15 USA Cheese Tours Worth Flying For

1.Los Angeles: Luxury Cruise with Wine, Cheese & Sea Lions

★★★★★★★★★★4.9 · 116 reviews · 2 hours · from $119Our pick

Spend two hours aboard a private or small-group electric Duffy boat in Marina del Rey. Your English-speaking captain, such as Tyler, Shaun, or Maxx, guides you past yachts, boathouses, sea lions, and water birds while you enjoy two glasses of red or white wine and a charcuterie board.

“The tour was great, especially our tour guide, Captain Shawn A. He was very knowledgeable and informative of the Marina,it's surroundings and sailing in general. He made us feel very comfortable. Overall good person!”

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2.Boston: North End Food Experience with Pizza, Meats & Cheese

★★★★★★★★★★4.9 · 111 reviews · from $75

Walk 1.3 miles through Boston’s North End with an English-speaking guide and a group of up to 12. Taste fresh bread, Italian meats and cheese, pizza, pastry, and cappuccino, with a historic church visit and local food tips along the way.

“I would definitely recommend this tour. The morning bakery was delicious. We could choose whatever type of coffee we wanted in the oldest coffeehouse in Boston. Our walk was very informative and the sandwich, pizza and cannoli were all excellent. It was a fun way to walk around Boston"s North End.”

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3.Wine, Bread, Cheese and Chocolate

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

Spend 2.5 hours tasting Washington wines, cheese, bread, jams, pasta, and chocolate around Pike Place Market. Guides Will and Maia are known for warm, flexible hosting and local food knowledge. The small group format makes this feel more like a friendly tasting walk than a standard sightseeing tour.

“Will was awesome. Funny and friendly. Knew great spots and tasting and pairings were divine. Would do this again.”

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4.Temecula Valley Afternoon Wine Tour with Tastings and Cheeseboard

★★★★★★★★★★5.0 · 65 reviews · 4 hours (approx.) · from $169

You’ll visit three Temecula wineries from 2:15 to 6:15 PM with Grapeline Wine Tours, tasting at each stop and enjoying cheeses, charcuterie, and nibbles at one winery. Guides such as Liz, Dave, Carlos, and Lonzo are known for keeping the group organized and upbeat. Round-trip Old Town transport means no one needs to drive.

“Dave our guide was fantastic!!! From the moment we got on the bus to the moment the tour ends. My bf and I had a great time with the other people that took part of the tour. I’d definitely recommend this tour.”

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

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

Take a 30 to 45 minute private flight from Lakefront Airport with an FAA-certified pilot, such as Lauren, Everett, Tanner, or Roy. Request sights, look over the French Quarter, Superdome, Mississippi River, and bayous, then enjoy champagne and chocolate or wine, cheese, and crackers.

“Our pilot was friendly and knowledgeable. It was an awesome way to see the city we grew up in. Thank you!”

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6.New York City: Champagne, Cheese, Caviar & Sightseeing Cruise

★★★★★★★★★★4.5 · 26 reviews · 1 hour 30 minutes (approx.) · from $134

Spend 90 minutes aboard a vintage-inspired Classic Harbor Line yacht, cruising from Pier 62 past One World Trade Center, the Statue of Liberty, Governors Island, and Lower Manhattan. You’ll enjoy three wine pairings, selected cheeses, and caviar, with indoor and outdoor viewing areas. Minimum age is 21.

“Great opportunity for photos, great experience all the way around. Would do this tour again in a heart beat”

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7.Sunset Wine & Cheese Emerald Bay Boat Charter

★★★★★★★★★★5.0 · 24 reviews · 2 hours (approx.)

Set out from Camp Richardson at 6:00 pm with your own group of up to four people. Your captain may visit Emerald Bay, Vikingsholm, Rubicon Bay, DL Bliss, or other points of interest. Expect white wine, gourmet cheese, fruit, crackers, safety gear, and a smooth private boat ride guided by captains such as Bryan, Jared, George, or Kevin.

“A beautiful experience! Bryan was professional, unbelievably kind and very knowledgeable. The views were amazing and the wine and cheese was delicious. A romantic and relaxing way to spend the evening on the lake. Would recommend to anyone looking to spend some quality time on the lake! Thanks for everything!”

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8.Fortune Reading with Cheese in Chicago

★★★★★★★★★★5.0 · 19 reviews · 1 hour (approx.) · from $65

At Beautiful Rind in Chicago, Jennifer Billock introduces you to the history of cheese in magic and tyromancy, then reads your fortune through up to four cheeses. You receive a tasting sheet and enjoy the cheese she purchases for the session. This private, English-language experience lasts about an hour and suits couples, friends, families, and solo visitors.

“We had such a good time! My friends and I all talked about how we need to tell everyone we know to do this when they come to Chicago now.”

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9.Seattle: Wine, Cheese and Chocolate Pairing Tour

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

Spend 150 minutes tasting Washington wines, cheeses, chocolates, and other local foods at several Seattle stops. Your English-speaking guide, possibly Maia or Will, shapes the route for your group of up to 10. Tastings change from day to day, so expect discovery rather than a fixed script.

“I LOVED our tour guide Maia! She was so informative and catered to the needs of our group. We couldn’t have asked for a better tour guide. We loved the food and all of the different stops along the tour. I went back to make more purchases the day after my tour. Thank you Maia for a fabulous time and tour!”

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10.Wine Tasting with Cheese, Charcuterie, and Dessert Experience

★★★★★★★★★★4.0 · 17 reviews · 1 hour (approx.) · from $74

At Blanchard Family Wines in Denver’s LoDo, you’ll taste four wines with cheese, a personal charcuterie board, and a choice of artisan sweets. Staff members such as Joe explain the selections, while the family-owned setting adds a personal touch. Plan on about an hour, with food and dessert choices subject to availability.

“Spent a great afternoon at Blanchard Wines in LoDo. Fabulous wines, charcuterie and recommendations - Joe suggested some great wines to try - he was friendly and knowledgeable. We went back for more drinks a few days later!”

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11.Epoxy Resin Cheese Board Art Class

★★★★★★★★★★5.0 · 15 reviews · 1 hour 30 minutes (approx.) · from $145

At Yulia Maui Art in Paia, you’ll learn to measure, color, mix, and pour resin while making an ocean-style cheese board and a mini practice board. Gloves, aprons, safety gear, drinks, and instruction are included. Your pieces need 24 hours to cure, so plan to collect them the next day.

“A great experience! So fun to learn how to create such beautiful art pieces. The instructor was very nice and helped us learn and assist with every step of the way!”

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12.Los Angeles #1: Luxury Boat Cruise-Wine, Cheese & Sea Lions

★★★★★★★★★★5.0 · 14 reviews · 2 hours · from $149

Spend two hours aboard a silent electric Duffy boat in Marina del Rey. Captain Shaun guides you past yachts, waterfront homes, and coastal wildlife while you enjoy a bottle of red or white wine, small charcuterie, snacks, beverages, and music. Private cruises are available, with dinner, sushi, flowers, cakes, and photography offered as paid extras.

“Shaun was an amazing captain with a wealth of knowledge and with his charismatic personality snd kind soul made it even more special. The weather was perfect which was an added bonus. I would highly recommend this cruise and would definitely do it again!”

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13.Romantic Boat Cruise with Wine & Cheese or Surprise Dinner

★★★★★★★★★★5.0 · 14 reviews · 1 hour - 90 minutes · from $129

Set out from Marina del Rey on a quiet electric Duffy boat with Captain Shaun or another experienced captain. You will pass yachts, waterfront homes, and coastal wildlife while enjoying two glasses of wine, blankets, music, and seasonal snacks. Add sushi, charcuterie, or a surprise dinner for a more polished date night.

“Shaun was the life of the party! He did great surprising my wife for her 30th birthday. She was not expecting anything and he helped me make her private boat experience exciting and worth while. FYI amazing photography skills! Would 100% book a million times again.”

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14.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 three-ounce pours: Conesus White and Runway Red with cheese, then Pebble Beach Blush and Max Black with chocolate. Staff such as Candi, Sam, Hailey, and Grace are known for warm service. The small setting feels personal, and lunch is available separately at the Tankroom Café.

“The wine +cheese/chocolate flight was amazing and for a great value. Our server Candi was incredible and refilled our waters while we sat around waiting to sober up. I highly recommend this place, thank you Candi for a fantastic experience!!!”

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15.Olive Oil, Cheese, and Wine Tasting with Local Expert

★★★★★★★★★★5.0 · 12 reviews · 2 hours (approx.)

Join Elisabeth at Il Fiorello Olive Oil Company in Fairfield for a two-hour walk and tasting. You’ll explore the olive grove, learn how to judge extra virgin olive oil, pair family-made oils with snacks, then taste Northern California wines and two local cheeses. Groups are limited to six for a personal visit.

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