch runs from noon to four, dinner service spans every night of the week, and the Friday and Saturday bar extends until two in the morning for those who came to dance as much as to dine. The restaurant participates in Long Island Restaurant Week, where its prix fixe menus showcase the same ingredient-driven approach at accessible price points.
From where I stand — as someone who has kept a diner alive on Route 25A for a quarter century, who understands the alchemy of cast-iron seasoning and the philosophy of showing up every morning regardless of the weather — Calissa represents something worth recognizing. It is what happens when Greek-American heritage, Manhattan restaurant sophistication, Hamptons ambition, and genuine community investment converge in a single address. The name comes from the brightest constellation in the summer sky. But the real light at 1020 Montauk Highway does not dim when the leaves fall. It burns all year.
Address: 1020 Montauk Highway, Water Mill, NY 11976 Phone: (631) 500-9292 Website: calissahamptons.com Reservations: OpenTable Delivery: DoorDash | Seamless Instagram: @calissahamptons Private Events: concierge@calissahamptons.com
Hours:
- Brunch: Sunday 12:00 PM – 4:00 PM
- Dinner: Monday–Wednesday & Sunday 5:00 PM – 10:00 PM | Thursday–Saturday 5:00 PM – 11:00 PM
- Bar: Friday & Saturday 5:00 PM – 2:00 AM
Dress Code: Resort Casual
Peter is a 25-year restaurateur at The Heritage Diner in Mount Sinai, NY, founder of Marcellino NY bespoke leather goods, and holds graduate degrees in Philosophy from Long Island University and The New School University in NYC.
