Our Story
At Bites of Boston Food Tours, we are passionate about all things Boston – and the fabulous food scene is no exception! For me personally, great food has always been an integral part of exceptional days and memorable vacations, and exploring different cultures through cuisine is one of my favorite parts of traveling. There’s a lot to love about Boston and being a part of this city means being surrounded by an abundance of delicious and eclectic food options every day. My love of food and local culture, and a desire to share both in the context of the urban Boston lifestyle, first inspired the creation of the first Bites of Boston food tour in 2011.
Mouth-watering food tastings provide the foundation for our tours but we firmly believe food is best enjoyed when served in the context of your local surroundings. Our neighborhood tours are carefully curated to create just that experience for our guests. By combining sweet and savory food tastings with fascinating stories, local culture, history and architecture, we have created the perfect recipe for a fun, one of a kind way to explore some of Boston’s most vibrant and tasty neighborhoods. We hope you’ll see Boston the way we do and feel more like a local at the end of your tour experience. We hope you will return to the neighborhoods on your own and feel confident navigating your way through the streets, back to your new favorite eateries and specialty shops.
We look forward to sharing our passion, knowledge, and favorite local foods with you on our tours. Join us and Stroll Boston. One Bite at a Time.
Our Team

Rachel DeSimone
Tour Operations Coordinator
Social Media & Food & Fun Blog Manager
Rachel’s Favorites
Local Eatery: Sofra Bakery & Cafe, Cambridge
Local Dish: Grilled Swordfish with coconut & cilantro rice, jumbo lump crab, mango & papaya salad from The Painted Burro, Somerville
Food Quote: “Knowledge is knowing a tomato is a fruit. Wisdom is not putting it in a fruit salad.” – Miles Kington
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Rachel was born and raised in Hells Kitchen, NYC where she was immediately exposed to a wide range of foods but her plate did not expand much past ice cream and apples as a kid. While these are still two of her favorite foods, she has found herself immersed in food in all senses of the word since she moved to Boston. She completed an undergraduate degree in hospitality at Boston University with a minor in journalism. She went on to earn a masters in gastronomy from BU as she began to pursue a path of food writing. She has two main focuses – storytelling and lifestyle/blog writing. She loves highlighting small, local food businesses and telling her own stories surrounding food. If you’re looking for her you will likely find her on a stoop in Brookline eating a treat from Clear Flour Bread in a brown paper bag.

Katie Barron
Tour Guide
Katie’s Favorites
Local Eatery: Barcelona, South End
Local Dish: Shakshuka from Tatte Bakery & Cafe, Boston, Cambridge
Food Quote: “Food brings People together on many different levels. It’s the nourishment of the soul and body. It’s truly lovely.” – Giada De Laurentiis
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Growing up in Denver, Colorado, Katie fell in love with Boston after visiting a friend who went to college in the city. Now living in the Boston area for 17 years, the history, architecture and culture – and of course the food – are still the things that attract her to this incredible city. After enjoying the the Sweet & Savory South End Tour so much as a tour guest, she decided she wanted to be a part of the fun and joined the Bites of Boston team as a tour guide! Katie is a First Grade teacher, and also enjoys spending the summer and weekends sharing all the things she loves about the South End with guests as a guide. Katie is a big fan of local food and loves to find fun, new restaurants to enjoy!

Katie Barrett
Tour Guide
Katie’s Favorites
Local Eatery: El Pelon
Local Dish: Chicken gyro from Gyro City (Brighton)
Food Quote: “Laughter is brightest in the place where food is.” – Irish Proverb
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Growing up an hour outside of Boston, Katie would often come to the more touristy neighborhoods for dinner with her family. It wasn’t until she moved to the city after college and started exploring that she discovered what the rest of the city had to offer. Exploring different neighborhoods through local restaurants (especially bakeries!) is one of her favorite pastimes. When she is not giving tours, baking, or watching cooking competition shows on Food Network, she works as a curator at a local museum.

Natalie Peña
Tour Guide
Natalie’s Favorites
Local Eatery: Beehive, South End
Local Dish: Crispy Chicken Basil from Siam Bistro, Financial District
Food Quote: “You don’t need a silver fork to eat good food.” – Paul Prudhomme
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After growing up just outside Denver, Colorado, Natalie fell in love with Boston during a college tour. She decided to make the move out East and ultimately received her undergraduate degree from Bentley University where she studied math and business. Eager to stay in Boston after graduation, Natalie signed her first lease in Boston’s Brighton neighborhood and began working in finance. She has since lived in neighborhoods all over the city including Brookline, South Boston, the West End, and Back Bay. She has loved exploring and trying the foods of each neighborhood and is excited to share her knowledge and love for the city through food tours. When she’s not trying new restaurants, Natalie can be found taking a stroll along the esplanade, jamming out at a concert (usually hip-hop), or cheering on the Celtics.

Jillian Meyer
Tour Guide
Jillian’s Favorites
Local Eatery: Pho Viets
Local Dish: Baklava pancakes from Brookline Lunch
Food Quote: “What’s good for you, must be good for all. If you are lost, share a plate of food with a stranger… you will find who you are.”
- Chef José Andrés
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Jillian was born and raised on Long Island, New York and moved to Boston in October 2022. Growing up she was quite the picky eater, however it was when she moved out for college and later moved to Spain after graduation that she really began to expand her palate outside of store-bought rotisserie chicken and Rice-A-Roni that she was used to. She will never forget her first food tour in the Basque Country, Spain where she ate such different but delicious foods than she was used to. After that experience, she wanted in on the action! The year after that she became a wine and tapas tour guide in Madrid and loved every second of it. After relocating to Boston, she wanted to replicate that experience and quickly stumbled upon the Bites of Boston website. When she’s not leading tours, you can find Jillian dancing salsa and bachata, playing pick-up soccer or riding her bike on the esplanade.