About Celeste

Booking travel has never been easier. Making the right choices has never been harder.

There are thousands of vacations you could book. My job is to help you choose the one you'll be happiest you booked.

Anyone can make a reservation online. I help you sort through the options, understand the tradeoffs, and choose the vacation that is genuinely the best fit for you.

Celeste Woodside of Traveling With Celeste

Hi, I'm Celeste

Boston-based travel advisor, frequent cruiser, theme park traveler, lifelong researcher, and the person in your corner from the first question through the trip home.

I help families, couples, groups, and busy professionals plan cruises, Disney World vacations, Universal trips, and all-inclusive getaways that are genuinely worth their time and money.

I am not here to take control of your vacation or tell you what you should want. You are still the decision maker. I bring the context that booking sites cannot: how one ship feels different from another, which Disney resort upgrade will actually change your experience, whether a promotion is truly valuable, and when spending more is unlikely to make the trip better.

You make the choices. I make sure they are informed ones.

The value of good advice

The wrong vacation can cost thousands. The right advice costs you nothing.

What you can expect from me

Honest guidance. Useful experience. A real advocate.

Advice that is actually personal

I do not believe there is one best cruise line, one best Disney resort, or one vacation that works for every family. I listen first, narrow the choices, and explain the tradeoffs without burying you in options.

Experience beyond the brochure

I sail the ships, stay at the resorts, visit the parks, and keep up with the constant changes that affect real trips. I want my recommendations grounded in what the experience is actually like, not just how it is sold.

Someone who stays in your corner

I monitor eligible price drops, keep track of the details, help coordinate multiple households, and know who to contact when something changes. You are not left to restart the conversation with a different call-center representative every time you need help.

Celeste traveling and researching vacations for her clients

Why my advice is different

I know what to look for before you book.

I am naturally the person who wants to understand how everything works: which cabin locations are quieter, what Club Level really adds to a Disney stay, why two similar itineraries can feel completely different, and which “included” cruise promotion may cost more than it saves.

That curiosity is useful when you are trusting me with your vacation. I notice the small details, ask the extra question, and am comfortable telling you when the more expensive option is not the smarter one.

I also work through an established travel agency with long-standing supplier relationships. That can mean access to preferred pricing, onboard credits, amenities, group inventory, and real contacts when a situation needs more than a generic customer-service answer.

A little more personal

Travel in the Middle.

Family travel looks different when your children are no longer little, but everyone still wants the trip to feel like time together.

I live just outside Boston with my husband, our teenage son, and our daughter when she is home from college.

Like many of my clients, we are in a stage of life where family vacations look different than they did a decade ago. Everyone has different schedules, different interests, and different ideas of what makes a trip memorable.

Helping families put those pieces together is one of my favorite parts of this job. Finding the cruise line that is a better fit than the obvious choice. Knowing when a Disney resort upgrade is worth the extra cost and when it is not. Recommending the itinerary that fits your family instead of simply recommending the newest ship or the biggest promotion.

Celeste traveling with her family

When I am not working on client trips, you will usually find me researching a new ship, updating a Disney or Universal strategy, building one of my travel guides, or planning my next research trip.

Ready when you are

Make one great vacation decision.

Tell me what matters to you. I will help you sort through the options, understand the tradeoffs, and plan the vacation that fits.

Let's Start Planning