
Jessica Sifrig
She/HerBased in St. Petersburg, Florida
English
Trip budgets start at $500/night
Ask me about
My Story
Luxury travel, tailored to you.
Travel Style
Travel has always been my favorite way to celebrate life’s best moments, and now I get to help my clients do the same. I’m Jessica Sifrig, founder of Henry Travel Co., and I specialize in creating personalized luxury travel experiences throughout the Caribbean and beyond. From dreamy honeymoons and relaxing babymoons to milestone group trips and carefully curated itineraries, I love helping my clients turn their travel dreams into reality. My journey began by planning my own adventures and discovering the best resorts, hidden gems, and unforgettable experiences to share with family and friends. Today, I bring that same passion and attention to detail to every trip I design, ensuring you enjoy VIP perks, trusted recommendations, and a seamless planning process.
Reviews (23)
Stella R.
7 days ago
Jessica is was extremely helpful planning my husband and I’s honeymoon trip. She answered every question we had in a timely manner and was so easy to work with. We will definitely use her again to book our next trip as well as recommend her to others!
Molly G.
24 days ago
It was a little off-putting that I had to reach out a week out for tee time details when her original email stated she would. I almost forgot!
Amanda A.
2 months ago
Jessica made choosing our 20 year anniversary trip the easiest and least complicated process! In this world, there are five million things to choose from but she listened to the things that were important to us for this trip and gave us the best options to choose from. She highlighted the cost differences which made choosing so much easier! 10 out of 10 would recommend using Jessica and we will definitely be doing so as well!
Brianna S.
2 months ago
Booking with Jessica was great. I was slightly disappointed regarding the transportation accommodations and a slight miscommunication but overall I was happy with the reservation and additives.
Tisha J.
2 months ago
Our Travel Advisor, Jessica, was lovely to work with. She gave us several options to choose from, and shared a lot of helpful information about each resort. The day before our trip to Grenada, we learned our flight was cancelled due to snow in Atlanta and she helped us push the entire trip back one day so we wouldn't miss a day of our vacation. I recommend hiring Jessica! We will definitely be working with her again.
Stella R.
7 days ago
Jessica is was extremely helpful planning my husband and I’s honeymoon trip. She answered every question we had in a timely manner and was so easy to work with. We will definitely use her again to book our next trip as well as recommend her to others!
Molly G.
24 days ago
It was a little off-putting that I had to reach out a week out for tee time details when her original email stated she would. I almost forgot!
Amanda A.
2 months ago
Jessica made choosing our 20 year anniversary trip the easiest and least complicated process! In this world, there are five million things to choose from but she listened to the things that were important to us for this trip and gave us the best options to choose from. She highlighted the cost differences which made choosing so much easier! 10 out of 10 would recommend using Jessica and we will definitely be doing so as well!
Brianna S.
2 months ago
Booking with Jessica was great. I was slightly disappointed regarding the transportation accommodations and a slight miscommunication but overall I was happy with the reservation and additives.
Travel ideas (2)

Ski, Sip, Stay: Plan Your Perfect Breckenridge Getaway with This Expert Guide
Breckenridge, a quintessential mountain town in the Rockies, is one of the most popular ski destinations in the world. Known for its world-class skiing, the resort offers terrain for every level, from wide-open beginner runs to thrilling expert bowls. Off the slopes, the town comes alive with a vibrant après-ski scene, buzzing bars and cozy spots perfect for unwinding after a day in the snow. With breathtaking mountain views, award-winning restaurants and a lively Main Street brimming with history and character, it’s easy to see why Breckenridge is a must-visit for every skier and snowboarder’s bucket list!

Ski, Sip, Stay: Plan Your Perfect Breckenridge Getaway with This Expert Guide
Breckenridge, a quintessential mountain town in the Rockies, is one of the most popular ski destinations in the world. Known for its world-class skiing, the resort offers terrain for every level, from wide-open beginner runs to thrilling expert bowls. Off the slopes, the town comes alive with a vibrant après-ski scene, buzzing bars and cozy spots perfect for unwinding after a day in the snow. With breathtaking mountain views, award-winning restaurants and a lively Main Street brimming with history and character, it’s easy to see why Breckenridge is a must-visit for every skier and snowboarder’s bucket list!

Your Perfect Barcelona Getaway: A Three-Day Guide to Must-Sees and Insider Spots
Barcelona is a city full of life, where vibrant culture, rich history and modern energy come together. Whether you're exploring stunning Gothic architecture, enjoying delicious tapas or experiencing the buzzing nightlife at some of the best cocktail bars in the world, every moment here is unforgettable. On top of all that, Barcelona is incredibly easy to get to, with a major international airport that makes it the perfect starting point for exploring the rest of Spain. In this three-day guide, I’m sharing my favorite spots, insider tips and local secrets to help you fall in love with Barcelona.

Your Perfect Barcelona Getaway: A Three-Day Guide to Must-Sees and Insider Spots
Barcelona is a city full of life, where vibrant culture, rich history and modern energy come together. Whether you're exploring stunning Gothic architecture, enjoying delicious tapas or experiencing the buzzing nightlife at some of the best cocktail bars in the world, every moment here is unforgettable. On top of all that, Barcelona is incredibly easy to get to, with a major international airport that makes it the perfect starting point for exploring the rest of Spain. In this three-day guide, I’m sharing my favorite spots, insider tips and local secrets to help you fall in love with Barcelona.

Ski, Sip, Stay: Plan Your Perfect Breckenridge Getaway with This Expert Guide
Breckenridge, a quintessential mountain town in the Rockies, is one of the most popular ski destinations in the world. Known for its world-class skiing, the resort offers terrain for every level, from wide-open beginner runs to thrilling expert bowls. Off the slopes, the town comes alive with a vibrant après-ski scene, buzzing bars and cozy spots perfect for unwinding after a day in the snow. With breathtaking mountain views, award-winning restaurants and a lively Main Street brimming with history and character, it’s easy to see why Breckenridge is a must-visit for every skier and snowboarder’s bucket list!

Ski, Sip, Stay: Plan Your Perfect Breckenridge Getaway with This Expert Guide
Breckenridge, a quintessential mountain town in the Rockies, is one of the most popular ski destinations in the world. Known for its world-class skiing, the resort offers terrain for every level, from wide-open beginner runs to thrilling expert bowls. Off the slopes, the town comes alive with a vibrant après-ski scene, buzzing bars and cozy spots perfect for unwinding after a day in the snow. With breathtaking mountain views, award-winning restaurants and a lively Main Street brimming with history and character, it’s easy to see why Breckenridge is a must-visit for every skier and snowboarder’s bucket list!

Your Perfect Barcelona Getaway: A Three-Day Guide to Must-Sees and Insider Spots
Barcelona is a city full of life, where vibrant culture, rich history and modern energy come together. Whether you're exploring stunning Gothic architecture, enjoying delicious tapas or experiencing the buzzing nightlife at some of the best cocktail bars in the world, every moment here is unforgettable. On top of all that, Barcelona is incredibly easy to get to, with a major international airport that makes it the perfect starting point for exploring the rest of Spain. In this three-day guide, I’m sharing my favorite spots, insider tips and local secrets to help you fall in love with Barcelona.

Your Perfect Barcelona Getaway: A Three-Day Guide to Must-Sees and Insider Spots
Barcelona is a city full of life, where vibrant culture, rich history and modern energy come together. Whether you're exploring stunning Gothic architecture, enjoying delicious tapas or experiencing the buzzing nightlife at some of the best cocktail bars in the world, every moment here is unforgettable. On top of all that, Barcelona is incredibly easy to get to, with a major international airport that makes it the perfect starting point for exploring the rest of Spain. In this three-day guide, I’m sharing my favorite spots, insider tips and local secrets to help you fall in love with Barcelona.
Travel photos




