Your travel advisor

Hi, I'm Courtney.
I plan the trips you'll never stop talking about.

One real person, not a call center, who handles everything from the first daydream to the day you land back home. Caribbean beaches, Hawaii, Mexico, cruises, and the mouse-eared kingdoms of Orlando.

Independent advisor · Pineapple Escapes Travel, LLC Free to you: resorts pay me Replies within 24 hours

Let's plan your trip No fees, no pressure, no obligation.

A family walking hand in hand along a palm-lined Hawaiian beach at golden hour

CaribbeanHawaiiMexicoCruisesDisney & UniversalHoneymoonsDestination WeddingsGroup trips

Credentials & Memberships

CLIA Certified

IATA / IATAN Accredited

Pineapple Escapes Travel, LLC

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"I plan the kind of trips I love to take."

I've walked the beaches, toured the resorts, and built the supplier relationships that get you upgrades, unpublished rates, and the little perks you won't find booking on your own.

When you work with me, you get one person who handles everything: comparing resorts side by side, lining up the room that actually fits your crew, and watching your booking until you're home. No fees, no pressure, just honest advice and a real human in your corner.

Start with the free calculators to find your budget, then tell me what you're dreaming about and I'll take it from there.

Courtney

How it works

From your first idea to a booked trip. Four steps, zero fees.

Price your trip

Free instant calculators give you an honest ballpark for a vacation, cruise, or theme-park trip in under a minute. No account, no sign-up.

Try the calculators →

Tell me about it

Send your dates, who's traveling, and what matters most. Everything carries over, so you never repeat yourself. (Skipping the calculator is fine too.)

Tell me about your trip →

I tailor your options

I compare resorts side by side and line up upgrades, resort credits, and unpublished rates through my supplier relationships. You get options that genuinely fit.

Book with confidence

I handle payments, documents, and requests, and I stay with you through the trip in case anything comes up. Nothing books until you say go.

Let's connect →

Real trips, real moments

A few favorites from the road, the beach, and everywhere in between.

Drag or swipe

My planning is free to you. And that's not a gimmick.

Resorts and cruise lines pay me a commission that's already built into the price you'd pay booking on your own. You pay nothing extra; you just get an expert in your corner. Nothing gets booked until you give me the go-ahead.

Good to know

Quick answers before you reach out.

Not at all. They're just an easy way to get a ballpark budget if you'd like one before we talk. If you'd rather skip straight to a conversation, reach out and tell me what you're dreaming about.

Caribbean and Mexico beach escapes, Hawaii, cruises, Walt Disney World and Universal Orlando, plus honeymoons, anniversaries, and group trips. If it's a vacation, odds are I can help.

I read every message myself and reply within 24 hours, usually much sooner. You'll always be talking to me, never a call center.

I'll follow up to learn a little more about what you're after, then put together a few options with real pricing. Nothing gets booked until you're happy and give me the go-ahead.

Yes. I'm an independent travel advisor with Pineapple Escapes Travel, LLC, a real person who plans and books real trips, every day.

Ready when you are.

Tell me where you're dreaming of and I'll take it from there.

Start the conversation Free · No obligation · Replies within 24 hours

Hi, I'm Courtney.I plan the trips you'll never stop talking about.