ENCOUNTER: That Slow Jam Party (April 30 – May 3) – various locations

This is the one people will plan their weekend around. ENCOUNTER brings together a series of experiences — wellness, yacht moments, and the signature R & B slow jam event that anchors the entire weekend.

The yacht party tonight sets the tone, while Saturday night’s ESSENCE pulls everyone into one space, one energy. It’s grown, it’s intentional, and it feels like more than just a party.

Why go: If you want to feel the shift into spring socially, this is it. The music, the people, the atmosphere, this is it.

Price: From $120 (full access pass) | VIP from $850

Tickets: https://www.ptix.bm/Event/8626/Encounter-Bermuda

The Lunar Table: Flower Moon Experience – May 1 at The Loren at Pink Beach

Spring at its peak, translated into a dining experience. The Flower Moon edition leans into fresh, seasonal ingredients and a lighter, more expressive menu, all set against a soft, intentionally designed atmosphere.

It’s not just dinner — it’s a shift in pace. Something slower, more considered and quietly indulgent.

Why go: For a reset. A reason to sit, stay and enjoy something that feels a little more elevated than your usual night out.

Price: $125 per person

Tickets: https://www.ptix.bm/Event/8746/Flower-Moon

Bloom & Brush Workshop, led by Demco & Alshante Foggo – May 10 at Magnolia Towers, First Floor

A hands on creative experience rooted in creativity and expression. Guided by Demco and Alshante Foggo, this workshop invites you to reimagine pieces you already love — painting directly onto garments while learning the art of floral arranging. Set within a fun, intentionally curated atmosphere, it’s an exploration of texture, colour and form across both canvas and bloom.

It’s not just a workshop, it’s a shift in how you engage with what you already have. A slower, more thoughtful approach to creating something new from something familiar, while leaving with fresh flowers of your own.

Why go: Because it’s spring. Because Mother’s Day calls for something meaningful. Because reconnecting with your creative senses and giving new life to pieces you already own feels both personal and lasting.

Price: $275 per person

Tickets:https://www.demco.bm/products/workshops

The Mother of All Portraits – May 9 at The Botanist Cafe & Garden Lounge

A completely different kind of outing and one of the more fun ones. This guided painting session flips the idea of portraits by having you paint each other. It’s less about skill and more about the experience — laughing through it, seeing what comes out, and leaving with something that actually means something.

You get a drink, all materials are included and you walk away with your own piece (whether it’s a masterpiece or not is beside the point).

Why go: It’s interactive, a little unexpected and perfect if you want something that feels social without defaulting to drinks.

Price: $100

Flag Invasion: World Cup Edition – May 16 at Fort St Catherine

The unofficial start of summer, and one of the few events that actually feels like it. Flag Invasion by DJ Rusty G returns with its World Cup edition, taking over Fort St Catherine with four stages, a full line-up of DJs and a crowd that shows up ready.

This isn’t a casual pop-out, it’s a commit. Jerseys, flags and energy from the minute the doors open. Multiple stages mean you can move with the vibe, not stay stuck in one lane, and the setting does a lot of the work for you. DJs include International DJs Noah Powa, Major Penny, Selecta Kerry, DJ Rusty G and Bermudian DJs Mista Genius, DJ IBreeze, QSkull, Jim Brown, Fresh Kidd and DJ Mystro.

Why go: It’s big, it’s high-energy and it marks the shift. If you’re looking for the moment spring turns into summer, this is it.

Price: From $75

Tickets: https://www.ptix.bm/Event/8750/Flag-Invasion

Hawkins Island Day Retreat – May 16

A completely different pace and exactly what some people will be looking for. This full-day retreat pulls you out of your routine and onto Hawkins Island for something quieter, more intentional.

It’s built around balance: movement, nourishment and time to actually switch off. You can lean into the guided sessions or ignore the structure completely and just be. Private boat transfer, a full day out, and no pressure to do anything but reset.

Why go: Not everything this season needs to be loud. If you’re looking for a proper exhale, this is it.

Price: $345 (members) | $375 standard, plus optional add-ons

Tickets: https://events.thewaterfront.bm/events/hawkins-island-day-retreat/