Sample Itinerary · Hawaiʻi · Honeymoon

Romantic Hawaii Honeymoon 14-Day Tour

Oʻahu · Maui · Kauaʻi · Hawaiʻi Island

Duration10 Days · 9 Nights
RouteOʻahu · Maui · Kauaʻi · Hawaiʻi Island
TransportPrivate Transfers · High-Speed Rail
Best ForFirst-Timers · Couples · Families
10 Days · 9 Nights
Oʻahu · Maui · Kauaʻi · Hawaiʻi Island
Private Transfers · High-Speed Rail
Designed for Two
Sample — Fully Customisable

This is a sample itinerary — for inspiration only. Every Juniper trip is designed from scratch around you. Many clients travel a very similar route — if this resonates, book a free consultation and a specialist will build something just like it (or better) specifically for your travel style, dates, and group.

1
Day One

Arrive in Honolulu, Oʻahu

Honolulu · Waikīkī

Aloha, and welcome to your honeymoon. A private driver brings you to a romantic hotel on Waikīkī Beach. An easy first evening — a sunset stroll and a cocktail as Diamond Head turns gold.

Two weeks for two, across four islands, begins gently.

Private airport transfer Waikīkī check-in Sunset for two
Overnight: Honolulu (Oʻahu)
2
Day Two

Oʻahu — Diamond Head & the Sea

Oʻahu · Waikīkī

A sunrise hike up Diamond Head, a snorkel in a protected cove, and the afternoon on the beach.

Sunset cocktails and dinner with a view to close a romantic opening on Oʻahu.

Diamond Head Snorkel & beach Sunset cocktails
Overnight: Honolulu (Oʻahu)
3
Day Three

Oʻahu to Maui

Maui · Wailea / Kāʻanapali

A short flight to Maui and a transfer to an ocean-view suite on the sunny coast.

The afternoon for the beach and the pool, and a Pacific sunset to ease into Maui time.

Inter-island flight Ocean-view suite Pacific sunset
Overnight: Maui
4
Day Four

Maui — The Road to Hāna

Hāna Highway

The Road to Hāna with a private guide-driver — waterfalls, bamboo forests, black-sand beaches, and pools to swim in, just the two of you.

Quiet stops, banana bread, and one of the world's great drives.

Road to Hāna Waterfalls & pools Private guide
Overnight: Maui
5
Day Five

Maui — Haleakalā & a Sunset Sail

Haleakalā · West Maui

An optional sunrise above the clouds at Haleakalā, then a slow day by the water.

In the evening, a private sunset sail along the coast, a glass in hand.

Haleakalā sunrise Private sunset sail Romance
Overnight: Maui
6
Day Six

Maui — Sea, Spa & Sand

Molokini · Wailea

A morning snorkel sail to the Molokini crater — turtles, clear water, and humpback whales in winter.

The afternoon for a couples' spa treatment and the beach.

Molokini snorkel Couples' spa Beach time
Overnight: Maui
7
Day Seven

Maui to Kauaʻi

Kauaʻi · North Shore

A short flight to Kauaʻi, the lush Garden Isle, and a transfer to a cliffside or beachfront retreat.

An evening walk on a long, quiet beach.

Inter-island flight Garden Isle retreat Quiet beach
Overnight: Kauaʻi
8
Day Eight

Kauaʻi — The Nā Pali Coast

Nā Pali Coast

A private boat cruise along the soaring Nā Pali cliffs — sea caves, waterfalls, and spinner dolphins.

The afternoon to relax, just the two of you.

Nā Pali coast cruise Sea caves & dolphins At leisure
Overnight: Kauaʻi
9
Day Nine

Kauaʻi — Waterfalls from the Air

Kauaʻi interior

A helicopter over the hidden heart of Kauaʻi — Waimea Canyon, the Nā Pali cliffs, and waterfalls you can reach no other way.

The afternoon for a couples' spa and a secluded beach.

Waterfall helicopter Couples' spa Secluded beach
Overnight: Kauaʻi
10
Day Ten

Kauaʻi at Leisure

Kauaʻi

A slow day on the Garden Isle — a quiet beach, a river kayak, or simply the two of you.

A private dinner before the final island.

At leisure River or beach Private dinner
Overnight: Kauaʻi
11
Day Eleven

Kauaʻi to Hawaiʻi Island

Kona · Kohala Coast

A flight to the Big Island and a transfer up the sunny Kohala Coast to an oceanfront suite.

A last island, with volcanoes and the manta-ray sea ahead.

Inter-island flight Oceanfront suite Kohala Coast
Overnight: Hawaiʻi Island
12
Day Twelve

Hawaiʻi Island — Volcanoes

Hawaiʻi Volcanoes National Park

A guided day in Hawaiʻi Volcanoes National Park — craters, lava tubes, and the living edge of the earth at Kīlauea.

Kona coffee on the way back, and the volcano glowing after dark if the timing is right.

Kīlauea & craters Lava tube walk Kona coffee
Overnight: Hawaiʻi Island
13
Day Thirteen

Hawaiʻi Island — Manta Rays & a Beach Dinner

Kohala Coast

A relaxed day on the Kohala Coast — beaches, snorkeling, and the spa — then the unforgettable night snorkel with the giant manta rays off Kona.

A private dinner on the sand to close the honeymoon.

Manta-ray night dive Beach & couples' spa Private beach dinner
Overnight: Hawaiʻi Island
14
Day Fourteen

Depart

Kona / KOA Airport

A last morning by the water, then a private transfer to Kona for your flight home — two weeks that ran from Waikīkī to the cliffs of Kauaʻi to the living volcanoes, all for two.

Your Juniper specialist remains reachable throughout departure day.

Private airport transfer Departure 24/7 specialist support

Love this itinerary? Make it yours.

This is a sample custom route — a starting point, not a fixed package. Many clients travel something very close to this. Book a free consultation and a specialist will build from here.

Accommodations
Eco-luxury lodges, boutique hotels, and beachfront retreats — chosen based on your preferences and travel style.
Transportation
Private transfers, high-speed rail, self-drive, or a mix — all confirmed before you travel.
Experiences
Pre-arranged tours and activities built around your interests — entrance tickets sorted, no queuing.
Available Experiences

Activities on this itinerary

Your specialist pre-arranges the right luxury experiences based on your interests and travel style. These are the custom experience types available on this route — specific choices are made with you, not for you.

Diamond Head & Waikīkī
Oʻahu
Road to Hāna
Maui
Haleakalā Sunrise
Maui
Private Sunset Sail
Maui
Nā Pali Coast Cruise
Kauaʻi
Waterfall Helicopter
Kauaʻi
Hawaiʻi Volcanoes NP
Kīlauea
Manta-Ray Night Dive
Kona
Couples' Spa
Throughout
Private Beach Dinner
Kohala Coast
Ocean-View Suites
Four islands
Designed for Two
Honeymoon

Activities are selected and pre-booked with your specialist based on your interests — not all activities are included in every trip version. Availability varies by season.

Your Top Travel Specialists

The people who will design your Hawaii trip

You work directly with a specialist who knows Hawaii deeply — not a call center or booking agent. Every consultation is with someone who has been there, stayed in those hotels, and knows the country inside out.

Your Hawaii Specialist
Hawaii · Custom & Honeymoon

Your Hawaii Specialist

A dedicated Hawaii specialist designs your trip from scratch — the right eco-lodge, private naturalist guides, the best windows for wildlife and weather, and the balance of soft adventure and beach time.

Book a Consultation
Your Hawaii Specialist
Ireland · Scotland · UK · Iceland

Your Hawaii Specialist

From volcano-view lodges to beachfront retreats, your specialist arranges every transfer, naturalist guide, and experience before you travel.

Book a Consultation
Questions

About this itinerary

Ready to Plan Your Hawaii Trip?

Build your luxury custom Hawaii trip with one of our top travel specialists.

30 minutes, completely free. Walk away with a clear picture of what your luxury custom Hawaii trip could look like — dates, route, 4 and 5-star accommodations, and all.