This post is part of Design in Motion—real-time reflections from the road as I test, refine, and live out a retirement built around solo travel. These entries are intentionally observational: small moments, logistics that matter, and lessons learned along the way.

Sometimes the best travel days aren’t flashy—they’re efficient. This was one of those days.

I boarded my nonstop flight from Newark to San Juan on United. We left about 30 minutes late, but because it was a direct flight, it barely registered. No missed connections, no sprinting through terminals, no stress. It was a good reminder of something I’ve learned the hard way: if a direct flight is an option, take it—especially before a cruise. Padding your schedule with simplicity is a gift to your future self.

After landing, I opted for a taxi rather than Uber—my usual preference in cruise ports—and it turned out to be a great choice. I had a genuinely good conversation with the driver on the short ride into Old San Juan, the kind that immediately helps you settle into a place. It felt welcoming and human, not transactional.

At San Juan airport, the taxi setup is refreshingly straightforward. The official taxis are clearly marked, and the drivers stand right there with signs. Honestly, if I’d been trying to locate a rideshare pickup area on my own, it would have taken longer. Instead, I was on my way within minutes.

The ride to the Rumbao Hotel was quick—and if you like easy logistics, this hotel is a gem. It’s literally across the street from the cruise pier. Drop your bags, take a breath, and you’re already where you need to be.

Dinner was an easy walk from the hotel at Reices—great food, relaxed atmosphere, and exactly what I wanted after a travel day. Back at the hotel, the night was quiet, the bed was comfortable, and I slept well. That kind of sleep-before-boarding is priceless.

By morning, four ships had arrived overnight—Princess, Viking, NCL, and Azamara—and the city had that familiar pre-boarding energy.

I took a lovely walk down to the San Juan Gate and back—fresh air, ocean views, and just enough movement to ease into the day before a long stretch at sea.

One small perk that made a big difference: my Marriott Bonvoy Silver Elite late checkout, which allowed me to pack up and leave the hotel without rushing or lingering. I gathered my things, went downstairs, and joined the cheerful crowd of cruisers heading toward the port.

My ship was at Pier 4. Rolling bags were easy to maneuver, port staff took my luggage immediately, and from curb to ship took maybe ten minutes. Hand off bags, check in, step onboard—done.

That’s my favorite kind of embarkation: calm, efficient, and already feeling like vacation.

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✨ Pro Tip: Keep the Pre-Cruise Simple

If you’re flying in the day before a cruise, stack the odds in your favor:

• Choose a direct flight whenever possible—even if it costs a little more.
• Use official taxis at cruise ports; they’re regulated, visible, and often faster than rideshares.
• Stay walkable to the pier if you can.
• Leverage elite perks like late checkout so your hotel stay flows seamlessly into boarding.

The goal isn’t just to arrive—it’s to arrive calm.