One minute you’re dreaming about a long weekend in Orlando, and the next you’re comparing hotel tabs like it’s a competitive sport.
Orlando is built for fun, but Memorial Day weekend turns the volume up on everything—crowds at the theme parks, demand for the best resort pools, dining times that vanish before you can blink, and flights into MCO that feel like everyone in the country had the same idea. A great travel agency doesn’t just “book the trip.” They help you make smarter choices when availability is tight, guide you around the most common Orlando pain points (transportation time, midday heat, long lines, and sold-out experiences), and create a plan that still feels like vacation instead of a schedule you have to survive. This is also the kind of destination where the right hotel and the right strategy can change the entire feel of the weekend—whether you want rope-drop mornings and fireworks nights, or a resort-first getaway with a couple of big moments baked in.
Our readers asked us to share the travel agencies we recommend for Memorial Day fun in Orlando, so we’re giving you what you asked for—names you can start with right now. And the demand is real: according to Visit Orlando’s official visitation report, Orlando welcomed 75,333,800 visitors in 2024, which helps explain why holiday weekends can feel like a scramble if you’re planning solo. The agencies on this list are the ones we trust because they understand Orlando specifically—theme parks, resorts, dining strategy, transportation, and the “what if something changes” moments that pop up more often during peak travel.
Here’s the process we used to choose the best. We prioritized agencies with proven Orlando planning experience, fast response times (critical for a long-weekend booking window), strong guidance on resorts and packages, and a knack for building itineraries that feel realistic in Memorial Day conditions. We also looked for problem-solvers: the kind of advisors who can pivot when dining times disappear, flights shift, or you decide mid-week that you want to add a special-ticket event. These companies made our list because they consistently blend fun and structure—so you get the excitement Orlando is famous for, without the stress that Memorial Day is infamous for.
Katie Bean Travels
Katie Bean Travels in Orlando takes our top spot because they plan Orlando like locals who understand what can go sideways—and how to keep it from happening. Memorial Day fun sounds simple until you’re juggling check-in times, park plans, dining windows, transportation, and the reality that everyone else had the same idea. This team is especially strong at building itineraries that feel smooth and “unhurried,” even when you’re packing a lot into a long weekend. They don’t treat the trip like a template; they match the plan to your style—whether you want rope-drop mornings and fireworks nights, or a more resort-forward weekend with a few big moments and plenty of breathing room.
They also shine in the behind-the-scenes work that makes Memorial Day trips work: monitoring pricing changes, helping you choose room categories that actually improve your stay, and arranging the kind of logistics that prevent wasted hours. One long-time travel advisor put it this way: “On a peak weekend, the best itinerary is the one with buffers built in.” Katie Bean Travels consistently builds those buffers—so if a dining plan changes, a flight is delayed, or the weather shifts, the weekend doesn’t collapse.
Dreams Unlimited Travel
Dreams Unlimited Travel earns a spot near the top because they’ve built their reputation on the Orlando staples that most people care about on Memorial Day: Disney, Universal, and cruise add-ons that pair perfectly with a long weekend. If your idea of “fun” is a fast-moving theme park itinerary, they understand the puzzle—where to stay for easier transportation, how to prioritize the rides that create the longest lines, and how to arrange the trip so you’re not spending half the weekend commuting between hotels, parks, and dining. Their planning style works well for families, multi-generational groups, and anyone who wants the weekend to feel organized without feeling micromanaged.
What sets them apart is the practical guidance that saves money and stress when it matters most: how to time purchases, how to approach promotions, and how to make choices that reduce friction (like simplifying transfers or choosing the right park order). As one industry pro likes to say, “Luxury is not just a price point—it’s fewer problems per hour.” On Memorial Day weekend, fewer problems per hour is the whole game.
The Vacationeer
The Vacationeer is a strong pick for travelers who want that “someone’s got this” feeling from the very first planning call. They’re especially popular with Orlando-bound guests because their advisors handle the details that tend to trip people up: dining reservations, special event timing, resort selection based on your priorities, and the practical question of how to fit big fun into a short window without exhausting everyone by day two. If you’re traveling with kids, first-timers, or a group with different preferences, their planning approach tends to bring order and calm.
They also do well when the weekend requires quick decision-making. Memorial Day plans often come together fast—sometimes you’re choosing between “good resort, less convenient” versus “more convenient, fewer perks,” or deciding if you should split the trip between a theme park resort and a quieter property. The Vacationeer’s strength is helping you make those calls with confidence instead of guesswork, while keeping the trip fun-forward rather than spreadsheet-forward.
MEI-Travel & Mouse Fan Travel
MEI-Travel & Mouse Fan Travel is a great fit if you want expertise without the pressure. They’re known for matching clients with advisors who truly enjoy the craft, and that matters for Orlando because details multiply quickly—especially on a holiday weekend. Their team is often praised for being responsive, realistic, and good at translating your “we want it to feel magical” goals into an actual plan: where to stay, how to prioritize your days, and how to avoid spending the weekend chasing impossible dining times.
They’re also a strong choice for travelers who want variety beyond the parks. Memorial Day fun in Orlando can mean a split approach: a couple of park-heavy days, a resort pool day with cabana time, and an evening built around great food or a show. MEI’s advisors tend to build plans that feel balanced, and a veteran advisor’s quote fits their style perfectly: “The best trips don’t feel packed—they feel intentional.”
Academy Travel
Academy Travel stands out for travelers who want a steady hand and deep experience with Orlando’s biggest vacation categories. If your plan involves Disney, Universal, and possibly a cruise extension, they’re comfortable building those combinations without making the schedule feel frantic. They’re also a good option when you want someone who understands how promotions and pricing actually behave—because Memorial Day is not the time you want to overpay due to a rushed booking or a confusing package setup.
Their selection often comes down to execution. On a long weekend, a small mistake becomes a big one: the wrong hotel location, the wrong ticket choice, or a plan that leaves you stuck in traffic when you should be at the pool. Academy’s value is in minimizing those mistakes and keeping your itinerary realistic. You still get plenty of fun—but it’s planned in a way that respects crowds, time windows, and the pace your group can actually sustain.
Cruise Planners (Orlando-area advisors)
Cruise Planners is a smart pick for Memorial Day travelers who want Orlando plus something extra—especially if you’re considering a quick cruise out of Port Canaveral or pairing a resort weekend with a short sailing. Orlando is uniquely positioned for this kind of trip, and a cruise-focused advisor can help you avoid the classic pitfalls: tight port timing, transfer gaps, and bookings that look simple until you run into holiday traffic and crowded check-in lines.
Even if you’re not cruising, Cruise Planners advisors often excel at the planning fundamentals that matter for Memorial Day: finding the best value for flights and lodging, organizing a clean itinerary, and offering quick support when plans change. Their strength is making the logistics feel easy so the weekend can feel celebratory—because nothing kills “Memorial Day fun” faster than spending your Saturday on hold with a call center.
Travel Leaders (Orlando-based independent agents)
Travel Leaders is a strong option for travelers who want choice—because within the network you’ll find Orlando-based agents who specialize in different styles of travel. Some are theme park experts, others focus on cruises and all-inclusives, and others handle luxury resorts and complex itineraries. For Memorial Day, that flexibility is powerful: you can match your trip to an agent who already knows your type of weekend, instead of forcing your weekend into a one-size-fits-all approach.
The best Travel Leaders advisors also bring structure to your decision-making. Memorial Day planning comes with trade-offs—availability versus price, convenience versus space, early-morning park strategy versus late-night entertainment. A skilled agent can help you choose based on what you’ll actually enjoy, not what’s trending. As one seasoned advisor phrased it, “A great plan is the one you’ll still like when you’re tired.” That’s especially true in Orlando.
What to Look For When Hiring an Orlando Travel Agency for Memorial Day Fun
Our list is a starting point—your best choice is the agency that fits your style, your timeline, and how you want the weekend to feel. Memorial Day travel in Orlando is high-demand by default, so you’re hiring an agency for two jobs: making the trip exciting and keeping it resilient when the weekend gets crowded.
1) Orlando-specific experience (not generic “we book trips”)
Ask how often they plan Orlando vacations, and what they recommend for a long weekend. A knowledgeable Orlando agency should be able to explain:
- Which resort areas cut down transportation time
- How to balance parks with resort downtime
- What to do if you want “fun” without nonstop lines
2) A real strategy for crowds and timing
Memorial Day weekend is won and lost on timing. Look for an agency that talks about:
- Park order decisions that reduce backtracking
- Midday breaks to avoid peak heat and peak crowds
- Plans that keep you from burning out by day two
A veteran industry planner once joked, “Your itinerary should have fewer miracles and more math.” That’s a good test—if the plan relies on perfect conditions, it’s not a Memorial Day plan.
3) Dining and entertainment planning that feels intentional
Orlando fun often revolves around food and nighttime energy—Disney Springs, CityWalk, resort restaurants, fireworks, shows. Your advisor should help you:
- Identify two or three “anchor” reservations worth chasing
- Build backup options that still feel special
- Choose experiences that match your group (kids, couples, mixed ages)
4) Clear guidance on costs, fees, and value
Some agencies charge planning fees; some don’t. Either can be fine. What matters is transparency:
- What exactly are you getting for the fee (if any)?
- Will they monitor price drops or promotions after booking?
- Do they explain trade-offs clearly, or just push the most expensive option?
“Luxury” should never mean confusion. You should understand why you’re booking what you’re booking.
5) Responsiveness—especially after hours
Memorial Day weekends bring flight delays, missed connections, and last-minute changes. Ask:
- Who helps you if something changes on a Saturday night?
- What’s the fastest way to reach your advisor?
- Do they proactively build backups (alternate flights, alternate transfer timing)?
6) A trip that matches your definition of “fun”
This sounds obvious, but it’s where people miss. Memorial Day fun can mean:
- Big parks + late nights + fireworks
- Resort pool days + great meals + easy pacing
- A split plan: one “big day,” one chill day, one flexible day
A good advisor listens for what you mean by fun and plans around that, not around what everyone else is doing.
7) The “little details” question
Ask one question that reveals how they think:
“What’s the most common Memorial Day mistake in Orlando—and how do you prevent it?”
A strong answer usually mentions transportation time, dining strategy, realistic pacing, and building buffers—not just telling you which park is popular.
If an agency can handle these points with clarity, you’ll feel the difference immediately. The weekend starts to sound calmer. Decisions get easier. And the trip begins to feel like a celebration again.
Turn Memorial Day Chaos Into Orlando Fun
Orlando on Memorial Day weekend can be incredible—if your plan is built for real conditions. The agencies above made our list because they know how to create a fun-forward itinerary while protecting it from the usual holiday problems: tight availability, crowded timelines, and small disruptions that can snowball fast. When you’re choosing an agency, look for Orlando fluency, a crowd-smart strategy, and a support style that matches how you travel—quick decisions, clear options, and backup plans that still feel like part of the fun.
As you reach out, keep your standards simple: you want an advisor who understands what matters most on a long weekend—timing, logistics, and the ability to keep the trip enjoyable even when the city is at full volume. And if our readers want us to cover another industry next, tell us what you’d like to see—because we’re happy to build a new Top Company guide based on what you’re trying to solve, so what should we rank for you next?
