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The Flying Dresses of Montego Bay — five women in pink, yellow, red, green and purple flying dresses by the sea

Bold. Beautiful. Breathtaking.

Your Jamaica vacation just became a fashion moment. Choose your setting and let your DRESS FLY and your SPIRIT SOAR!

MONTEGO BAY + SURROUNDING AREAS·BOOK YOUR OWN DRIVER
THE FLYING DRESS EXPERIENCE
THE FLYING DRESSES OF MONTEGO BAY

Our flying dresses feature extra-long, silky tails designed to create dramatic movement in the Caribbean breeze. Video is for promotional purposes only.

THE FLYING DRESSES OF MONTEGO BAY

Not just a photoshoot.
A Jamaica memory in motion.

CHOOSE YOUR EXPERIENCE

Luxury in Motion

Solo Flying Dresses of Montego Bay package
YOUR MOMENT

Solo

Your moment. Your dress. Your spotlight.

US$285PER PERSON · 60 MIN
  • 1 flying dress
  • Private pop-up dressing room
  • Professional camera photography
  • Drone content when conditions & permissions allow
  • Wind fan for dramatic movement
  • Dedicated assistant
  • Location of your choice, subject to confirmation
  • Calico Jack rum punch
  • Red Stripe & flavored beers
  • Snacks + complimentary water
Bestie Flying Dresses of Montego Bay package
DOUBLE THE DRAMA

Bestie

Two friends. Two flying dresses. Twice the fun.

US$5192 FRIENDS · 2 DRESSES · 90 MIN
  • 2 flying dresses
  • Private pop-up dressing room
  • Professional camera photography
  • Drone content when conditions & permissions allow
  • Wind fan + movement direction
  • Dedicated assistant
  • Friendship + individual portraits
  • Calico Jack rum punch
  • Red Stripe & flavored beers
  • Snacks + complimentary water
Trio Flying Dresses of Montego Bay package
TRIPLE THE DRAMA

Trio

Three friends. Three flying dresses.

US$189PER PERSON · 90 MIN
  • 3 flying dresses
  • Private pop-up dressing room
  • Professional camera photography
  • Drone content when conditions & permissions allow
  • Wind fan + movement direction
  • Dedicated assistant
  • Trio + individual portraits
  • Calico Jack rum punch
  • Red Stripe & flavored beers
  • Snacks + complimentary water
Group Flying Dresses of Montego Bay package
BRING YOUR CREW

Group(4–6)

Bring your crew. Your group. Your private experience.

US$189PER PERSON · 2 HOURS
  • Flying dress for each participant
  • Multiple dress colors
  • Private pop-up dressing room
  • Professional camera photography
  • Drone content when conditions & permissions allow
  • Wind fan + dedicated assistant
  • Individual + group photographs
  • Calico Jack rum punch
  • Red Stripe & flavored beers
  • Snacks + complimentary water
Takeover Flying Dresses of Montego Bay package
TAKE OVER THE BEACH

Takeover(7–10)

Seven to ten guests. One unforgettable fashion takeover.

US$169PER PERSON · 2.5 HOURS
  • Flying dress for each participant
  • Multiple dress colors & sizes
  • Private pop-up dressing room
  • Professional camera photography
  • Drone content when conditions & permissions allow
  • Wind fan + dedicated assistant
  • Individual, group & creative portraits
  • Extra time for a larger group experience
  • Calico Jack rum punch
  • Red Stripe & flavored beers
  • Snacks + complimentary water
Horseback Flying Dresses of Montego Bay package
SIGNATURE ADVENTURE

Horseback

Flying dress. Horseback. Caribbean shoreline.

US$415PER PERSON · 90 MIN
  • 1 flying dress
  • Guided horseback experience through an approved equestrian partner
  • Professional camera photography
  • Drone content only when location + JCAA + property permissions allow
  • Wind fan where safe for horse and rider
  • Dedicated assistant
  • Beach, ranch or scenic equestrian setting subject to confirmation
  • Partner/equestrian fees included only when stated in your confirmed quote
  • Snacks + complimentary water
NOW BOOKING
OPENING DAY

Saturday, March 6, 2027.

Bookings are now open for Flying Dress experiences beginning Saturday, March 6, 2027. Choose from our recommended locations or request a location of your choice. A non-refundable deposit is required to secure your reservation.

DEPOSIT POLICY: Deposits are non-refundable unless weather conditions prevent the experience and/or the vendor cancels the reservation.

EVERYTHING NEEDED TO FLY

The magic is already here.

We bring the production. Bring your personality.

THE DRESSES

Beautiful flowing silk flying dresses with extra-long tails in multiple colors and sizes, designed to move dramatically in the breeze.

THE CAMERA

Professional photography equipment for your shoot.

THE DRONE

Aerial content when weather, safety and permissions allow.

THE WIND FAN

Dramatic movement that makes your dress come alive.

THE ASSISTANT

A dedicated assistant helps with movement, positioning and flow.

THE COOLER

Complimentary water and on-site refreshments.

COMPLETE YOUR EXPERIENCE

Make your Jamaica moment spectacular.

Enhance your flying-dress session with carefully selected experiences. Book each specialist directly—no middleman, no unnecessary upsells.

CELEBRATIONS

MAKE IT A MOMENT

Flowers, bouquets, balloons and celebration styling for birthdays, anniversaries, honeymoons and special moments.

CURATED PROVIDERS
VIDEO + DRONE

CAPTURE THE MAGIC

Professional video, cinematic reels and aerial content for clients who want more than still photos.

CURATED PROVIDERS
RIVER EXPERIENCE

FLYING DRESS + RIVER

Take your flying dress experience onto the river for a one-of-a-kind Caribbean fashion moment surrounded by flowing water, lush scenery and movement.

CURATED PROVIDERS
MAKEUP + BEAUTY

SLAY MY FACE

Professional makeup and beauty preparation so you arrive camera-ready.

BOOK / EXPLORE
LUXURY

AFTER THE SHOOT

Luxury picnic, spa and relaxation experiences to turn your photoshoot into a full day of indulgence.

CURATED PROVIDERS
PRIVATE CHEF

PRIVATE DINING

Private chef and curated dining experiences for couples, families and groups celebrating in Montego Bay.

CURATED PROVIDERS
HOW IT WORKSChoose your add-on → connect directly with the specialist → arrange and pay them directly.
SIMPLE BY DESIGN

From arrival to iconic.

01

BOOK YOUR EXPERIENCE

Choose Solo, Couples, Bestie, Trio or Group.

02

GO TO YOUR SELECTED LOCATION

Meet us at your confirmed shooting location.

03

CHOOSE YOUR DRESS

Select your preferred available color, style and size.

04

GET READY

Use our private pop-up dressing room.

05

LET IT FLY

Our assistant, camera, drone and wind fan help create dramatic images.

06

POSE. PLAY. CREATE.

Capture beautiful Caribbean fashion content.

07

LEAVE WITH MEMORIES

Take the experience home as part of your Jamaica story.

The Flying Dresses of Montego Bay at a Caribbean beach location
YOUR EXPERIENCE. YOUR SETTING.

CHOOSE YOUR LOCATION

MONTEGO BAY + SURROUNDING AREASRecommended locations or your location of choice

Your Flying Dresses experience doesn't have to happen in one place. Choose from our recommended locations, or tell us where you want to create your memories. We'll help confirm access, availability, travel logistics and any commercial photography requirements before your shoot.

LOCATION TRAVEL FEE

Locations of your own choosing outside of the Montego Bay area will incur additional costs. Any applicable travel, access, permit or location fees will be confirmed with you before your booking is finalized.

SUN + SEABEACHES

Turquoise water, sandy shores and dramatic Caribbean breeze.

ELEGANTLUXURY & RESORTS

Elegant resort, hotel and villa settings for a polished destination-fashion look.

TROPICALNATURE & SCENIC

Lush tropical gardens, waterfront scenery and distinctive Jamaican landscapes.

CUSTOMYOUR LOCATION

Have a special place in mind? Tell us where you want to fly and we'll check access, availability and requirements.

ADVENTUREHORSEBACK + FLYING DRESS

Pair your flying-dress session with a guided horseback beach experience and create editorial-style images with the sea, sand and horses.

WATER + ADVENTURERIVER EXPERIENCE

Take your flying dress onto the river for a flowing Caribbean fashion moment surrounded by lush scenery and moving water.

LOCATION DIRECTORYKnow the rules before you book.

We track access, commercial-shoot approval, horseback availability and drone restrictions for the locations we recommend. A location is never treated as automatically approved.

One Man BeachMontego Bay · Beach
REQUEST / CONFIRM

DRONE: NO DRONE BY DEFAULT — JCAA airspace + site permission must be confirmed

HORSEBACK: Horseback: partner request only

CONTACT: Public beach — no official contact. Our team confirms access.

Doctor's Cave BeachHip Strip, Montego Bay · Managed Beach
REQUEST / COMMERCIAL SHOOT APPROVAL

DRONE: NO DRONE BY DEFAULT — within the Sangster airport restriction area; commercial flight requires JCAA authorization

HORSEBACK: Horseback: not a standard beach-shoot location

Harmony Beach ParkMontego Bay · Public Beach Park
REQUEST / UDC CONFIRMATION

DRONE: NO DRONE BY DEFAULT — airport proximity plus UDC/site permission

HORSEBACK: Horseback: not currently listed as a standard beach-ride site

CONTACT: Managed by the Urban Development Corporation (UDC).

Dead End BeachKent Avenue, Montego Bay · Public Beach
REQUEST / CONFIRM

DRONE: NO DRONE BY DEFAULT — airport proximity; commercial JCAA authorization required

HORSEBACK: Horseback: partner request only

CONTACT: Public beach — no official contact. Our team confirms access.

Cornwall BeachMontego Bay · Beach
REQUEST / CONFIRM ACCESS

DRONE: DRONE: PERMISSION + JCAA REVIEW REQUIRED

HORSEBACK: Horseback: partner request only

CONTACT: No official beach contact. Our team confirms access.

Walter Fletcher BeachMontego Bay · Managed Beach
REQUEST / CONFIRM

DRONE: DRONE: PERMISSION + JCAA REVIEW REQUIRED

HORSEBACK: Horseback: partner request only

CONTACT: No official beach contact. Our team confirms access.

Sunset BeachMontego Bay · Public Beach
REQUEST / CONFIRM

DRONE: DRONE: PERMISSION + JCAA REVIEW REQUIRED

HORSEBACK: Horseback: partner request only

CONTACT: Public beach — no official contact. Our team confirms access.

Burwood Beach — FalmouthTrelawny · Beach + Equestrian Partner
PARTNER LOCATION

DRONE: DRONE: PERMISSION + JCAA REVIEW REQUIRED

HORSEBACK: HORSEBACK AVAILABLE THROUGH BEACH OPERATOR PARTNER

CONTACT: Public beach — horseback partner details shared on confirmation.

Private Hotel / ResortMontego Bay + Rose Hall · Private Property
OWNER / RESORT APPROVAL REQUIRED

DRONE: NO DRONE UNLESS PROPERTY + JCAA APPROVE

HORSEBACK: Horseback only where an approved equestrian partner is available

CONTACT: Contact details depend on the property you choose.

Private VillaMontego Bay + Surrounding Areas · Private Property
OWNER APPROVAL REQUIRED

DRONE: NO DRONE UNLESS PROPERTY OWNER + JCAA APPROVE

HORSEBACK: Horseback only by separate approved partner arrangement

CONTACT: Contact details depend on the villa you choose.

Tropical Garden / Scenic LocationMontego Bay + Surrounding Areas · Scenic / Private / Public
REQUEST / CONFIRM

DRONE: DRONE: LOCATION-SPECIFIC PERMISSION + JCAA REVIEW REQUIRED

HORSEBACK: Horseback by separate partner arrangement

CONTACT: Contact details depend on the site you choose.

Your Requested LocationClient selected · Custom
REQUEST / CONFIRM

DRONE: DRONE STATUS CHECKED BEFORE BOOKING

HORSEBACK: Horseback availability checked separately

CONTACT: Share the location's contact with us and we'll handle the rest.

DRONE + COMMERCIAL PHOTOGRAPHY NOTE

Jamaica's Civil Aviation Authority requires a Special Aerial Work Permit for professional/commercial drone operations before each flight. Drone flights also have airspace, people, property and airport restrictions. Our team will not promise drone content until the location, property/site manager and JCAA requirements are confirmed.

NEW SIGNATURE EXPERIENCE

FLYING DRESSES + HORSEBACK

Bring the fashion moment to the shoreline. Horseback photo sessions are offered through approved equestrian partners and are scheduled around rider safety, horse welfare, beach access and weather conditions.

STARTING ATUS$399per person · 90 minutes
AFFILIATE PROGRAM

Share the experience. Earn 20%.

Anyone can apply to become an affiliate and earn 20% on eligible completed bookings referred through their approved code.

VIEW AFFILIATE PROGRAM
QUESTIONS, ANSWERED

Frequently Asked Questions.

Everything you need to know before you let your dress fly — from booking and dress selection to transportation, horseback riding and our river experience.

Where is the Flying Dresses experience located?

Our main service area is Montego Bay and surrounding areas. We recommend locations based on access, scenery and your requested experience. You may choose one of our recommended locations or request your own location. Locations outside the Montego Bay area may incur additional travel, access, permit or location costs, which will be confirmed before your booking is finalized.

When can I book?

Bookings are open for experiences beginning Saturday, March 6, 2027. Your requested date and time are not final until our team confirms availability and your reservation is secured according to the booking terms.

What packages are available?

We offer Solo, Couples, Bestie, Trio, Group and Takeover packages, plus a Horseback + Flying Dress experience. Package pricing, guest counts, durations and inclusions are displayed on the home page and may vary by experience.

What is included in my Flying Dress package?

Depending on the package, your experience includes the flying dress, private pop-up dressing room, professional photography, a dedicated assistant, wind-fan movement support and complimentary water and refreshments. Drone content is included only when weather, safety and required permissions allow. Always review the specific package inclusions before booking.

Can I choose my dress color and size?

Yes. We offer multiple colors and sizes. You can request your preferred color and provide your dress size during booking. Dress availability is subject to the inventory available for your date and your final selection is confirmed by our team.

Do I have to bring my own dress?

No. The flying dress is provided as part of the applicable experience. Our team helps you select an available dress and use the private pop-up dressing area to get ready.

Is photography included? What about video and drone?

Professional photography is included in the listed packages. Additional video or cinematic content may be available through curated providers. Drone content is never guaranteed because weather, wind, safety, airspace, property permission and Jamaica Civil Aviation Authority requirements can affect whether a flight is permitted.

How does transportation work?

Transportation is separate from your Flying Dress booking. You may use our open driver directory or choose any driver of your own. Transportation is arranged and paid for directly with your driver. If you identify your driver to us, we can record the transportation provider connected to your booking for our internal referral tracking.

Do drivers or makeup artists receive a 20% commission?

No. The 20% affiliate commission is for approved affiliates who refer eligible completed bookings through their assigned affiliate code. Drivers and makeup artists do not receive the 20% affiliate commission simply because a client found or booked them through the Flying Dresses directory. Their directory relationship and any applicable referral/provider fee are handled separately.

Can I book makeup?

Yes. Our Slay My Face experience connects guests with makeup and beauty services. Makeup providers are separate specialists, so their service, pricing, timing and payment arrangements are handled directly with the provider.

Can I bring family or friends who are not participating?

Yes, subject to the rules and capacity of the selected location. Non-participating guests should follow all location and safety instructions and are responsible for their own transportation and personal belongings.

Can I book a birthday, honeymoon, girls trip, proposal or other special occasion?

Yes. The experience can be requested for birthdays, girls trips, honeymoons, anniversaries, proposals, bridal events, family vacations, content creation and other celebrations. Celebration styling, flowers, balloons and other add-ons may be available through curated providers.

What is the Horseback + Flying Dress experience?

It combines a flying-dress photoshoot with a guided horseback experience through an approved equestrian partner. The experience is designed around rider safety, horse welfare, beach or equestrian access, weather and the rules of the partner property. Horseback availability is location-specific and must be confirmed before the experience.

Where can I do horseback riding?

Horseback options are available through approved partner locations rather than automatically at every beach. Current partner possibilities include Half Moon / Rose Hall, Chukka Ocean Outpost in Sandy Bay and other approved equestrian arrangements. The exact riding route, duration, beach access, weight/height or riding-experience requirements, age limits and availability are determined by the equestrian partner and confirmed before booking.

Can the flying dress be used while riding the horse?

The dress can be incorporated into the photography experience only when the equestrian partner and our team determine that it is safe. A flowing dress, wind fan, posing and horse movement can create additional safety considerations. We will not ask a rider or horse to perform an unsafe pose or movement for a photograph.

What is the Flying Dress + River Experience?

It is a planned signature experience that brings the flying-dress concept onto a Jamaican river setting, combining flowing water, tropical scenery, movement and fashion photography. River availability, exact location, water conditions, access, transportation, vendor arrangements and pricing must be confirmed for the requested date. Because the river experience is location- and vendor-dependent, it should not be treated as automatically included in a standard beach package unless your confirmed booking specifically says so.

Is the river experience available now?

The river experience is being developed as a separate experience offering while the luxury raft production and operating details are finalized. Availability will depend on the confirmed river site, raft readiness, weather, water conditions, safety requirements and operating partners. Ask our team for current availability before making travel plans specifically for the river experience.

Can I combine horseback riding and the river experience?

A combined itinerary may be possible as a custom request, but it is not automatically included in either experience. We would need to confirm timing, locations, transportation, partner availability, safety requirements and any additional costs before accepting the itinerary.

What happens if the weather is bad?

Weather, wind, water, beach and site conditions can require an experience to be delayed, relocated, modified or cancelled. Safety comes first. Deposits are non-refundable unless weather conditions prevent the experience and/or the vendor cancels the reservation, subject to the booking terms communicated at reservation.

How much is the deposit?

A non-refundable US$59 deposit per person is required to secure a reservation unless a different amount is specifically stated for a particular service or booking. The remaining balance and payment timing are shown during the booking process or confirmed by our team.

What should I wear or bring?

Bring personal items you need for comfort, sunscreen and anything else appropriate for an outdoor Caribbean experience. Wear something easy to change out of and arrive ready for movement and photography. For horseback or river experiences, follow the additional clothing, footwear and safety guidance provided by the applicable partner.

How will I receive my photos?

Photography deliverables and delivery details depend on the package and service booked. Your confirmed booking will provide the applicable content and delivery information. Additional video, reels or other media may be available separately.

Are permits or location approvals required?

Some locations may require commercial-shoot approval, property permission, access fees or permits. Drone operations have additional airspace and authorization requirements. We check location requirements before confirming the experience and will not represent a location or drone flight as approved until the necessary permissions are confirmed.

What if I want a location outside Montego Bay?

You can request your own location. Locations outside the Montego Bay area may incur additional travel, access, permit and location costs. We will confirm applicable costs with you before finalizing the booking.

What if I need to cancel or change my booking?

Contact us as soon as possible. Changes are subject to availability and the terms attached to your reservation. Deposits are generally non-refundable except where the stated weather/vendor cancellation policy applies.

What about my personal belongings?

You are responsible for your money, phone, jewelry, clothing, luggage and other personal property during the experience. Do not leave valuables unattended. Our team and vendors are not responsible for loss, theft, damage or misplacement of personal belongings except where liability cannot legally be waived.

How can I ask a question before booking?

Message us on WhatsApp for help with dates, packages, dress options, locations, transportation, horseback riding, the river experience or other booking questions. We will confirm details that depend on current availability before you make plans.

READY TO FLY?

Choose your setting in Montego Bay or request a location that fits your vision, and let us turn your Jamaica vacation into a breathtaking fashion experience.

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Flying Dresses · Your Location