The Plan-B Summit Is Coming to Orlando

The Escape Artist Plan B Summit is coming to Orlando, Florida, on March 6 and 7, 2027, bringing together attorneys, bankers, developers, investors, and expat experts for two focused days on international diversification. Designed for people serious about residency, offshore banking, asset protection, and geographic optionality, the summit is built to deliver practical clarity, real access, and a 90-day action framework attendees can use immediately.

What the Plan-B Summit Is

On March 6 and 7, 2027, the Plan-B Summit will bring together attorneys, developers, bankers, and international investors for two focused days of conversation, strategy, and direct access. This is not a seminar built around theory or aspiration. It is a working room designed for people who are serious about building a life with more geographic and financial resilience, and who want to do so legally, intelligently, and with clarity.

The format is deliberately different from what most conference-goers are used to. Attendance is capped to keep speaker access real. Sessions are built around outcomes, not presentations. And the people on stage are not motivational speakers or online influencers. They are operators: lawyers who structure international assets for a living, bankers who run offshore institutions, developers who have built communities for expats across Latin America, and investors who have spent decades navigating cross-border wealth.

By Sunday afternoon, attendees leave with a shortlist of two to three residency programs matched to their income, family, and timeline; a clear understanding of how U.S. citizens are legally taxed abroad; an international banking path they can act on within 60 days; a real estate diversification framework; and a written 90-day action plan built inside the room. That is the offer.

A New Location, the Same Standard

Las Vegas hosted the inaugural summit in March 2026. The atmosphere was exactly what the format intended: less like a conference, more like a working room where assumptions could be challenged and ideas pressure-tested against real-world experience. The conversations continued long after the sessions ended.

For 2027, the summit moves to Orlando, Florida. The location reflects both the expanding reach of the Escape Artist community and the practical reality that central Florida is among the most accessible cities in the country for domestic travel. The specific venue will be announced to ticket holders well in advance of the event, with plenty of time to arrange accommodation and travel.

What will not change: the dates (March 6 and 7, 2027), the city (Orlando), and the daily schedule (8:00 AM to 5:15 PM both days).

The Voices Behind the Conversations

The 2027 summit brings together an experienced and globally diverse lineup of speakers, each offering a different vantage point on what it means to build resilience outside traditional systems.

Together, they offer practical insight into what it actually takes to build a life beyond borders.

Already announced:

Michael K. Cobb, Chairman and CEO of ECI Development, brings decades of experience helping individuals and families find property and build lives abroad. His insights into international real estate go beyond market cycles, focusing instead on livability, governance, and long-term value.

Joel M. Nagel, Founding Partner of Nagel and Associates, is widely regarded as a pioneer in international asset protection. His work centers on safeguarding wealth legally across jurisdictions, with an emphasis on understanding and managing risk before it becomes a problem.

Luigi Wewege, President of Caye International Bank, demystifies offshore banking, offering clarity on how international accounts work, who they are for, and how they fit into a broader, compliant financial strategy.

Dan Wilhelm, an American expat living in Portugal, shares firsthand insight into the realities of relocation, from navigating bureaucracy to integrating into daily life, offering a grounded counterpoint to overly idealized narratives.

Rich Checkan, President and COO of Asset Strategies International, brings a long-term perspective on wealth preservation, speaking to the enduring role of precious metals in an increasingly digital financial landscape.

Isha Sesay, Editor-in-Chief of Escape Artist, brings a global editorial perspective shaped by more than a decade of living and working across multiple continents, anchoring the summit’s conversations in realism and lived experience.

Ryan L. Palmer, Founder and Operations Manager of Teak Craft Solutions, explores how teak investments can function as both generational wealth-building tools and pathways to residency in countries such as Panama.

Alyssa Esquivel brings fifteen years of expat experience to the stage, having built a life abroad across India, Turkey, Nicaragua, Panama, and Belize, offering insight into long-term relocation from a deeply personal perspective.

Peter Zipper, President Emeritus of Caye International Bank, contributes decades of experience in international banking and geopolitics, shaped by a career spanning European finance and United Nations peacekeeping service.

John Maisto, former U.S. Ambassador and President of the U.S.-Philippines Society, offers a diplomatic perspective on global affairs, governance, and the geopolitical forces shaping international decision-making.

John Davis, combat veteran, Harvard graduate, and co-founder of Veterans in Paradise, speaks to the growing community of veterans building lives overseas, with a focus on mental health, community, and purpose abroad.

Joe Cronin covers international health coverage as a practical foundation for anyone considering life outside their home country, and how to choose the right policy for their specific situation.

More speakers will be announced soon.

Why Orlando, and Why Now

Choosing Orlando as the location for the 2027 summit is intentional. It is one of the most accessible cities in the United States, sitting at the center of a domestic travel network that makes it genuinely easy to reach from almost anywhere in the country. For an event that draws attendees from across North America, that accessibility matters. The goal is to remove every possible barrier between the people who need this information and the room where it is being shared.

Timing matters too. March sits at a natural inflection point in the year, far enough from January resolutions to allow for seriousness, yet early enough to act on new thinking before the year accelerates. For many attendees, the summit functions as a catalyst, not necessarily for immediate relocation, but for the kind of informed decision-making that unfolds over the months and years that follow. People leave not just with clarity about their options, but with the contacts and the framework to actually execute on them.

There is also something fitting about Florida as a location for a conversation about international living and financial optionality. It is a state that has long attracted people in search of a different arrangement, one that asks less of them in certain ways while offering more in others. That instinct, the desire to find a place that works better for the life you are trying to build, is exactly what the Plan-B Summit is designed to serve.

Who This Weekend Is Built For

The summit is designed for U.S. and Canadian citizens or green card holders with investable assets who have thought seriously about a second residency or international diversification but have not yet pulled the trigger. It is for people who want straight answers from operators rather than a sales pitch from a relocation agency, and who would rather spend one weekend gaining clarity than two years getting confused online.

It is not for people seeking a tax dodge or anything that skirts U.S. reporting requirements. Everything taught at the summit is fully compliant. It is also not a free seminar with a hard backend close. This is a paid working summit with a capped room and real speaker access.

What the Plan-B Summit has always done well is connect finance to lifestyle, legality to lived experience, and aspiration to execution. It is not about abandoning one life for another. It is about understanding your exposure, building optionality, and making decisions with your eyes fully open.

The Escape Artist Plan-B Summit takes place March 6 and 7, 2027, in Orlando, Florida. For anyone serious about building a future that is not dependent on a single country, a single system, or a single set of assumptions, it is two days well spent.

Reserve your seat at escapeartist.com/orlando2027

About the Author

Isha Sesay is Escape Artist’s Editor-in-Chief. Born in London, she has spent the past decade living and working across the globe, and now calls Spain home.

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