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Travel Designed by Experienced Experts Who Care About the Details

River & Expedition Cruises Crafted for Connection, Comfort, and Confidence

Meet the owners of Yellow Umbrella Travel

Cheryl and Shea Bailey, owners of Yellow Umbrella Travel

Yellow Umbrella Travel was created by Cheryl & Shea Bailey, owners of Yellow Umbrella Events – one of the top group travel agencies in the US, known for crafting seamless, all-inclusive experiences at Mexico’s best resorts. 

After guiding thousands of companies, couples, and families through international travel logistics, Cheryl saw a growing need among her clients – they were ready to explore beyond Mexico in more elevated and expertly organized ways. They wanted the same thorough, personalized service they’d come to trust, but in a new setting: the rivers of Europe and the remote coastlines of the world.

That’s how Yellow Umbrella Travel was born – a sister brand dedicated to river cruises and small-ship expedition travel, serving our clients who wanted what we’re known for (personalized, seamless, expert-guided planning) but for a different kind of journey: one that sails beyond the beach and into the world’s rivers and remote coastlines. Our past clients get to continue to enjoy the all-inclusive style of travel they grew accustomed to, while experiencing more of what this amazing world has to offer!

Our team of travel professionals brings the same trusted approach our clients already know and love:

  • Integrity and transparency in every recommendation
  • Proactive communication so you always know what’s next
  • Thorough, curated itineraries tailored to your interests
  • Partnerships with only the best cruise lines and tour operators. 

When you travel with Yellow Umbrella Travel, you’ll feel confident, cared for, and inspired – because we’ve thought through every detail long before you start your journey.

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The Yellow Umbrella Difference

Our process goes far beyond simply booking a ship – we deliver end-to-end planning designed to make group travel effortless.

  • InsiderMatch™ Ship Pairing
    Our proprietary system matches you to the perfect river or expedition cruise line and itinerary based on you or your group’s size, style, destination goals, and budget.
  • Expert Group Logistics
    From group room blocks to international transfers, we coordinate every moving part so every guest enjoys a seamless experience.
  • Personalized Service
    You’ll always work with a dedicated, experienced planner – not a call center.
  • Responsive, U.S. Based Support
    Our team is quick to respond, transparent, and ready to troubleshoot anything – from payment questions to what to wear.
  • Proven Expertise
    After more than a decade managing group travel worldwide, we know how to prevent problems before they happen.

Let us take the complexity out of planning, so you can focus on the unparalleled adventure that awaits.

Uniworld River Cruises Christmas Market

Yellow Umbrella Travel’s InsiderMatch™ Process

Because every great trip starts with the right ship!

Finding the perfect river or expedition cruise can feel overwhelming – hundreds of ships, countless itineraries, endless cabin options. That’s where our InsiderMatch™ comes in.

It’s our signature system for pairing your group with the ideal ship, itinerary, and experience – designed to fit your travel style, group size, sense of adventure, and budget.

How InsiderMatch™ Works

  1. Share Your Vision
    Tell us what you’re celebrating, where you’d love to go, and how you want your experience to feel – intimate and cultural, adventurous and wild, or luxurious and laid-back.
  2. We Curate the Perfect Match
    Using our insider knowledge of the world’s top river and expedition fleets, we match you with the best-fit cruise line, ship, and itinerary for your group’s personality and budget.
  3. We Handle Every Detail
    From individual reservations to group room block contracts to international transfers and payments, we manage all the logistics – so you can focus on enjoying the journey.

 

Why Clients Love InsiderMatch™

  • It saves time. We narrow the world of river & expedition cruise options down to the few that truly fit your needs.
  • It can often save you money. We know how to secure group rates and added value through our river cruise line partnerships.
  • It’s seamless. We manage the details and the deadlines so nothing slips through the cracks.
  • It’s personalized. Every recommendation comes from our team of nine seasoned travel experts – not an algorithm.

Ready to Find Your Perfect River or Expedition Cruise Match?

Let’s design your river or expedition journey together - curated for connection, culture, and comfort. Contact us today.

GET STARTED

The Yellow Umbrella Travel Difference

5 Reasons Groups Trust Us With Their River & Expedition Journeys

RHINE River Cruise Ama waterways by Yellow Umbrella Travel
  • Expert Knowledge, Perfect Match We know the world’s best river and expedition ships inside and out - from Europe’s legendary waterways to the polar regions and beyond. Our team of experts helps you choose the right vessel, itinerary, and cabin category for your group’s exact needs.
  • Clarity From the Start No hidden surprises here - just complete transparency. We clearly outline what’s included, what’s not, and how far your budget will go, so you can make confident decisions before you ever set sail.
  • Seamless Guest Coordination Managing a group doesn’t have to be stressful. We handle the contracts, room blocks, guest bookings, payments, and international transfers - all with the precision and communication you’d expect from a dedicated concierge team.
  • Real Support, Real People When you need us, we’re here - quick to respond, proactive, and based right here in the U.S. From pre-departure questions to in-transit assistance, you’ll always have a reliable partner looking out for you.
  • Your Vision Comes First Before we talk ships or contracts, we start with you. Using our background in high-end event and group planning, we design every journey around your goals and what you want this experience to mean - for you and your guests.

This Is What “Above the Current” Feels Like

A team that’s thorough, up front, and invested in your experience from day one.
Because when every detail is handled with care, all that’s left for you to do is enjoy the journey.

Frequently Asked Questions

Because cruise lines sell cabins; we design experiences. We handle every aspect of your group journey – from choosing the right ship and managing contracts to coordinating guest bookings and transfers – so you can actually enjoy the trip, not manage it.

We plan both individual trips and group trips. Whether you’re a party of 1 or 100, we’d love to plan your river or expedition travel!

Our river cruise and expedition travel services are complimentary at this time.

However, for advanced and extremely detailed itineraries (like corporate event or incentive travel planning services) there could be a fee. Once we learn about your group size, destination, and travel style, we’ll provide transparent pricing for any potential fees upfront. No surprises, ever!

Reach out to us anytime. You’ll get clear answers, fast responses, and honest guidance from our expert team (never a call center). Contact Us Here.

Get Cruising Today