Real couples. Real love. Epic destinations. All captured by you.
This is Love in Retreats - where we capture love in epic ways. From multi-day international retreats consisting of stunning locations to the storytelling styled moments featuring real couples to local excursions, luxury lodging, and a full immersive experience of bucket-list destinations.
Imagine your 2026 calendar booked out with weddings and elopements you thought you could only dream of.
And when a dream inquiry does pop up, your stomach drops. Because when they ask, “Can we see your destination portfolio?” … you don’t have it. *Cue the stress, the doubt, the “fake it til you make it” spiral.*
You’ve even offered to cover travel costs just to get the chance—and still, no bites.
You’re pouring hours into Instagram, tagging #destinationphotographer, shouting, “I’ll travel anywhere for love!”… but your inbox is crickets (even with offering allll the discounts!)
That plane ticket to your dream location? Still sitting in “add to cart” because the thought of going solo feels scary without support, a game plan, or a community to say “we got you, girl!”
You’re shooting beautiful weddings, but at the same venues on repeat—your creative spark is starting to dim.
Meanwhile…
Jetting off to bucket-list locations, capturing epic love stories, and finally feeling like you’re living that “pinch-me” career you’ve always wanted.
So, you Google “how to be a destination wedding photographer”...and what do you get? A vague list: market yourself, build a portfolio, network with the right people.
Cool… but what does that even look like in real life? You’re still lost, overwhelmed, and wondering if this dream is even possible.
Destination Wedding Photographer
The dream is…
You’ve always dreamt of traveling the world to capture all the romance, but it seems like a far-fetched dream. That was once me too...
The truth? Growth doesn’t happen by staying comfortable. It happens when you say yes—even when you’re scared. That’s why I created Love in Retreats: a space to step outside your comfort zone, connect with like-minded photographers, and experience the kind of transformative adventures that remind you why you picked up your camera in the first place.
I’ve walked this path. Now I want to guide you through it, so you can step into your own story with courage, clarity, and unforgettable experiences that shape not only your portfolio—but your life.
When I first started, imposter syndrome felt like my constant travel companion. The idea of photographing love in dream destinations sounded incredible, but also impossible.
Fast forward to today—I’ve photographed over 125 weddings (from traditional ceremonies to intimate elopements, wild adventures, and epic destination “I do’s”) and traveled to 17+ countries in the last 7 years with my camera in hand. Along the way, I’ve learned what works, what doesn’t, and what it truly takes to build confidence while chasing your photography dreams around the world.
hey friend, I’m kailee rose!
That’s exactly why Love in Retreats exists—to help you turn the “someday” dream into “let’s freaking do this.”
What you need is a supportive community, epic portfolio-building experiences in real dream destinations, and the confidence that comes from finally stepping outside your comfort zone.
You don’t need to hustle harder, discount yourself into the ground, or wait for some magical opportunity to fall into your lap.
The bottom line is…
And the best part? You’re not doing it alone. You’ve got a community of photographers who cheered you on, traveled with you, and get it. You finally feel supported, inspired, and part of something bigger.
Instead of feeling stuck shooting the same venues over and over, you’re traveling the world, inspired, and proud of the art you’re creating. Your confidence is magnetic.
Dream clients are sliding into your inbox—excited to book you for their destination day. They trust you, because they can see your experience. You’re no longer “hoping someone takes a chance”—you’re confidently showing up with proof of your worth.
You’re shooting real couples in epic destinations like Lake Como, Greece, or Bali—crafting the kind of storytelling galleries that instantly set you apart. No more faking it until you make it. You’ve got the real thing in your portfolio.
You wake up in a stunning villa overlooking a bucket-list location. The air feels electric—you’re not just traveling, you’re creating.
Imagine this…
Discover golden beaches, explore picturesque towns, and capture love against the Algarve’s breathtaking backdrop.
The south of Portugal awaits… all we need is YOU!
September 8-11, 2026
What we have planned…
Right in the beautiful town of Lagos, we have our own little oasis! A quaint private villa for us to have as our “home base” for the retreat. Perfect to relax, connect, have community time together by the fire, take a dip in the pool or hot tub, and cook in the kitchen if your heart desires! This villa, called the Tiny Whale Lodge has even been used to host weddings and elopements, so how special that we will make our own memories here.
3 Nights and 4 Days in a Beautiful Lodge
Each shoot is designed to feel like a real wedding day—getting ready, vows, portraits, and those intimate in-betweens that clients crave. You’ll walk away with more than epic photos—full storytelling galleries that prove your expertise.
And we’re not talking about just one shoot—you’ll photograph three different styled destination elopements over the course of the retreat, each crafted with a different couple, location, and story. Every detail—from the florals to the attire to the emotion—is designed to help you build a dynamic, high-end portfolio that screams experience, artistry, and trust. You won’t just learn how to capture love stories—you’ll learn how to create them.
3 Styled Destination Elopements
Because destination weddings are more than just one day. From a romantic sunrise beach walk to poolside fun and a dreamy picnic with a view—you’ll capture multi-day experiences that show future couples the true value of bringing you along.
What better way to create multi-day experiences than capturing your elopement couples the day before or after - think romantic picnic with a view, romantic morning on the beach, and poolside vibes. Destination weddings are more than a one day event, and having these sessions will help add to that portfolio for future clients to see the value in a true multi-day experience with you.
2 Casual Couple Sessions
You’ll see the most epic views of the south of Portugal on this boat tour, including Ponta de Piedade, as well as other stunning coastal views, cliffs, and rock formations. The perfect dreamy backdrop for an adventurous elopement ceremony.
Yes, it’s as dreamy as it sounds. Explore Portugal’s iconic cliffs, hidden caves, and turquoise waters while photographing an adventurous ceremony on the water. Bucket-list content, unlocked.
Private Boat Tour of the Algarve Coast
Boudoir and Wedding Photographer, Rachel Tenpenny, will be joining us throughout the retreat as an expert. With 10+ years of experience, she will be guiding us through a special getting-ready photo session with an extra fun twist - spicy and editorial vibes that adds creativity to the boring “normal” getting-ready photos. You’ll be confident in guiding your every day couples towards feeling spicy and beautiful on their day!
Special Guest: Rachel Tenpenny
Forget the stress of navigating a new country. We’ll take care of transportation to every shoot and retreat event so you can focus on creating and connecting.
Transportation during the Retreat
I will send you all the information you need in a downloadable PDF guide prior to the retreat. All the facts about the area, popular hikes, things to do (just in case you are extending your stay or to share with future couples!) as well as preparing for the trip with what to pack, how to get to the hotel, important international travel tips, and more.
Before you even pack your bags, you’ll get a downloadable guide filled with local tips, must-see spots, hikes, restaurants, and travel hacks—perfect for your trip and for impressing future clients.
South of Portugal Informational Guide
Traveling solo? Don’t stress. You’ll be plugged into our private group chat to connect, share ideas, and even plan adventures together before we ever touch down in Portugal.
Access to VIP Attendee Group Chat
From exploring the streets of Lagos to enjoying local cuisine, this retreat is about more than just photos. You’ll experience the heartbeat of Portugal while building memories that fuel your creativity with the built in time to explore!
Immersive Experience
Love in Retreats is about more than growing your wedding portfolio and expanding your knowledge about epic destinations. One of the best experiences you’ll receive is meeting other photographers in your shoes, getting to collaborate, create, and grow your community – not only in the professional wedding industry, but by making life long friends as well. You’ll make epic memories you simply can’t replace!
Love in Retreats isn’t just about stunning galleries—it’s about friendships, support, and a creative family that continues long after the retreat ends.
A Focus on Community & Collaboration
Not included: flights, transportation to/from the hotel, and meals
We know that social media is the secret weapon to reach your ideal clients. Any videos captured by me and my team will be shared on the cloud so you can make content highlighting your expertise and travels from the retreat. This is gold for your socials—because showing the world you’re out there doing the work is half the battle when it comes to booking dream clients.
Content Cloud
Provided by yours truly, you’ll also get updated branding photos of yourself in an epic destination setting—perfect for showing your clients that you are a destination photographer.
Professional Destination Headshots
This is the transformation waiting for you inside Love in Retreats.
Not just beautiful images (though you’ll get plenty)—but the confidence, community, and experience you need to book destination weddings with ease.
The world is wide open. Your portfolio, your confidence, your dream career—it all starts here.
Love in Retreats offers multi-day international destination retreats for photographers consisting of stunning locations, elopement-styled content shoots with real couples, local excursions, luxury lodging, and immersive experience of the local culture.
September 8-11, 2026
Because at the end of the day, this retreat isn’t about me—it’s about you stepping into your dream. I’m just here to light the path.
You won’t just be getting beautiful photos for your portfolio—you’ll have a leader who can guide you, cheer you on, and create a safe space for you to step into the photographer you’re meant to be.
This is the same energy I’ll bring to Love in Retreats.
Culture, cuisine, adventure, and community that will fuel your creativity long after the retreat ends.
Immersive experiences & unforgettable memories
Build your brand, show off your expertise, and grow your social presence effortlessly.
Content Cloud
What’s better than headshots in epic locations to show you truly are what you’ve always dreamed: a destination photographer!
Professional headshots
Connect, collaborate, and make friends with other photographers before you even arrive.
Access to the VIP attendee group chat
Everything you need to know about the area, from local excursions to packing tips, so you feel fully prepared.
South of Portugal informational guide
No stress, no logistics, just show up and create.
All transportation during the retreat
Bringing spicy and editorial vibes to bridal getting ready moments.
Special guest speaker, Rachel Tenpenny
Epic views, unique content, and memories you’ll never forget.
Private boat tour of the Algarve Coast
Your home base for rest, connection, and inspiration.
3 nights / 4 days in luxury local lodgine
Realistic, storytelling shoots that give you the portfolio you need to book dream clients.
Three multi-day destination “elopement-styled” weddings in the Algarve, Portugal
What You’re Really Investing In:
All of this—luxury accommodations, private boat tour, curated multi-day shoots, transportation, VIP community access, and expert guidance—is included in one all-inclusive experience designed to set your destination wedding career on fire.
When you break it down, what you’re getting is way more than just a retreat. You’re walking away with:
Spots are limited to the first five photographers, so if this sounds like your kind of adventure, don’t wait!
Create unforgettable memories—and images—that you simply can’t get anywhere else.
Experience a popular destination in a private, exclusive way.
Add one-of-a-kind content to your portfolio that will wow future elopement couples.
The first five photographers to secure their spot will be invited on an exclusive bonus excursion to the stunning Benagil Caves.
Imagine capturing a couple for an adventurous swim shoot in one of Portugal’s most iconic, bucket-list-worthy locations. The cave’s dramatic cliffs and turquoise waters create a shoot that feels epic, intimate, and truly unique.
This is your chance to:
5 Photographers will get the Epic Couple Swim Session – you can be one of them!
Who Doesn’t Love a Bonus?!
Hit that waitlist button and stay in the know on the launch!
Step 1 – Join the Waitlist!
Applications are open! Apply for your spot and tell me about your photography dreams. This helps us make sure this retreat is the perfect fit for you. Be one of the first to get access to the exclusive bonus shoot!
Step 2 – Applications Open
I’ll check out your application and send you an email letting you know… you’re in! 🎉
Step 3 – Review & Accept
Once accepted, you’ll have 24 hours to sign your contract and make your first payment. Do it fast—spots are limited, and we want you on this adventure!
Step 4 – Lock It In
Cue confetti! Your spot is secured, your portfolio adventure is ready to begin, and I can’t wait to create memories, content, and epic experiences with you.
Step 5 – It’s Official!
How you can go from “I want in” to your spot officially secured!
Let’s break it down…
Let me ease your worries…
How do I sign up for the retreat?
If tickets are available, apply for the retreat. If tickets are sold-out, put your info on the waitlist. If you are accepted, you’ll receive an email with the contract & invoice for the first payment. The contract must be signed & invoice paid within 24 hours of receiving to secure your spot.
How do I sign up for the retreat?
What airport should I fly into?
The closest international airport I suggest is Humberto Delgado Airport in Lisbon, Portugal.
What airport should I fly into?
Is transportation provided to/from the airport?
Transportation is not provided from the airport. Transportation is only provided during the retreat to get us to/from shoots. You’ll have to travel via car or bus after to get to…. You will also be able to use the VIP Group to carpool with other attendees!
Is transportation provided to/from the airport?
Will meals be included?
No. I want this to be an immersive experience that encourages you to get out in the city and try local cuisine! Don’t worry - I will provide restaurant recommendations!
Will meals be included?
I’m new to photography. Is this for me?
Yes! Anyone's level of expertise is welcome to attend!
As long as you’re comfortable with your camera and excited to learn, this retreat is perfect for newer photographers.
You’ll get tons of guidance, support, and hands-on experience — plus leave with a portfolio that actually helps you start booking dream clients. It’s all about growth, connection, and creating at your own pace. You've got this!
I’m new to photography. Is this for me?
What if I have never traveled internationally before? Can I still attend? Is this for me?
Yes absolutely! You will need to make sure you have all your travel documents arranged prior to the retreat, mainly your passport. Follow the guidelines on the US Department of State’s website on how to prepare and apply for a passport. Keep in mind, passports can take 4-6+ weeks to arrive and you must have it before purchasing your flights as well.
If you have your passport but haven’t traveled internationally before, don’t worry! Once your spot is secured, I will share an informational guide to help prepare you and connect you with other attendees incase you want to coordinate carpools/travel schedules!
What if I have never traveled internationally before? Can I still attend? Is this for me?
What are the shooting group sizes like?
Whenever possible, every time we shoot, there will be 2 couples present so that we can break into 2 separate shooting groups, making them smaller and more intimate! Styled shooting etiquette is briefed during the welcome and it’s important to me that everyone is kind, gets equal shooting time, and works together as a team!
What are the shooting group sizes like?
What happens if I can’t attend?
You can sell your ticket to another interested attendee! All previous paid payments will be transferred to you from the new attendee, and they will take over all future payments! If you can no longer attend, email me and I can guide you on selling as well as help share!
What happens if I can’t attend?
When are the payments due?
Payment dates are dependent on which payment plan you choose. Payments are evenly spread out between signing up & 30 days prior to the retreat.
When are the payments due?
What happens after I sign up?
As soon as your spot is secured, you’ll receive the informational guide to the area, access to the VIP attendee group as well as emails leading up to the retreat with all the updated information and schedules.
What happens after I sign up?
Can I book a non-lodging ticket & still attend the styled shoots & other parts of the retreat?
Yes! If you prefer to lodge elsewhere (or are traveling with your partner/family) or simply don’t need to stay overnight with us, you can book a discounted ticket without lodging per request.
Can I book a non-lodging ticket & still attend the styled shoots & other parts of the retreat?
How can I get in contact with you?
Please email me at kailee@kaileerose.com, and I’d be happy to answer any more questions!
How can I get in contact with you?
Luxury accommodations, curated shoots, transportation, and expert guidance.
Everything is taken care of
Portfolio-ready images, travel content, and confidence to book dream clients anywhere.
You’ll gain real experience
A supportive community of photographers and expert mentors are here to guide you every step.
You’re not alone
Spots are exclusive, and early-bird bonuses won’t last.
The opportunity is limited
You’ve dreamed of destination weddings, epic shoots, and travel that transforms your portfolio—and this is your chance.
Let’s Make This Happen
© 2018-2025 Kailee Rose Photo
Here’s what people who’ve worked with me say:
Because this isn’t my first rodeo. I’ve guided over 125 couples through some of the most important moments of their lives—and every single time, I’ve shown up with the same energy I’ll bring to this retreat: calm, organized, flexible, and 100% invested in making sure you feel supported and empowered.
So, why me?
You’re not just signing up for a styled shoot. You’re trusting someone to guide you through an experience that pushes you out of your comfort zone, grows your confidence, and helps you create the kind of work that transforms your business.
Let’s be real—