We curate vacations personalized for your style, vision and interests.

We help busy travelers design trips without the endless scrolling, review reading and hours of research.

Tired of spending hours searching for "the perfect trip?"

You have 20 tabs open, resort reviews become blurry, and every destination looks amazing—but also could be “too good to be true.” One blog says it’s the best ever, another says it’s a disaster. You start comparing prices and obsessing over details you never cared about before.

We know how easy it is to get lost in a sea of resorts, recommendations, and reviews that all promise the world. You want something amazing, but between TikTok tips, shiny Instagram reels, and everyone’s “must-do” list, it’s hard to know what’s real—and what’s just good marketing. We get it, and you’re not alone.

We believe planning travel shouldn’t feel like guesswork

We handle the details, you make the memories.

Allow our team to help you travel confidently. No algorithms. No stock advice. Just firsthand knowledge, transparent recommendations, and a whole lot of heart! Whether it’s a luxury catamran in the Caribbean, a safari in South Africa, or pasta making in Rome, we’ll help get you there.

As experienced travel designers, our team has visited every continent, enjoyed every Sandals resort, stayed at every Disney property or experienced Alaska like a local! We have guided thousands of clients with vacations that actually fit their style. We utilize our professional training, destination experience, trusted tour operators and travel partners to craft the trip of your dreams.

And we’d love to do the same for you!

Travel Designed For You

Dreamy Weddings and Honeymoons

Gorgeous, stress-free celebrations in paradise, from save-the-date to honeymoon.

Best All-Inclusive Resorts

Handpicked resort vacations in sun-soaked destinations we’ve personally explored and vetted in Mexico, the Caribbean and beyond.

Passport Stamp Collectors

Curated, custom travel plans throughout the globe. From the Eiffel Tower to the Vatican, Tokyo’s neon lights to Iceland’s northern lights.

Wildlife and Adventure

Chasing kangaroos, elephants and northern lights? We’ve got you! Glamping, chasing kangaroos, elephants and northern lights? We’ve got you!

Family Vacations

Thoughtfully designed trips for all ages, from todders to grandparents.

Theme Park Vacations

Tickets, tips, and guidance for each magical park around the globe.

River and Ocean Cruises

Curated sailings for every style, whether you’re island hopping or sailing by castles and vineyards.

The Pink Pineapple Difference

Travel Should Be Personal

With hand-crafted itineraries built for you, every experience is personalized to your interests.

Real Resort Insight

With firsthand experience at 120+ resorts, you’ll get honest, tailored recommendations—which means no more guessing what’s worth your time or investment.

Peace in Mind

With comfort knowing you have a travel designer to assist before, during and after your travels.

Our Personalized Process

Love Notes from Happy Travelers

"Super Useful!"

"Jess was amazing! She listened to what we were looking for and gave us great resort options as well as excursion options. Jess checked in throughout the process, provided us with packing and super useful travel tips. We will 100% be using Pink Pineapple for our next trip!"

Nikki M.

"Top Notch!"

"Sarah helped us in every aspect of planning our Mexican vacation. The attention to our individual requests and general questions was top notch."

Jessica C.

"Very Helpful and Detailed!"

"Lorryn was fanastic to work with. We had a 50 person wedding in Mexico and she helped coordinate our contract with the hotel along with booking rooms for our guests and providing us and them with all of the information for the trip. All of our guests said she was very helpful and detailed. My wife and I highly recommend Lorryn for your travel/Destination wedding needs!"

Stephen K.

"Amazing!"

"They've made our trip planning so smooth and have made travel dreams come true! We've worked with several agents and they've all been amazing!"

Patrice S.

"Travel Was Seamless!"

"I booked a recent trip through Pink Pineapple and was so impressed. Every detail was accounted for and thoroughly explained. We got a great deal and the planning and travel was seamless!"

Allison A.

Our Favorite Ways to Make Your Trip Easy and Meaningful

Resort Matching

You’ll get handpicked resort options that actually fit your travel style—so you can stop second-guessing and feel excited to book.

Custom Itinerary Design

You’ll enjoy a trip designed around how *you* want to travel—so your days flow naturally, with time to truly connect and relax.

Support Before, During & After Travel

You’ll have expert help every step of the way—so you never feel alone if something unexpected pops up.

Clear Quotes & Budget Guidance

You’ll get pricing that makes sense and matches your goals—so you don’t waste money on the wrong fit.

Destination Wedding Planning

You’ll get real support from “yes” to “I do”—so your big day feels beautiful and breezy, not chaotic.

Family Travel Expertise

You’ll get age-appropriate options for everyone—so the whole crew feels included (and no one’s bored).

Special Occasion Add-Ons

You’ll get help adding meaningful extras like candlelit dinners or spa time—so your trip feels truly special, not just standard.

Travel Protection Education

You’ll understand how to protect your trip and your wallet—so you can book with confidence, not worry

Door-to-Door Travel Support

You’ll get help arranging smooth arrivals and easy departures—so you can focus on the fun parts, not figuring out how to get there or back.

You deserve all of this and much more…