I Travel with Sterling

I Travel with Sterling I help women 55+ plan unforgettable travel experiences—from weekend escapes to dream cruises—with ease, style, and heart.

At Travels with Sterling, I offer personalized planning, real-world insights, and a joyful push to finally go.

06/17/2026

✨ YOUR CONSTRAINTS ARE NOT ROADBLOCKS — THEY'RE CLUES. ✨

Sometimes the perfect trip, opportunity, or next chapter doesn't happen when everything aligns perfectly.

It happens when you stop focusing on what's standing in your way and start asking:

👉 What if this challenge is actually showing me the path?

The schedules that don't match.
The budget that feels tight.
The timing that seems impossible.

Often, those very limitations become the strategy that makes the experience unforgettable.

Travel intentionally.
Dream creatively.
Plan courageously.

Because extraordinary journeys aren't built from perfect circumstances.

They're built from people willing to see possibilities where others see obstacles.

✈️ Where is life asking you to think differently right now?

For this Mediterranean cruise:✅ We researched every port individually✅ We chose depth over coverage (yes, we let *The La...
06/12/2026

For this Mediterranean cruise:

✅ We researched every port individually
✅ We chose depth over coverage (yes, we let *The Last Supper* go)
✅ We protected our sea days
✅ We added Milan for both experiences *and* savings
✅ We made every decision together

The result?

A trip that feels completely ours.

I documented the entire planning process, including:

→ How we researched each destination
→ Our excursion vs. free-day decision framework
→ Port-by-port choices and trade-offs
→ Why we added a Milan extension
→ Train logistics and transportation tips
→ Everything we learned along the way

Link in bio.

My hope is that this encourages you to travel more intentionally—to ask better questions, make thoughtful choices, and design trips that are rich, rewarding, and exactly right for *you*.

What's your dream cruise destination? 👇

"Life rewards those who dare to leave the shore, trust the journey, and embrace the NEXT ADVENTURE ahead." 🚢✨18 days unt...
06/10/2026

"Life rewards those who dare to leave the shore, trust the journey, and embrace the NEXT ADVENTURE ahead." 🚢✨

18 days until we set sail on our Mediterranean cruise! 🌊☀️

After 30+ cruises, I've learned that the best trips aren't about seeing everything—they're about creating experiences that matter.

This journey is the result of intentional planning, thoughtful choices, and making memories we'll treasure for years to come.

What's one destination that's at the top of your travel bucket list? Tell me below! 👇🌍

06/05/2026

POV: 23 days until our Mediterranean cruise adventure begins. 🚢🌊☀️

After 30+ cruises, here's what I've learned:

The best trips aren't planned perfectly.
They're planned intentionally.

Every port asks a different question:
✨ Excursion or free day?
✨ Guided tour or independent exploring?
✨ Adventure or rest?

For this cruise, we chose:
✅ Depth over checking boxes
✅ Experiences over rushing
✅ Protected sea days
✅ A Milan extension for extra memories (and savings!)
✅ Decisions we were both excited about

The result? A trip that feels completely ours.

I've put together the full planning guide covering:
📍 Our research process
📍 Excursion vs. free-day framework
📍 Port-by-port decisions
📍 Milan extension strategy
📍 Train logistics
📍 Lessons learned from 30+ cruises

Link in bio.

My hope is that this inspires you to travel with intention and create a trip that's exactly right for YOU.

🌍 What's your dream cruise destination?

The July 4th strategy that made our Mediterranean cruise possible 🎆 I run an event planning business. Summer = wedding s...
06/03/2026

The July 4th strategy that made our Mediterranean cruise possible 🎆

I run an event planning business. Summer = wedding season.

My sister works hospital payroll. Her schedule is LOCKED.

Finding a week where we could both disappear? Seemed impossible.

Then we realized: July 4th week.

✅ No one books event planners when everyone's at the lake
✅ Elizabeth gets an extra paid holiday
✅ Suddenly our "impossible" week = perfect

The lesson:

Your constraints can become your strategy.
→ Look for weeks your industry goes quiet
→ Holiday weeks
→ Shoulder seasons
→ The "impossible" week might be exactly right

We turned a scheduling problem into a travel solution.

Question for you:
What week would work best for YOUR schedule?
When does your industry slow down?

Full planning story on the blog. Link in bio.

We could have rushed to the cruise port. Instead, we added 2.5 days in Milan. 🇮🇹 Here's what we're doing: The Duomo → Sk...
05/28/2026

We could have rushed to the cruise port.

Instead, we added 2.5 days in Milan. 🇮🇹

Here's what we're doing:

The Duomo → Skip-the-line rooftop tickets (non-negotiable)

Lake Como → Full-day private boat tour (Bellagio, Lugano, 11 hours of views)

Brera district → Cobblestone streets, art galleries, cafes. No schedule. Just wandering.

The strategy: Use the cruise as your anchor, then add cities around it.

Milan flights were $200/person cheaper than Rome.
That $400 savings funded 2.5 days exploring a city we'd never seen.

Then: scenic train through Alps to Rome.
Then: 7-night Mediterranean cruise.

The result? We turned a 7-night cruise into a 10-day Italian adventure.

The lesson: Stop thinking cruise OR city. Think cruise AND gateway cities.

That's when travel becomes extraordinary.

Full Milan planning on the blog. Link in bio.

Have you been to Milan? What shouldn't we miss? 👇

Unpopular opinion: Sea days are NOT wasted days 🌊 I've met cruisers who view sea days as crossed-out time. Days that "do...
05/27/2026

Unpopular opinion: Sea days are NOT wasted days 🌊

I've met cruisers who view sea days as crossed-out time. Days that "don't count."

After 30+ cruises, I want to say this clearly:

Sea days are the infrastructure of your cruise. They make the port days possible.

Before your first port:
Sea day before Corfu = we board, breathe, and arrive rested
→ One day of recovery changes how you show up at every port after it

Before big days:
Naples = 9-hour strenuous excursion
→ Sea day before Naples = you sleep, hydrate, arrive ready

As the destination itself:
The ship is remarkable.
Open water. Perfect deck chair. A book. A nap with no alarm.
3 PM cocktail because you're at sea and that's exactly right.

Some of my best cruise memories live on sea days.

Our Mediterranean cruise:
✅ 2 sea days
✅ Both protected
✅ Both non-negotiable

Sea days aren’t wasted days.
They’re the space between the adventures that makes the adventures possible. ✨

How do you feel about sea days? 👇

05/22/2026

40 days until Janet leaves for her Mediterranean & Adriatic cruise — and she’s doing the research before she goes. ✈️🌊

What’s actually worth buying in each port?
What local phrases make travel easier?
What should you skip?
And what are the hidden gems most tourists miss?

This guide covers:
🇮🇹 Milan leather, farmacia skincare & pantry finds
🇬🇷 Corfu kumquat liqueur & local specialties
🇭🇷 Dubrovnik artisan jewelry & Croatian wine
🇲🇪 Kotor hidden shopping finds & local culture
🇮🇹 Naples espresso culture, limoncello & cameo jewelry

Plus:
✔️ local language phrases
✔️ shopping strategies
✔️ packing tips
✔️ customs/VAT guidance
✔️ content & travel inspiration

Comment:
👉 MedCruise27

and I’ll send you the guide and tips.

Need help planning your own Mediterranean cruise or custom journey? Reach out anytime 💙

How we decided: excursion, free day, or sea day for every port. Not one decision was a default. Every one was researched...
05/16/2026

How we decided: excursion, free day, or sea day for every port.

Not one decision was a default. Every one was researched.

Swipe through for our decisions 👉

The framework:
→ Read each port individually
→ Distance, walkability, logistics
→ Protect your sea days
→ Choose what's rich & rewarding for YOU

Full breakdown on the blog: : https://travelswithsterling.com/mediterranean-cruise-planning-tips/

2 hours of research that will save you if you're cruising from Italy 🚂Getting from Milan to Civitavecchia (Rome's cruise...
05/12/2026

2 hours of research that will save you if you're cruising from Italy 🚂

Getting from Milan to Civitavecchia (Rome's cruise port) took me 2 hours to figure out. The info online is scattered. So here's exactly what we booked:

The Frecciarossa (Italy's high-speed train)
→ Milan to Rome: 3 hours through Alps
→ Then transfer to Civitavecchia

What I learned:
✅ Book left-side seats heading south (best Alps views)
✅ Business class worth it (under €75, table service)
✅ Confirm seat numbers (trains charge separately sometimes)
✅ Senior discount available

Pro tip: We booked facing seats with a table. Bringing a card game. The journey IS the experience.

Luggage hack: Radical Storage near train stations = explore hands-free.

Full Milan + train details on the blog: https://travelswithsterling.com/mediterranean-cruise-planning-tips/

Questions? 👇

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