THE BEST TIME TO TRAVEL TO THE CARIBBEAN
One question my clients frequently ask is, "When is the best time to travel to _____?" As a professional travel agent who specializes in...
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Endless Adventures Travel
THE WORLD IS WAITING
I curate travel itineraries with concierge service for clients and families of all types. Whether you need a mom's getaway, have a blended family, special needs considerations, or friends who are like family, I create vacations full of Beyond the Bucket List experiences with treasured memories for years to come.
PERSONALIZED ITINERARIES
TAKE BACK YOUR TIME
PROFESSIONAL NETWORK
Your life is busy enough already...
Between juggling a career, swimming lessons for the kids, and getting a healthy meal on the table each night, you're stretched thin and time is precious.
Pulling together all the details for a great trip can be overwhelming, even for people who enjoy the planning process.
Which resort has the best spa services? Which cruise line will take you beyond the typical ports and into quaint European villages? Does your child with special needs qualify for a Disability Access Pass at Disney (and what does that even mean)?
You want someone who has the expertise AND the connections to make your dream vacation a reality.
Let me collaborate with you on a vacation that lets your entire family or favorite travel partners experience the world in a new way, with the relief of knowing that a professional travel advisor will be supporting you every step of the way.
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Let's keep in touch...
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I love sharing inspiring itineraries, my clients' favorite destinations (or up and coming hot spots) and amazing experiences.
Your next Instagram-worthy moment may be closer than you think!
What You Get When You Work with a Professional Travel Planner (me!)...
HIGHLY CUSTOMIZED ITINERARIES
There's a vacation for everyone, but not every vacation is for everyone.
My focus is matching the right vacation to your travel style.
Whether you're a serious foodie, history buff, literary geek, or adventurous family, I've developed local contacts to offer the type of authentic experiences most travelers never even know about.
YOUR TIME IS VALUABLE
Have you ever heard the phrase "Time is money?"
My clients don't like wasting either, which is why I take a comprehensive approach to travel planning.
I'll guide you through all the details, from creating the itinerary to booking accommodations, flights, ground transfers, guided tours, and travel insurance - with complete transparency.
A NETWORK OF PROFESSIONALS
Business is all about who you know.
I've built relationships with some of the best known and most respected travel brands in the world. These industry partners offer the ability to access exclusive amenities or additional guest privileges.
Should the unexpected occur, I have direct contact with a team of trusted professionals ready to support you.
Before I was a professional travel advisor, I felt just like you...
After over 20 years planning vacations for family and friends, I started my own travel agency because I wanted to help other families (like mine, with Autism and ADHD) build lifelong memories.
And, for every client, I wanted to do more - create trips that weren't just about checking marks off a bucket list, but diving deep into the culture, history, and experiences that make a destination truly special.
That's where a professional travel advisor comes in. I have planned hundreds of successful trips, from cruises, theme parks, and all-inclusive resorts to self-drive tours through Canada and Alaska.
In addition to finding the best accommodations for your lifestyle, I can book safe and reliable transportation, dining reservations, and unique experiences.
My extensive customer service and event planning background drive me to deliver the VIP extras that make travel special, like room upgrades, celebration surprises, and more.
FAMILY TRAVEL
You're not an average family - you're a single mom, a mega-family, grandparents suddenly raising young children again, or someone you love has special needs. Every family deserves to experience travel that is extraordinary for their lifestyle and preferred financial investment. For large family gatherings, such as reunions or celebration travel, I can plan the perfect vacation even your in-laws can't complain about.
GIRLS GETAWAYS
Whether you live just across town or 1000 miles away, a girls getaway brings everyone together again. From bachelorette parties in the Riviera Maya to 50th birthdays in California Wine Country (and everything in between), it all begins with a plan. Let me coordinate all the details while you sit back with a smile and watch them flawlessly delivered.
COUPLES ESCAPES
When it's time to reconnect with your partner, let me do the work while you focus on each other. Is your idea of romance an overwater bungalow with couples massages and the highest quality champagne? Or, are you an adventurous couple who would rather explore ancient ruins before trying out the best local brew? Either way, there's an itinerary perfect for you.
I specialize in...
Services
Hey there!
I'm Jen Gillespie - solo mom of two, lover of all cheese, Swiftie, and owner of Endless Adventures Travel.
I know you want that incredible feeling of sharing once-in-a-lifetime moments with loved ones, to marvel at the beauty of places you've only ever seen in pictures, and to cast your worries aside... at least, for a little while.
I understand, because I want the same things.
My favorite trips are the ones I spend with my children and those I love. We've snorkeled in St. Thomas, explored monuments and museums in Washington D.C., cruised the Caribbean, and marveled at the magic of Disney. I've loved experiencing the Christmas markets in Germany, celebrating turning 40 on a girls cruise, and soaking up the beauty of Paris.
From a weekend adventure to a global journey, I'll help you go from just saving Instagram photos of dream destinations to actually experiencing them.
What it's like to have your vacation planning done for you...
– STEP 1 –
SCHEDULE A QUICK HELLO
We'll initially connect with a quick, 15-minute chat. This is a great chance to introduce ourselves and for you to share your travel plans. I'll explain my services, what you can expect from me, and Professional Travel Planning Fee.
– STEP 2 –
TIME TO PLAN YOUR TRIP
After our quick hello, we'll need a full planning meeting. We're going to dive deeper into your expectations for your upcoming trip. I want to know about favorite past vacations, what you're passionate about, and even the things you absolutely can't stand.
– STEP 3 –
ITINERARY PRESENTATION
Once I have a clear picture of your travel goals, I'll research, meticulously plan, and create a itinerary full of recommendations that match your unique lifestyle and travel preferences with my industry experience.
– STEP 4 –
BOOK & TRAVEL WITH CONFIDENCE
In this stage, I confirm the travel details & begin the booking process. Your travel documents will be delivered electronically, and I'll stay in touch before, during, and after your travel to assist in any way. All you have to do is enjoy.
ABOUT
Take a peek at some of the dreamworthy destinations I send my clients to...
Get Inspired For Your Next Trip...
TESTIMONIALS
What my clients are saying...
Nothing makes me happier than catching up with my clients after they return home. Seeing their beautiful pictures and knowing they had the trip of their dreams drives me to continue developing my professional skills in the travel industry.
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