Lavish Lovers’ Escape in Kailua-Kona
RomanticWeekend
$$$$$ Ball Out

Kailua Kona

Lavish Lovers’ Escape in Kailua-Kona

Indulge in a luxe, oceanfront weekend on the Kona Coast with private sails, sunset dinners, and spa-level relaxation. This itinerary focuses on ultra-romantic experiences, VIP treatment, and the area’s best high-end dining and resorts for an unforgettable couples’ getaway.

Where to Stay

Four Seasons Resort Hualalai
Stay

Four Seasons Resort Hualalai

Ultra-luxury oceanfront resort north of Kailua-Kona with multiple pools, world-class golf, an onsite swimmable aquarium, spa, and exceptional dining.[1]

$1,500-2,500/night
Kona Village, A Rosewood Resort
Stay

Kona Village, A Rosewood Resort

High-end, bungalow-style resort on the Kona Coast with private hale accommodations, beautiful pools, beach access, and serene grounds.[4]

$1,800-3,000/night

Good to Know

k
Know

Book Signature Experiences Well in Advance

Reserve manta ray night snorkels, Mauna Kea summit tours, and top restaurants like Merriman’s and Ulu Ocean Grill several weeks out, especially for weekend dates and sunset time slots.

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Know

Splurge on Private or Small-Group Options

When choosing cruises, tours, or transfers, favor private charters or limited-capacity groups for more space, better service, and a calmer vibe.

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Know

Time Your Days Around Sunrises and Sunsets

Plan at least one sunrise (on the coast or up Mauna Kea) and both a waterfront and high-elevation sunset; build meals and activities around these golden hours.

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Know

Pack Smart for Luxe Meets Adventure

Bring resort-casual outfits and light layers along with reef-safe sunscreen, water shoes, and motion-sickness remedies if you’re prone to seasickness.

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Know

Respect Local Culture and Natural Sites

Learn a few Hawaiian words, heed kapu (no entry) signs, stay on marked paths, and never touch coral or wildlife—even on guided tours.

Your Weekend Itinerary

Merriman's Big Island
Eatevening

Merriman's Big Island

Upscale farm-to-table Hawaiian cuisine in a romantic setting; order the nightly fresh catch and the paniolo steak.

2h 30m
$90-150 per person
Papa Kona Restaurant & Bar
Eatmorning

Papa Kona Restaurant & Bar

Waterfront spot in Kailua-Kona with great brunch and cocktails; try the loco moco or crab cake eggs Benedict.

1h 15m
$30-45 per person
Umekes Fish Market Bar & Grill
Eatafternoon

Umekes Fish Market Bar & Grill

Casual-upscale spot known for excellent poke bowls and fresh fish, plus creative cocktails.

1h
$25-40 per person
d
Domorning

Kona Style - Deluxe Morning Snorkel & Sail

Catamaran cruise from Kailua-Kona or Keauhou with snorkeling at Kealakekua Bay and lounging on deck.

4h
$150-220 per person
Fair Wind Cruises - Kealakekua Bay Snorkel
Doafternoon

Fair Wind Cruises - Kealakekua Bay Snorkel

Premium snorkel cruise with slides, platforms, and excellent gear to explore one of Hawaii’s top marine preserves.

3h 30m
$160-200 per person
Fair Wind Cruises - Manta Ray Night Snorkel
Doevening

Fair Wind Cruises - Manta Ray Night Snorkel

Evening boat tour to snorkel with giant manta rays under lights in Keauhou Bay.

2h 30m
$160-225 per person
Ulu Ocean Grill at Four Seasons Resort Hualalai
Eatevening

Ulu Ocean Grill at Four Seasons Resort Hualalai

Oceanfront fine dining with sushi, seafood, and Pacific Rim dishes; reserve a table right by the water for sunset.

2h 30m
$120-180 per person
Hualalai Trading Company
Eatmorning

Hualalai Trading Company

Chic café/market at Four Seasons Hualalai offering excellent coffee, pastries, and light breakfast.

45m
$20-35 per person
d
Doevening

Mauna Kea Summit Adventures (Mauna Kea Sunset & Stargazing Tour)

Guided luxury tour from Kona up to Mauna Kea for sunset above the clouds and telescope stargazing at 9,000+ feet.

6h
$250-300 per person
Kona Coffee Living History Farm
Domorning

Kona Coffee Living History Farm

Outdoor museum and working coffee farm in Captain Cook, showcasing the history of Kona coffee with tastings and guided walks.

1h 30m
$25-30 per person
d
Doafternoon

Ensemble Therapy Massage & Wellness (Kailua-Kona)

Boutique spa offering couples massages and customized treatments in a peaceful setting.

1h 30m
$160-260 per person

14 activities across 3 days

Map

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