Private Sunset Sailboat Proposal

Once you reserve your all-inclusive proposal package, you’ll receive access to our photography partner’s Planning Lounge, filled with expert proposal tips, a full walkthrough of the surprise strategy, and Hawaii travel resources to help you plan an unforgettable trip. You’ll also enjoy a complimentary proposal strategy call with your photographer before the big day, where they’ll walk you through every step of the plan so you feel confident, prepared, and fully ready before we set sail.

Not at all. With our dedicated crew, undercover photographer, and carefully coordinated plan, your partner will think it’s a normal private sunset sail charter. The surprise remains completely hidden until the exact moment you’re ready to propose.

Your photographer blends in naturally as part of the crew, and we coordinate every detail in advance, including timing, positioning, and the signature reveal moment. Everything happens quietly behind the scenes so nothing ever feels suspicious.

Hawaii weather can change quickly, but sunset sails are typically calm and comfortable. If conditions become unsafe or less than ideal, our captain will guide you through the safest options, and we’ll reschedule or cancel the sail when necessary for weather-related safety reasons.

For personal schedule changes, we generally allow rescheduling or canceling with 48 hours’ notice. Cancellations made within 48 hours, as well as no-shows, are typically non-refundable due to limited availability and the preparation required for each private charter. We always recommend reaching out as early as possible if your plans shift.

Photography coverage is reserved exclusively for your scheduled time, and planning begins well in advance. Because of this, photography payments are non-refundable, though we’re always happy to reschedule if your charter is moved due to weather or operational changes. If we need to postpone your sail for safety reasons, we’ll coordinate a new date and adjust your proposal plan so everything flows smoothly.

Our goal is to make your entire experience safe, seamless, and unforgettable, no matter what nature has in mind.

Absolutely. You’re welcome to bring personal touches, and we can also arrange custom enhancements such as premium champagne upgrades, vegan or vegetarian meal options, or sweet treats to elevate your celebration.

Each proposal package includes a 60-minute photo session that captures the proposal, the celebration that follows, and romantic engagement portraits at sunset.

Yes! You’ll receive a same-day iPhone video of the proposal moment, along with a gallery of more than 100 high-resolution, professionally edited images to browse through. Your final selections are delivered within two weeks, with the option to purchase additional images or upgrade to the full gallery.

We recommend booking as early as possible so we can coordinate timing, planning, and the undercover strategy with our photographer. Sunset sails fill quickly, especially during peak travel seasons.

Choose outfits that feel like you and move comfortably in the ocean breeze. You’ll also receive wardrobe tips and inspiration inside your Planning Lounge to help you and your partner look and feel your best.

Absolutely. Whether you imagine florals, a message in a bottle, a special song, or specific décor color requests, we can personalize the experience to match your vision.

Our photographer specializes in helping couples feel relaxed and natural in front of the camera. The experience blends candid moments with light direction so nothing feels forced or overly posed.

Of course. Loved ones are always welcome, and having your closest friends or family on board can make the celebration even more meaningful!