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The Regatta Inn

From $235/night • Score: 4.9★ (310 reviews)

Exterior 1Exterior 2Interior 1Interior 2Surroundings

First Impressions & Architecture

Approaching The Regatta Inn on Centre Street is akin to stepping backward into a more refined, deliberate century, yet with all the crisp, effortless polish that modern luxury demands. Situated on a quiet, residential stretch of upper Centre Street, this restored Federal-style mansion commands its historic plot with understated grace. Unlike the bustling, sometimes frenetic energy found closer to Straight Wharf during the peak summer months, this pocket of Nantucket offers a sanctuary of tranquility. As a hospitality critic who has reviewed properties across the globe, I am often wary of historic restorations that either lean too heavily into dusty museum-piece antiquity or strip away soul in favor of sterile minimalism. The Regatta Inn, however, achieves that elusive design alchemy: a seamless, respectful dialogue between 19th-century maritime heritage and contemporary coastal-chic sophistication.

The exterior immediately establishes the tone. Classic shingle-style architecture, crisp white trim, and a welcoming front facade invite you past manicured hydrangeas and up historic steps. Crossing the threshold, the foyer acts as a sensory palate cleanser from the outside world. Original wide-plank pumpkin pine floors, lovingly restored and gleaming with a soft satin patina, anchor the space. The design narrative here is anchored in a maritime palette—navy accents, crisp whites, brushed brass, and natural textures like jute and rattan. There is no pretension in the air; instead, you are greeted by an atmosphere of residential intimacy. It feels less like checking into a commercial hotel and more like being welcomed as an esteemed houseguest into the private estate of a well-traveled sea captain with an immaculate eye for interior design. Every architectural detail, from the restored crown moldings to the period-appropriate sash windows, speaks to a profound respect for Nantucket’s storied past, thoughtfully curated for the discerning traveler of today.

The Room Experience

Accommodations at The Regatta Inn elevate the boutique hotel experience through a steadfast commitment to both aesthetic harmony and uncompromising comfort. Stepping into the guest quarters, one is immediately struck by the generous proportions—a rare luxury in historic island properties where rooms can often feel compressed. The design philosophy here continues the coastal-chic motif established in the lobby, but with a softer, residential warmth that encourages immediate relaxation.

At the center of the room sits an exceptionally plush pillow-top mattress, dressed in high-thread-count crisp white linens and accented with textured throw pillows that evoke the colors of the Nantucket dunes and surrounding Atlantic waters. Flanking the sleeping quarters are bespoke bedside tables outfitted with modern charging ports and reading lamps that offer a warm, flattering glow. During the cooler shoulder-season evenings, the gas fireplace serves as the room's focal point, casting a flickering, ambient warmth that transforms the space into a cozy retreat after a brisk walk along Steps Beach. It is the kind of thoughtful amenity that turns a standard hotel stay into a deeply restorative experience.

The architectural integrity extends seamlessly into the en-suite marble bathroom, a sanctuary of polished stone, chrome fixtures, and spa-quality bath products. A spacious walk-in glass shower with high-pressure rainfall showerheads ensures an invigorating start to the morning, while plush, oversized bath sheets wrap you in luxury afterward. Thoughtful touches abound: abundant natural light, ample wardrobe space that avoids the dreaded cramped closet syndrome, silent and efficient climate control, and artisanal local touches that remind you precisely where you are in the world. Whether you are curling up with a book by the fireplace or preparing for a night out in town, the rooms at The Regatta Inn provide an impeccably appointed backdrop to your island getaway.

Signature Amenities & Atmosphere

True luxury in hospitality is rarely defined by ostentatious displays; rather, it is found in the rhythm of daily pampering and the creation of spaces that foster genuine relaxation. The Regatta Inn excels in this regard, offering a curated suite of amenities that elevate the guest experience without ever feeling intrusive.

Chief among these is the tranquil garden terrace—a hidden oasis tucked away from the gentle hum of the street. Surrounded by lush plantings, climbing ivy, and comfortable seating, this courtyard serves as the social and contemplative heart of the property during the sun-drenched afternoons. It is an ideal setting to page through a novel, enjoy a quiet moment with a book, or simply breathe in the salt-kissed air of the island.

Service throughout the property is characterized by an intuitive, warm professionalism. The staff possesses an encyclopedic knowledge of the island, ready to offer bespoke recommendations or secure difficult reservations with a gracious smile. The atmosphere cultivated here is one of effortless exclusivity. There are no crowded elevators, no chaotic lobby check-ins, and no rigid, impersonal corporate policies. Instead, the pacing of the day is dictated by your own desires. Afternoon baked cookies—often still warm from the oven and served with artisanal flair—become a delightful ritual, drawing guests back to the common areas for quiet conversation before the evening settles in. It is these small, consistent gestures of hospitality that cement The Regatta Inn’s reputation as a premier boutique sanctuary on the island.

Food, Drink & Local Nightlife

While boutique hotels in historic districts often forgo extensive culinary operations, The Regatta Inn approaches the morning routine with the devotion of a destination dining room. The experience begins each morning with a chef-curated breakfast that sets a vibrant, delicious tone for the day ahead. Eschewing the tired, institutional steam-table breakfast formats common in lesser establishments, the inn presents a rotating menu highlighting fresh, locally sourced ingredients and artisanal preparations. Expect dishes like lemon-ricotta pancakes infused with local berries, perfectly poached eggs over house-made hash, and freshly baked pastries alongside artisanal granolas, local yogurts, and expertly extracted espresso drinks. Served in the sunlit dining spaces or out on the garden terrace, it is a meal meant to be savored slowly, accompanied by the morning light filtering through the historic windows.

When the sun dips below the horizon, the inn’s location on upper Centre Street proves to be an ideal strategic advantage. You are far enough from the late-night revelry to guarantee an undisturbed, silent night of sleep, yet you are merely a short, charming stroll away from the vibrant heart of Nantucket’s culinary and nightlife scene. Within a ten-minute walk, you can find yourself seated for world-class seafood at Straight Wharf, sipping craft cocktails at a chic harbor-view lounge, or exploring the historic cobblestone alleys framed by whaling captains' homes. The staff’s curation of local dining options ensures you bypass tourist traps in favor of the island’s genuine culinary pulse, making your evening excursions as seamless as your mornings at the inn.

Who This Stay Is For

Practical Travel Notes

Planning a stay at The Regatta Inn requires a few logistical considerations to ensure your Nantucket holiday goes off without a hitch. At $235 per night, the property represents astonishing value given the current landscape of island luxury pricing, making early reservations an absolute necessity—particularly for the summer high season and the vibrant shoulder months of September and October.