Cruise Deals, Pricing & Value
A Great Private Tour Comes Down to the Guide, Not the Stops
A gray day in Bar Harbor transformed into a delightful adventure thanks to our guide Carli, whose knowledge of Acadia enhanced our experience. The rain revealed beautiful waterfalls and led us to the stunning Asticou Terraces. In contrast, our Saint John tour showcased great logistics but left us wanting more depth in storytelling. Finding the right guide can make all the difference … Read more
3 min read
Reflections on Rebranding
The name change from Cruise Made Easy to Squared Away Travel reflects a broader vision for trip planning, allowing for diverse travel experiences beyond cruises. The old name limited the perception of services offered, but the new one embraces the full spectrum of travel options while maintaining the same personal touch and dedication to getting it right.
3 min read
The Greek Isles Peak Season Is Two Weeks Long, in September
The 2027 Mediterranean deployment shows a significant price increase for the Greek Isles, with the cheapest weeks skyrocketing from $1,429 to $2,369. This shift highlights the intricacies of planning a Greek Isles trip.
8 min read
The Fare Drop I Catch for You Is About to Get Rare
Norwegian Cruise Line is shifting its pricing strategy, reducing the likelihood of fare drops before sailing. This means booking early could become more advantageous as initial prices will be closer to fair value. The traditional practice of waiting for discounts may not yield the same benefits … Read more
4 min read
Notes Before Thursday's Norwegian Q2 Report
Elliott Investment Management's demands for Norwegian Cruise Line include stronger marketing and improved guest experience, but the tension arises between cost discipline and guest satisfaction. With the second quarter results arriving soon, we can finally assess how these changes materialize. The report will provide insights into occupancy rates and revenue yield, revealing the delicate balance between pricing strategies and guest experiences … Read more
5 min read
The Glacier Comes to the Whole Ship
The ship doesn't just glide past the glacier; it rotates to give everyone aboard a perfect view. Choosing your stateroom should be about your trip's experience, not just strategy. Whether you book a Balcony or an Inside, you'll have access to stunning sights and shared moments with fellow travelers. Prioritize what kind of trip you want over mere logistics … Read more
3 min read
2028 Summer Schedule Drops Soon. Here's What I'm Watching.
Norwegian Cruise Line's upcoming schedule drop isn't just about new itineraries; it's a critical insight into fleet strategy. The key question is whether the new ship, Norwegian Aura, signals net-new capacity or a reshuffle of existing routes. The implications for markets, homeports, and itineraries could be significant… Read more
5 min read
When Competent Isn’t Enough: A Conversation About Cruise Value
Norwegian Cruise Line's recent shake-up reveals a critical truth: the difference between competent service and compelling experiences. My recent cruise was smooth but lacked that standout moment that makes a trip unforgettable. As competitors push for higher standards, Norwegian's solid but steady approach may risk diminishing perceived value… Read more
4 min read
NCL Black Friday Hot Take: Half-off, with Some Bonuses
Norwegian Cruise Line just launched their Black Friday sale TWO DAYS before Royal Caribbean and Celebrity. Here’s what they’re doing right – and what’s hidden in the fine print. 🔥 THE TRIPLE PLAY (All Live Now) 1. 50% Off All Cruises Real half-price base fares (not “up to” marketing BS) 2. New Free at Sea Unlimited drinks, specialty dining, WiFi, excursion credits – INCLUDED 3. CruiseNext TripleUp Stack THREE credits (was two) on Balcony+ bookings … Read more
4 min read
MORE at Sea is Dead: Here’s What Changed (And What You’re Losing)
Norwegian Cruise Line just killed MORE at Sea after barely a year. Starting November 5, 2025, it’s back to “Free at Sea” – but this isn’t your 2022 Free at Sea. Here’s the evolution: 🍹 BEVERAGE PACKAGE: The 5 Cap That Vanished (Then Came Back as Tier Exclusions) OLD Free at Sea (2022-2024): – 5 price cap – want that 7 cocktail? Pay difference + 20% gratuity – Premium brands limited – Daily gratuity: ~38.60/person for 7 … Read more
4 min read
The Sunday Compass – Issue #2 (October 12, 2025)
📧 Newsletter Format: The Sunday Compass with persona-specific intro sections Ships in Motion Ships are on the move this month—and with them, opportunities that exist only during these brief windows of seasonal transition. Whether you’re drawn to fall foliage, repositioning adventures, or Mediterranean shoulder seasons, October reveals how Norwegian’s fleet movements create extraordinary experiences. This … Read more
2 min read
The Sunday Compass – Issue #1
Published October 5, 2025 Fall is here, and while everyone else is chasing sales, we’re chasing seasons. This week I’ve been exploring why the smartest guests plan now for 2026 — from New England’s foliage to Alaska’s glaciers, Europe’s shoulders, and even across-ocean repos. If you’ve been thinking about a milestone celebration, this is your … Read more
2 min read
Make It a Season, Not a Sale: Smarter Fall Cruising Starts with the Calendar
Every fall, I witness the same rush. Ads shouting “last chance,” inboxes flooded with deals, and guests scrambling to grab whatever stateroom is left. It feels more like coupon clipping than dream planning. But that’s not how cruising should work — especially not in fall, when the season itself is the reward. The Season Has … Read more
3 min read
Alaska or Europe in 2026? A Practical Comparison to Help You Decide
I sat with a client recently who opened her notebook and drew three columns. At the top of each: Alaska, Mediterranean, and Northern Europe. “We want a milestone celebration in 2026,” she said, “but we don’t know which direction to go.” That’s where most guests find themselves: too many good choices, too little time. Let … Read more
3 min read
Weekend Wanderlust: Fall Foliage from the Sea (And Why 2026 Is Your Better Play)
[Image suggestion: Dramatic fall foliage coastline view from ship deck – golden maples and brilliant red oaks cascading down to rocky New England coast with ship’s rail in foreground] There’s something magical about witnessing fall foliage unfold from the deck of a cruise ship that landlubbers simply cannot experience. 🍂✨ But here’s the reality check: … Read more
5 min read
How I Learned Alaska Cruise Planning Has a “Sweet Spot”
After three years of helping families book Alaska cruises, I’ve discovered a game-changing insight: there’s a “sweet spot” window that transforms planning from overwhelming stress to confident decision-making. 🌟 Watching dozens of families navigate Alaska planning revealed this sweet spot, which has become the cornerstone of how I assist first-time Alaska cruisers in avoiding the … Read more
4 min readWeekend Wanderlust: Alaska 2026 – The Planning Begins
There’s something truly magical about the moment you first glimpse Alaska from a cruise ship deck. 🌊 The glaciers stretching endlessly, the thrill of wildlife around every corner, and the sheer vastness of untouched wilderness all come together to create an unforgettable experience. But here’s what I’ve learned after three years of helping families turn … Read more
3 min read
Norwegian Cruise Line’s Latest Results: Looking Beyond the Headlines
Norwegian Cruise Line's latest financial results reveal a surprising trend: while corporate efficiency is under scrutiny, spending on guest experiences has actually increased. However, post-pandemic changes in service models may leave travelers feeling a shift in service quality. The company is strategically positioning itself between Royal Caribbean and Celebrity Cruises, aiming for a more refined experience … Read more
4 min read