Each year Frank Reynolds crawls naked out of a leather couch on Christmas, and somehow that's still not the most unhinged holiday tradition in my life. Mine is opening a box with 24 little doors every morning and pretending the vibrator behind door 9 is for her.
The rise of the advent calendar is the telltale sign that capitalism has breached our hobbies and pastimes. What used to be a small piece of chocolate has worked its way into everything, sex toys included. So before the hordes clear the shelves, DYG rounded up the best sex toy advent calendars 2026 has to offer, plus a few kink boxes, whether you're going solo or with a partner. As of Nov 4, every item here is still available to buy, but they're disappearing fast, so make your move today.
Liberator Kinkmas Boxes ($199 to $299)
Liberator announced three Kinkmas Boxes on Nov 3. Each ships in a designed gift box (no wrapping required) with a free mystery toy "valued at over $80," a holiday date night scene and checklist, and a scannable playlist. A checklist for sex, which I'd tape to the fridge.
Merry & Wild ($269) is the cozy one, "just naughty enough": the Faux Fur Fascinator in black and grey, a blindfold and a cuff kit.
Wrapped Up & Ravished ($299) is the Red Bondage Ravish Pillow, with positioning support and built-in restraints, plus a blindfold, and the pillow is most of what you're paying for here.
Ho Ho Ooooh ($199) packs the Royal Blue Bondage Wedge, a blindfold, a cuff kit and a flogger. Cheapest box, most in it, so it's my pick for couples easing into bondage.
Womanizer Couples Advent Calendar ($179)
The Couples calendar is 24 days for $179, and Womanizer puts the value at $609. Headliners are a Womanizer Liberty 2 for her and a We-Vibe Sync Lite for both of you, then a USB bullet with a remote and seven sleeves (stroker, cock ring and prostate, so I'm covered too). Also lube, cuffs, a satin paddle, hogtie restraints, massage oil, a sex positions card game and a Womanizer ornament. If you buy one calendar for two, I'd make it this one, mostly for the Sync Lite.
Womanizer x We-Vibe Luxury Calendar ($369)
The splurge. The Luxury calendar is 24 pieces, worth $909 by Womanizer's count: Womanizer Enhance, We-Vibe Sync Lite, an Arcwave Zing, a remote bullet with six sleeves, a Lovehoney mini wand, lace top hold-ups, bed restraints, dice and card games, and a candy cane glass dildo. Yes, a candy cane, and I have follow-up questions for whoever pitched it. It's for the couple whose toy drawer is already full, and it's excluded from Womanizer's free-toy promo on orders over $240.
Lily Allen Enjoy Advent Calendar ($129)
We covered Lily Allen's Lovehoney collab on DYG, and her Enjoy calendar is part of that 'Love, Lily' collection. It's 24 days, worth $346, anchored by the Womanizer Starlet 3 and a rechargeable mini wand. Then a bullet with sleeves, an egg stroker, a penis ring, a feather tickler, five meters of rope, a paddle, a card game and a storage bag. Sold out on Lovehoney but still on Womanizer's US store, and at $129 it's the easiest yes here for a couple who's just getting curious.
Womanizer Romance Calendar ($129)
Seven days, for anyone without 24 nights of stamina in December (hand raised). The Romance calendar is built around the We-Vibe Moxie+, a wearable you run by app or remote, plus a USB bullet with remote, cock ring and prostate sleeves, a crystal plug, a blindfold, satin restraints, lube, wipes and a card game. Worth $292, says Womanizer. The Moxie+ is the reason to buy it, and I'd want that remote in my pocket at whichever family dinner comes first.
LELO Couples Calendar ($349)
LELO's first calendar. The LELO Couples Calendar has 12 pieces, and five are full LELO toys: TOR 3, TIANI Harmony, SONA 2 Travel, SURFER 2 and MIA 3. The rest is a Flickering Touch Massage Candle (vanilla and creme de cacao), an inflatable LELO Sex Pillow, handcuffs, a blindfold, Pleasure Enhancing Serum, personal moisturizer and toy cleaning spray. Fewer doors than the Womanizer calendars for more money, but you get five real toys instead of a stack of sleeves, which is the trade I'd make.
Ann Summers 12 Nights of Naughtiness ($160)
Half off its $320 tag. 12 Nights of Naughtiness leans toward her: a pink rechargeable petite rabbit, a purple bullet, a pink wand, a pink rechargeable tickler and a pink rechargeable G-spot vibrator, plus a navy masturbator, a cock ring and a purple beaded plug. Satin ties, a paddle, lube and tip cards round it out. Ann Summers is a UK shop showing US prices, and international shipping gets priced at checkout, so check that number before you fall for it.
Ann Summers 12 Nights of Pleasure ($285)
The couples version, down from $560. 12 Nights of Pleasure fits 13 pieces into 12 nights: a teal rechargeable thrusting rabbit, a navy rechargeable cock ring, a bullet, a rechargeable wand, a dual love egg, a metal jewelled plug and a teal couples tickler, plus a paddle, cuffs, orgasm gel, lube and tip cards. If it's really a gift for both of you, I'd take this over Naughtiness, and the 13th piece is basically a free night. Same shipping caveat, priced at checkout.
Organic Loven Luxury Holiday Pleasure Box ($425)
Not a calendar, and not a 2026 edition either, since it's been around a few holidays. The Luxury Holiday Pleasure Box lets you pick by who's in your bed: one vulva and one penis, two vulvas, two penises, or a solo version of either. Inside are two luxury toys valued over $100 each, full-size organic lube, massage oil, intimate oil, three sex-positive books and "intimate sundries," over $550 in value per the shop. Pricey, but it's the most grown-up gift here. Usually ships in 3 to 4 business days.
Arcwave Dream Team Set ($118)
Not a holiday edition, just $50 off its regular $168. The Dream Team Set pairs the Arcwave Pow, a manual stroker with a suction-control valve and CleanTech silicone, with the Womanizer Pro40 clitoral vibrator. One for each of you. If he already grabbed something from Fleshlight's Penthouse Pets drop, this is the set that gets her in on it, and it's the cheapest buy-in on the list.