Because Some Moments Deserve More Than a Long Weekend in Napa
A Bay Area travel agent’s guide to planning the Hawaii romance trip you’ll never forget.
Hawaii has been the #1 honeymoon destination in the United States for decades — and for good reason. Warm water, dramatic landscapes, world-class resorts, candlelit dinners on the beach, and a culture built around hospitality and love. Add the fact that you’re just 5.5 hours from San Jose with a direct flight, and it’s hard to argue with.
Whether you’re newly married and planning your honeymoon, or celebrating 10, 25, or 40 years together, here’s my guide to doing Hawaii romance right — from which island to choose, to the experiences that make it truly unforgettable.
First Things First: Which Island Is Right for You?
Not all Hawaiian islands are the same, and the right one for your romance trip depends on your vibe as a couple. Here’s how we think about it:
Maui — The Classic Honeymoon Island
Maui is Hawaii’s most popular honeymoon destination, and it earns that reputation. It has the best combination of luxury resorts, stunning beaches, fine dining, and adventure activities of any island. Wailea on the south shore is pure romance — upscale resorts, calm turquoise water, and spectacular sunsets. If you want the full Hawaii honeymoon experience with zero compromises, Maui is your island.
Kauai — The Most Dramatic & Intimate
Kauai is Hawaii’s oldest and most untouched island — lush, green, and jaw-droppingly beautiful. The Na Pali Coast alone is worth the trip. Kauai is smaller and quieter than Maui, with fewer crowds and a more private feel. It’s perfect for couples who want adventure mixed with seclusion — hiking, helicopter tours, remote beaches, and cozy boutique resorts. If Maui is a romantic dinner at a rooftop restaurant, Kauai is a candlelit cabin in the mountains.
The Big Island — For Couples Who Want It All
The Big Island of Hawaii is unlike any place on earth. You can watch lava flow into the ocean, snorkel with manta rays at night, and stay at a world-class resort — all in the same trip. It’s ideal for adventurous couples who want to feel like they’ve truly explored somewhere extraordinary. The Kohala Coast on the west side has some of Hawaii’s finest resorts and most beautiful beaches.
Oahu — Best for Couples Who Want City + Beach
Oahu is Hawaii’s most vibrant island — home to Honolulu, Waikiki, incredible food, nightlife, and iconic landmarks like Diamond Head. It’s a great choice for couples who want the energy of a city alongside the beauty of the ocean. It’s less secluded than the neighbor islands, but the range of experiences is unmatched.
💡 Travel Agent Tip: Can’t choose? Multi-island itineraries are a beautiful option for honeymoons — spend 4 nights on Maui and 3 on Kauai, for example. Inter-island flights are short (30–45 minutes) and inexpensive. I put these together regularly for my Bay Area clients.
The Best Romantic Resorts in Hawaii
Where you stay sets the tone for the entire trip. Here are our top picks by island for romance:
Maui
The Wailea resort corridor is the crown jewel of Maui romance. The Four Seasons Maui at Wailea, the Fairmont Kea Lani, and the Andaz Maui at Wailea Resort are consistently among the top romantic resorts in the country. Expect private lanais with ocean views, couples spa treatments, and beach butler service. For something more intimate, boutique properties in Napili and Kapalua on the west side offer a quieter, more secluded experience.
Kauai
The St. Regis Princeville on Kauai’s north shore sits on a cliff above Hanalei Bay with views that will make your jaw drop. The 1 Hotel Hanalei Bay is another stunning option — sustainable luxury with unbeatable scenery. On the south side, the Grand Hyatt Kauai Resort & Spa in Poipu is a perennial favorite for honeymoon couples.
Big Island
The Mauna Kea Beach Hotel and the Fairmont Orchid on the Kohala Coast are iconic. For something ultra-luxurious, the Four Seasons Resort Hualalai is widely considered one of the finest resorts in all of Hawaii.
Oahu
The Halekulani in Waikiki is legendary — old-world elegance, impeccable service, and one of the most romantic settings in Honolulu. For something more modern and design-forward, the Ritz-Carlton Residences Waikiki Beach is a standout.
💡 Travel Agent Tip: As your travel agent, I have preferred relationships with many of these properties — which often means room upgrades, complimentary amenities like champagne or spa credits on arrival, and early check-in. These are perks you simply don’t get booking on your own through a hotel website or Expedia.
Romantic Experiences Worth Splurging On
Hawaii is full of once-in-a-lifetime experiences. For a honeymoon or anniversary trip, here are the ones we recommend prioritizing:
Sunset Sail or Private Catamaran Charter
There is nothing more romantic than watching the Hawaiian sun dip below the Pacific horizon from the deck of a sailboat with a glass of champagne in hand. Most islands offer both group sunset cruises (more affordable) and private charters (more intimate). For a honeymoon, the private charter is worth every penny.
Couples Spa Day
Every major Hawaiian resort has a world-class spa, and most offer couples treatment rooms. A side-by-side massage followed by time in a private outdoor jacuzzi with ocean views is a peak Hawaii romance experience. Book in advance — spa appointments at top resorts fill up fast.
Helicopter Tour
Seeing Hawaii from the air is truly breathtaking — waterfalls, volcanic craters, sea cliffs, and remote valleys that are inaccessible any other way. On Kauai, a doors-off helicopter tour over the Na Pali Coast is the single most spectacular thing you can do on the island. On Maui, a helicopter flight over Haleakala and the Hana rainforest is equally stunning.
Stargazing at Mauna Kea
On the Big Island, the summit of Mauna Kea sits above the clouds at nearly 14,000 feet — one of the best stargazing locations on the planet. Watching the Milky Way stretch across the sky together is a deeply memorable experience for couples. Guided summit tours are available and highly recommended.
Private Beachside Dinner
Many Maui and Kauai resorts offer private beachside dinner setups — a table for two on the sand, personal butler service, a customized menu, and tiki torches flickering in the ocean breeze. It’s not cheap, but for a honeymoon or milestone anniversary, it’s an experience you’ll talk about for years.
💡 Travel Agent Tip: Tell me your anniversary or honeymoon date when booking and we’ll work with the resort to arrange a special welcome — whether that’s flowers and champagne in the room, a private dinner setup, or a personalized touch that makes arrival day unforgettable.
Flying from SJC: What Romantic Travelers Should Know
Direct flights from San Jose to Hawaii make this trip remarkably easy for Bay Area couples. Here’s what to know:
Best Islands to Fly Direct from SJC
- SJC → OGG (Maui) — Direct flights available on Southwest, United, and Alaska
- SJC → HNL (Oahu) — Most frequent service, multiple airlines
- SJC → KOA (Kona, Big Island) — Seasonal direct service available
- SJC → LIH (Kauai) — Limited direct service; may require a connection through HNL or LAX
Upgrade the Flight
For a honeymoon, consider upgrading to first or business class for at least one leg of the journey — it sets the tone beautifully and turns the travel day into part of the celebration. If you have airline miles or credit card points sitting around, a honeymoon is exactly what they’re for.
💡 Travel Agent Tip: I can help you use points and miles strategically to upgrade flights or cover hotel costs — often getting you more value than you’d get redeeming them on your own.
Best Time to Go
For romance, we love April through early June — perfect weather, fewer families (school is still in session), and shoulder season pricing that leaves more budget for the experiences that matter. February is also lovely — and if your anniversary falls near Valentine’s Day, Hawaii is far more romantic than a crowded restaurant back in San Jose.
Sample 7-Night Maui Honeymoon Itinerary
Here’s a taste of what a perfect Maui honeymoon week looks like:
Night 1 — Arrive & Settle In Check into your Wailea resort, order room service, and fall asleep to the sound of the ocean.
Day 2 — Beach Day & Sunset Sail Spend the morning on the beach, then board a private sunset catamaran in the evening with champagne and appetizers.
Day 3 — Road to Hana Take your time on the world-famous coastal drive — waterfall hikes, black sand beaches, and roadside banana bread. End with dinner in Hana.
Day 4 — Haleakala Sunrise & Upcountry Wake before dawn for the most spectacular sunrise of your lives above the clouds. Spend the afternoon exploring the farms and lavender fields of Upcountry Maui.
Day 5 — Molokini Snorkel & Couples Spa Morning snorkel at Molokini Crater, then afternoon couples massage at the resort spa.
Day 6 — Helicopter Tour & Private Beach Dinner See Maui from the air in the morning, then end the trip with a private beachside dinner at sunset.
Night 7 — Slow Morning & Fly Home One last sunrise walk on the beach, shave ice at Ululani’s, and a late checkout before heading to OGG.
How Far Out Should You Book a Hawaii Honeymoon?
For peak season travel (summer and holidays), book 4 to 6 months out — especially for the top romantic resorts, which fill their best ocean-view rooms first. For shoulder season travel, 2 to 3 months is usually sufficient, though we always recommend booking sooner rather than later when the trip matters this much.
Don’t leave the rental car for last — even on a romantic trip, you’ll want a car for day trips, and inventory gets thin fast.
Let Me Plan It For You
A honeymoon or anniversary trip to Hawaii isn’t something you want to piece together on your own across a dozen browser tabs. The right resort, the right room category, the right activities booked in the right order — it all matters, and getting it right makes the difference between a good trip and a truly unforgettable one.
As a Bay Area travel specialist flying clients out of SJC and SFO, I’ve planned numerous Hawaii romance trips. I know which resorts deliver on their promises, which experiences are worth the splurge, and how to make sure everything goes smoothly from the moment you leave your driveway to the moment you return home.
📞 Contact me today to start planning your Hawaii honeymoon or anniversary trip.
Your Bay Area travel agent — proudly serving San Jose and the greater Bay Area.