What It’s Like to Plan a Trip Together

Christie Costello
May 6
5 min read

Three people smiling and raising wine glasses in a toast outdoors at sunset. Table with cacti, corn, and a wine bottle. Warm, joyful atmosphere.

Because the best memories are made when you're fully present—with the people who matter most.

Hi there—and welcome! I’m so glad you found your way here.

This might be your first time working with a travel advisor—or maybe you’ve planned plenty of trips before but are curious what it would be like to have expert support this time. Whether you’re celebrating something special, craving a deeper experience, or simply want your next vacation to be smoother and more enjoyable, you’re in the right place.

At Toastable, our entire ethos is built around connection—to places, to people, and to the moment. Our name was born from this belief: You can’t toast alone.

We believe in memory-making over checklist-chasing, in sharing laughter over a beautiful meal, in finding those little moments that make you say, “This is exactly where I’m supposed to be.” Whether you’re traveling with family, friends, a significant other—or even yourself—you deserve to feel grounded, joyful, and well taken care of.

Group of smiling people on a red suspension bridge in a lush green forest, some holding cameras. Bright, cheerful atmosphere.

Why Work With Toastable Travel?

Anyone can book a flight. But a trip that leaves a lasting imprint on your life? That takes intention, listening, and thoughtful design.

At Toastable, I don’t just match you with destinations—I match you with the right experience for your travel style, values, and the people you’re traveling with. That might mean choosing the right cruise line or small-group tour, or building a custom journey from scratch. But it always starts with connection and ends with a trip that reflects who you are.

And here's the best part: you don’t have to figure it all out first. I’ll walk you through everything, step by step.

What You Can Expect:

Step 1: Discovery

Hands typing on a silver laptop in a relaxed setting. Person wearing a white sweater. Blurred background with subtle colors.

We’ll start with a relaxed, friendly call where I get to know you. Not just where you want to go, but what you’re celebrating (if anything!), who you’re traveling with, and how you want to feel while you’re there. You don’t need all the answers—just bring your ideas, your questions, and your excitement.

I’ll also ask if you’ve worked with a travel advisor before. If not, no worries at all—I’ll guide you through what to expect and how we’ll collaborate. If you have, I’d love to hear what worked well and what didn’t. Either way, we’ll tailor the process to fit you.

Step 2: Choose Your Planning Level

Once we understand your trip goals and needs, we’ll choose one of three ways to work together. Each one offers a different level of service and support—but all are designed to make your travel planning easier, better, and way more enjoyable.

Support Level

You already know exactly which cruise, tour, or resort you want—amazing! But even when the decision is made, there’s still a lot to coordinate.

That’s where I come in.

I’ll handle all the logistics, bookings, upgrades, and behind-the-scenes details to make sure everything flows smoothly. I’ll also walk you through any trip extras, help you avoid common pitfalls, and make sure nothing gets overlooked.

Plus, through my professional travel network, you’ll often get access to perks and amenities you wouldn’t get on your own—things like room upgrades, early check-in, onboard credits, or exclusive experiences.

You still get the trip you want—but elevated, stress-free, and personalized with thoughtful care.

Advisor Level

You know the type of trip you want, but don’t know which cruise line, resort, or tour company to choose? That’s where having an experienced guide makes all the difference.

There are hundreds of great travel brands out there—but they’re not all created equal. I spend time getting to know them, just like I get to know you. I understand the personalities, inclusions, pacing, and clientele each one is built for—and I use that knowledge to match you with the best possible fit.

Instead of sifting through an overwhelming list of options, you’ll get a short list of curated recommendations—each one aligned with your style, values, and travel goals.

It’s a smarter, more confident way to book, with an experienced voice in your corner.

Concierge Level

This is where I do my most transformative work—and where many of my clients find the greatest value.

The Concierge Level is for travelers who want something custom-built from the ground up—a trip that’s as unique as they are.

Whether it’s a multi-stop adventure across countries, a slow and immersive regional itinerary, or a blend of culture, food, nature, and rest, I’ll design it all for you with care and intention. Think: hotels with soul, transport that makes sense, meaningful experiences, and room to breathe.

You'll get a full itinerary tailored to your preferences, with thoughtful details that make your trip feel effortless and immersive. From big-picture flow to on-the-ground logistics, everything is handled—beautifully.

This is more than just a vacation. It’s a trip that reflects who you are, what you care about, and what you want to remember.

For a full breakdown of what's included in each planning package level, click here.

What About Booking and Payments?

Depending on your trip, I’ll either book components directly through my trusted supplier network or use your securely provided payment details to reserve pieces on your behalf. Whether it’s a fully packaged itinerary or custom elements pulled together, I handle the booking process to ensure everything runs smoothly and is backed by excellent service.

Either way, you’ll always know what’s happening, and I’ll keep the process clean, simple, and clear.

Is This the Right Fit?

We might be a great match if…

You want a real person (hi, that’s me!) guiding your travel planning
You value quality time with the people you love
You appreciate thoughtful details, insider tips, and seamless logistics
You’d rather enjoy the journey than stress about the spreadsheets
You’re open to collaboration and trust the process

On the other hand, if you prefer to shop solely on price or enjoy booking things yourself for fun, we might not be the best fit—and that’s totally okay.

I work best with clients who want a curated, connected, and low-stress experience—people who want their trip to feel just as good on the inside as it looks in the photos.