Sunday, December 28, 2025

Early Arrival

Slip in a day early, exhale, and make The Resort yours—unpack, wander, and ease into the week at your own pace.

Monday, December 29, 2025

Arrival & First Sunset

Touchdown at MBJ
Your week begins the moment you land at Montego Bay (MBJ). A Resort driver will meet you outside Customs, manage the bags, and ease you along the coastal road—cane fields, sea views, and bright bougainvillea setting the tone.

Settle in & explore
Check-in is from 3:00 p.m., and we’ll do our best to host you sooner if your suite is ready. Until then, stroll the grounds, claim a poolside lounger, or—if you’re feeling bold—head to the cliff ledge for a jump into the clear Caribbean.

First sunset, First toast
As the light turns gold, join us on the western terrace for welcome cocktails. It’s an easy way to meet fellow Members, swap a few stories, and watch the sun slide into the sea.

Dinner under the Almond Tree
When dusk settles, we’ll gather on the open-air terrace beneath our half-century-old shade tree. Expect a chef-led menu that marries island ingredients with polished technique.

After-dinner ease
Close the evening at The Cliff Bar, where a local guitarist keeps things mellow beneath hanging lanterns. Enjoy a nightcap, the salt air, and a soft landing into island rhythm.

Tuesday, December 30, 2025

Unwind & Connect

Morning, your way
Wake to the hush of the Caribbean and choose your pace. Have Blue Mountain coffee and fruit delivered to your suite, linger over breakfast on the patio, settle into a table in the restaurant, or grab a quick espresso before a workout. If leisure wins over lunges, reserve an open-air massage by the surf—or have the therapist come to your villa for a private session.

Midday vibe
By early afternoon the heartbeat moves to the toptional main lagoon pool, where a guest DJ lays down easy grooves over the sound of the sea. Attendants make the rounds with classics—mojitos, daiquiris, and bright zero-proof coolers—while conversations start naturally among new arrivals. With every room and villa due to be occupied by dusk, you’ll feel the property slip into full celebration mode.

Arrivals, simplified
Still traveling? Member Services can upgrade the last leg from Montego Bay to a quick flight into Negril Aerodrome, trimming the journey to minutes. However you arrive—by road or by sky—a chilled towel and a welcome cocktail will be waiting.

Golden hour
Meet on the western terrace as the sun unspools toward the horizon. Champagne in hand and a local duo setting the mood, it’s an effortless way to reconnect with friends and meet a few more.

Dinner that lingers
Evening unfolds at an unhurried pace—courses shared, stories traded, and perhaps a nightcap under torchlight. Stay for the last song, or slip away early to savor the quiet of your villa. It’s your week; shape the night exactly as you like.

Wednesday, December 31, 2025

New Year’s Eve: The Black Tie & Lingerie Ball

Morning & Afternoon
Ease into the day and save your energy for the night ahead. The spa and salon team will be on standby for tux pressings, gown steaming, blowouts, and makeup. Sound checks begin mid-afternoon; you’ll hear the first notes floating across the terraces as the sun starts to lean west.

5:00 p.m. — Golden-Hour Portraits
Meet on the western lawn for couple’s photos at sunset. Champagne service begins; a jazz trio sets a low, elegant pulse.

6:30 p.m. — Reception
Black tie gathers on the cliff-edge terrace: canapés, martinis, and quiet conversation beneath lantern light. Gentlemen in tuxedos or dinner jackets; ladies in evening gowns or long dresses.

7:30 p.m. — Gala Dinner “Under the Tree”
A multi-course chef’s menu celebrates island ingredients with polished technique. Wine pairings flow at an unhurried pace; the sea keeps time just beyond the rail.

9:30 p.m. — Lila Iké (Live)
Our new favorite, Lila Iké takes the stage with a soulful, roots-forward set—intimate, magnetic, and perfectly tuned for a seaside ballroom.

10:45 p.m. — Maxi Priest (Live)
Maxi Priest turns the dial toward celebration, carrying us toward midnight with the unmistakable warmth of his catalog.

11:59 p.m. — Countdown
Couples gather along the balustrade; flutes are charged; the sky deepens. Ten…nine… and the New Year arrives in a shimmer of corks and coastline.

12:15 a.m. — The After Party
The Black Tie & Lingerie Ball earns its playful name after midnight. It’s a bit of a misnomer at the start—this evening begins in classic formalwear—but as tradition (never obligation) has evolved, some of the more brazen women slip away and reappear in couture lingerie for the after-party—think La Perla and Agent Provocateur—paired with Jimmy Choo or Christian Louboutin stilettos. The mood stays refined and consensual; tuxedos remain very much in fashion.

Thursday, January 1, 2026

Late Morning — Sleep-In Breakfast & Reset
Ease into the year with a long, lazy breakfast: fresh fruit, Blue Mountain coffee, pressed juices, and made-to-order favorites served late so night owls aren’t punished. A gentle stretch class and a “reset bar” (hydration, herbal tonics) are on standby for those who overachieved at midnight.

1:00–4:00 p.m. — “The Game” in Our Pop-Up Sports Bar
We turn a corner of the lounge into a make-shift sports bar: big screens, comfortable seating, and a casual menu of wings, sliders, and ice-cold Red Stripe. Settle in for the game with friends old and new. (Programming subject to broadcast availability.)

4:30–6:30 p.m. — Pool Party with Guest DJ
Slide over to the toptional main lagoon pool for a sun-splashed DJ set as the afternoon hits its stride. Expect an easy, feel-good playlist, cocktail service (plus zero-proof coolers), and that unmistakable first-day-of-the-year glow.

6:30–7:30 p.m. — Sunset Happy Hour: Island Live Music
As the light goes gold, a local trio takes the terrace for an acoustic set—rootsy, warm, and unmistakably Jamaican. It’s the perfect bridge from pool to dinner.

From 7:30 p.m. — Dinner, À La Carte
No prix fixe tonight—choose freely from our new menu. Island ingredients meet polished technique: charcoal-kissed seafood, bright garden sides, hand-rolled pastas, and a few classics for the comfort-minded. Your server will happily steer you toward the night’s best pairings. (Reservations recommended.)

After Dinner — Nightcaps & Sea Air
Linger at The Cliff Bar for a final pour, or take a quiet walk under the stars. Tomorrow, the pace picks back up—tonight, just enjoy being exactly where you are.

Friday, January 2, 2026

Choose Your Mid-Day Adventure
Start slow: a late breakfast, Blue Mountain coffee, and a stretch on the terrace. If you’re feeling energetic, take a coastal walk or slip into the pool for a few easy laps—today’s built for sunshine and choice.

Mid-Day Adventures (pick your pace)
Please note: off-property outings may involve transport, entry, charter, or guide fees. Your concierge will confirm details and pricing before you commit.

Seven-Mile Beach Stroll
For a quieter rhythm, your driver can drop you at the north end of Negril’s famous powder-white strand. Kick off your sandals and wander south as the tide brushes your ankles. Stop wherever the music and a cold Red Stripe call your name, then we’ll collect you when you’re ready.

Mayfield Falls (River Hike & Cascades)
Set out on a scenic 90-minute drive inland to Mayfield Falls, then wade upstream with a local guide through clear mountain water, ascending more than twenty natural waterfalls and limestone pools. It’s playful and refreshing—expect rock-pool jacuzzis, gentle climbs, and short swims. Bring water shoes, swimwear, and a dry change; moderate fitness is recommended. Your concierge will arrange transport, guide, and towels, and can secure a waterproof phone pouch if you’d like photos en route.

On the Water: Snorkel, Dive, or Sail
Sea lovers can slip out to coral gardens with mask and fins, book a guided PADI dive, or charter a catamaran for a lazy tack along the coast. Member Services will match you with a trusted captain, right-sized boat, and the reef conditions of the day—equipment and charter particulars outlined in advance.

Rick’s Café Cliff Show
If spectacle is your mood, head to Negril’s iconic cliff-side bar for live music, rum punches, and the legendary jumpers who draw cheers all afternoon. Watch a palm-top salute and a fearless plunge into blue water, then return to the calm of The Resort when you’ve had your fill.

Late-Afternoon Cool-Down
Back at the property, slip into the toptional pool or claim a lounger and let the day exhale. Our attendants will keep the spritzers and coolers coming while the sun tilts west.

Sunset Happy Hour
As golden hour arrives, a local trio sets an acoustic groove on the terrace—easy conversation, sea air, and a glass of something celebratory as the horizon glows.

Dinner — À La Carte
No prix fixe again tonight. Explore our new menu at your own pace—grilled island catch, bright garden sides, hand-rolled pastas, and a few indulgences for the table. Your server will point you to the evening’s best pairings and off-menu surprises.

After Hours
Close the night with a rum nightcap at The Cliff Bar or a moonlit walk past the water’s edge. Tomorrow can be an adventure; tonight is yours to savor.

Saturday, January 3, 2026

Morning light
Draw the curtains and let the Caribbean blue set the tone. By now, the island rhythm should feel natural—slow coffee, deep breaths, no hurry.

Breakfast, your way
Choose the verandah, your villa courtyard, or the comfort of bed. Fresh-cut mango, Blue Mountain coffee, and chilled coconut water are on standby, with a full breakfast menu if you’re ready for more.

Equity-Member Business Huddle (optional, mid-morning)
Equity Members are invited to a concise financial briefing covering current holdings and next-quarter priorities. Expect coffee, pastries, and panoramic views; we’ll keep it tight and useful.

Lagoon pool session 
The energy shifts to our lagoon-style pool—palm-crowned island, swim-up bar, and underwater stools. A guest DJ blends laid-back soca with deep-house edits while bartenders keep daiquiris, rum punches, and cold-brew tonics moving. Sun, music, and an easy come-as-you-are vibe.

Dinner is yours to design
Make the evening exactly what you want. Reserve a table under the almond tree on the property, slip over to Ivan’s for a local favorite, visit Rockhouse for pepper pot soup and curried chicken, or have grilled lobster delivered to your patio and dine under the stars.

One last After-party

We close the week on home turf with an on-premise celebration in a crisp white theme—linen, silk, and pearl tones to mark the clean slate of 2026. Invitations read 9:00 p.m. — until, because this one isn’t about the clock; it’s about momentum.

A surprise musical act keeps the tempo high while our head mixologist keeps you well lubricated with bright, icy pours and late-night riffs on the classics. Expect low candlelight, sea breeze, and a room full of sleek silhouettes and confident energy—the kind of finale where the dance floor does the talking and the night trims itself to your best angles.

Dress code is simple: white on white. Show up polished, stay as long as the rhythm carries you, and let this be the week’s last, irresistible hurrah.

Sunday, January 4, 2026

Farewell

The week winds down with our Farewell Brunch beneath the broad canopy of the old almond tree—linen-draped tables, soft morning light, and the gentle shimmer of the sea just beyond. A steel-pan duo sets an easy rhythm while servers pass rum-kissed brioche French toast, bite-size ackee-and-saltfish sliders, tropical fruit, and carafes of bottomless mimosas alongside strong Blue Mountain coffee. It’s unhurried by design: time to trade photos, exchange numbers, and raise one last glass to the memories you’ve just made.

When you’re ready to roll, our drivers will meet you at the porte-cochère. Bags are whisked into the car, chilled towels are offered, and you’ll settle in for a comfortable ride back to Montego Bay (MBJ)—the coastline glinting in the rearview and your next visit already taking shape.

Monday, January 5, 2026

Oh, You Decided to Linger

You missed the convoy to MBJ—and honestly, we suspected you might. After cliff-top sunsets and generous mimosas, clocks run on island time. Whether you wanted one more slow morning with your favorite person or tapped snooze with conviction, we’re glad you’re still here.

Breakfast goes wherever you are: trays in bed, a breezy patio table, or barefoot at the bar ordering “the usual.” By now, you know the rhythm—tell us what you’re craving and it appears.

Need a pretext for the bonus day? The concierge can line up a scuba refresher, a couples’ spa session, a coastal drive, or the finest plan of all: absolutely nothing. “Horizontal by the pool” qualifies as a scheduled activity in our book.

A quick note on billing: Monday isn’t part of the published package. If you’d like to extend, email george@thecliffjamaica.com and we’ll add the night, update your folio, and keep the good vibes rolling.

Pro tip — The Residence Program: Resort and Equity Members can travel lighter next time. Leave a capsule wardrobe—linen shirts, sundresses, even that half bottle of miracle sunscreen. We’ll launder, press, and store your things in our climate-controlled facility, then place everything in your room, suite, or villa before you arrive. It’s complimentary for Members and makes spontaneous returns effortless.

Take your time. Soak up a few more rays. Let departure chase you for once—paradise isn’t in a hurry to say goodbye.