Travel Diaries: How A Matchmaker Explores The World

Name: Tennesha Wood
Age: 37
Occupation: Matchmaker and founder of The Broom List
Home: San Juan, Puerto Rico and New York, New York
Handle: @tenneshawood

Plane, train, or automobile? Plane. It's the best way to squeeze a little work in with WiFi.

Beach or mountains? Beach, sand, and sun. I was born on an island and my heart is still there.

What's your biggest vacation splurge? Booking a five-star hotel in Madrid last minute for my birthday.

What’s your minibar weakness? Fiji Water. It's hands down the best water on Earth, and I plan on traveling to Fiji to verify that fact.

What is the first big trip you ever took? I came to America from Jamaica when I was four all by myself. My mother still brags about it.

Tell us about your best travel experience. In 2016, I had a crazy year — my relationship ended and I quit my job. On New Year's Eve I decided that 2017 had to be different, so I booked a random flight based on the cheapest international flight from JFK. At the time, that was Stockholm. From there, I continued booking based on the next cheapest destination. I ended up going to seven different countries and spent seven weeks traveling alone on an eat, pray, love kind of journey.

Tell us about your worst travel experience. I ended up spending the night in a Moroccan airport after a bomb threat happened on our flight. Scary is an understatement. 

What is your favourite place to visit? My favourite place is somewhere new. I rarely go to the same place twice, I like the excitement of seeing somewhere new for the first time. 

What is your go-to travelling outfit? Comfy leggings, slip-on tennis shoes, and a big cozy sweatshirt. It's always cold on the plane!

Do you arrive at the airport three hours early? Or 30 minutes before boarding? About an hour before boarding. Pre-check, no check bags, and snacks at the ready.

What are your favourite traveling snacks? Cheez-Its and Godiva dark chocolate.

What's your favourite part about staying in a hotel? Fluffy robes and room service.

Where do you want to go next? Dubai — sometimes I like opulence and excess.

Where would you travel if it were the end of the world? I’d head back to Minnesota and spend my last days with my family. 

What’s your most frequent trip? Jamaica. I go back every year to see my grandparents and listen to my parents point out everything that's changed since they were kids.

What’s your packing style? I have travel-sized containers of all my favourite toiletries, robe, slippers, PJ’s and I pack other things based on the weather.

What was your last trip? Hawaii.

What's your next trip? Bali. After 2020, the peace and tranquility of Bali is calling my name. 

What’s your best travel hack? Be open, there’s something interesting to see everywhere! My best trips have been to the places I never really planned on going to.

What’s better: solo trips or traveling in groups? Solo trips. You can do whatever you want whenever you want.

What’s a touristy spot that’s actually worth it? Every patisserie in Paris!

Window, middle, or aisle? Window. It's the best place to rest your head and I never get up, so I’m undisturbed.

Hotels: splurge or save? Splurge.

What’s your go-to airplane drink? Red wine.

Domestic or international travel? Both. I love crossing an ocean but there’s still so much to discover in America.

What’s the best meal you’ve ever eaten while traveling? In Costa Rica, a local elderly woman had a restaurant that consisted of her personal kitchen and two chairs on her front porch. I get hungry recalling that plate.

Podcast, audiobook, or playlist? Playlist. I’m still in awe of airplanes and the fact that a huge piece of metal can transport us to somewhere completely different, so I like getting lost in that wonder to the perfect songs. 

What’s your favourite airplane movie? The last one I remember watching is Girls Trip, which was hilarious.

What’s at the top of your bucket list? Spend a few months traveling to the top-rated restaurants in the world.