James & Caitlin’s Surprise Proposal, Resort at Longboat Key Club, Longboat Key, FL

Man proposing on longboat key beach during sunset photographed by Juliana Montane Photography

Engagements & Proposals

Sarasota Sunset Surprise Proposal

There’s something undeniably magical about a sunset beach proposal. The sky painted in hues of orange and pink, the gentle sound of waves lapping against the shore, and two hearts beating in anticipation of a life-changing moment. When James decided to ask Caitlin—his high school sweetheart of ten years—to marry him, he knew the setting had to be nothing short of spectacular. And what better backdrop than the stunning shores of Longboat Key during golden hour?

High School Sweethearts

Some love stories are written in the stars long before we realize it. James and Caitlin’s journey began in the hallways of their high school, where stolen glances eventually led to a first date that would mark the beginning of their decade-long adventure together. Through college, career changes, and all of life’s ups and downs, their bond only strengthened with time.

As their 10th anniversary approached, James knew this milestone deserved a celebration that would honor their past while embracing their future. A Sarasota sunset surprise proposal seemed like the perfect way to begin the next chapter of their love story.

Planning the Perfect Sarasota Sunset Surprise Proposal

Planning a surprise proposal is no small feat—especially when you’re trying to keep it secret from someone who knows you better than anyone else! James reached out to me weeks in advance, sharing his vision for a sunset beach proposal that would take Caitlin’s breath away.

Together, we crafted a plan that would unfold seamlessly at the Resort at Longboat Key Club—a luxurious escape nestled along the Gulf Coast that offers the perfect blend of elegance and natural beauty. With its pristine white-sand beaches and unobstructed views of the Gulf of Mexico, this location provides an idyllic setting for couples looking to create unforgettable memories.

James chose a secluded spot on the beach where I could discreetly position myself to capture every emotion of their special moment. We coordinated timing down to the minute, ensuring we’d catch that perfect golden glow as the sun began its descent into the horizon.

Captured in Golden Light

On the evening of their anniversary, James suggested a “casual” sunset stroll along the beach. Little did Caitlin know that this walk would change everything. As they made their way down the shoreline, the Resort at Longboat Key Club provided a stunning backdrop with its tropical landscaping and elegant architecture peeking through the palm trees.

When they reached our predetermined spot, James gently took Caitlin’s hands in his. The look of surprise that washed over her face when he dropped to one knee was absolutely priceless—a mixture of shock, joy, and overwhelming love that I was privileged to capture through my lens.

Her “yes” was immediate and emotional—a moment of pure, unfiltered joy that exemplifies why I’m so passionate about planning a surprise proposal photography.

Why The Resort at Longboat Key Club

The Resort at Longboat Key Club isn’t just another beachfront property—it’s a destination that elevates any romantic occasion. With 223 spacious accommodations adorned in relaxed tropical decor, couples can extend their proposal experience into a romantic getaway.

What makes this venue particularly special for a Longboat Key proposal is its versatility. The resort boasts over 33,000 square feet of customizable event space, a celebrated full-service spa, and amenities that allow couples to celebrate their engagement in style—whether that means a romantic dinner at one of their exceptional restaurants or a champagne toast by the pool.

For photographers like me who specialize in capturing love stories, the location offers endless creative possibilities. From the pristine beach to the lush landscaping, every corner of this resort provides a stunning canvas for immortalizing these life-changing moments.

Planning Your Own Sarasota Sunset Surprise Proposal

Inspired to create your own magical proposal moment on the shores of Sarasota or Longboat Key? Here are some tips I’ve gathered from helping countless couples plan their perfect surprise:

  • Consider the timing carefully—the “golden hour” before sunset offers the most flattering natural light for photos
  • Scout your location in advance to find the perfect spot away from crowds
  • Have a “Plan B” in case of weather changes (the Resort at Longboat Key Club offers beautiful indoor spaces as backup)
  • Consider how you’ll get your partner to the location without raising suspicion
  • Communicate your vision clearly with your photographer so they can position themselves discreetly
  • Be present in the moment—the photos will capture everything, so focus on your partner and the emotions you’re sharing

Remember that the most beautiful proposals aren’t necessarily the most elaborate ones—they’re the ones filled with genuine emotion and personal significance. Whether you’re high school sweethearts like James and Caitlin or you’ve found love later in life, your story deserves to be celebrated and captured in a way that honors your unique journey.

Book Your Sarasota Sunset Surprise Proposal

There’s something profoundly beautiful about beginning your engagement journey against the backdrop of a Sarasota sunset. The moment you ask that life-changing question deserves to be documented with the same care and artistry as your wedding day.

Whether you’re planning a Longboat Key proposal, a sunset beach proposal elsewhere in Sarasota, or even a destination proposal, I’d be honored to help you plan and preserve this milestone moment. Ready to plan your own breathtaking Sarasota sunset surprise proposal? Let’s create a moment as unique and beautiful as your love story. Reach out today, and let’s start planning a proposal that will take their breath away—just like James did for Caitlin on their unforgettable anniversary.