Allison Jackson's approach to entertaining is shaped by her roots — born in San Francisco and raised in the South — where modern sophistication meets timeless hospitality. 

With decades of experience, Allison has grown Pineapple Productions into a trusted, full-service event planning and design firm known for its discerning eye, calming presence, and wholehearted service. Inspired by nature, travel, and history, she leads with intuition and purpose, translating each client’s story into layered, immersive experiences that feel both effortless and unforgettable.

Allison is supported by a dedicated in-house team that brings structure, creativity, and care to every celebration. Together, they uphold Pineapple’s signature standard: refined, gracious, and deeply personal. The result is a joyful atmosphere where guests feel fully seen and celebrations unfold with ease, meaning, and lasting beauty.

Q: Where do you start when planning a gathering?

A: I always start with the feeling I want people to walk into.

Allison begins each gathering by setting the emotional tone — thinking first about how she wants her guests to feel when they arrive. Once that’s defined, everything else flows naturally: a menu that reinforces the mood, décor that enhances it, and small, personal touches that make the night feel thoughtful and effortless.

Q: What are your favorite ways to break the ice or entertain guests?

 A: I love creating natural, gentle ways for guests to ease into a gathering — nothing forced, just thoughtful moments that make people feel instantly included.

Allison sets the tone with small details that invite connection: a seasonal welcome drink, a sentimental object with a story, or a shared tray of oysters. When the group is right, she’ll add an interactive moment like a spritz station or communal toast — keeping it relaxed and organic. It’s never about structured icebreakers, but about shaping an atmosphere that helps guests connect without effort.

Q: If you had a limited budget for a dinner party, what would you focus on for the tablescape?

A: I focus on the elements that create the most atmosphere. I always start with lighting.

With candlelight as her first layer, Allison adds texture with seasonal greenery or a single floral varietal — even a few simple stems can do the trick. Then she incorporates one or two warm, intentional pieces like beautiful napkins or ceramic details. A softly lit, cohesive table will always feel elevated — no big budget required.

Q: What advice would you give to someone who feels overwhelmed by hosting?

A: If hosting feels overwhelming, simplify the plan and elevate the intention.

Allison recommends choosing one element to feel confident about — maybe it’s a great cocktail, a cozy playlist, or simply candlelight that sets the mood. Prep in advance where you can, release the pressure of perfection, and take a breath before guests arrive. A calm host creates a calm space.

Q: What’s your signature recipe when entertaining?

A: We almost always start the evening with an elevated Old Fashioned — it’s such a classic, but with great bourbon it becomes something extraordinary. My husband Arthur collects beautiful bottles, and there’s something special about opening one when we have friends over. It instantly sets the tone: warm, celebratory, and a little indulgent.

Arthur’s Signature Old Fashioned

Ingredients:

• 2 oz very good bourbon
• 1 bar spoon spiced demerara syrup (recipe below)
• 2 dashes Angostura bitters
• 1 dash orange bitters
• 1 large clear ice cube
• Orange peel
• Optional garnish: fresh fig slice or star anise pod

Method:
Add the bourbon, spiced demerara syrup, and bitters to a mixing glass filled with ice. Stir until well chilled. Strain over one large clear ice cube. Express the orange peel over the drink, then add it to the glass along with a fig slice or star anise for a subtle seasonal finish.

Spiced Demerara Syrup

Ingredients:

• 1 cup demerara sugar
• 1 cup water
• 1 cinnamon stick
• 3 whole cloves
• 1 strip orange peel
• Optional: 2–3 pink peppercorns

Method:
Heat all ingredients until sugar dissolves. Steep for 20–30 mins, strain, and refrigerate.

Allison’s Signature Bar Snack‍

To pair with an Old Fashioned, Allison reaches for something savory, warm, and elevated — her go-to:

Rosemary Marcona Almonds with Citrus Zest & Sea Salt

Warm the Marcona almonds in a low oven just until fragrant. Toss with fresh rosemary, a touch of orange or lemon zest, and flaky sea salt. Serve in a pretty bowl near the bar — they disappear quickly.

Q: What’s your ideal dinner party playlist?

Evening Light: A party playlist by Pineapple Productions

Listen on Spotify

Allison curates her playlists with care — a flow that supports the rhythm of the evening without overpowering it.

Q: What’s your favorite party trick when hosting?

A: Creating a moment that feels spontaneous but is quietly planned. I love introducing one unexpected element—a nightcap tray, a late-night round of oysters, or a surprise family-style dessert—right when the evening needs a little spark. It doesn’t have to be elaborate; the magic is in the timing and giving guests a moment they didn’t see coming

Q: What do you love about Partytrick?

A: Partytrick understands that a great gathering is about both beauty and ease. I love that the platform makes hosting feel elevated but still approachable. My favorite feature is the inspiration-to-execution flow — you can discover ideas that feel aspirational and then immediately translate them into a real, achievable plan.

For her, that mix of beautiful ideas and actionable tools is a game-changer.

Q: What’s the most memorable event you’ve ever hosted?

A: A surprise 80th birthday celebration for my dad.

Allison and her brother designed a heartfelt evening honoring their father’s Italian heritage and California roots. It was filled with subtle, meaningful details — nothing overdone — and the look on his face when he realized what was happening made it a night they’ll never forget.

Q: What are your favorite products to use when hosting?

A: A very good Italian olive oil — Partanna, Castello di Ama, or Frantoia.  A drizzle over warm bread or a finished dish adds an instant sense of luxury. I’m also never without Maldon flaky salt. That final pinch of good salt is the simplest way to make anything feel restaurant-worthy at home.

Inspired by Allison’s thoughtful approach to hosting? Follow her journey at Pineapple Productions and stay connected on Instagram @pineappleprodc to see how she continues to create meaningful, elevated gatherings. Ready to host your own moment of connection? Partytrick makes it simple — with customizable templates, expert tips, and a streamlined planning flow that brings your vision to life. Create your free Partytrick account today.