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  1. Home
  2. Wine Gifts
  3. Wine & Chocolate Gifts

Wine and Chocolate Gift Baskets & Boxes

Toast to a delicious match made in heaven—fine Harry & David™ wines paired with smooth, rich chocolates.

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  • Price: High to Low
Lucca & Sons Cellars Red Wine with Chocolate Truffles
Passport Eligible

Lucca & Sons Cellars Red Wine with Chocolate Truffles

★★★★
★
☆
27 Reviews

available to ship now

Chest of Chocolates with Wine
Passport Eligible

Chest of Chocolates with Wine

available to ship now

Chocolate Obsession Gift Basket with Wine
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Chocolate Obsession Gift Basket with Wine

available to ship now

Sweet Treats Wine Pairing Collection - Two Bottles
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Sweet Treats Wine Pairing Collection - Two Bottles

★★★★★68 Reviews

available to ship now

Belgian Chocolate Bento Box with Reserve Pinot Noir
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Belgian Chocolate Bento Box with Reserve Pinot Noir

★★★★★5 Reviews

available to ship now

Chocolate Truffles with Harry & David® Wine
Passport Eligible

Chocolate Truffles with Harry & David® Wine

available to ship now

Artisanal Belgian Chocolate with Reserve Cabernet Sauvignon
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Artisanal Belgian Chocolate with Reserve Cabernet Sauvignon

available to ship now

Truffles, Red Wine, and Personalized Wine Box with Tools
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Truffles, Red Wine, and Personalized Wine Box with Tools

available to ship now

Reserve Pinot Noir and Artisan Belgian Chocolate
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Reserve Pinot Noir and Artisan Belgian Chocolate

★★★★★8 Reviews

available to ship now

Thank You Red Wine Gift Box
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Thank You Red Wine Gift Box

★★★★★90 Reviews

available to ship now

Deluxe Thank You Gift with Wine
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Deluxe Thank You Gift with Wine

★★★★★73 Reviews

available to ship now

Birthday Red Wine Box
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Birthday Red Wine Box

★★★★★149 Reviews

available to ship now

Savor and Celebrate Gift Box with Copper Tray
Passport Eligible

Savor and Celebrate Gift Box with Copper Tray

available to ship now

Scharffen Berger® Chocolatier's Collection - 20 Piece with Freehaven Cellars™ Red Wine Blend
Passport Eligible

Scharffen Berger® Chocolatier’s Collection - 20 Piece with Freehaven Cellars™ Red Wine Blend

available to ship now

Springtime Wine Gift
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Springtime Wine Gift

available to ship now

Deluxe Chest of Chocolates with Wine
Passport Eligible

Deluxe Chest of Chocolates with Wine

available to ship now

Sympathy Red Wine Gift Box
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Sympathy Red Wine Gift Box

★★★★★36 Reviews

available to ship now

Belgian Chocolate Bento Box with Reserve Cabernet Sauvignon
Passport Eligible

Belgian Chocolate Bento Box with Reserve Cabernet Sauvignon

available to ship now

Elegant Birthday Wine Gift
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Elegant Birthday Wine Gift

★★★★★71 Reviews

available to ship now

Congratulations Gift with Wine
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Congratulations Gift with Wine

★★★★☆8 Reviews

available to ship now

Gourmet Drizzled Strawberries™, Chocolate Truffles, and Wine
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Gourmet Drizzled Strawberries™, Chocolate Truffles, and Wine

available to ship now

WYNY Wine Co. Gift Basket
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WYNY Wine Co. Gift Basket

available to ship may 12 2025

Sparkling Wine with Glasses and Truffles Gift Set
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Sparkling Wine with Glasses and Truffles Gift Set

available to ship now

Mother's Day Cherished Blooms Bouquet, Chocolate Truffles, and Wine
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Mother’s Day Cherished Blooms Bouquet, Chocolate Truffles, and Wine

available to ship now

Lucca & Sons Cellars™ Wine and Sweets Basket
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Lucca & Sons Cellars™ Wine and Sweets Basket

available to ship may 12 2025

Ultimate Sparkling Wine Gift Basket
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Ultimate Sparkling Wine Gift Basket

available to ship now

Assorted Roses & Peruvian Lilies, Chocolate Truffles, and Wine
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Assorted Roses & Peruvian Lilies, Chocolate Truffles, and Wine

available to ship now

Freehaven Cellars™ Wine Gift Basket
Passport Eligible

Freehaven Cellars™ Wine Gift Basket

available to ship now

Vintner's Choice Birthday Red Wine Box
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Vintner’s Choice Birthday Red Wine Box

★★★★★2 Reviews

available to ship now

Cheryl's® Cookies and Cupcakes, Gourmet Drizzled Strawberries™, and Wine
Passport Eligible

Cheryl’s® Cookies and Cupcakes, Gourmet Drizzled Strawberries™, and Wine

available to ship now

Reserve Pinot Noir with Glasses and Truffles Gift Set
Passport Eligible

Reserve Pinot Noir with Glasses and Truffles Gift Set

available to ship now

Cheryl's® Cookies, Chocolate Truffles, and Wine
Passport Eligible

Cheryl’s® Cookies, Chocolate Truffles, and Wine

available to ship now

Scharffen Berger® Chocolatier's Collection - 36 Piece with Freehaven Cellars™ Red Wine Blend
Passport Eligible

Scharffen Berger® Chocolatier’s Collection - 36 Piece with Freehaven Cellars™ Red Wine Blend

available to ship now

Scharffen Berger® Valentine Chocolatier's Collection - 20 Piece with Reserve Cabernet Sauvignon
Passport Eligible

Scharffen Berger® Valentine Chocolatier’s Collection - 20 Piece with Reserve Cabernet Sauvignon

available to ship now

Vintner's Choice Wine Barrel Gift
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Vintner’s Choice Wine Barrel Gift

★★★★
★
☆
3 Reviews

available to ship now

Vintner's Choice Deluxe Thank You Gift with Wine
Passport Eligible

Vintner’s Choice Deluxe Thank You Gift with Wine

★★★★★2 Reviews

available to ship now

Two Dozen Red Roses, Chocolate Truffles, and Wine
Passport Eligible

Two Dozen Red Roses, Chocolate Truffles, and Wine

available to ship march 31 2025

Harry & David™ Wine and Chocolate Subscription Box
Passport Eligible

Harry & David™ Wine and Chocolate Subscription Box

available to ship now

Cheryl's® Cookies, Gourmet Drizzled Strawberries™, and Wine
Passport Eligible

Cheryl’s® Cookies, Gourmet Drizzled Strawberries™, and Wine

available to ship now

Scharffen Berger® Chocolatier's Collection - 72 Piece with Freehaven Cellars™ Red Wine Blend
Passport Eligible

Scharffen Berger® Chocolatier’s Collection - 72 Piece with Freehaven Cellars™ Red Wine Blend

available to ship now

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Wine & Chocolate Gift Basket Delivery

Wine and chocolate are a classic combination, and Harry & David pairs them perfectly in an assortment of wine and chocolate gift baskets and other unique gifts. Wine and chocolate gifts include premium Harry & David red and white varietals in combinations with our signature chocolate truffles, chocolate covered cherries, unique chocolate confections, and decadent desserts, crafted in our own Southern Oregon candy kitchens. Harry & David wines are made with only Oregon-grown grapes and are crafted in Southern Oregon, tended carefully by watchful winemakers every step of the way. With many varietals to choose from, including robust reds, delicate whites, and fragrant dessert wines, creating exceptional wine and chocolate gifts is easy.

Wine and chocolate gifts are perfect for any occasion. Whether sending a unique gift to celebrate a holiday, a milestone, or just to show you care, a wine and chocolate gift basket is an ideal choice. Host your own chocolate and wine party pairing different wines and chocolates. You can’t go wrong, and any combination will be a winner with your guests.

You’ll also fine chocolate and wine gifts for special occasions, such as birthdays, Christmas, and Valentine’s Day. There’s no better way to recognize an important occasion than with a chocolate and wine gift basket or gift box that pairs two of the most delicious and appreciated gifts in one.

Wine and Chocolate Boxes

Our exquisite wine and chocolate boxes and gift baskets feature pairings with our signature chocolate truffles and other delicious goodies in a variety of one-of-a-kind containers. Whether you’re planning to host a get-together, surprising a friend, or treating yourself to a luxurious indulgence, a wine and chocolate gift delivery is sure to delight. Say happy birthday, thank you, congratulations, thinking of you, or celebrate any occasion with one of our Harry & David™ Oregon wine and chocolate gifts. Don’t forget to look at our wine gift baskets collection.