Stress-free planning for
YOUR BIG ISLAND ADVENTURE
Aloha, I’m Jen
I'm longtime Big Island resident, mom, concierge with a deep passion for helping people create once-in-a-lifetime vacations on this truly one-of-a-kind island. As Your Big Island Concierge, I offer helpful and personalized travel planning, itineraries, activities for your upcoming stay to the Big Island!
For over 20 years, I’ve called the Big Island home. Living here and working in the travel and tourism industry has given me a front-row seat to the magic this island holds and I’ve made it my mission to help visitors experience that same magic in their own unique way.
Planning the perfect trip can feel overwhelming, but that’s where I come in. With a background in life coaching, I naturally connect with people to understand their vision, their pace, and their travel style. I know how important these vacations are. Many people dream and plan for years to finally make it to Hawai‘i. Being part of that process is something I take to heart.
Over the past 7 years, I’ve worked as a concierge with top companies like Expedia, Hilton Grand Vacations and the Fairmont Orchid; Carefully matching guests with experiences that fit their needs and desires from relaxed beach days and local markets to helicopter tours, snorkeling with manta rays, lava viewing, and waterfall adventures and even 1-1 guided seaside meditations. By the end of their stay, many of my guests say the same thing: “That was the best trip we’ve ever had.”
Services I Offer
Whether you’re dreaming of swimming under waterfalls, hiking a lava field, tasting fresh island cuisine, or catching the sunset from Mauna Kea, I’d love to help you craft your perfect Big Island experience.
Grand Circle Island Tour
Explore the Big Island’s ecosystems, from rainforests to Kilauea’s active volcano, on this full-day guided tour. Visit a Kona coffee farm, waterfalls, Punalu’u beach, and spot sea turtles, all while learning about the island’s geology and wildlife. Lunch and transportation included; Private tours available.
Big island Travel Itinerary & Discovery Call
Uncover the best of the Big Island with a personalized daily itinerary designed for adventure and relaxation. Discover volcanic wonders, hidden beaches, lush rainforests, hikes and best dining experiences including unique experiences like coffee farm tours and stargazing under the Hawaiian skies.
Custom Big Island Itineraries
Your dream trip, planned with purpose and aloha.
Tired of generic travel guides?
The Big Island is special and you deserve to experience it without the overwhelm, decision fatigue, or hours of Googling.
I can help!
Whether you’re chasing waterfalls, looking for quiet beach days, or craving a little bit of everything, I’ll create a custom itinerary that reflects your unique rhythm, style, and vacation style.
How It Works
Tell me the kind of experience you want:
This helps me design your trip around your energy not just your dates.
Step 1: Choose Your vacation experience
Step 2: Share a Few Quick Details
Once you select your vibe, I’ll ask for a few more things like your travel dates, daily pace, budget, food preferences, and who’s coming with you. It’s short and sweet (because planning a trip should be fun, not frustrating).
Step 3: Pick Your Package & Pay
Itinerary Planning Packages
3 Days
Price $ 97
Ideal for a long weekend
5 Days
Price $ 147
Perfect for a full getaway
7 Days
Price $ 197
Our most popular option
10 Days
Price $ 267
Includes Local Tips & bonus Spots & dining Reservations
Custom Length
$30/day
Flexible option for Unique Trips​
Want help booking activities or restaurants?
Add concierge-style booking support for just
$25–$50 extra.
Step 4: Receive Your Personalized Itinerary
Once payment is complete:
• You’ll get a confirmation email with a summary of your answers.
• Your custom itinerary will be delivered within 5–7 business days.
• You can request a quick 15-minute call to go over anything.
Once payment is complete:
• You’ll get a confirmation email with a summary of your answers.
• Your custom itinerary will be delivered within 5–7 business days.
• You can request a quick 15-minute call to go over anything.
🌺 Personalized Paradise Starts Here
Let’s create your perfect trip—crafted with care and built for your joy.
From Dream to Departure – Let’s Make It Magical
“Planning a trip for a family of seven, including 5 adult children and 1 teenager, is no small feat, but Jennifer Connery made it feel effortless. She helped organize every detail of our family vacation to Kona, Hawaii, from suggesting and securing reservations at incredible restaurants to booking unforgettable excursions and suggesting hidden-gem day trips we would have never discovered on our own. Her knowledge of the island, along with her thoughtfulness and attention to detail, truly made this the best family trip we've ever had. Jennifer is smart, kind, and incredibly resourceful. I would wholeheartedly recommend her to anyone planning a trip to Kona or anywhere, really. She turned our vacation into an unforgettable experience.”
Berylin Schwab, New Jersey