Ashley Wilson
Based in Dallas, Texas
Jet Set Wilsons
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Our Story
Obsessed with planning itineraries so you don’t have to be.
Travel Style
Hi, I’m Ashley! If you’ve met me, you know that I am a planner. And I love to plan vacations. A good itinerary is my love language! My goal is to elevate the family vacation experience to one that both parents and children will enjoy. As a mom of three and frequent traveler myself, I understand the unique needs of traveling with children. I specialize in creating unforgettable luxury vacations for families and groups who want to explore the world together—without sacrificing comfort, style, or ease. Whether it’s a European exploration, a tropical beach escape, a mountain adventure, or a city tour, I’m here to make family and group travel effortless, personalized, and extraordinary. Let’s jet, set, and explore!
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Reviews (16)
Steven W.
travel to San Miguel de Allende
11 days ago
Ashley did an amazing job of planning the perfect activities for a short 4-day trip - time relaxing at the resort pool, visiting art galleries and other shops, a cooking class, and a day outside the city going to wineries.
John D.
travel to Hawai'i
18 days ago
Working with Ashley to plan our family vacation in Maui was awesome! She had the best recommendations, she helped us book an incredible hotel and the perfect room at the hotel, and she put together an absolutely amazing custom tour. Her attention to detail in making sure this vacation was perfect for our whole family was amazing. Thank you, Ashley!!!
Jacque G.
travel to Boston
29 days ago
Ashley is the best! She is very thorough, helpful, and detail oriented.
Ryan M.
travel to Ireland
3 months ago
As always, Ashley helped us put together a wonderful trip! This was a guys’ golf trip to Ireland to celebrate the members of the group all turning 50 this year. Ashley (and her partners) really helped us focus our itinerary while providing us with an excellent driver and great hotel stops along the way.
Brian B.
travel to Bahamas
5 months ago
Ashley planned us a wonderful vacation and took care of everything. We especially liked the excursions she planned for us. She did everything she said she was going to do and more and the entire trip ran smoothly. It was the first time we’ve used a travel agent since our honeymoon and it was definitely nice to have someone do the lifting for you. We would definitely use Ashley again.
Steven W.
travel to San Miguel de Allende
11 days ago
Ashley did an amazing job of planning the perfect activities for a short 4-day trip - time relaxing at the resort pool, visiting art galleries and other shops, a cooking class, and a day outside the city going to wineries.
John D.
travel to Hawai'i
18 days ago
Working with Ashley to plan our family vacation in Maui was awesome! She had the best recommendations, she helped us book an incredible hotel and the perfect room at the hotel, and she put together an absolutely amazing custom tour. Her attention to detail in making sure this vacation was perfect for our whole family was amazing. Thank you, Ashley!!!
Jacque G.
travel to Boston
29 days ago
Ashley is the best! She is very thorough, helpful, and detail oriented.
Ryan M.
travel to Ireland
3 months ago
As always, Ashley helped us put together a wonderful trip! This was a guys’ golf trip to Ireland to celebrate the members of the group all turning 50 this year. Ashley (and her partners) really helped us focus our itinerary while providing us with an excellent driver and great hotel stops along the way.
Travel ideas (5)
Pura Vida in Peninsula Papagayo, Costa Rica
Costa Rica is a popular travel destination for a reason. It has beautiful resorts, stunning beaches, lush rainforests, and incredible biodiversity. This destination is great for all types of travelers, from families to couples to solo adventure seekers. Costa Rica truly encompasses the Pura Vida or "pure life" culture. While many visitors opt to split their stay between the rainforests and the beach, if you are short on time or prefer to stay near the beach, you can easily make Peninsula Papagayo in Guanacaste your home base.
Pura Vida in Peninsula Papagayo, Costa Rica
Costa Rica is a popular travel destination for a reason. It has beautiful resorts, stunning beaches, lush rainforests, and incredible biodiversity. This destination is great for all types of travelers, from families to couples to solo adventure seekers. Costa Rica truly encompasses the Pura Vida or "pure life" culture. While many visitors opt to split their stay between the rainforests and the beach, if you are short on time or prefer to stay near the beach, you can easily make Peninsula Papagayo in Guanacaste your home base.
Sun, Sand & Stingrays: Why Families Love Grand Cayman
There’s just something special about Grand Cayman for me. My brother went to medical school there, and my husband and I have been multiple times—with and without kids. Grand Cayman checks all the boxes for an easy, memorable family vacation. With plenty of direct flights from major US cities and a clean, modern airport, getting there is easy, especially when traveling with kids. Once you arrive, the island feels calm and manageable: It’s small, extremely safe, and easy to navigate. Many families choose to rent a car (just remember you’ll be driving on the left!), making it simple to explore at your own pace.
Sun, Sand & Stingrays: Why Families Love Grand Cayman
There’s just something special about Grand Cayman for me. My brother went to medical school there, and my husband and I have been multiple times—with and without kids. Grand Cayman checks all the boxes for an easy, memorable family vacation. With plenty of direct flights from major US cities and a clean, modern airport, getting there is easy, especially when traveling with kids. Once you arrive, the island feels calm and manageable: It’s small, extremely safe, and easy to navigate. Many families choose to rent a car (just remember you’ll be driving on the left!), making it simple to explore at your own pace.
Nashville Notes: Boots, Bites & Beats
I grew up going to summer camp in Tennessee and my daughters go there now, so Tennessee has always had a special place in my heart. Nashville is now a go-to weekend trip for me (at least yearly!) and I never get tired of going. Whether it’s a trip with the kids to the Gaylord Opryland (amazing Soundwaves water park!), or a weekend with my husband or girlfriends at the Noelle downtown, Nashville blends southern character with good vibes and great music. From live music on Broadway to incredible food and cool neighborhoods to explore, I have yet to get bored in Music City!
Nashville Notes: Boots, Bites & Beats
I grew up going to summer camp in Tennessee and my daughters go there now, so Tennessee has always had a special place in my heart. Nashville is now a go-to weekend trip for me (at least yearly!) and I never get tired of going. Whether it’s a trip with the kids to the Gaylord Opryland (amazing Soundwaves water park!), or a weekend with my husband or girlfriends at the Noelle downtown, Nashville blends southern character with good vibes and great music. From live music on Broadway to incredible food and cool neighborhoods to explore, I have yet to get bored in Music City!
Gelato, Gladiators & Great Views: Your Guide to Rome
Rome is a fantastic destination for families where history comes to life around every corner—from exploring the Colosseum, admiring ancient masterpieces, to tossing coins into the Trevi Fountain. Kids will love wandering through ancient ruins, climbing the Spanish Steps, and tasting authentic Italian pasta and gelato. The city’s walkable layout and open piazzas make it easy for families to explore. Step back in time and feel the magic of the stories of emperors, gladiators, and gods in the heart of the Eternal City.
Gelato, Gladiators & Great Views: Your Guide to Rome
Rome is a fantastic destination for families where history comes to life around every corner—from exploring the Colosseum, admiring ancient masterpieces, to tossing coins into the Trevi Fountain. Kids will love wandering through ancient ruins, climbing the Spanish Steps, and tasting authentic Italian pasta and gelato. The city’s walkable layout and open piazzas make it easy for families to explore. Step back in time and feel the magic of the stories of emperors, gladiators, and gods in the heart of the Eternal City.
A Big Easy Blueprint: A 3-Day Itinerary
While my roots lie in Texas, my spirit lives in New Orleans. I grew up in New Orleans and was married there. New Orleans is quite literally a city that marches to the beat of its own drum. Known as The Big Easy, it blends French, Spanish, African, and Caribbean influences into something completely unique. You’ll taste it in the gumbo, hear it in the brass bands, and see it in the colorful balconies and oak-lined streets. New Orleans feels like a party that never ends.
A Big Easy Blueprint: A 3-Day Itinerary
While my roots lie in Texas, my spirit lives in New Orleans. I grew up in New Orleans and was married there. New Orleans is quite literally a city that marches to the beat of its own drum. Known as The Big Easy, it blends French, Spanish, African, and Caribbean influences into something completely unique. You’ll taste it in the gumbo, hear it in the brass bands, and see it in the colorful balconies and oak-lined streets. New Orleans feels like a party that never ends.
Pura Vida in Peninsula Papagayo, Costa Rica
Costa Rica is a popular travel destination for a reason. It has beautiful resorts, stunning beaches, lush rainforests, and incredible biodiversity. This destination is great for all types of travelers, from families to couples to solo adventure seekers. Costa Rica truly encompasses the Pura Vida or "pure life" culture. While many visitors opt to split their stay between the rainforests and the beach, if you are short on time or prefer to stay near the beach, you can easily make Peninsula Papagayo in Guanacaste your home base.
Pura Vida in Peninsula Papagayo, Costa Rica
Costa Rica is a popular travel destination for a reason. It has beautiful resorts, stunning beaches, lush rainforests, and incredible biodiversity. This destination is great for all types of travelers, from families to couples to solo adventure seekers. Costa Rica truly encompasses the Pura Vida or "pure life" culture. While many visitors opt to split their stay between the rainforests and the beach, if you are short on time or prefer to stay near the beach, you can easily make Peninsula Papagayo in Guanacaste your home base.
Sun, Sand & Stingrays: Why Families Love Grand Cayman
There’s just something special about Grand Cayman for me. My brother went to medical school there, and my husband and I have been multiple times—with and without kids. Grand Cayman checks all the boxes for an easy, memorable family vacation. With plenty of direct flights from major US cities and a clean, modern airport, getting there is easy, especially when traveling with kids. Once you arrive, the island feels calm and manageable: It’s small, extremely safe, and easy to navigate. Many families choose to rent a car (just remember you’ll be driving on the left!), making it simple to explore at your own pace.
Sun, Sand & Stingrays: Why Families Love Grand Cayman
There’s just something special about Grand Cayman for me. My brother went to medical school there, and my husband and I have been multiple times—with and without kids. Grand Cayman checks all the boxes for an easy, memorable family vacation. With plenty of direct flights from major US cities and a clean, modern airport, getting there is easy, especially when traveling with kids. Once you arrive, the island feels calm and manageable: It’s small, extremely safe, and easy to navigate. Many families choose to rent a car (just remember you’ll be driving on the left!), making it simple to explore at your own pace.
Nashville Notes: Boots, Bites & Beats
I grew up going to summer camp in Tennessee and my daughters go there now, so Tennessee has always had a special place in my heart. Nashville is now a go-to weekend trip for me (at least yearly!) and I never get tired of going. Whether it’s a trip with the kids to the Gaylord Opryland (amazing Soundwaves water park!), or a weekend with my husband or girlfriends at the Noelle downtown, Nashville blends southern character with good vibes and great music. From live music on Broadway to incredible food and cool neighborhoods to explore, I have yet to get bored in Music City!
Nashville Notes: Boots, Bites & Beats
I grew up going to summer camp in Tennessee and my daughters go there now, so Tennessee has always had a special place in my heart. Nashville is now a go-to weekend trip for me (at least yearly!) and I never get tired of going. Whether it’s a trip with the kids to the Gaylord Opryland (amazing Soundwaves water park!), or a weekend with my husband or girlfriends at the Noelle downtown, Nashville blends southern character with good vibes and great music. From live music on Broadway to incredible food and cool neighborhoods to explore, I have yet to get bored in Music City!
Travel photos
