This week on Where We Roam, we’re playing Travel Would You Rather — the ultimate vacation debate episode.

John, Dayna, Jess, and Shawn are choosing between some seriously tough travel scenarios: a full week at Walt Disney World or Universal Orlando, a suite on an older cruise ship or an inside cabin on the newest ship, flying economy with an ultra-luxury resort stay or flying business class with more moderate accommodations, and whether swim-out suites beat butler service.

We also get into Disney fireworks vs. character meet-and-greets, iconic historic hotels vs. brand-new luxury resorts, traveling with extended family, peak season crowds, loud hotel neighbors, and plenty of vacation hot takes along the way.

It’s a fun, chaotic, and surprisingly revealing conversation about how we each travel, what we prioritize on vacation, and which “would you rather” choices are harder than they sound.

Perfect for fans of Disney vacations, Universal Orlando, cruises, luxury resorts, family travel, and travel planning debates.

Jess is official official!

This week on Where We Roam, we officially welcome Jess as a regular co-host and give listeners a chance to get to know her better. Jess shares how her love of travel started, what led her into the travel advisor world, and why Hawaii has become one of her deepest areas of expertise.

We talk Maui memories, favorite Hawaiian resorts, bucket-list trips, traveling with kids before they leave the house, and what it was like being a travel advisor before, during, and after the pandemic. Then we put Jess to the test with a Disney resort guessing game and rapid-fire favorites covering Disney parks, Disney snacks, favorite cruise lines, and the eternal travel debate: cruise or all-inclusive?

If you love Hawaii, Disney resorts, Royal Caribbean, travel advisor behind-the-scenes talk, or just want to meet the newest voice on the show, this is the perfect episode to jump into.

In this episode, we discuss:

• Jess officially joining Where We Roam
• Her background in travel and life in New England
• Why Hawaii, especially Maui, is so special to her
• Bucket-list trips including Asia, Tuscany, safari, and Norway
• Disney resort trivia and favorite Disney parks
• Royal Caribbean vs. Disney Cruise Line
• Cruises vs. all-inclusive resorts
• What makes a great travel experience for families with older kids

Listen now and help us welcome Jess to the show!

Thinking about upgrading to The Haven on Norwegian Cruise Line? Before you spend the extra money, this episode breaks down what you really need to know.

After John’s recent stay in a Haven Penthouse with Balcony on Norwegian Luna, we’re answering the most common NCL Haven questions: what The Haven actually is, what perks are included, how the private restaurant compares to specialty dining, whether the service feels elevated, and who this luxury “ship-within-a-ship” experience is really for.

We talk through the food, the cocktails, the stateroom, butler service, concierge perks, priority boarding, private spaces, kids in The Haven, Vibe Beach Club access, line-skipping benefits, and whether the upgrade feels worth it compared to a regular Norwegian cruise experience.

If you’re considering The Haven on Norwegian Luna, Norwegian Prima, Norwegian Viva, or another NCL ship, this episode will help you decide whether it’s the right splurge for your next cruise.

In this episode, we cover:

What The Haven is on Norwegian Cruise Line What’s included with The Haven Norwegian Luna Haven Penthouse review Haven restaurant food and service Haven bar and elevated cocktails Free at Sea Plus in The Haven Butler service and concierge perks Kids in The Haven Vibe Beach Club and thermal spa access Priority boarding, shows, tendering, and line-skipping Whether The Haven is worth the upgrade

Listen before you upgrade — this is your NCL Haven FAQ.

Universal’s Epic Universe is officially raising the stakes—and Disney is responding with a massive $10 billion investment across its parks. But is it enough?

In this episode of Where We Roam, we break down the growing battle between Disney and Universal, including what’s coming to Walt Disney World through 2030, how Epic Universe is already changing the game, and why this feels like a full-blown theme park arms race.

We also dive into the latest Disney news, including the release of 2027 bookings, what it means for pricing and availability, and key updates like potential changes to perks, dining plans, and bounceback offers.

From new lands like Encanto and Monsters Inc. to long-term projects like Villains Land, we’re analyzing what excites us, what concerns us, and whether Disney is moving fast enough to keep up.

If you’re planning a future Disney or Universal trip—or just love theme park strategy—this is a must-listen.

Norwegian Luna is one of the most stunning new ships at sea—but is it enough to take down Royal Caribbean?

Fresh off the first public sailing, we’re breaking down our full experience onboard NCL’s newest ship—from embarkation and ship design to dining, entertainment, and The Haven.

But the real question: 👉 When you compare it head-to-head with Royal Caribbean… who actually comes out on top?

In this episode, we cover:

• First impressions and embarkation (and where it falls short)
• Solo cabins vs suite life in The Haven
• Specialty dining vs main dining—and why it didn’t feel so “special”
• Entertainment differences between NCL and Royal
• Ship layout, flow, and overall design
• Where Norwegian Luna shines—and where Royal still dominates

Plus, we share honest onboard reactions from Megan and Lisa to round out the conversation.

If you’re trying to decide between Norwegian Cruise Line and Royal Caribbean for your next cruise, this is the real-world comparison you’ve been waiting for.

Disney Cruise Line now has two private destinations… but which one actually delivers the better day?

In this episode of Where We Roam, John, Dayna, and special guest Jess break down Castaway Cay vs. Lookout Cay at Lighthouse Point—and it gets surprisingly competitive.

Dayna just sailed back-to-back itineraries hitting BOTH islands in the same week, giving us a rare side-by-side comparison, while Jess brings fresh perspective from recent sailings.

We’re scoring each destination across what actually matters:

• Beaches (spoiler: this one isn’t close 👀)
• Layout & ease of getting around
• Activities (snorkeling, biking, water play & more)
• Vibe (classic Disney vs. authentic Bahamas feel)
• Food (and yes… we go there)

From crystal-clear Bahamian water and pink sand beaches to nostalgia, crowd flow, and real-world usability, this is the honest breakdown Disney cruisers need.

If you’re deciding between itineraries—or just want to know if Disney’s new island lives up to the hype—this episode gives you the answer.

This week on the Where We Roam Podcast, we’re breaking down Royal Caribbean’s Utopia of the Seas with our brand new Roamer Rating system—and nothing is off limits.

Joined by special guest Corinne from Royal Caribbean, we dive into a real-world review of a 3-night weekend sailing out of Port Canaveral—covering everything from embarkation to entertainment.

We rate:

• 🚢 The Ship (layout, crowds, overall vibe)
• 🍽️ Food (Coastal Kitchen vs main dining vs specialty)
• 🛏️ Stateroom (Junior Suite for a family of 5)
• 📍 Itinerary (Nassau, CocoCay, and the new Beach Club)
• 👏 Service (and why Royal continues to stand out)
• 🎭 Entertainment (Aqua 80s, ice shows, live music)
• 💰 Value (is a short cruise actually worth it?)

Plus, we talk:

• Weekend cruise vs weekday cruise vibes
• Is Utopia too crowded?
• The Galentine’s takeover 👀
• And whether 3 nights is enough (spoiler: probably not)

If you’ve been considering a short Royal Caribbean cruise, this is the episode you need before you book.

What happens when two travel advisors get invited on one of the first sailings of a brand-new cruise ship?

In this episode of the Where We Roam Podcast, John and Dayna preview the Norwegian Luna, the newest ship from Norwegian Cruise Line’s Prima Plus class, before sailing on board in just a few weeks.

We talk about what makes the Luna different from other ships — including the Aqua Coaster, expanded outdoor spaces, new dining concepts like the Indulge Food Hall, and how NCL’s Freestyle Cruising compares to other cruise lines like Royal Caribbean and Disney Cruise Line.

We also break down what our clients are actually booking for Summer 2026 travel, including:

• Alaska cruises • European cruises and river cruises • Caribbean family sailings • All-inclusive resorts in Mexico and Turks & Caicos • New ships like Disney Destiny, Royal Caribbean Star of the Seas, and Norwegian Luna

Plus we discuss:

• Why cruise ships are getting bigger (and sometimes smaller)

• New private island upgrades at Great Stirrup Cay

• The best cruise experiences to book for next summer

• And John’s plan to test the bourbon selection on board.

If you’re planning summer travel in 2026, considering a cruise vacation, or just love hearing about the newest ships and destinations, this episode is packed with inspiration.

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