Caitlin Humphreys, Co-Principal, Travel Sommelier

Caitlin Humphreys - NP Alumni Profile

Tell us about your current role at Travel Sommelier, and what you typically handle. How do you use your legal skills in your current role?

I am the co-owner of Travel Sommelier, along with my husband Darren. Travel Sommelier is a high-end travel advisory company—we customize trips for multi-generational families, groups, honeymoons, celebrations, etc. Darren is from South Africa so we have a special affinity for safari travel, as well as food and wine travel (we were named to Travel & Leisure’s “A List of Travel Advisors,” with special recognition for wine and gastronomy travel).

My role at the company is to head our marketing team, oversee any legal and contractual issues, and work with Darren on business strategy and planning. My legal skills have been extremely helpful with employment agreements and client participation agreements, as well as drafting and editing marketing content. I have also served on the board of an industry association called Safari Professionals of the Americas and played an integral role with legal questions for the organization. My legal background has been of use on a cross-border basis, as we have a global footprint and there are a myriad of considerations in different source markets.

What is the most enjoyable aspect of your current role?

Of course, I enjoy the international travel! We go to “research” destinations firsthand so we know the management, form local ties, and can experience all the pitfalls and VIP perks for our clients. We love nothing more than finding local hot spots and connections! We also travel for charitable events, for industry trade shows, and to brainstorm with international travel industry movers and shakers on a “think tank” basis. Apart from travel, I love the business strategy portion of my role—the same predilection for analytical thinking that led me to the legal field serves me well in this position.

How has your experience at NP influenced the direction of your career? What was your career trajectory, and what brought you to Travel Sommelier?

I started at Nixon Peabody in the general Business Litigation practice group in the Boston office. Some of my first mentors were Marcus Cohn, Tim Mungovan, Leigh-Ann Durant, David Mack, and Christine Colmey. I was fortunate to be part of trial teams early on in my career—although I have a quieter personality, I always loved the excitement of trial. I was also drawn to the research, writing, and analytical thinking that litigation entails. One day, a new leveraged buyouts team from the New York office (Dom DeChiara and Brad Vaiana) visited us to speak about the mid-cap private equity climate in NYC. I was enthralled by their energy and the thought of New York City.

Being young and single, I requested a transfer to the New York office, working in their group. I loved the New York office, being in the center of midtown, and the excitement of working on big deals in the heart of the financial hub. I admittedly did not like corporate work as much as I had liked litigation due to my particular skill set, and ended up moving to a smaller litigation boutique named Hoguet, Newman, Regal & Kenney (started by partners from Simpson Thatcher and White & Case). I had a tremendous couple of years at HNRK, including second chairing a big trial in the SDNY. I enjoyed being the savvy but even-tempered litigator who served as the communication point person among our team, client, co-defendant, co-counsel, the judicial clerk and the U.S. attorney’s team. I felt like I was truly on my favorite TV program, Law & Order!

After my last (intense and high-profile!) trial ended, I took time off to travel the world, which is my passion. I met and married Darren, who had worked all over the globe in the financial markets and recently left the industry to start Travel Sommelier. As I figured out what I wanted my next career move to be, I started brainstorming ideas and business development plans for Travel Sommelier. It soon became apparent that my joining Darren and making TS a family business would be a perfect fit. I feel truly blessed that I am able to combine my passion, skills, and legal experience.

Are there any other developments in your professional and/or personal life you’d like to share with the NP Alumni community?

We run Travel Sommelier out of Duxbury, Massachusetts (where I grew up), with employees in both Connecticut and Massachusetts. We have two amazing sons—Charlie (5) and Soren (3)—future junior safari rangers! I look forward to showing them the world….

How do you plan on using NP Alumni to keep in touch with former colleagues?

I am connected to many NP folks on LinkedIn, but I am excited to become more active in the alumni program. We recently joined the Algonquin Club (now the Quin House) in Boston, and I hope to get into the city more to meet up with colleagues for lunch and a chat (the Quin has reciprocity with clubs in NYC, so I hope to do the same there). I also find the NP newsletters quite helpful, especially regarding employment issues during COVID.

Outside of your profession, what do you like to do in your free time?

I love to read (mysteries, memoirs, historical fiction, psychology), clam and oyster in Duxbury bay, golf, eat seafood, collect shells, and decorate. I am also drawn to fitness and wellness. I love to learn about other cultures, but that is technically not outside of my profession!

Are you involved with any organizations? If so, what drew you to these causes?

Travel Sommelier is deeply involved with multiple charities to which we donate trips and attend annual events. Some of these are the Emeril Lagasse Foundation, the Boston Medical Center, the Boston Ballet, the South Shore Conservatory, the Nantucket Boys & Girls Club, and IFAW. We put a lot of research into the charities with which we become involved—it is important that funds raised go to the bottom line and that the people who run them have big, genuine hearts.

What is your industry outlook? What’s your outlook on how COVID-19 is shifting your professional approach?

Our industry was, for the most part, put on hold during the pandemic. Our focus during this time was to strengthen ties with our clients (the vast majority of our business is repeat and referral), do any operational clean-up that we do not usually have time to do, and participate in industry think tank groups. We used Zoom to solidify old relationships and form new connections with suppliers “on the ground” at different destinations, so we always know what is new and can offer clients unique destinations, VIP treatment, and special local access. We also invested in some self-travel to locations including South Africa, Kenya, Tanzania, Uganda, and the Caribbean. It was crucial to see what it was like “out there” so we could provide clients with honest, impartial advice based on tangible, firsthand knowledge.

Post-vaccine, we have experienced colossal pent-up demand for travel. We have seen a rise in multi-generational trips, bucket list trips, honeymoons, exclusive-use “pod travel,” and wellness-focused travel. The pandemic highlighted the need for a travel advisor—someone who can deal with health requirements and local testing facilities, and can also handle emergencies and insurance, etc. However, with regulations and airlines constantly changing, each trip continues to be much more work! We have been forced to become more easily adaptable and more readily available to our clients.

Key Contact

Dorsey Breslin

Senior Manager, Marketing, Attorney and Alumni Engagement

Phone: 202-585-8397

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