Jennifer Santos Has Sailed Oasis of the Seas Three Times — Here's What She Tells Every Client Before They Book

There is a moment, Jennifer Santos says, when the tender pulls toward Coco Cay and the island comes into full view, that everything shifts. The cruise ship disappears behind you. The ocean opens up. And what greets you feels less like a port stop and more like checking into a luxury resort for the day. "If I could go on a cruise that stopped here multiple times, I would," Santos says, her enthusiasm unguarded and immediate. "I absolutely love cruising with everything there is to do, but this island is like arriving at a resort for the day." For a travel advisor who chooses her words with professional care, that kind of unfiltered joy says everything.

Santos recently returned from a family trip aboard Royal Caribbean's Oasis of the Seas, a sailing that marked the third time she has boarded the same ship in five years, always with her children in tow. What began as a family favourite has quietly become one of her most powerful professional tools. Because when a travel advisor can speak to a destination not from a brochure, but from memory, from the feel of salt air and the texture of a sun-warmed cabana cushion, clients notice the difference.

The Cabana Secret That Changes Everything

Ask Santos for her single most-shared tip from any Coco Cay visit and the answer comes without hesitation: rent the cabana. It sounds simple. Most travelers scroll past the add-on without a second thought. Santos has watched that mistake play out too many times to stay quiet about it. "Rent the cabana," she says, listing the reasons in the efficient shorthand of someone who has given this advice dozens of times. "Save space for your belongings, top VIP service, golf cart shuttle around the area, direct beach access, amazing drink service, as well as somewhere safe to store belongings, but also becomes a set meet-up spot for your group, as well as a nice area to cool off and refresh throughout the day."

The cabana, in Santos's framing, is not a luxury splurge. It is a logistics solution, a comfort guarantee, and a social anchor all at once. For families travelling with children or groups spread across a sprawling private island, having a fixed home base changes the rhythm of the entire day. It is the kind of field-tested intelligence that travel advisors accumulate over years of experience and that no algorithm can replicate.

Why the Same Ship Keeps Winning

What makes Santos's relationship with Oasis of the Seas genuinely compelling is not that she booked it once and loved it. It is that her family has chosen it again and again, even as her children have grown from toddlers into young teenagers. "I have been on Oasis of the Seas three times with my children over five years and they still keep choosing this ship," she says, with the quiet pride of a parent who has managed to find something that holds a family's attention across an entire childhood.

That loyalty, Santos explains, is not accidental. It is a reflection of what mega-ships do better than almost anything else in travel: scale. The Oasis of the Seas is not merely a cruise ship. It is a floating resort, dense with activity, designed to meet travelers wherever they are, whether that means a toddler's first splash in a pool or a teenager's first rock-climbing wall. Santos is direct about who this experience is built for. "Mega cruises are amazing for groups and those looking for action-packed vacations," she says. But she is equally direct about who should look elsewhere. Travelers seeking quiet, adults-only atmospheres or unusual, off-the-beaten-path port stops will find mega-ships a poor fit. The size that makes them extraordinary also limits the ports they can enter, keeping itineraries anchored to major destinations rather than hidden harbours.

The Insider Rules That Protect Every Cruise

Beyond Coco Cay and the ship itself, Santos carries a set of practical principles that have evolved through years of watching clients make the same avoidable mistakes. The first is deceptively simple. Always fly in the night before. "I used to suggest this only for winter travel due to weather delays," she says, "but now the reality is, schedules, flights, last-minute emergencies happen." Arriving the evening before departure means the first morning of the cruise begins with energy and anticipation rather than the frayed nerves of a connecting flight barely caught.

The second rule lives in the carry-on bag. Santos has seen it too many times: passengers stepping off the ship at their first port stop with skin already raw and red, their sunscreen packed deep in checked luggage that did not reach their stateroom until the ship departed that evening. The image is uncomfortable precisely because it is so preventable. A change of clothes, a bathing suit, and sunscreen in the carry-on are, in Santos's world, non-negotiable. They are the difference between a perfect first day and spending day two paying for a mistake that took thirty seconds to avoid.

The Case for Booking Early

Santos's professional philosophy extends well beyond what to pack. She is, at her core, an advocate for early planning, and her reasoning is grounded in years of watching the cruise booking market reward those who move first. Low deposits lock in not just price but selection: the best cabins, the most desirable ships, the premium sailing dates that sell out months before the general public thinks to look. "Selling last-minute cruise travel isn't ideal for the majority of customers," she says, "and wouldn't be my first option for a new cruiser, as they won't have the same type of experience."

This is the philosophy she brings to every client conversation now. When a new sailing launches, Santos is already talking to her clients about it. Not because she is selling urgency for its own sake, but because she has watched the alternative play out, and it rarely ends well for the traveler who waited.

A Traveler Still Growing

For all her expertise in family cruise travel, Santos is candid about the fact that her own travel identity is shifting. A decade of family-focused itineraries, shorter flight times, and single-destination trips has given her children a remarkable foundation as travel companions. Now, with that foundation in place, she is ready to push further. Thailand and the surrounding region sit at the top of her bucket list, part of a broader turn toward multi-destination, culture-rich journeys that she has been quietly building toward for years.

It is a telling detail about the kind of advisor Santos is. She does not recommend experiences she has outgrown. She grows alongside her clients, always reaching toward the next horizon, always carrying back something worth sharing. "My travel bucket list is always growing," she says. "There isn't many places I wouldn't go." For the clients who trust her with their own adventures, that restless curiosity is not just reassuring. It is the whole point.