Our Sightseeing Tour Guides

Meet the guides

Circle Line's tour guides work from narration developed with the New York Historical Society, so you're getting real research behind every joke and landmark story.

Here's a bit about the guides who'll be talking your ear off, in the best way.

Chris Mason

Chris Mason was born and raised in Bay Ridge, Brooklyn, and Circle Line runs in his family. His father, John Mason, was a legendary guide here, and Chris picked up the microphone himself in 1985. Since then he's built a style that's entirely his own, even while carrying on the family name.

He's logged nearly four decades and thousands of tours. His narration mixes history, comedy, and the occasional pop quiz. Guests never know when he'll throw out a surprising statistic or ask them to guess a landmark's backstory, but they know they'll be entertained.

Chris says New York is the greatest city on earth, and every tour is a chance to prove it.

"We laughed, we learned, and we left knowing more about New York than we ever expected. Chris made the tour unforgettable." — Daniel K., London

David Parker

David Parker grew up near the Pittsburgh airport and came to New York in 1985 for an M.F.A. in acting. After some summer theater and adjunct teaching, he landed a job with Circle Line's onboard concession contractor and quickly became their top salesman. That led to an audition as a tour guide. He started as a substitute, split shifts with the Statue of Liberty information booth for a while, and became a full Circle Line guide in 1994.

In October 2001 he met his future wife while narrating a tour. He and Leslie married in December 2002 and now live in Jersey City.

Outside of guiding, David's into aviation, cars, and racing. He's a member of the New Jersey Diecast Car Club and has built a collection running into the thousands.

"David's knowledge was endless. He knew the history, the architecture, even fun little details we never would have noticed on our own." — Michelle T., Boston "He has such a warm and engaging style. It felt like we were exploring New York with a friend who happens to be a walking encyclopedia." — Greg W., Sydney

Alexis Moore Eytinge

Alexis found tour guiding almost by accident, on a chocolate tour in New York City in November 2013. She knew right away it was what she wanted to do. With a background in theater, sociology, and food culture, she stood out when she applied to a tour company in Portland, Oregon, where she spent six years leading everything from history walks to beer, wine, and waterfall tours.

Eventually she came back to New York, where her mother grew up, and now lives in Astoria. Circle Line turned out to be a natural fit for someone who loves both boats and storytelling. She calls her approach "edu-tainment," a mix of history, humor, and heart, and as a performer who's written and produced several one-woman shows, it's not unusual for her to break into song mid-tour.

Outside of guiding, Alexis runs a life coaching business that helps young people transition into college and independent living, and she wrote 21 Strategies for Thriving at College, available on her website www.TheConfidenceSociety.com.

"Her passion for New York and her ability to connect with the group made the cruise feel so personal. She even sang for us, which was unforgettable!" — Claudia S., Madrid "Alexis turned the tour into more than sightseeing. It felt like a show, a history lesson, and a comedy act all rolled into one." — Patrick D., Chicago

Andy Sydor

Andy was born in Manhattan, raised in New Jersey, and now lives in Queens. He has a BA in anthropology from Rutgers, and given his lifelong ties to the city, guiding tours felt like a natural direction. He's been at it for more than 17 years and joined Circle Line in 2015.

When he's not on a boat, he's playing music around Astoria, a regular at spots like Irish Whiskey Bar, Shillelagh, and the Wild Goose in Woodside.

One of his most memorable moments came during the 2003 blackout, when he was guiding a double-decker bus and helped a full bus navigate from Lower Manhattan back to Midtown in the dark, keeping everyone's spirits up along the way.

"Andy's storytelling was incredible. He explained the city in a way that made us see New York completely differently." — Laura K., Dublin "Between his knowledge of the city and his stories from years of guiding, Andy kept everyone hooked from start to finish." — Marcus H., Florida

Debbie Mason

Debbie was born and raised in southernmost Brooklyn and is a photographer, storm chaser, and lifelong explorer of the city. History, architecture, food, neighborhoods, she finds something to love in all of it.

She spent more than 30 years in telecommunications before switching to tourism, and she hasn't looked back since. She's led thousands of tours, from sightseeing buses to harbor cruises to student groups and private corporate trips, and she brings the same energy to all of them.

Her style feels less like a scripted tour and more like exploring with an old friend who happens to know every secret corner of the city, alongside all the famous ones.

For Debbie, New York isn't just where she's from. It's who she is.

"Debbie made us feel right at home in New York. It was like exploring the city with a friend who knows every story and secret corner." — Hannah G., Seattle "We loved how Debbie balanced the big landmarks with the hidden gems. She showed us a side of the city we never would have discovered on our own." — Claire J., Paris

Malachy Murray

Malachy Murray is a Queens native descended from 17th-century sailors, and his name literally means "Sea Warrior." Fitting, given how his career turned out.

After serving in the Navy's Special Forces, he joined Circle Line in 1996 as a deckhand. Three weeks in, a guide fell ill and Malachy picked up the microphone for the first time. Guests still talk about that tour.

He's built a reputation on sharp wit and deep knowledge of the city. Beyond the water, he's a SAG-AFTRA actor with credits in The Departed and Law & Order, wrote the best-selling book Unique New York, and hosts the podcast NEW YORK TALK NYC.

"Malachy's energy is incredible. He had the whole boat laughing, learning, and completely engaged the entire time." — Caroline D., Edinburgh

Timothy Ries

Tim Ries has more than two decades in New York City tourism. He founded Tourist New York, is a licensed NYC tour guide, and is known for digging up hidden gems alongside the obvious landmarks.

Before starting his own tour company in 2019, he served as Director of Visitor Services at the High Line and has spoken at industry events including The New York Times Travel Show. He's a member of the Guides Association of New York City, has led thousands of tours across the five boroughs, and contributed to a New York City food encyclopedia.

Tim is originally from the Midwest and now lives in southeast Brooklyn with his wife and son. He collects vintage New York postcards from the 1920s through 1940s, a hobby that fits his interest in the city's history.

"Tim has an incredible way of connecting the dots between New York's past and present. His stories made the city feel alive." — Olivia B., Toronto "We loved Tim's tour. He shared not only the big highlights but also small details and hidden gems that we never would have noticed on our own." — Rajesh P., Mumbai

Bobby Hedglin-Taylor

Bobby Hedglin-Taylor, known as "Flying Bobby," is an actor, comedian, author, singing impressionist, and trapeze artist with more than 40 years on stage, in the air, and on screen. His circus choreography has shown up on Broadway, and he's appeared in nine reality shows.

He's lived in New York since the 1980s and is excited to bring his focus to tour guiding. Several landmarks hold personal weight for him: his father was stationed on the USS Intrepid during the Korean War, his Sicilian relatives came through Ellis Island, and he once worked in the South Tower of the World Trade Center.

As a performer, he's toured nationally in musicals, plays, and circuses, designed and trained aerial sequences for Broadway productions, and performed as an acrobat at Madison Square Garden. In 2022 he received the Legacy Award from Dancers Over 40.

He's also the author of #Sh*tMyMamaSays, a tribute to his late mother that inspired his solo show Escape to Ravioli Mountain, a mix of memoir, storytelling, and live cooking.

Jennifer Wright-Tubbs

Jennifer's version of New York is never just one thing. She brings that same range to her tours, whether by bike, on foot, by bus, or now by ferry.

She's carried a Macy's Thanksgiving Day Parade balloon, watched the ball drop on New Year's Eve, run the NYC Marathon, and completed the Great Saunter walk around Manhattan. She finds just as much meaning in the smaller stuff, coffee with friends, sunsets on the Hudson, volunteering, the surprises the city throws at you.

She shares New York with her husband, son, daughter, and dogs, whether that's dressing up the pups for the Tompkins Square Halloween Dog Parade or riding the ferries together.

Check out "Jennifer's NYC Basics," her tips tested over 20 years and updated weekly.

Jerry Kaiser

Jerry Kaiser has spent more than 15 years in travel and tourism and has been with Circle Line since 2017.

He's guided with Grayline Sightseeing, helped launch the Top of the Rock Observation Deck, and supported major events at Rockefeller Center. He's also worked internationally, building tour packages in India and collaborating with the American Consulate in Mumbai.

He's known for being easy to talk to, clear, and good at bringing the city's history and hidden corners to life.

"Jerry was fantastic. He made the city feel welcoming and easy to understand, and his stories were both fun and informative." — Allison M., Chicago "Jerry explained the landmarks so clearly and kept us laughing the whole time. He really brought the city to life." — Hiroko T., Osaka

Tim Hollon

Tim has spent more than five decades leading tours across the U.S. and Europe. He started out as an Army Intelligence Russian specialist during the Cold War, later worked with the CIA, and eventually found his real calling in bringing history to life for travelers.

He studied at George Washington University and the University of Wisconsin and has guided groups through Gettysburg, Boston, Monticello, and sites across the British Isles and Europe. He's known for sharp research and a knack for finding the landmarks everyone else overlooks, often weaving in the voices of people who actually lived through the history he's describing.

Congressman John McCain's office selected him twice to lead top Arizona students on government tours in Washington, D.C.

"A true historian and entertainer. Tim made sites I thought I already knew feel fresh and meaningful." — Leonardo M., Rome "We were amazed by Tim's knowledge. He kept our group engaged with fascinating details and a great sense of humor." — Emily W., Vancouver