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Dorchester Center, MA 02124

Experience a private Maui flying dress photoshoot for $795, lasting about 1.5 hours, with professional guides, stunning sunset views, and high-res photos.
Capturing the spirit of Maui in breathtaking photos, the Maui Flying Dress Photoshoot Experience offers a unique blend of style and scenery. For $795 per group, this 1 hour 30 minutes private session provides a personalized photoshoot with high-resolution images delivered straight to your inbox. The experience is ideal for celebrating special occasions or simply indulging in a memorable adventure—plus, it’s suitable for most participants, with most bookings made about 41 days in advance.
Set against the mesmerizing sunset backdrop at Ulua Beach in Wailea-Makena, this tour features a choice of several colorful long-train flying dresses. The private photographer guides you through a variety of poses, making sure every shot captures your best angles. An upgrade option allows for a luxe photoshoot in Hana, adding extra charm to an already special experience.


The tour begins at Ulua Beach in Wailea-Makena, a stunning location known for its soft sands and beautiful sunset views. Participants meet their private photographer between 5:00 PM and 7:00 PM during the designated sunset hours. The start time depends on the season, but the experience typically takes about 90 minutes.
This mobile ticket experience allows flexibility to meet at the beach, where the photographer has the dresses ready and a variety of poses planned. The location choice enhances the photos with Maui’s natural beauty, especially as the golden hour casts a warm glow over the scene.
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Participants receive a selection of up to two vibrant flying dresses. These dresses feature long trains that flow dramatically in the breeze, making for eye-catching photos. The dresses are designed to complement the sunset lighting, creating visually stunning images.
The selection process involves guidance from the photographer, who helps match dresses to your style and skin tone. The dresses are a key part of the experience, adding a touch of glamour and fun. The variety of colorful options ensures you find a look that makes you feel beautiful.

The private photographer leads the session, offering personalized attention and expert guidance. Based on positive reviews, guides like Jude, Laurence, and Regina are praised for being professional, patient, and talented. They provide posing tips and ensure you feel comfortable throughout the shoot.
Their attention to detail and ability to capture natural, flattering shots turn a fun experience into professionally crafted artwork. The photographers are skilled at working with different body types and confidence levels, promising photos that highlight your best features.

The shoot coincides with Maui’s spectacular sunset, often considered the best time to capture romantic and vibrant images. The golden hour enhances the colors of the dresses and creates a warm, flattering light.
Participants can expect the photos to include ocean views, beach scenery, and Maui’s natural beauty as backdrops. The timing ensures a romantic, dreamy atmosphere that elevates every shot. Weather is a factor, but if canceled due to poor conditions, a full refund or alternative date is offered.

All high-resolution JPG files are delivered on a disk after the session, with additional edited images available for download through a link. This dual delivery ensures flexibility—photos can be printed or shared online.
Guests consistently praise the quality of the images, describing them as stunning and professional-looking. The process of receiving the photos is straightforward, making the experience both enjoyable and stress-free.

For those wanting an even more luxurious adventure, an upgrade option to a Hana photoshoot exists. This allows participants to experience Maui’s lush, scenic east coast while capturing more exclusive images. Although details are limited, this upgrade adds a special dimension to the experience.

The tour is booked most often about 41 days in advance, highlighting its popularity. The free cancellation policy allows full refunds if canceled more than 24 hours before the scheduled start. If weather conditions are unfavorable, the photographer will offer an alternative date or a full refund.
The experience is suitable for most women, and most you will find it accessible. It is a private activity, so your group enjoys undivided attention from the photographer.

Based on glowing reviews, this tour is frequently described as “amazing,” “fantastic,” and “a highlight of Maui.” Guests highlight the professionalism, creativity, and friendliness of the team, especially noting guides like Jude and Laurence for making the shoot fun, relaxing, and confidence-boosting.
The beauty of the Maui scenery combined with elegant dresses results in captivating images that guests cherish long after their trip. Many mention that it’s an experience worth treating yourself to—a memorable gift that lasts a lifetime.
The Maui Flying Dress Photoshoot offers a personalized, scenic, and stylish way to commemorate your visit. For $795, you receive a luxurious photoshoot with a trained photographer, high-quality images, and the chance to wear beautiful, colorful dresses in Maui’s iconic sunset setting.
While weather can impact the schedule, the team’s flexibility and professionalism shine through in the reviews. This experience suits anyone looking to add a touch of glamour and elegance to their Maui memories, especially for special milestones or just because.
If you want professional photos in a stunning location with a fun, relaxed vibe, this tour delivers a beautiful, memorable experience you’ll cherish for years to come.
“I meanthese folks are the best people and do very talented! 5 stars!!! They were fun, patient and sent great directions!”
What is the cost of the Maui Flying Dress Photoshoot?
The experience costs $795 per group, which includes all photos, dresses, and guidance.
Where does the photoshoot take place?
The session begins at Ulua Beach in Wailea-Makena and uses the beach’s scenic sunset views as a backdrop.
How long does the photoshoot last?
The session lasts approximately 1 hour and 30 minutes.
Can I choose my dress?
Yes, participants select from several colorful long-train flying dresses provided for the shoot.
What do I receive after the session?
All high-resolution JPG images are delivered on a disk and via a download link, including some edited photos.
Is this experience suitable for everyone?
Most women can participate, and the activity is private, tailored to your comfort and style.
Can I upgrade to a Hana photoshoot?
Yes, there’s an option to upgrade to a photoshoot in Hana for an even more exclusive Maui experience.
What about weather cancellations?
If weather cancels the session, a full refund or rescheduling is offered.
How far in advance should I book?
Most bookings are made about 41 days ahead; early reservations are recommended.
Is there a cancellation policy?
Yes, cancellations made more than 24 hours in advance are fully refunded; less than that, no refund is available.
Who operates the Maui Flying Dress Photoshoot?
The experience is provided by Wailea Photo, known for professional, friendly service and stunning results.