Traveling in 2026: Part 5

Part 5 of 6 about traveling in 2026
by Jenny Buschauer

Portugal’s Secret Island and the Conversation Every Traveler Should Have

Madeira: Even Better Than You Imagined

Most Americans have heard of Madeira, if at all, as a wine, or perhaps as the birthplace of Cristiano Ronaldo. What they do not know is that it is one of the most strikingly beautiful islands on earth: a Portuguese archipelago floating in the Atlantic, closer to Morocco than to Lisbon, with a landscape so dramatic it genuinely stops people in their tracks. The cliffs really are that steep. The flowers really are that extraordinary. And the sheer range of what is available, from boutique wine hotels to cliffside pousadas to lively harbor-side dining in Funchal, means there is a version of Madeira for almost every type of traveler.

What most visitors do not realize is how much exists beyond Funchal and the coastline. The island’s famous levadas, ancient irrigation channels that double as hiking trails, wind through laurel forests that have been UNESCO-protected for decades, past waterfalls and valleys that feel like they belong in a different century entirely. And scattered across the island are experiences that simply do not exist anywhere else: whale and dolphin watching in some of the most productive waters in the Atlantic, canyoning through volcanic gorges, and the extraordinary Monte Palace Tropical Garden, a place so lush and theatrical it is almost impossible to believe it is real.

Madeira rewards travelers who know to look a little deeper. The experience most people have there is already excellent. The experience available to those who plan it well is genuinely exceptional.

Funchal and Beyond

Funchal is the island’s capital and the natural starting point for most visits, a genuinely beautiful city built into a hillside above a natural harbor, with a covered market full of tropical fruits and flowers, cobblestone streets lined with restaurants and wine bars, and the famous wicker toboggan ride down from Monte that has been delighting visitors since the 1850s. The food scene here is better than most travelers expect: fresh Atlantic tuna and espada, Madeiran black scabbardfish, prepared in ways that bear no resemblance to anything you have had before.

The west and north coasts of the island are where Madeira gets truly wild. São Vicente, on the north shore, sits in a valley where waterfalls pour directly onto black volcanic beaches, a landscape unlike anything in the Mediterranean or the Caribbean. Porto Moniz, at the island’s western tip, is famous for its natural lava rock pools that fill and drain with the Atlantic tides. The drive along the northern coast road alone is worth the flight. Madeira is a small island. It does not feel like one.

Ready to See What Madeira Really Has to Offer?

Madeira is a destination that consistently surprises the people who go. Most arrive not knowing quite what to expect. Most leave wondering why they waited so long. Whether you have been to Portugal before or this would be your first visit, there is a version of this island that will genuinely stay with you.

Part of what I do is help clients understand what they are actually going to experience, before they arrive. The traveler who shows up with the right information, the right itinerary, and the right coverage has a dramatically better trip than the one who figured it all out on a booking website. When you are ready to start that conversation, I am happy to help.

What Coverage?: The Insurance Conversation Most Travelers Skip

Planning a trip to Madeira, or anywhere internationally, is a good moment to talk about something that does not get enough attention: what travelers are actually protected against when something goes wrong.

Many people assume their travel credit card covers them, and some cards do include meaningful protections. But benefits vary widely, coverage amounts can fall far short of what a serious trip interruption actually costs, and even the strongest cards usually don’t include comprehensive medical coverage abroad. The gaps are rarely obvious until you read the fine print, and most people never do.

A private travel insurance plan is designed to fill exactly those gaps, with comprehensive medical coverage and medical evacuation included, which can cost tens of thousands of dollars on its own.

One of the most common questions I get is about cancellation coverage, and specifically what is and is not actually covered. This is where Cancel for Any Reason coverage, or CFAR, becomes genuinely valuable.

Unlike standard cancellation policies, CFAR protects a significant portion of your investment in scenarios you simply did not see coming, a friend’s destination wedding that gets postponed, a work obligation that cannot be moved, a family situation that changes everything. It reimburses typically seventy to seventy-five percent of non-refundable costs, for any reason at all. One important detail many travelers miss: travel insurance generally must be purchased within a short window of your initial booking, so the time to think about it is at the very beginning of the planning process, not the week before departure.

Part of what I do is make sure this conversation happens early, when the options are widest and the protection is strongest. The right coverage depends on the trip, the investment, and the traveler. It is worth a conversation before you book, not after something goes wrong.

Looking Ahead

Next week brings the final installment of this series, and we are closing with one more destination that belongs on every traveler’s radar for 2026. If the last five weeks have sparked any ideas for a trip of your own, I would love to help you turn them into something real.

About Jenny’s Across States & Seas Travel

I’m Jenny Buschauer, founder of Jenny’s Across States & Seas Travel. With over 15 years of experience in the travel industry and firsthand travel across more than 50 countries and 40 U.S. states, I help clients plan thoughtful, well-organized trips that reflect their budget, interests and travel style.

From historic European cities to wildlife experiences, cultural destinations and relaxed getaways closer to home, my goal is to handle the details so my clients can focus on enjoying the journey.

If you’d like to start talking about ideas for a future trip, I’d be happy to help.

Jenny Buschauer
Across States & Seas Travel
Email: jenny@stateseatravel.com
Website: www.stateseatravel.com
Phone: 203-693-1289