After your flight, enjoy a seamless private transfer to Four Seasons Resort Maui at Wailea (or your chosen Wailea luxury property) for a VIP check-in and prosecco welcome. Settle into your suite, then stroll the resort grounds to discover Polo Beach for a gentle first swim and the adults-only Ho'ola Spa pool or a couples' welcome treatment to melt travel fatigue before a relaxed poolside lunch.
After a leisurely resort lunch, take a short private drive to the dramatic coastal bluff at Makena State Park (Big Beach) for a romantic stroll and sunset photos, then cool off with a couples' swim at the sheltered cove of Keawakapu Beach. Return to the resort for a sunset cocktail on the lanai and an intimate beachfront dinner at Merriman's Kapalua (or your resort's signature oceanfront restaurant) to ease into island time and set the tone for your honeymoon.
As twilight falls, enjoy a private beachfront torch-lit stroll to Wailea Beach Walk followed by an aperitif at the oceanfront cabana of The Lobby Bar at Andaz Maui (or your resort's signature sunset terrace). Later, savor a romantic tasting menu for two at Spago Maui (or an elevated in-suite chef's tasting) with wine pairings and a private dessert served on your lanai to end your first Hawaiian night in intimate luxury.
Wake early for a private catamaran pickup from Wailea Beach Resort marina and glide to the pristine marine reserve at Molokini Crater, where you'll enjoy guided snorkeling with a marine naturalist and optional underwater photography to capture vibrant coral and Hawaiian green sea turtles. After the snorkel, return toward shore for a luxe beachside brunch at The Restaurant at Hotel Wailea with ocean-view seating and a celebratory mimosa before a restorative couples' float or light paddle around the calm waters of Ulua Beach to linger in island serenity.
After your marine reserve morning, enjoy a private luxury picnic on the quiet shoreline of Kapalua Bay, where an on-call chef prepares fresh poke, tropical fruit and chilled champagne served on a shaded beach blanket; linger with a guided coastal walk to the hidden tide pools at Honolua Bay for intimate wildlife spotting. Later, transfer to a chartered 40-foot yacht for a pampered late-afternoon cruise out of Lahaina Harbor, complete with a sunset champagne toast, live ukulele accompaniment and a couples' stargazing guide as the sky darkens.
After your yacht stargazing, slip into a private chauffeured ride to Lahaina's historic Front Street for an early evening art stroll and gallery hop, pausing for handcrafted cocktails on the oceanfront lanai at Fleetwood's on Front St.; enjoy live acoustic music as the sky deepens. Later, board a secluded two-person outrigger for a moonlit paddle to a quiet cove near Kapalua Coastal Trail, where a chef-led beachside tasting of local cacao and macadamia sweets with a sparkling wine toast closes your romantic day.
Depart pre-dawn in a private SUV with a local naturalist guide for a sunrise ascent to Haleakalā National Park-sip warm kona coffee from a thermos as you watch the sky bloom over the crater and capture unforgettable sunrise photos from the Red Hill (Puʻu ʻUlaʻula) lookout. After descending, linger in Upcountry with a leisurely brunch at Kula Lodge & Restaurant overlooking the slopes, then stroll the gardens and visit a nearby boutique farm such as Surfing Goat Dairy for a private tasting of fresh chèvre and a behind-the-scenes tour that connects your morning's high-altitude calm to the island's pastoral charm.
After descending from the crater, return to sea level for a pampered afternoon at The Spa at Four Seasons Resort Maui at Wailea, where a signature Hawaiian lomi lomi couples massage is followed by a private hydrotherapy ritual in a seaside garden grotto. Continue your indulgence with a late-afternoon visit to TEDDY'S Bigger Burgers Wailea for a casual gourmet bite or opt for a chef's tasting and wine pairing at Humuhumunukunukuapuaʻa (or your resort's seasonal tasting menu) before a quiet sunset stroll along Wailea Beach Path to connect the high-country serenity of the morning with the island's elegant coastal evening.
As the day cools, enjoy a private transfer to Kīpahulu's Oheo Gulch for a tranquil twilight walk among lush bamboo and cascading pools, then pause at Kīpahulu Visitor Center for a brief cultural talk if available. Follow with a seaside reservation at The Preserve Kitchen + Bar for an intimate farm-to-table dinner featuring local seafood and a signature tropical cocktail, then return to Wailea for a nightcap on your lanai or a moonlit stroll along Palauea Beach to unwind under the stars.
Begin before mid-morning with a private driver-guide who whisks you along the scenic Hana Highway to explore the lesser-known coastal gems: pause for a refreshing swim at Red Sand Beach (Kaihalulu) and enjoy a cliffside coffee and pastry from the local kiosk at Ke'anae Peninsula while taking in taro fields and ocean vistas. Continue with a short guided hike to the secluded cascade at Alelele Falls (a quieter alternative to the main pullouts) and a shore-side picnic prepared by your resort featuring fresh island fruit, smoked kālua pork, and chilled champagne to savor before the day unfolds further toward Hāna.
After your secluded morning swims, continue deeper into Hana with a private driver to the misty valley surrounding Waiʻānapanapa State Park for a guided coastal cave exploration and a walk along the black sand shoreline where a local naturalist will point out sea arches and native seabirds. Late afternoon, enjoy a private farm-to-table tasting at Hāna Farms-fresh fish ceviche, taro flatbreads and tropical sorbets-then take a quiet stroll to the cliffside viewpoint at Hāna Lava Tube Lookout to watch golden light spill across the coastline before your chauffeured return to Wailea.
As twilight settles after the Hāna road, unwind with a private sunset soak at the secluded oceanfront pools of Honokalani Black Sand Beach (a quieter cove adjacent to the main park), followed by a couples' fresh-ingredient dinner at Hāna Ranch Restaurant where locally caught fish and island-grown greens are paired with boutique Maui wines. Finish the night with a slow, scenic drive back to Wailea, pausing for stargazing and a sweet shave ice from a roadside vendor near Nahiku Marketplace to savor one last taste of Hana's laid-back charm before returning to your resort.
Enjoy a relaxed final Maui morning with a private beachfront breakfast delivered to your lanai at Andaz Maui at Wailea (or your resort), then take a slow walk along Wailea Beach Path to collect a few last sunrise photos and pick up a curated picnic from Monkeypod Kitchen for the short transfer to Kahului Airport. Board an inter-island first-class flight to Honolulu, where a private car will meet you for a scenic coastal drive past Diamond Head to your chosen Oʻahu luxury property - settle into your suite with a signature welcome mai tai at Halekulani's House Without a Key (or your North Shore resort's oceanview lounge) before a light beachside swim to refresh after travel.
After settling in, enjoy a curated afternoon of shoreline discovery: take a private guided coastal drive to Makapuʻu Lookout for dramatic ocean vistas and a chance to spot migrating whales from the cliffs, then continue to Nuuanu Pali Lookout for panoramic windward views and a short, shaded stroll through fragrant plumeria groves. Finish with a late-afternoon seaside tasting at The Pig and the Lady (chef's tasting menu or a tropical cocktail on the patio) or, if you choose the North Shore, a luxe beach cabana service at Turtle Bay Resort with chilled champagne and an optional couples' surf coaching session to ease into island life together.
As the sun dips, enjoy a private transfer to Kaimana Beach for a quiet shoreline walk and a brief couples' snorkel to meet nocturnal reef life before cocktails; afterward, savor a curated farm-to-table dinner at Salt at Our Kakaʻako featuring island-grown produce and locally sourced seafood with bespoke wine pairings. Cap the night with a rooftop nightcap at The SURFjack Hotel's Mahina & Sun's lounge for live local music and sweeping views of the Waikīkī skyline, or-if you're on the North Shore-reserve a sunset table at The Point Sunset & Surf for a secluded dinner and a starlit stroll along a private stretch of sand.
Start your day with a private guided tour through the lush valleys of the windward coast, beginning with a sunrise visit to Kualoa Ranch for a behind-the-scenes movie site drive and a tandem ATV ride through secret ridgelines, then continue to Byodo-In Temple for a peaceful koi-feeding and a short private Shinto blessing tailored for honeymooners. Afterward, savor a leisurely farm-to-table brunch at Kualoa Ranch's Ranch Cafe featuring locally raised produce and guava pastries before a private cultural talk with a kumu hula who will introduce you to traditional oli (chant) and simple hula steps to carry the morning's aloha into the rest of your day.
After your morning at Kualoa Ranch and Byodo-In Temple, enjoy a curated afternoon exploring the windward shore with a private guide: wander the coastal botanical displays and cultural exhibits at Hoʻomaluhia Botanical Garden, then kayak together in the calm inlet of Kahana Bay where a local naturalist will point out native birds and explain traditional fishpond practices. Finish with a private farm-to-table tasting at Kahala Mall's artisanal pop-up or a reserved tasting flight at Koko Head Cafe's wine partner (chef-curated small plates), keeping the day's cultural immersion relaxed and intimately connected to Oʻahu's living landscapes.
As twilight settles, enjoy a private transfer to La Mariana Sailing Club for classic tiki cocktails in a retro oceanfront setting, followed by a short drive to Kawaikui Beach Park for a serene sunset picnic prepared by a local chef featuring pickled ahi, sweet potato poi cakes and chilled pineapple prosecco. After dinner, attend an intimate evening hula & mele performance at Hawaiʻi Theatre (reserve a front-row table or private box) and finish with a moonlit stroll along Pōhākea Point to listen for nocturnal seabirds and reflect on the day's cultural discoveries.
Board a private helicopter from John Rodgers Terminal (HNL) for a thrilling morning circle-island flight that dips into the lush Windward cliffs above Makapuu, threads the dramatic Koolau pali, and sweeps over the emerald valleys of Kaʻena Point with live narration from your pilot-guide and panoramic glass windows for unobstructed photos. Alternatively, choose a luxury launch from Haleʻiwa Harbor for a morning coastal cruise beneath sea cliffs toward Kaʻena Point Natural Area Reserve, where a guided zodiac will drop you at a secluded reef for a private snorkel and a gourmet seaside brunch prepared on board featuring fresh island poke, tropical fruit and chilled champagne.
After your morning flight or snorkel, slip into a privately chauffeured drive to Lulumahu Falls for a short guided rainforest walk and a secluded picnic beside the cascading pool set up by a local chef; linger while your guide shares kōkua stories about the valley's history. Later, continue along the windward coast to Kaiaka Bay for a luxury beach cabana experience with chilled champagne and an expert stand-up paddle instructor who'll take you to nearby tide pools for intimate reef spotting before a late-afternoon return to your resort to refresh for the evening.
As dusk falls, take a private transfer to Ala Moana Beach Park for a curated beachfront champagne tasting and live ukulele duo on a reserved lawn-perfect for golden-hour photos-then stroll the nearby boardwalk to watch city lights awaken. Later, enjoy an intimate multi-course dinner at Roy's Ko Olina (reserve a chef's tasting table or private dining alcove) featuring Hawaiian fusion seafood with bespoke wine pairings, followed by a moonlit walk along Ko Olina Lagoons to end the night in secluded coastal romance.
Wake to a private beachfront breakfast delivered to your cabana at Turtle Bay Resort's Ocean Club before a guided snorkel with a local naturalist at the nearby sheltered reef off Kuilima Point to spot reef fish and honu (green sea turtles). After snorkeling, indulge in a couples' seaside wellness session - choose a restorative oceanfront yoga class on Kuilima Cove or a sand-scrub ritual followed by chilled sparkling rosé served on your shaded lounger, then take a short electric-bike ride along the coastline to discover a quiet tide pool for an intimate photo moment.
Spend a leisurely afternoon luxuriating in a private cabana at Turtle Bay Resort's Kawela Bay Club, where chilled champagne service, a curated grazing board of island cheeses and poke, and personalized reef-safe sunscreen touch-ups keep you pampered between dips. When you want a change of pace, take a short escorted boat shuttle to Sunset Beach's secret cove for guided tandem snorkeling among coral gardens and a sunset surf coaching session with a pro instructor, then return to your cabana for a couples' beachfront coconut oil massage as golden light softens into evening.
As the sun softens, enjoy a private sunset sail from Kahuku Harbor aboard a two-person launch with chilled sparkling wine and a chef-led tasting of island crudo and grilled opakapaka; glide past sea cliffs as the sky warms to coral. After the sail, savor a candlelit table at The Point Sunset & Surf Clubhouse for a locally sourced tasting menu-think citrus-cured fish, macadamia crusted scallops and a tropical dessert flight-then finish with a moonlit walk along the resort's private stretch of sand, pausing at Pounders Beach overlook for stargazing and the rhythmic sound of the surf.
Begin your day with an adrenaline-tinged adventure: take a private early-morning charter from Haleʻiwa Harbor for a guided shark-viewing expedition off Waimea Bay with a marine biologist on board who'll explain local shark behavior and offer optional cage viewing for unforgettable close-up encounters. If you prefer surf over sea life, meet a world-class instructor at Queens Surf in Waikīkī for a tailored couples' surf lesson focusing on pop-ups and wave selection, then refuel with an oceanfront brunch at Hula Grill Waikiki before choosing a restorative afternoon option.
For a thrilling alternative to your morning, take a private transfer to Shark Explorers' Waimea Bay base for a shore-based marine talk and optional surface snorkel with reef sharks in shallow clear water (no cage) guided by a marine biologist, followed by a seaside recovery lunch at Giovanni's Shrimp Truck for fresh garlic shrimp and cold tropical drinks. If you prefer calm water, enjoy an afternoon of tandem stand-up paddle boarding and reef exploration with a pro instructor from Ala Moana Beach Park-they'll guide you to sheltered coral gardens and finish with a sunset paddle back to the beach club; or surrender to luxury with a late-afternoon couples' treatment at SpaHalekulani featuring a Hawaiian herbal body wrap and private plunge pool time to melt into honeymoon relaxation.
As dusk settles, enjoy a private transfer to Kaimana Beach for a calm twilight snorkel with a local naturalist who will point out evening reef life, then head to Ala Moana Center's Roy Street Tavern (or a reserved seaside table at The Beach House at Ko Olina) for a relaxed tapas-style dinner featuring island ceviche and a craft tropical cocktail. Finish the night with a rooftop cocktail at The Modern Honolulu's Café Chanel (or a moonlit stroll along Sherwood Forest Park if you're on the North Shore) to soak in the island night air and reflect on your day's adventure together.
Ease into your final Hawaiian morning with a leisurely seaside breakfast at The Surfjack's Mahina & Sun's rooftop, followed by a private guided stroll through the artisan stalls of Kakaʻako Farmers Market to pick up last-minute locally made gifts like koa wood jewelry and small-batch chocolate. Afterward, enjoy a calm couples' soak and light treatment at The Spa at Halekulani with time in their signature plunge pool before a relaxed transfer to the airport, savoring a final cup of kona coffee prepared to-go by Island Vintage Coffee.
Spend a relaxed afternoon wandering the boutique-lined streets of Kaimana Plaza and hunting for last-minute aloha pieces at Hawaiian Quilt & Gift before slipping into a late lunch at the ocean-view terrace of House Without a Key for fresh poke and a final mai tai toast. Afterward, enjoy a private couples' mani-pedi and floral lei-making mini-class at Līhuʻe Spa & Salon to leave with a handmade souvenir, then take a scenic drive to Magic Island Lagoon for a gentle shoreline stroll and golden-hour photos before your private transfer to the airport.
As twilight settles, enjoy a private sunset sail departing from Kewalo Basin Harbor for a last romantic cruise with chilled sparkling wine and a narrated skyline view of Honolulu as lights come alive. After disembarking, savor a farewell dinner at the intimate chef's-counter at Mud Hen Water featuring island-forward tasting plates and bespoke cocktails, then take a slow moonlit walk through the nearby gardens of Fort DeRussy Beach Park to soak in your final Hawaiian night before your private transfer to the airport.
| Place / Activity | Cost |
|---|---|
| Private transfer (airport to resort) - Maui | $120 |
| Four Seasons Resort Maui at Wailea - welcome/prosecco (approx. minibar/welcome amenity) | $0 |
| Polo Beach | Free |
| Ho'ola Spa pool / couples' welcome treatment | $350 |
| Poolside lunch (per person, resort dining) | $60 |
| Makena State Park (Big Beach) - parking/entry | Free |
| Keawakapu Beach | Free |
| Merriman's Kapalua - dinner (per person, upscale) | $120 |
| Wailea Beach Walk (torch-lit stroll) | Free |
| The Lobby Bar at Andaz Maui - cocktail (per person) | $20 |
| Spago Maui - tasting menu (per person) | $150 |
| Private catamaran to Molokini (private charter, per person) | $250 |
| Guided snorkeling with marine naturalist (included in private charter) | Included |
| Underwater photography (optional add-on) | $75 |
| The Restaurant at Hotel Wailea - beachside brunch (per person) | $55 |
| Ulua Beach - float / paddle (rental) | $30 |
| Private luxury picnic at Kapalua Bay (per person) | $120 |
| Honolua Bay tide pool walk (guided) | $40 |
| Chartered 40-foot yacht from Lahaina Harbor (sunset cruise, per person) | $220 |
| Fleetwood's on Front St. - cocktail (per person) | $25 |
| Two-person outrigger moonlit paddle (guided) | $80 |
| Chef-led beachside tasting (per person) | $65 |
| Private SUV sunrise to Haleakalā with naturalist guide (per person) | $175 |
| Haleakalā National Park entry (per vehicle; per person estimate) | $8 |
| Kula Lodge & Restaurant - brunch (per person) | $40 |
| Surfing Goat Dairy - private tasting & tour (per person) | $25 |
| The Spa at Four Seasons - lomi lomi couples massage & hydrotherapy (per person) | $280 |
| TEDDY'S Bigger Burgers Wailea - casual bite (per person) | $18 |
| The Preserve Kitchen + Bar - dinner (per person) | $90 |
| Kīpahulu's Oheo Gulch (ʻOheʻo Gulch) visit | Free |
| Private driver-guide for Road to Hāna (full-day, per person) | $200 |
| Red Sand Beach (Kaihalulu) | Free |
| Ke'anae Peninsula coffee & pastry (per person) | $8 |
| Alelele Falls guided hike (per person) | $30 |
| Seaside picnic prepared by resort (per person) | $65 |
| Waiʻānapanapa State Park (parking/entry) | $10 |
| Hāna Farms - farm-to-table tasting (per person) | $45 |
| Hāna Lava Tube Lookout | Free |
| Honokalani Black Sand Beach | Free |
| Hāna Ranch Restaurant - dinner (per person) | $70 |
| Private beachfront breakfast delivery to lanai | $45 |
| Inter-island first-class flight (Maui to Oʻahu) - per person | $180 |
| Private car to hotel in Honolulu (including Diamond Head drive) | $80 |
| Halekulani - welcome mai tai (approx.) | $18 |
| Makapuʻu Lookout visit | Free |
| Nuuanu Pali Lookout | Free |
| The Pig and the Lady - tasting or meal (per person) | $55 |
| Turtle Bay Resort - cabana service with champagne (per person) | $150 |
| Kaimana Beach snorkel (twilight) - rental/guided | $35 |
| Salt at Our Kakaʻako - dinner (per person) | $85 |
| Private guided tour Kualoa Ranch (movie sites + ATV tandem) - per person | $220 |
| Byodo-In Temple - visit / koi-feeding (admission) | $5 |
| Hoʻomaluhia Botanical Garden | Free |
| Kahana Bay kayak with naturalist (per person) | $75 |
| La Mariana Sailing Club - classic tiki cocktails (per person) | $16 |
| Hawaiʻi Theatre - evening hula & mele performance (per person) | $45 |
| Private helicopter circle-island from John Rodgers Terminal (per person) | $650 |
| Luxury launch from Haleʻiwa Harbor (per person, alternative) | $220 |
| Lulumahu Falls guided rainforest walk (per person) | $40 |
| Kaiaka Bay beach cabana with SUP instructor (per person) | $95 |
| Ala Moana Beach Park - curated beachfront champagne tasting (per person) | $60 |
| Roy's Ko Olina - multi-course dinner (per person) | $120 |
| Turtle Bay Resort Ocean Club breakfast (per person) | $45 |
| Kuilima Point snorkel with naturalist (per person) | $60 |
| Oceanfront yoga or sand-scrub wellness session (per person) | $40 |
| Kawela Bay Club cabana with grazing board (per person) | $140 |
| Sunset sail from Kahuku Harbor (per person) | $110 |
| The Point Sunset & Surf Clubhouse - tasting menu (per person) | $95 |
| Shark-viewing expedition from Haleʻiwa Harbor (per person, private charter) | $200 |
| Queens Surf - private surf lesson (per person) | $120 |
| Hula Grill Waikiki - oceanfront brunch (per person) | $45 |
| Giovanni's Shrimp Truck - meal (per person) | $15 |
| Ala Moana SUP tandem session (per person) | $65 |
| SpaHalekulani - herbal body wrap & private plunge (per person) | $260 |
| Kaimana Beach twilight snorkel with naturalist (per person) | $35 |
| Roy Street Tavern / Beach House at Ko Olina - dinner (per person) | $70 |
| The Surfjack's Mahina & Sun's - rooftop breakfast (per person) | $28 |
| Kakaʻako Farmers Market - artisan shopping | $40 |
| The Spa at Halekulani - couples' soak & light treatment (per person) | $150 |
| Island Vintage Coffee - kona coffee to-go (per person) | $6 |
| Kaimana Plaza / Hawaiian Quilt & Gift shopping | $60 |
| House Without a Key - late lunch / mai tai (per person) | $45 |
| Līhuʻe Spa & Salon - mani-pedi & lei-making mini-class (per person) | $85 |
| Magic Island Lagoon stroll | Free |
| Kewalo Basin Harbor sunset sail (per person) | $95 |
| Mud Hen Water - chef's-counter dinner (per person) | $110 |
| Private transfer to airport (final) | $120 |
| Estimated Total (per person) | $7,278 |