Meet the Advisors Who've Sailed 80+ Times
(So You Don't Have to Make the Mistakes)
Roam with Rosen was founded in November 2024 by Melissa Rosen and Heather Maastricht because busy professionals deserved better than generic cruise packages and overwhelming research.
With 80+ combined sailings and certifications across 15+ cruise lines, we help you choose the ship, cabin, and timing that actually fit your travel style. Not a cruise line's marketing brochure. Not someone else's idea of luxury. Yours.
We're not just booking agents. We're strategic partners who've done the research, made the mistakes, and figured out how to cruise smarter.
MELISSA ROSEN - FOUNDER & CRUISE ADVISOR
Melissa Rosen founded Roam with Rosen to help busy professionals cruise smarter. Without the research overwhelm.
With 80+ personal sailings across ocean, river, and expedition cruises, I don't read cruise line brochures. I've been on the ships. I know which cabins to avoid, which dining strategies work, and which shore excursions are worth your time.
What sets me apart:
I'm a Virgin Voyages Gold Tier specialist. The only tier that actually means you've sailed enough to know what you're talking about. I'm certified across 15+ cruise lines including Virgin, Celebrity, Silversea, Disney, Viking, Oceania, Seabourn, and more.
I'm a Chief network member, which means I understand how busy professionals think about travel and time off. I know what it's like to negotiate vacation days. To feel guilty about unplugging. To need forced rest because "doing nothing" doesn't come naturally.
I'm the co-creator of Sailing Sisters, a women's leadership voyage series that blends networking, rest, and intentional connection. Because cruising isn't just about the destination. It's about who you become when you give yourself permission to step away.
“Luxury for less isn’t about cutting corners. It’s about knowing the system.”
I don't chase the cheapest price. I chase the best value. That means knowing which cabin categories get free upgrades. Which sailing dates have the best weather. Which on-board credits are worth negotiating for.
I've been the person who booked the cabin above the theater. I've been the person who didn't reserve dining early enough. I've made the mistakes so you don't have to.
80+ personal sailings (ocean, river, expedition)
Virgin Voyages Gold Tier Specialist
Certified across 15+ cruise lines
Chief network member
Sailing Sisters co-creator
Based in Tampa Bay, serving clients nationwide
80+ personal sailings (ocean, river, expedition) Virgin Voyages Gold Tier Specialist Certified across 15+ cruise lines Chief network member Sailing Sisters co-creator Based in Tampa Bay, serving clients nationwide
When you work with Roam with Rosen, you get:
Strategic cabin selection.
Location matters more than cabin class. I know which cabins on specific ships are worth the upgrade and which are a waste of money.
Shore excursion guidance.
Which ones are worth it, which to skip, and which you can do on your own for half the price.
Dining and entertainment planning.
Book key reservations before boarding, or you'll be eating at 9:30pm every night.
Real-time support during your sailing.
We’re available if issues arise. Not just during business hours.
Packing and pre-cruise preparation.
What you actually need versus what cruise lines recommend. Spoiler: you don't need formal wear for most ships.
HEATHER MAASTRICHT - CO-FOUNDER & COO
Heather Maastricht co-founded Roam with Rosen with Melissa in 2025. If there's a way to make it happen, she's already three steps ahead. Spreadsheet open, details locked in, backup plan ready.
Her story didn't start in travel. It started with purpose.
At a camp for individuals with disabilities, Heather learned early on that experiences shouldn't have limits. That belief became a 30-year career helping people live fully, independently, and boldly. She didn't just manage programs. She traveled alongside clients and made sure they experienced the world in ways that felt accessible, joyful, and completely their own.
Then came that cruise.
Melissa invited Heather as her plus one on a Sailing Sisters voyage. When things didn't go as planned, they naturally stepped in together. Handled issues. Answered questions. Kept the trip on track. By the end, people weren't just grateful. They were telling Melissa, "You should do this yourself."
So Melissa started thinking. Researching. And Heather casually offered to "help out."
That help turned into a partnership. One conversation became a plan. The plan became a business. And Heather officially became part of Roam with Rosen.
Now she brings that same calm-in-the-chaos energy to every trip. Operational excellence meets deep personal understanding of what travel can mean in someone's life. She makes sure everything works exactly the way it should, so you can just show up and enjoy.
What Heather brings to RWR:
While Melissa focuses on voyage strategy and cabin selection, Heather ensures the operational side runs smoothly. Client coordination. Pre-cruise planning. Logistics management. The behind-the-scenes work that makes your cruise planning feel effortless.
You shouldn't have to chase down confirmations, wonder about payment schedules, or worry about whether everything is handled. That's her job.
And while she's busy helping everyone else check destinations off their lists, her own wanderlust is very real, fueled by a growing list of "next places to go" that's getting slightly out of control (in the best way).
Heather's philosophy: Travel isn't just about where you go. It's about making sure everyone gets the chance to go. And she's here to make sure it actually happens.
Background:
Co-Founder, Roam with Rosen (2024)
30+ years in disability services and accessible travel
Program management and client advocacy
“Travel isn’t just about where you go. It’s about making sure everyone gets the chance to go. And she’s here to make sure it actually happens.”
THE BECOMING OF ROAM WITH ROSEN
How RWR Started
Roam with Rosen didn't start as a business plan.
It started as a question people kept asking Melissa:
"How do you cruise so much?"
The answer: I know how to make it work.
I know which cabins to book. When to sail. How to get luxury experiences without luxury budgets. I know how to take 4-day sailing weekends without burning all my vacation time. I know how to unplug completely because being on a ship (literally unable to check one more thing off my to-do list) is the only way I've learned to rest.
After years of fielding questions from Chief network members, friends, and colleagues, Melissa realized there was a gap in the market:
Busy professionals who wanted to cruise but didn't have time to research.
They didn't need generic packages. They needed someone who understood their constraints. Limited vacation time. Guilt about unplugging. The need for both rest and stimulation. And could plan accordingly.
In 2025, Melissa partnered with Heather Maastricht to turn this insight into Roam with Rosen.
Why "Roam with Rosen"?
The name reflects what we do: we help you roam smarter. Not just book cruises, but explore the world in a way that fits your actual life.
"Rosen" is Melissa's last name, but it's also a nod to the personalized approach. You're not working with a faceless agency.
You're working with someone who's been there, done that, and knows what works.
What We Believe:
Cruising isn't just about the destination. It's about perspective. When you're watching the sun set over Santorini or having dinner with strangers who become friends, you remember what matters. You come back sharper. Clearer. More strategic.
Luxury for less isn't about cutting corners. It's about knowing the system. It's knowing which cabin next door costs $400 more but offers nothing different except a higher deck number.
Rest isn't optional. It's strategic. Leaders who take time off perform better. But "rest" doesn't mean doing nothing. Sometimes it means exploring Iceland. Sometimes it means networking with other professional women at sea. Sometimes it means both.
.Why We're Different:
Most cruise advisors help you book. We help you plan strategically.
We don't just find you a cruise. We help you choose the ship, cabin, and timing that fit your travel style, your budget, and your actual vacation constraints.
We don't just send you a confirmation email. We monitor for price drops after booking. We negotiate on-board credits. We provide real-time support if something goes wrong during your sailing.
We don't just sell cruises. We help busy professionals build travel strategies that actually work for their lives.
What's Next:
Since launching in 2024, Roam with Rosen has grown from 1:1 planning to include hosted group voyages (Sailing Sisters), Virgin Voyages specialist services, and curated small-group sailings for professional women.
But we're still small by design. We're not trying to be the biggest cruise agency. We're trying to be the best. For a very specific type of traveler.
If you're a busy professional who wants to cruise without the research overwhelm, who values expertise over generic packages, and who's ready to actually use those vacation days you've been hoarding? We're here.