All things Family Travel in New England

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Diane Donovan, Travel Agent in Pittsfield, MA

Diane Donovan

Pittsfield, MA Travel Agent

Diane Donovan

Pittsfield, MA

Shared Suitcase Travel, an independent agent with WorldVia, a Travel Leaders Agency
5.0
(1)
100% Recommended
Diane was truly wonderful to work with. I was very overwhelmed planning a trip to Costa Rica and really went back and forth with where... Read More >
About
Reviews
My Places

Areas of expertise

Destinations:

Massachusetts, Ogunquit, Kennebunkport

Interests:

Family Vacations, LGBTQ+ Travel, Gluten-Free

About Me

Rainbow over the Atlantic Ocean (Maine)
Rainbow over the Atlantic Ocean (Maine)

Hi, I’m Diane, your go-to travel concierge for New England getaways that blend charm, comfort, and core memories. I help busy parents who are juggling it all.  You are the people I want to help and why I founded Shared Suitcase Travel. I specialize in finding the right place and connecting all the details so you basically just get to show up and make the memories! I have a deep love (and lifetime of experience) vacationing and exploring New England. I was born and raised in Massachusetts and make it a point to find all the right lodging, adventures and culinary experiences.

I know firsthand how overwhelming travel planning can feel, especially when you're trying to juggle work, school schedules, activities, and everything else that lands on a parent's plate. That’s where I come in. Whether you're dreaming of a relaxing luxury resort on the Maine coast, a quaint inn tucked into a quiet historical Massachusetts town, or a leaf peeping family tour I help you plan every detail with care.

My goal is simple: to make vacation feel like a real break. Not just a change of scenery where you're still doing all the things, just in a different zip code. While my formal career as a travel advisor is new, my experience is not. I’ve spent over 20 years planning travel, first for myself, then for friends, family, and now for busy families like yours. I bring not only first hand expertise and insider tips, but also warmth, humor, and a relational approach. I'm not just here to book a trip. I want to understand your family, your needs, and what kind of vacation feels like a win for you. 

I specialize in:

  • New England getaways with heart, especially Maine and Massachusetts 
  • Luxury and boutique stays that are family-friendly without losing their sparkle
  • Itineraries designed to balance activity with rest, and connection with independence
  • Thoughtful details that make travel easier for parents and more magical for kids

And because I live here, I don’t just know where to go, I know when to go, how to go, and the little extras that can make this an unforgettable trip. Think of me as your travel loving bestie and local insider who can take care of it all.  You focus on making the memories, laughing and getting the rest needed on this trip.

REVIEWS

Rating: 5.0
1 review
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Amazing trip, thank you!
Reviewed By KASNY - Huntington, NY | Traveled to Costa Rica | Central America
Diane was truly wonderful to work with. I was very overwhelmed planning a trip to Costa Rica and really went back and forth with where to go and what to do. Diane was incredibly patient with discussing the options and helping plan adventures that were right for my family. Every tour we did was amazing and it was a really special trip that hit everything we had hoped for, can't thank you enough!
Diane Donovan responded
"It was such a pleasure working with you and your family! Thank you for the kind words!"
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.
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