Hi, I’m Jessi Boynton!
I create immersive, experience-driven adventures for travelers who want to go far beyond the surface and truly understand the places they visit.
From national parks, city deep dives, and glamping adventures to extraordinary honeymoons, cultural events, food discoveries, and once-in-a-lifetime natural phenomena, I’ll help you build the kind of trip you’ll reminisce about for decades.
About Me
You don’t simply visit a destination. You experience it.
I’m based in the vibrant beach town of New Smyrna Beach, Florida, and my travel style centers on exploring nature, seeking out hidden food gems, and absorbing the rhythm of local life.
My professional background has taken me around the world. I’ve spent 20 years as a hotel, home, and apparel designer, more than a decade organizing adventure-focused social clubs, over 20 years touring domestically and internationally as a professional dancer, and more than seven years mixing cocktails for fun.
That whirlwind career sparked my love of hospitality and travel early. It also taught me to notice the details most travelers miss: how a hotel is designed, how an itinerary flows, what makes an experience feel effortless, and which moments transform a vacation into a story you’ll tell forever.
My wife, Ashley, is my adventure partner for life. Whether we’re exploring a national park, tracking down an unforgettable meal, or standing in the middle of an atmospheric river on our wedding day, no seat is better than the one next to her.
Quick Snapshot
What I love to plan
- ✔Adventure-rich North American city dossiers
- ✔National parks, nature, wildlife, and outdoor exploration
- ✔Extraordinary honeymoons and romantic adventures
- ✔Europe by backpack, boutique stay, or elevated glamping
- ✔Concerts, museums, fine arts, architecture, and cultural events
- ✔Food-focused itineraries and hidden local gems
By the Numbers
A lifetime of creativity, hospitality, and adventure brought to every trip.
My Approach
Boots on the ground. Research in hand. Adventure dialed all the way up.
I love creating travel dossiers grounded in experiences I’ve tried and tested myself—or that come exceptionally well recommended, researched, and reviewed.
Bring the Energy
I genuinely light up when learning what you’re imagining. Your ideas become the creative spark for the entire trip.
Make It Crystal Clear
My clients love my ultra-clean, easy-to-follow itineraries that make even complex adventures feel manageable.
Research Deeply
I look beyond the obvious choices to find the experiences, neighborhoods, flavors, and details that give a trip its personality.
Build in Buffers
Thoughtful breathing room keeps travel calm and creates space for rest, lingering meals, and unplanned discoveries.
How I Can Help
What kind of adventure are you ready to remember forever?
I build layered trips that combine the things you already love with the places, experiences, and unexpected discoveries you may never have found on your own.
North American City Dossiers
Go beyond a generic weekend guide with a tried-and-tested mix of neighborhoods, music, food, architecture, art, and local experiences.
National Parks & Nature
Build an adventure around dramatic landscapes, wildlife, hiking, glamping, scenic drives, and the natural events worth traveling to see.
Extraordinary Honeymoons
Celebrate somewhere unforgettable—from the Azores to the Maldives—with romance, adventure, and meaningful shared experiences.
Arts, Music & Culture
Let concerts, museums, historic architecture, performances, and once-in-a-lifetime cultural events become the anchor of your itinerary.
Food-Driven Travel
Find the restaurant worth flying in early for, the local specialty you’ll never stop talking about, and the hidden places that define a destination.
Backpacking to Glamping
Explore Europe, North America, or South America with the right balance of movement, comfort, creativity, and immersion for your travel style.
My Travel Style
Explore nature. Find the food. Feel the local rhythm.
I’m not the kind of traveler who stays in one place for the entire trip. I want to see what’s around the corner, what’s off the map, and what most people miss.
Favorite Destination
Costa Rica
The unparalleled beauty of its biodiversity and the warmth of its people feel healing, refreshing, and endearing all at once.
I Could Return Again and Again
Portugal
Its history, architecture, and the wild beauty of the Azores continually inspire me. Every visit feels like I’ve only scratched the surface.
Favorite Hotel Experience
The Fairmont San Francisco
Its one-of-a-kind, overstated elegance and refined whimsy—cultivated through generations of historic preservation—make it unforgettable.
A Travel Story I’ll Never Forget
An atmospheric river, a rainforest elopement, and one elk witness.
In 2024, my wife and I eloped in Washington’s Hoh Rainforest in the middle of a deluge caused by an atmospheric river.
It was dramatic, wildly beautiful, completely soaked, and somehow made even more surreal when an elk stood nearby as our unexpected wedding witness.
That day captured everything I love about travel: extraordinary nature, a little chaos, an unforgettable story, and the person I most want beside me for every adventure.
Travel Personality
A few quick things to know about the way I travel.
Next Dream Vacation
A few unforgettable weeks exploring Greece.
I’m dreaming of Santorini wineries, volcanic-caldera hot tubs with life-changing views, and tracking down the famous manakriti mushrooms at a vegan restaurant in Chania.
In Crete, I want to swim in the protected blue-green cove of Seitan Limania, explore the caves around Agia Triada and Gouverneto, buy olive oil from local monks, and visit Elafonissi.
Then I’d finish in Rhodes, surrounded by the fascinating blend of Ottoman, Byzantine, and Hellenistic architecture—castles, mosques, ancient temple ruins, and cosmopolitan energy all sharing one extraordinary cityscape.
Jessi’s Don’t-Miss Recommendation
Fly into Denver early—and go directly to Pit Fiend Barbecue.
This tiny Dungeons & Dragons-themed smokehouse in Denver’s RiNo Art District serves what I consider the best brisket of your life.
They make their own sauces, and the live-fire, all-natural smoker sitting out front is bigger than the restaurant itself. It is also exceptionally friendly for travelers managing food allergies.
Go early, because they sell out. This is exactly the kind of memorable, highly specific local experience I love building into a trip.
Who I Work Best With
We might be a perfect fit if you want to truly know a place.
My ideal clients want to immerse themselves in the food, fine arts, architecture, nature, music, history, and everyday life of the destinations they visit.
We’ll probably work beautifully together if...
- ✔You want a vacation that feels like a deep dive rather than a surface-level visit.
- ✔You get excited about nature, local food, architecture, art, music, and hidden gems.
- ✔You want your itinerary to combine planned highlights with room for spontaneous exploration.
- ✔You appreciate creative ideas, extensive research, and a clean itinerary that is easy to follow.
- ✔You want to anchor a trip around a concert, natural phenomenon, cultural event, or major milestone.
- ✔You want a long-term advisor who will continue learning the way you love to travel.
We may not be the right fit if...
- ✕You want to remain inside an all-inclusive resort for the entire vacation.
- ✕You have no interest in exploring what exists beyond the most obvious tourist attractions.
- ✕You want a generic, pre-built itinerary that could belong to anyone.
- ✕You prefer a schedule packed so tightly that there is no room to rest, linger, or discover something unexpected.
Ready When You Are
Let’s plan a trip you’ll still be talking about twenty years from now.
Whether you’re dreaming about a national-park adventure, a city deep dive, a spectacular honeymoon, an unforgettable natural event, or a trip built around the food, music, art, and culture you love, I’m ready to help you experience it fully.