The trip won’t happen twice. Let’s get it right.

From milestone trips to luxury cruises, I design custom trips built around the specific moments that matter to you, the experiences you want to have, and the access you can't get on your own.

Meet Jessie Riley

Founder & Chief Travel Advisor

I've planned 5-star anniversary trips across the Amalfi Coast and the Scottish Highlands, coordinated multi-country group itineraries around major sporting events, and designed Disney cruises with the same level of polish as any luxury hotel stay. I've been to most of these places myself - which is the part that actually makes a difference when the details matter.

Learn More About Me

Samples of Trips I’ve Designed

  • Anniversary

    ROME & AMALFI, ITALY

    Twelve days across Rome and Amalfi for the mix of city and coastal experiences. Signature moments in Rome included a private tours of St. Peter’s Basilica (including the dome), the Colosseum, and the Roman Forum, as well as a private cooking class with a local chef. In Amalfi, an arranged tour of one of the oldest lemon groves and a day trip to Ravello.

  • Honeymoon

    MAUI, HAWAII

    For newlyweds, I planned a 10-day Hawaii honeymoon centered on a relaxing Maui getaway with a touch of local experiences from small group snorkeling to experience sea turtles, to a private Luau, an all day Road to Hana experience, and a chartered Catamaran at sunset.

  • Anniversary

    LA FORTUNA & GUANACASTE, COSTA RICA

    An anniversary trip to Costa Rica designed to hit the balance between luxury and adventure. A 5 day stay at a 5-star resort in the jungles of La Fortuna at the base of Arenal volcano, included an anniversary dinner made up of a 14-course tasting menu and private violinist, a tour of the hanging bridges with sightings of toucans and sloths. Another 5 days in Guanacaste to relax and enjoy a slower beach pace.

  • Milestone Birthday

    ASHEVILLE, NC

    For a client marking a milestone 60th birthday, I built out a longer weekend in Asheville, NC including exclusive experiences at The Biltmore Estate, an arranged birthday dinner at a 5-star steak house, and an upgraded suite at The Grand Bohemian.

  • Reunion (Mid-size)

    IRELAND & SCOTLAND

    For a group of four friends, I designed a 14-day reunion trip through Ireland and Scotland, built around core experiences such as a Castle stay in Scotland, a falconry experience, visiting the Cliffs of Moher, a tasting at a distillery, a day trip on the Jacobite Steam Train, and a visit to the Isle of Skye.

  • Reunion (Small)

    LONGBOAT KEY, FL

    An annual girls weekend hosted in Longboat Key, FL and attended by friends who flew in from all over the country. A suite was arranged in addition to added white sand beach and F&B amenities to help make their reunion even more enjoyable and comfortable.

  • Reunion (Large)

    Disney Cruise

    For a large family group of 34, I helped with itinerary selection, room blocking design, booking management, and pre-cruise hotel arrangements.

Ready to Start Planning?

  • "I’ll be honest, I was always a little skeptical about using a travel advisor. I assumed it would cost more money and that I could probably do everything myself. Working with Jessie completely changed my perspective. Not only did she make the entire process incredibly easy, but she also helped us access benefits and perks that we never would have received on our own. The experience ended up being better than expected, and more than anything, Jessie gave us peace of mind. Instead of worrying about the details, we were able to focus on enjoying the trip, knowing everything had been taken care of. If you’re on the fence about using a travel advisor, I was too. After working with Jessie, I can confidently say I’d do it again."

    -Derrick B.

  • “My family and I just returned from a 7-night cruise to the Caribbean and had an amazing experience, thanks to Jessie's attention to detail and clear communication planning each component of the trip in advance. We were completely looked after and knew what to expect from the second we walked on the ship. My family and I would recommend Jessie's services to anyone who doesn't want to plan or like to plan but loves to travel!”

    - Steve R.

  • “Worth every penny. I personally don’t mind planning vacations but I’m at a point in life where I don’t really have a lot of extra time to do it the way it needs to be done. Which is important - especially when traveling with four kids. Knowing Jessie was managing the planning and booking for us was a weight off my shoulders. I plan to use Emerald Atlas for all my future trips because she does a great job and it’s one less thing I need to have on my to do list!”

    - Jamie D.

  • "I basically gave her a little basic information and she took it from there and did an amazing job. So much that she is planning another trip for us now."

    -John S.

  • "Jessie did a wonderful job booking our mother-daughter weekend! As a busy mom and graduate student, it would have been a challenge to find extra time to plan a vacation. Jessie took the stress out of that! She listened to what we were interested in and planned an itinerary to accommodate the things we wanted to do while also leaving room for flexibility. She included the little details that made a difference, from what to see first at the aquarium, to the cute little brunch place and even a suggested time to leave for the airport. Jessie helped make this a relaxing and memorable vacation for my daughter and me! We plan to book with her again."

    -Jenny S.

  • "Jessie made our entire travel planning process incredibly easy. She provided several great options and helped us choose the perfect location for our trip. Since we had never been there before, the detailed information she shared was especially helpful. She even handled an on-site issue for us so we could keep enjoying our vacation without any stress. Highly recommend working with Jessie!"

    - Nicole Y.