Jenna Casper
She/Her
Based in Charlotte
Jenna Casper
Ask me about
My Story
I’m a mom of two young girls and I am passionate about seeing the world and sharing this passion with my daughters. Family travel is so important to me, but so is a romantic getaway with my husband, or a girls’ trip with my besties. Traveling is multi-faceted. There’s a time for luxury and romance on the Italian coast, a time for experiencing culture and showing your children the world in Costa Rica, and also a time for cocktails and giggles with the girls on St. John. If any of these trips sound up your alley (or maybe all three do), I’m the advisor for you. Let’s chat!
Travel Style
My travel style includes a specific itinerary, but not a packed one. We are sure to hit the must-see spots, some lesser-known hidden gems, but also leave time for discovery. Some of the best memories are the unexpected ones, so we always leave room for a destination to surprise us. That does not mean unprepared though. We always have a clear vision of how to best experience a place.
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Reviews (7)
Erica B.
17 days ago
Jenna is a ROCKSTAR and we could not have done this trip without her! I really appreciated her taking initiative and keeping the planning-ball rolling even when I was swamped at work and slow to respond. She took the time to learn about our preferences and travel-vibe and curated an amazing itinerary - all of her recommendations were top notch! She booked all of our accommodations, transfers and excursions (food tour, cooking class, Pompeii tour, Coliseum tour) and everything went so smoothly, no issues at all. Also shout out to the Fora app - so helpful to have everything for our itinerary in one place to reference (even when we didn't have WiFi!)
2 months ago
Jenna was an absolute gem to work with when planning this 40th bday couples trip. The best travel agent ever. She was clear with communication and followed through on all tasks and requests and went above and beyond, even finding a rare catamaran excursion that was on our wish list. She got us a steal on quality airport transfer to hotel and we could not be more thankful for her making this trip so seamless. Will be asking her to book all our trips in the future!
Ashley S.
2 months ago
Working with Jenna was a total game-changer for our trip! From the very first planning session, it was clear she wasn’t just booking a vacation—she was crafting an experience.
She took the stress out of every single detail, from finding the perfect boutique hotel to snagging reservations for a food tour we never would have found on our own. Jenna has an incredible eye for detail and a knack for knowing exactly what kind of vibe we were looking for.
What really stood out was how seamless everything felt. We didn’t have to worry about a thing; we just showed up and enjoyed. If you want a trip that feels personal, polished, and perfectly executed, Jenna is the person to call. We’re already looking forward to having her plan our next adventure!
Rachael M.
2 months ago
Jenna listened to all of my feedback and worked with us to find a location for our trip that was very specific to us. She gave lots of options in various price ranges, all staying within the budget I gave her. She was very responsive anytime I had questions and went above and beyond in every aspect! I will definitely use her for our next trip!
Melissa B.
3 months ago
Jenna planned the perfect little girls trip for us to Riviera Maya this month and it truly couldn’t have been easier! She listened to what we wanted out of the trip and presented options that fit our vibe and our budget perfectly.
She handled everything from narrowing down locations to booking and coordinating airport transfers, which saved us hours of research. I definitely struggle with decision paralysis when there are too many options, so having her guidance was exactly what I needed!
We had the best time and it was exactly what we hoped for. I’m already looking forward to using Jenna again for future trips with my husband and family! Highly recommend her if you want a seamless, stress-free experience!
Erica B.
17 days ago
Jenna is a ROCKSTAR and we could not have done this trip without her! I really appreciated her taking initiative and keeping the planning-ball rolling even when I was swamped at work and slow to respond. She took the time to learn about our preferences and travel-vibe and curated an amazing itinerary - all of her recommendations were top notch! She booked all of our accommodations, transfers and excursions (food tour, cooking class, Pompeii tour, Coliseum tour) and everything went so smoothly, no issues at all. Also shout out to the Fora app - so helpful to have everything for our itinerary in one place to reference (even when we didn't have WiFi!)
2 months ago
Jenna was an absolute gem to work with when planning this 40th bday couples trip. The best travel agent ever. She was clear with communication and followed through on all tasks and requests and went above and beyond, even finding a rare catamaran excursion that was on our wish list. She got us a steal on quality airport transfer to hotel and we could not be more thankful for her making this trip so seamless. Will be asking her to book all our trips in the future!
Ashley S.
2 months ago
Working with Jenna was a total game-changer for our trip! From the very first planning session, it was clear she wasn’t just booking a vacation—she was crafting an experience.
She took the stress out of every single detail, from finding the perfect boutique hotel to snagging reservations for a food tour we never would have found on our own. Jenna has an incredible eye for detail and a knack for knowing exactly what kind of vibe we were looking for.
What really stood out was how seamless everything felt. We didn’t have to worry about a thing; we just showed up and enjoyed. If you want a trip that feels personal, polished, and perfectly executed, Jenna is the person to call. We’re already looking forward to having her plan our next adventure!
Rachael M.
2 months ago
Jenna listened to all of my feedback and worked with us to find a location for our trip that was very specific to us. She gave lots of options in various price ranges, all staying within the budget I gave her. She was very responsive anytime I had questions and went above and beyond in every aspect! I will definitely use her for our next trip!
Travel ideas (2)
Outer Banks Travel Guide: Choosing the Right Town for Your Trip
The Outer Banks has always been deeply personal to me. My dad, an avid surfer, and my mom, a devoted beach lover, built a house on Cape Hatteras when she was pregnant with me—on a street known for some of the best waves on the East Coast, a reputation it still holds today. I’ve spent 37 summers there since, falling in love with every mile of the National Seashore. For the past 15 summers, I’ve shared it with my husband, with our wedding in nearby Avon, and over the past five, I’ve watched my daughters fall in love with it, too. Now I’m raising the next generation of beach lovers there—drawn to nothing but surf, sand, and seclusion.
Outer Banks Travel Guide: Choosing the Right Town for Your Trip
The Outer Banks has always been deeply personal to me. My dad, an avid surfer, and my mom, a devoted beach lover, built a house on Cape Hatteras when she was pregnant with me—on a street known for some of the best waves on the East Coast, a reputation it still holds today. I’ve spent 37 summers there since, falling in love with every mile of the National Seashore. For the past 15 summers, I’ve shared it with my husband, with our wedding in nearby Avon, and over the past five, I’ve watched my daughters fall in love with it, too. Now I’m raising the next generation of beach lovers there—drawn to nothing but surf, sand, and seclusion.
Barefoot Luxury in Anguilla
Anguilla will always have a special place in my heart, as it's where I had the honor of standing beside my college best friend on her wedding day, right on the beach at Meads Bay in front of Straw Hat. From that moment on, I fell in love with the island’s easygoing rhythm. It's the kind that invites you to slow down and settle in. The beaches feel untouched, stretching effortlessly along the coast, and the beach bars, warm people, and iconic views make it all feel both simple and unforgettable. It’s that rare balance of upscale luxury that still feels accessible. It's refined, but never pretentious. I still think about sunsets from the lounge at the Four Seasons—those golden, quiet moments that seem to linger a little longer there. In Anguilla, rum punch is the house wine, time feels irrelevant, and the only thing you’re meant to feel is a sense of complete ease.
Barefoot Luxury in Anguilla
Anguilla will always have a special place in my heart, as it's where I had the honor of standing beside my college best friend on her wedding day, right on the beach at Meads Bay in front of Straw Hat. From that moment on, I fell in love with the island’s easygoing rhythm. It's the kind that invites you to slow down and settle in. The beaches feel untouched, stretching effortlessly along the coast, and the beach bars, warm people, and iconic views make it all feel both simple and unforgettable. It’s that rare balance of upscale luxury that still feels accessible. It's refined, but never pretentious. I still think about sunsets from the lounge at the Four Seasons—those golden, quiet moments that seem to linger a little longer there. In Anguilla, rum punch is the house wine, time feels irrelevant, and the only thing you’re meant to feel is a sense of complete ease.
Outer Banks Travel Guide: Choosing the Right Town for Your Trip
The Outer Banks has always been deeply personal to me. My dad, an avid surfer, and my mom, a devoted beach lover, built a house on Cape Hatteras when she was pregnant with me—on a street known for some of the best waves on the East Coast, a reputation it still holds today. I’ve spent 37 summers there since, falling in love with every mile of the National Seashore. For the past 15 summers, I’ve shared it with my husband, with our wedding in nearby Avon, and over the past five, I’ve watched my daughters fall in love with it, too. Now I’m raising the next generation of beach lovers there—drawn to nothing but surf, sand, and seclusion.
Outer Banks Travel Guide: Choosing the Right Town for Your Trip
The Outer Banks has always been deeply personal to me. My dad, an avid surfer, and my mom, a devoted beach lover, built a house on Cape Hatteras when she was pregnant with me—on a street known for some of the best waves on the East Coast, a reputation it still holds today. I’ve spent 37 summers there since, falling in love with every mile of the National Seashore. For the past 15 summers, I’ve shared it with my husband, with our wedding in nearby Avon, and over the past five, I’ve watched my daughters fall in love with it, too. Now I’m raising the next generation of beach lovers there—drawn to nothing but surf, sand, and seclusion.
Barefoot Luxury in Anguilla
Anguilla will always have a special place in my heart, as it's where I had the honor of standing beside my college best friend on her wedding day, right on the beach at Meads Bay in front of Straw Hat. From that moment on, I fell in love with the island’s easygoing rhythm. It's the kind that invites you to slow down and settle in. The beaches feel untouched, stretching effortlessly along the coast, and the beach bars, warm people, and iconic views make it all feel both simple and unforgettable. It’s that rare balance of upscale luxury that still feels accessible. It's refined, but never pretentious. I still think about sunsets from the lounge at the Four Seasons—those golden, quiet moments that seem to linger a little longer there. In Anguilla, rum punch is the house wine, time feels irrelevant, and the only thing you’re meant to feel is a sense of complete ease.
Barefoot Luxury in Anguilla
Anguilla will always have a special place in my heart, as it's where I had the honor of standing beside my college best friend on her wedding day, right on the beach at Meads Bay in front of Straw Hat. From that moment on, I fell in love with the island’s easygoing rhythm. It's the kind that invites you to slow down and settle in. The beaches feel untouched, stretching effortlessly along the coast, and the beach bars, warm people, and iconic views make it all feel both simple and unforgettable. It’s that rare balance of upscale luxury that still feels accessible. It's refined, but never pretentious. I still think about sunsets from the lounge at the Four Seasons—those golden, quiet moments that seem to linger a little longer there. In Anguilla, rum punch is the house wine, time feels irrelevant, and the only thing you’re meant to feel is a sense of complete ease.