Honeymoons and Girls Getaways

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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
(4)
100% Recommended
Working with Diane as my travel agent was such a great experience. From the very beginning, she really took the time to listen to what I... Read More >
About
Reviews
My Places

Areas of expertise

Destinations:

Aruba, Italy, Puerto Rico, Jaco Beach

Interests:

Honeymoons, Overwater Bungalows, Women's Travel, All Inclusive, Celebration Travel

Suppliers:

Sandals and Beaches Resorts, Small Luxury Hotels, Iberostar

About Me

All Inclusive Resort in Mexico, view of the lagoon
All Inclusive Resort in Mexico, view of the lagoon

I specialize in planning trips that feel personal, thoughtful, and worthy of the reason you are traveling in the first place. Whether it is a honeymoon, a girls trip, an anniversary, or simply time away with people you love, I believe the right trip should reflect your energy, your pace, and what you need most from the experience.

What my clients often tell me after working together is that they felt understood. I listen closely, ask the right questions, and pay attention to the details that often get overlooked when people try to plan on their own. Some travelers want a beautiful beachfront stay where everything feels easy and restorative. Others want walkable charm, memorable meals, a little nightlife, and a balance of relaxation and discovery. My role is to help shape a trip that matches your travel style rather than forcing you into a destination that looks good on paper but does not feel right once you arrive.

I frequently plan honeymoons and girls getaways in destinations such as Costa Rica, Aruba, Mexico, and Italy, but destination is only one piece of the experience. The right resort, the right room category, the right location within a destination, and even the right dinner recommendations can completely change how a trip feels. I help clients think through those layers so the experience feels seamless and well matched from the start.For honeymoon clients, that often means creating space for both celebration and ease. I may recommend a property with privacy, thoughtful service, and memorable dining, while also adding small personal touches to help the trip feel even more special. For girls trips, it may look like finding a beautiful beach setting with easy access to cocktails, spa time, and just enough energy nearby to keep the trip fun without feeling busy.

I also believe the details matter just as much as the destination itself. I help with everything from choosing flights that do not drain the first day of your trip, to recommending meals worth planning ahead for, to identifying the kind of atmosphere that fits the mood you are hoping to create. Sometimes it is the smallest touch that ends up becoming what clients remember most.

Shared Suitcase Travel was built on the idea that travel planning should feel supportive, intentional, and highly personal. I offer concierge level planning with a strong emphasis on relationship, communication, and fit. I am not interested in quick bookings. I want my clients to feel cared for before they leave, while they are away, and when they return home with stories they are still talking about months later.

If you are looking for someone who will truly listen, help narrow the options thoughtfully, and make sure the trip feels right for you, I would love to help you begin planning.

REVIEWS

Rating: 5.0
4 reviews
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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Showing 4 reviews

Great experience with Diane!
Reviewed By AliG - Leominster, MA | Traveled to Punta Cana | Dominican Republic | Caribbean
Working with Diane as my travel agent was such a great experience. From the very beginning, she really took the time to listen to what I wanted out of our trip and made me feel like she truly understood our family’s needs. She was incredibly patient with me while I worked through different options and decisions, never making me feel rushed or pressured. Instead, she provided thoughtful, well-matched recommendations that made choosing so much easier. Her communication was excellent throughout the entire process—clear, responsive, and proactive—which I really appreciated. As a busy mom, having someone handle the details and present great options in a simple way made all the difference. Diane made what could have been a stressful planning process feel easy and even enjoyable. I would absolutely recommend her to anyone looking for a smooth, personalized travel planning experience.
I would recommend this agent to my family and friends.
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Amazing Trip!!
Reviewed By Adrienne - Massachusetts | Traveled to Costa Rica | Central America
Diane went above and beyond!! She set up our trip with such attention to details. All the tours were guided to our families specific needs. The guides were all on time and professional and accommodating. We got a good mix of Costa Rican culture, interactive things for the kids, wild life, and relaxation. Our child had some last minute medical stuff come up and Diane helped with each step of the way! Highly recommend Diane and her services to anyone looking to book a memorable stress free trip!
I would recommend this agent to my family and friends.
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Can’t wait to continue our Costa Rican adventure
Reviewed By Bostonmom - Boston ma | Traveled to Costa Rica | Central America
Had an adventure filled trip to Costa Rica spanning two areas. Accommodations, transportation, and activities were perfection. Our family can’t wait to go back and explore more areas.
I would recommend this agent to my family and friends.
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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.
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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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