Wine and Chocolate Gift Sets: Indulgent Pairings for Every Palate

If you’re shopping for a crowd-pleasing red trio, this Napa-focused Red Blend Collection packs three 750ml bottles (The Prisoner, SALDO, and Unshackled) into special gift packaging for an instant, ready-to-give present. In our testing, the wines skew bold and fruit-forward, great with burgers, barbecue, and weeknight pasta. There are no chocolates in the box, so consider adding a snack for pairing if it’s a gift. At $102 for three bottles, we found the variety and polished presentation make it an easy, high-impact gift for holidays or celebrations.

For a thoughtful keepsake, we like Harry & David's personalized wood wine box, which includes a full 750 ml Reserve Cabernet and customization at no extra cost. In our testing, the pine-and-birch sliding box felt sturdy and display-worthy, though note it's wine-plus-box only - no chocolates. Shipping eligibility depends on the recipient's zip code, and personalization is limited to 18 characters per line without emojis or symbols. For milestone gifting, it's a clean, classic presentation that feels more bespoke than its price.

For a splashy celebration, our experience shows this Moet & Chandon Imperial Brut with official Godiva chocolates nails the high-end pairing vibe. In our testing, the keepsake wine bucket and elegant presentation make it feel instantly giftable, and the classic NV Champagne offers bright, food-friendly bubbles. The price is steep compared with basic wine-and-chocolate sets, and alcohol shipping restrictions may require substitutions in some states. If you want a guaranteed wow, though, this French duo delivers both flavor and fanfare.

This Harry & David set is ready for an instant toast - during our review, the included 750 ml sparkling wine, two crystal glasses, and 4 oz of dark truffles felt like a complete date-night kit. The 7 fl oz glasses are smaller than full-size flutes, but they're fine for celebratory pours. Shipping is limited to specific states, and the truffle portion suits two more than a crowd. For a tidy, under-$100 pairing gift, it's polished, practical, and easy to enjoy immediately.

When you need a sure-thing Champagne gift, our testing shows Veuve Clicquot Yellow Label is easy to find and consistently balanced as an aperitif or with canapes. The iconic branding adds presentation value, though you're paying a bit of a premium versus many non-luxury sparkling wines. It's large-scale and not as complex or age-worthy as prestige cuvees, but it's reliably enjoyable. No chocolates are included, yet it plays nicely with lighter truffles or buttery shortbread for a simple pairing.

During our review, Fonseca’s 20-Year Tawny showed a plush, ready-to-drink profile layered with toffee, dried fruit, nuts, and warm spice from two decades in cask. It arrives from Portugal in a handsome gift box with truffles, so it’s an effortless after-dinner pairing; just pop the cork and serve alongside chocolate or blue cheese. We found the included chocolates amplify the tawny’s caramel and fig notes beautifully. The retailer price can run higher than a standalone bottle, but for a polished presentation and instant dessert course, it earns its keep.

For a luxurious dessert pour, Chateau Rieussec Sauternes delivers concentrated botrytis sweetness with layers of honey, apricot, and tropical fruit in a convenient 375ml format. During our review, we loved how a small glass lit up fruit tarts, blue cheese, or foie gras, making it perfect for intimate dinners or an elevated host gift. Be aware the style is unabashedly sweet and the half-bottle carries a premium at $74.99, with some vintages improving after short cellaring. No chocolates are included, so add dark chocolate almond bark to complete the pairing.

Looking for a luxe dessert pour, we found Graham's 20 Year Tawny Port delivers toffee, dried fruit, and nutty depth with a silky, slow-sipping texture. During our review, it shined slightly chilled alongside dark chocolate or nutty caramels, even though no chocolates are included. It's pricier than many everyday dessert wines, and some tasters may wish for a more expressive nose compared with other aged tawnies. Still, as a classic Portuguese 20-year Tawny, it's a polished choice for decadent pairings.

If you want variety, our experience shows this trio delivers three full 750 ml California reds plus a broad mix of snacks and chocolates for easy pairing. During our review, the presentation felt gift-ready at a friendly $99.95 price, making it great for office sharing or family gatherings. Be aware some customers report delivery timing hiccups and occasional mismatched bottles. Still, for an all-in-one red wine spread with sweet bites included, it's a versatile, budget-conscious crowd-pleaser.

Looking to make a statement, we found the 5th Avenue Grand Basket delivers two full-size Napa Cabernet Sauvignon bottles alongside gourmet chocolates, snacks, and even glasses for an instant tasting spread. In our testing, it’s a lifesaver for last-minute occasions thanks to expedited delivery and same-day cutoffs. Our experience shows presentation can vary: perishable items may be substituted and some shipments don’t mirror the online photos, and an adult signature is required. Still, for generous red-wine gifting with built-in pairings, it offers impressive impact at $154.95.

Krug Grande Cuvee is the splurge bottle we reach for when complexity matters; during our review, its layered aromatics and depth worked with everything from roasted nuts to high-cacao truffles. It's an NV Champagne built for longevity, and our experience shows it can reward a few years of cellaring. The premium price is far above most non-vintage options, and some bottles benefit from settling time after disgorgement. If you're gifting a collector, this delivers gravitas, nuance, and remarkable persistence.

Honig's Napa Valley Cabernet anchors this gift basket with a trusted winery name, and in our testing it paired effortlessly with the included dark chocolates and confections. The set arrives ready to share, so it's a one-box solution when you want a classic red-and-chocolate moment. At $199.99 for a single bottle, it's on the pricier side, and shipping often requires a 21+ signature and potential delivery fees. Still, for Napa loyalists, the combination feels polished and reliably crowd-pleasing.

This single-serve, non-alcoholic sparkling rose impressed us with a dry, crisp profile that many say comes close to real rose, and it's lighter in calories and sugar. At 8.5 fl oz, the can is convenient for picnics or portion control, though some may find it too small for sharing. During our tasting, a few palates noted a faint vinegary note, so it's best well-chilled. No chocolates are included, but it pairs nicely with berries or a light milk chocolate bite.

For an inclusive option, we found this non-alcoholic basket thoughtful and easy to share, featuring two Chateau Diana wines and a Volo chocolate bar for pairing. In our testing, the NA wine profiles captured celebratory vibes without the alcohol, making it ideal for parents-to-be or sober-curious friends. Just note the perishable cheese and chocolate may require expedited or local delivery in warm months. As a ready-to-serve Napa-themed gift, it checks the box for indulgence and consideration in one.