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 fit your travel style. Your budget. Your actual vacation constraints.
We've done the research, made the mistakes, and know how to cruise smarter. That's what you're hiring when you work with us.
Melissa Rosen
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, she doesn't read cruise line brochures. She's been on the ships. She knows which cabins to avoid, which dining strategies work, and which shore excursions are worth your time.
What Sets Her Apart:
Melissa is a Virgin Voyages Gold Tier specialist. The only tier that actually means you've sailed enough to know what you're talking about. She's certified across 15+ cruise lines including Virgin, Celebrity, Silversea, Disney, Viking, Oceania, Seabourn, and more.
She's a Chief network member, which means she understands how busy professionals think about travel and time off. She knows what it's like to negotiate vacation days. To feel guilty about unplugging. To need forced rest because "doing nothing" doesn't come naturally.
She's the co-creator of Sailing Sisters, a women's leadership voyage series that blends networking, rest, and intentional connection.
"Luxury for less isn't about cutting corners. It's about knowing the system."
Melissa doesn't chase the cheapest price. She chases the best value. That means knowing which cabin categories get free upgrades, which sailing dates have the best weather, and which on-board credits are worth negotiating for.
On her honeymoon, she booked an inside cabin at the bottom of the ship, right next to the anchor. It dropped every morning. Very unromantic alarm clock. She's also been the person who didn't reserve dining early enough. She's made the mistakes so you don't have to.
When you work with Melissa, you get:
- Strategic cabin selection: Location matters more than cabin class. She knows which cabins on specific ships are worth the upgrade and which are a waste of money.
- Dining and entertainment planning: Book key reservations before boarding, or you'll be eating at 9:30pm every night.
- Shore excursion guidance: Which ones are worth it, which to skip, and which you can do on your own for half the price.
- Packing and pre-cruise preparation: What you actually need versus what cruise lines recommend. Spoiler: you don't need formal wear for most ships.
- Real-time support during your sailing: She's reachable if issues come up. Not just during business hours.
Heather Maastricht
Heather Maastricht co-founded Roam with Rosen with Melissa in 2024. If there's a way to make something happen, she's already three steps ahead. Spreadsheet open, details confirmed, backup plan ready.
Her career didn't start in travel. It started with a belief that experiences shouldn't have limits. That conviction drove 30 years in disability services, traveling alongside clients, managing programs, making sure people experienced the world in ways that felt accessible and genuinely 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 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."
That conversation became a plan. The plan became a business. And Heather officially joined Roam with Rosen.
Now she handles the operational side so Melissa can focus on voyage strategy: client coordination, pre-cruise planning, logistics, the behind-the-scenes work that means you show up and everything's already handled. You shouldn't have to chase confirmations or wonder about payment schedules. That's her job.
Her own list of places to go is getting slightly out of control. In the best way.
What Heather Brings to RWR:
While Melissa focuses on voyage strategy and cabin selection, Heather runs the operational side. Client coordination. Pre-cruise planning. Logistics management. The work that happens before you ever step on the ship.
"Everyone deserves the chance to go. She makes sure it actually happens."
The Becoming of Roam with Rosen
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: she knows how to make it work. Which cabins to book. When to sail. How to get luxury experiences without luxury budgets. How to take 4-day sailing weekends without burning all her vacation time. Being on a ship, literally unable to check one more thing off a to-do list, is the only way she's learned to truly unplug.
After years of fielding questions from Chief network members, friends, and colleagues, Melissa saw a real gap: busy professionals who wanted to cruise but had no 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 around them.
In 2024, Melissa partnered with Heather Maastricht to build 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, and a nod to the personal approach. You're working with someone who's been there, made the mistakes, and knows what works.
What We Believe
Perspective Shifts
The destination matters. So does who you are when you come back. Watching the sun set over Santorini or having dinner with strangers who become friends, that's when perspective shifts. Leaders who take real time off come back sharper. The research backs it up. So does our own experience.
System Knowledge
Luxury for less means knowing the system. The cabin next door costs $400 more and offers nothing different except a higher deck number. We know which upgrades are worth it and which aren't.
Strategic Rest
Rest is part of the strategy. "Doing nothing" rarely works for people wired to produce. Sometimes rest looks like exploring Iceland. Sometimes it looks like networking with other professional women at sea. Either way, it has to be intentional.
Why We're Different
Most cruise advisors hand you a confirmation email and call it done.
We start with your travel style, budget, and vacation constraints, then choose the ship, cabin, and timing around those. We monitor for price drops after booking, negotiate on-board credits, and stay reachable if something goes sideways during your sailing.
We're small by design. We're trying to be the right agency for a very specific type of traveler: busy professionals who want to cruise without research overwhelm, value expertise over generic packages, and are ready to actually use the vacation days they've been hoarding.
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.
We're still small by design. If you're a busy professional ready to cruise without the overwhelm, we're here.
Our Values
Expertise Over Sales
We're not here to put you in the most expensive cabin. We're here to put you in the right one. Sometimes that's the cheapest option. Sometimes the upgrade is worth it. We'll tell you which.
Transparency
No hidden fees. No surprise charges. You pay the same price as booking direct, often less, because we're compensated by the cruise lines.
Personalized Planning
You're a person with specific travel goals, constraints, and preferences. We plan around those.
Real-Time Support
If something goes wrong during your cruise, we're reachable. Not just during business hours. Not just via email.
Common Questions
The things people ask before they book a call.
How much does working with a cruise travel advisor cost?
Nothing. The initial consultation is free, and we're compensated by the cruise lines when you book. You pay the same price as booking direct, often less, because we have access to advisor-exclusive promotions, on-board credits, and cabin upgrades. No hidden fees. No planning charges.
What is a cruise travel advisor, and why use one instead of booking direct?
A cruise travel advisor helps you choose the right ship, cabin, and timing for your travel style and budget, then handles the booking, monitors for price drops, and secures on-board perks. Booking direct with a cruise line gets you a reservation. Working with an advisor gets you a strategy. The price is the same. The experience isn't.
What makes Roam with Rosen different from other cruise advisors?
Melissa has 80+ personal sailings across ocean, river, and expedition cruises. She's not reading cruise line marketing materials. She knows which cabins to avoid on specific ships, which dining reservations to book before you board, and which shore excursions deliver on their promises because she's been on them. She's a Virgin Voyages Gold Tier specialist, certified across 15+ cruise lines, and the co-creator of Sailing Sisters, a hosted voyage series for professional women. You get that experience working for you from the first call.
Ready to stop hoarding your vacation days?
Book Your Free 30-Minute Consult