Wine and Chocolate Tours in the USA: Our 13 Favourites

1.Wine, Bread, Cheese and Chocolate

★★★★★★★★★★5.0 · 81 reviews · 2 hours 30 minutes (approx.) · from $119Our pick

Spend about 2.5 hours with a small group of up to 10, tasting Washington wine, artisan cheese, bread, jams, pasta, and chocolate around Pike Place Market. Guides Will and Maia are especially praised for their humor, local knowledge, and personal touch. Meet at SELEUŠS Chocolates and finish there.

“I love the small group setting. Our host was very knowledgeable of the town. We love the variety of all the different chocolates and wines and cheeses that we tasted. It was a very fabulous experience while in town of Seattle. And we did get a special dessert at the end that was amazing thank you to the hosts you were amazing.”

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2.New Orleans VIP Sightseeing Flight with Champagne & Chocolates or Wine & Cheese

★★★★★★★★★★5.0 · 50 reviews · 30 to 45 minutes (approx.) · from $197

Take a private 30 to 45-minute flight from Lakefront Airport with up to two companions. Your FAA-certified pilot points out the French Quarter, Superdome, Mississippi River, and bayous while you enjoy champagne and chocolates or wine, cheese, and crackers. The small plane offers an intimate view, though summer flights can be warm.

“Enjoyed our flight around the city with Tanner. He was very informational. Highly recommend this trip.”

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3.Nashville: Whiskey or Wine and Chocolate Pairing Experience

★★★★★★★★★★4.8 · 22 reviews · 45 min · from $40

At Nashville Barrel Co., choose a spirits flight with bourbon, rye, and agave, or four wines, two red and two white. Your English-speaking guide, including Justin on some sessions, explains production and pairing while you taste chocolates alongside each pour. Plan on 45 relaxed minutes, and bring ID.

“Justin was super knowledgeable about both the whiskey and wine. His passion about what he does really showed. He was a lot of fun.”

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4.Chocolate and Wine Pairing in Chantilly

★★★★★★★★★★5.0 · 21 reviews · 1 hour (approx.) · from $65

At River-Sea Chocolates in Chantilly, you’ll taste five small-batch chocolate bars with three wines from local vineyards. A guide such as Eli explains bean-to-bar methods, then shows you the factory machines that turn roasted cacao into chocolate. The one-hour visit is capped at 10 people.

“We were hosted by Eli. He gave us wonderful chocolates with wines that complimented each special morsel. These chocolates are amazing. This business is about making chocolate in a sustainable and pure way. All my future chocolate purchases will be from here. My palate now knows the difference and there’s no going back to commercially made chocolate. ❤️”

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5.Santa Barbara’s Ultimate Wine and Chocolate Walking Tour

★★★★★★★★★★5.0 · 19 reviews · 3 hours 30 minutes (approx.) · from $149

Meet Melissa or another Totally Cali Tours guide at 209 State Street for a small-group walk through downtown Santa Barbara, La Arcada, the County Courthouse, and the Funk Zone. You will taste wines from two boutique tasting rooms and sample chocolate, while learning about local architecture, theater, food, and wine culture. The tour ends downtown.

“Melissa was an excellent tour guide and made sure we had a wonderful time. She went out of her way to make sure we knew the history of Santa Barbara, different types of wines, the chocolate and even the ice cream! She was awesome!”

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6.Wine, Cheese and Chocolate Pairing Tour

★★★★★★★★★★4.4 · 17 reviews · 2h 30m · from $119

Spend 150 minutes tasting Pacific Northwest wines, cheeses, chocolates, and other foods at several Seattle stops, with time at Pike Place Market. The small group is capped at 10, and guides such as Maia and Will bring different strengths in wine, food, and local stories. Tastings change from day to day, so expect discovery rather than a fixed flight.

“The wine was so good! The stops along the way were sooo good! Delicious wine, cheese and chocolate. Highly recommend 😊. Our good, Maia was phenomenal”

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7.Taste of the Wild: Chocolate and Wine Pairings in the Alaskan

★★★★★★★★★★4.5 · 15 reviews · 3 hours (approx.) · from $109

Meet in downtown Anchorage at 5 pm for a three-hour tasting with Alaskan Sights and Bites. Ride in an air-conditioned van to 61 Degree North Winery, sample local chocolates, then pair them with five wines using tasting cards. Chris may lead the experience, and the group is limited to nine people.

“I loved all the stories about Alaska heroes while we sipped wine and nibbled chocolate. It was chill and fun”

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8.Whiskey or Wine Pairing with Chocolate Experience

★★★★★★★★★★5.0 · 13 reviews · 40 minutes (approx.) · from $40

At Nashville Barrel Co, you’ll spend about 40 minutes tasting either four whiskeys or four wines with Ghirardelli chocolates. A guide leads the pairing, explains the spirits, and takes questions as you sip. David has guided this tasting, and some sessions may offer both wine and whiskey, so ask when booking.

“This was a great experience for us. Our guide, David, was knowledgeable and made the tasting one we won’t forget. Being able to do both wine and whiskey in the same tasting allowed for us to both enjoy the entire experience.”

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9.Shared Wine, Chocolate and Cheese Tasting in Conesus Lake

★★★★★★★★★★5.0 · 13 reviews · 45 minutes (approx.) · from $20Best value

At Deer Run Winery near Conesus Lake, you’ll sit down for four 3-ounce wine pours paired with cheese and chocolate. Try Conesus White, Runway Red, Pebble Beach Blush, and Max Black while staff such as Candi, Hailey, Sam, or Grace explain the wines. The 45-minute tasting ends at the winery, with lunch available separately.

“Fun experience. Servers were was fantastic. Enjoyed our time. Wine was fantastic. Bought your product and will do it again.”

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10.Anchorage: Chocolate and Wine Tasting Tour

★★★★★★★★★★5.0 · 6 reviews · 3 hours · from $110

Meet your English-speaking guide at the Egan Center, then ride in a small van to Chugach Chocolates and 61 Degree North Winery. Taste up to six chocolates, five locally crafted wines, and pair them using tasting cards. Guide Chris may lead the tour, sharing Alaska stories and practical food insight along the way.

“We had a great tour! We are local but wanted something unique. We sampled a lot of great chocolate and were each able to customize our wine tasting to our specific tastes. Chris was a great guide - very knowledgeable about Alaska and fun to have at the helm.”

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11.Santa Barbara: Wine, Chocolate and History Walking Tour

★★★★★★★★★★5.0 · 4 reviews · 3h 30m · from $135

Spend 210 minutes walking downtown Santa Barbara with an English-speaking guide such as Melissa or Time. Visit two boutique tasting rooms for two wines, sample two local chocolates, and see the County Courthouse, La Arcada, and State Street. Expect a small group of up to eight, plus possible olive oil or vinegar extras.

“Our tour was amazing! Our guide Time was knowledgeable, interesting, and fun! We loved the places we visited - a wonderful introduction to Santa Barbara! Top rate all the way!”

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12.Grapevine’s Wine & Chocolate Happy Hour

★★★★★★★★★★5.0 · 4 reviews · 2 hours (approx.) · from $128

Spend two relaxed hours along Grapevine’s Main Street with guides such as Andy and Jennifer, tasting sparkling and Texas wines with chocolate, bruschetta, and small bites. You’ll learn saberage, opening a bottle with a sword, then finish at Wine Fusion Winery. The $128 price includes wine and food, with a $10 gratuity suggested separately.

“It was so much fun! I don’t even drink, and it was a great time! The host was wonderful, and she brought us to some great places where the people were so warm and welcoming. We also learned a little about wine that we didn’t know.”

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13.Kansas City’s Sweet Escape Private Tour: Chocolate & Wine Tour

★★★★★★★★★★5.0 · 4 reviews · 3 hours (approx.) · from $855

Spend about three hours with your private group exploring Kansas City, the Power and Light District, and Crossroads through chocolate shops, wine, art, and dining. Pickup is offered from Kansas City, and the tour runs in English. It suits couples and small groups who want a polished food outing without sharing a vehicle or guide.

“Wonderful chocolate shops and wine bar, professional and knowledgeable operator. Highly recommended tour for any romantic couple!”

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