Unique Wine Tasting Experiences in the U.S. and Canada

By | Food, Travel, Wine, Finance and Lifestyle Journalist
Last Updated: June 2, 2023
Unique Wine Tasting Experiences in the US and Canada

Unique Wine Tasting Experiences in the United States and Canada

When hospitality and wine meet, magic can happen.

When making a pilgrimage to visit a winery, it isn’t always just about the wine.

The winemaking process, the educational component and the actual wine tasting is paramount, but it’s the uniqueness of the experience that makes a true memory, one that is often created by showcasing the vineyard’s individual definition of hospitality. 

North America is home to many wine regions—everywhere from California to Oregon to Eastern Long Island to Ontario Wine Country and beyond—and each has their own identity. Many boutique, family-owned and operated wineries are learning to highlight what makes them special and thinking beyond a pedestrian wine tasting experience for their guests.

It rings true, especially for private, small group experiences where wineries can use their own creativity and personal touch. When hospitality and wine meet, magic can happen. For those seeking unique, memorable, private tasting experiences, see below a list of distinctive experiences found throughout North America.

Long Island

Macari Winery

150 Bergen Ave, Mattituck, NY 11952

(631) 298-0100

unique places to taste wine in the united states
Image courtesy Macari Winery.

Nestled in the North Fork of Long Island is the Bergen Road Bungalow experience at Macari Vineyard. This luxe hospitality experience takes place in the vineyard’s collection of private heated luxury tents for a party of six people or fewer. The tents were created in conjunction with local North Fork artisans including TENTRR, White Duck Outdoors, Terra Glamping, Jesse Elliott Design and White Flower Farmhouse.

RELATED: The Best Wineries to Visit This Year in Long Island

The goal was to design and stage tents that include special touches like vintage furnishings and a vinyl record player that also hooks up to a Bluetooth speaker, should guests wish to DJ their own gathering. The tent experience can be reserved for an entire afternoon that includes a wine tasting and lunch from local Chef Lauren Lombardi. The winery is also poised to roll out additional experiences within the tented spaces, including guest chef dinners and other culinary partnerships.


Bricoleur Vineyards

7394 Starr Rd, Windsor, CA 95492

(707) 857-5700

unique wine tasting experience in California - Inglebook Winery
Pergola Private Lounge at Inglenook Winery. Image courtesy Inglenook.

Nature lovers will be compelled to visit Bricoleur Vineyards located in Sonoma’s Russian River Valley – just south of Healdsburg, California. This 40-acre picturesque gathering- place with 21 acres of Pinot Noir and Chardonnay vineyards – is arguably best known for its popular Sip & Savor tasting – which includes six wines expertly paired with small, hearty dishes crafted by the estate chefs. But for those who crave a nature-focused experience, private groups are invited to fish for bass and bluegill in the larger of Bricoleur’s two ponds. All they need to do is reserve a tasting for their party and pack their own gear to enjoy an afternoon of fishing and wine tasting.


1991 St Helena Hwy, Rutherford, CA 94573

(707) 968-1161

Napa Valley-based Inglenook vineyard, which holds the title for being Napa’s first estate winery founded in 1879, has recently launched the new Pergola Private Lounge offered seasonally May through October.

The organic winery, owned by acclaimed film director Francis Ford Coppola, has created this exclusive experience for private groups of eight or fewer. The lounge setting with vineyard views is accompanied with a complete culinary experience created by estate chef Alex Lovick. The menu is paired with a cheese and charcuterie platter and a selection of Inglenook’s Sauvignon Blanc, Blancaneaux, Edizione Pennino Zinfandel, Estate Cabernet Sauvignon, and Rubicon. Guests are also offered traditional board games and magazines to pass the time in a leisurely fashion while taking in the breathtaking views.

Breathless Wines

499 Moore Ln, Healdsburg, CA 95448

(707) 395-7300

The female-led team comprised of three sisters Sharon Cohn, Rebecca Faust, and Cynthia Faust are at the helm of Breathless Winery in Healdsburg, CA. The winery’s mantra is about celebration, which is why they believe in the breathless moments of life.

While they have a variety of tasting and small group event options, the most unique offering is the sabrage experience for groups up to 10 people. Guests are brought together to learn the fine, historic art of sabering that has a connection to Napoleon and the French Revolution.

As the story goes, during Napoleon’s victorious battles, soldiers would ride on horseback through villages and towns with bottles of champagne to mark their victory. Without the ability to use their hands, they would strike the bottle with their sabers to pop the cork. Groups can learn the history of the experience along with the “how-to” led by a private instructor. After the instruction, they are left to enjoy the bottle along with optional charcuterie and cheese plate options and additional pairings.

Hoopes Vineyard

6204 Washington St, Napa, CA 94558

(707) 944-1869

This newly-opened winery in Napa Valley boasts not only a suite of award-winning wines, but also a picturesque setting for animal lovers especially. Guests will be wowed by the organic gardens and sleek airstreams that line the property that are also available to have tastings in. It also boasts an animal sanctuary home to pigs, chickens, goats, a donkey and two dogs. The entire wine tasting experience, coined Oasis by Hoopes, is retreat-like in nature, offering private, small groups choose-your-own adventure tastings in private patio setups next to their airstreams. For the ultimate luxury experience, guests can also rent the farmhouse for a private stay and a highly curated experience.


unique places to taste wine in Canada
Image courtesy Stratus Vineyards.

Stratus Vineyard

2059 Niagara Stone Rd, Niagara-on-the-Lake, ON L0S 1J0, Canada

+1 905-468-1806

Teknion Corporation designer/owner David Feldberg launched Stratus Vineyard on Niagra-on-the-Lake in Ontario, Canada in an attempt to create the most sustainable and environmentally-friendly winery as possible. The winery, which is the first LEED-certified winery in the world, offers a private tasting hosted in the Teknion room.

RECOMMENDED: Book a Full-Day Niagara-on-the-Lake Scooter or E-Bike Wine & Cider Tour

The wine tasting is paired with a supreme culinary offering, all hosted in the private space that is decked out with all Teknion furniture and furnishings. The company began as a response to the emergence of technology in the workplace and fans of Teknion and their products will no doubt enjoy geeking out over this unique experience.

Cave Springs

4043 Cave Spring Rd, Beamsville, ON L0R 1B1, Canada

+1 905-563-9393

For those who prefer private wine experiences to take place in the comfort of their own home, Cave Springs located in Niagra-on-the-Lake in Ontario, Canada has a variety of options that marry elevated cuisine with wine tasting experience. These virtual experiences celebrate both the art of cooking and the art of wine pairings. Each individual virtual class provides two guests the tickets to the event, the ingredients to cook along with the instructor and two bottles of wine meant to pair with the dinner.

Most recently, the winery hosted a lobster cooking demonstration led by a local chef who walked guests through the step-by-step process of properly cooking a lobster, along with industry trade tips. The meal was paired by Cave Spring’s traditional Method Blanc de Blanc Sparkling and a Chardonnay. Next up is a Celebration of Spring menu hosted by winemaker Gabe Demarco and chefs Jody and Kirstie of The Culinary Studio. The chefs will walk through the preparation and pairing of the spice roasted fish taco and a pork loin chop.

Frequently Asked Questions about Unique Wine Tasting Experiences in the United States and Canada

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