By Island Jewel Yacht Charters – Oahu's Highest-Rated Private Yacht Charter
Few moments in life are as unique as asking the love of your life to be yours forever and no more picturesque setting than the endless ocean, painted in warm gold, caressing waves, and vistas of Oahu's coast.
At Island Jewel Yacht Charters, we’ve helped countless couples create that once-in-a-lifetime proposal moment, romantic, private, and completely unforgettable.
Here’s your guide on how to plan the perfect proposal aboard a private yacht in Oahu.
1. Choose the Perfect Time of Day
Timing sets the mood and in Oahu, every hour brings its own kind of magic.
Sunset: Top proposal choice. The heavens are painted in hues of golden oranges and pinks, creating a movie-magic backdrop for your special moment.
Midday: Best for those who want bright blue ocean hues, shining waters, and stunning photos.
Evening: A moonlit night proposal under the stars, quiet, intimate, and softly romantic.
Pro Tip:
Book your charter 4–6 weeks in advance to get the ideal time and yacht for the big day.
2. Pick the Right Yacht Experience
Your proposal is more than a boat tour, it's an experience worthy of luxury, intimacy, and personalization.
Island Jewel offers a couple of private yacht experiences tailored to your style:
2-Hour Sunset Charter: Ideal for classic, intimate proposals with champagne and sunset.
Half-Day Experience: Combine your proposal with a beach picnic or snorkel break.
Full-Day Luxury Charter: Make it an entire-day experience with ocean activities, music, and dining.
We will help put all the pieces together from playlists to flower arrangements so everything feels unstudied and specially yours.
3. Set the Scene
The best part of a private yacht proposal is the possibility of customizing it according to your own taste.
Here are some ways to make it a cut above:
Decor: Top with fresh tropical flowers, fairy lights, or an elegant rose-petal path on deck.
Drinks & Dining: Pop the question over champagne or indulge in a private catered dinner on board.
Capture the Moment: We can arrange a photographer or discreet videographer to catch your "yes."
Music: Play your song at the proposal, what is more romantic than your favorite tune while the sun sets over the ocean.
4. Choose the Perfect Venue
Oahu's coast has literally thousands of beautiful spots for your proposal. These are a few of our favorites:
Diamond Head Viewpoint: For traditional Hawaii photos.
Waikiki Skyline: City lights twinkling behind you as you take a knee.
Secret Bays and Reefs: Secluded, intimate areas where it's just the two of you and the sea.
Our captains know the most peaceful and romantic locations, just tell us your fantasy, and we'll take you there.
5. Surprise Them (If You Dare)
We've organized many "secret" proposals where your partner thinks it's just a regular yacht ride or photo shoot.
Our staff is experienced at maintaining your secret and will signal everyone in top form from the champagne transfer right on down to when you descend on bended knee.
You can even pre-arrange with us for special surprises like:
A "decoy" sunset photo shoot
The perfect song to play right before proposing
A celebratory toast the moment they respond with "yes"
6. Celebrate Afterwards
Once you’ve popped the question, celebrate your engagement right there on the water!
Enjoy a private dinner, take photos at sunset, and watch the stars appear over Waikiki.
Many couples choose to extend their charter and celebrate with family or friends later in the evening.
You’re already in paradise, why not make it a memory that lasts forever?
7. Book with the Experts in Romance
Here at Island Jewel Yacht Charters, we've established a reputation as the go-to private yacht in Oahu for milestone romantic moments — from surprise proposals to anniversary cruises and vow renewal ceremonies.
Leave the details to us so you can focus on what matters most: the moment, the view, and the person you love.
Whether you like a simple, intimate one or an over-the-top gesture with the whole shebang, we'll make it happen with the aloha and luxury you deserve.
Ready to Plan Your Yacht Proposal?
Your fairy tale "yes" starts with an intimate yacht and a breathtaking Hawaiian sunset.
Only select dates in high season, book early to reserve your place!
Book Your Private Proposal Charter
Call Now to Speak with Our Team