As summer travel surges, families are once again embracing the opportunity to explore the world not just for leisure, but for legacy. Whether it’s a multi-generational cruise, a remote villa rental, or a business-tinged escape abroad, successful families are redefining what it means to travel well.
But behind every picture-perfect getaway lies a series of choices with financial, logistical, and emotional weight. From tax considerations to family dynamics, summer travel has evolved into a multifaceted experience, one that intersects with your broader wealth strategy.
Here’s how to plan intentionally, travel meaningfully, and avoid the financial missteps that can derail an otherwise unforgettable summer.
Travel as a Financial Planning Topic
At Wealthspire, we often remind clients: travel isn’t separate from financial planning, it is financial planning. The way you approach summer travel reflects values, risk tolerance, tax posture, and sometimes even real estate strategy. When you’re investing five or six figures into a single trip, it’s worth asking:
- Are there tax-deductible elements to this trip?
- Could this qualify as part business, part personal?
- Are we thinking about privacy, legacy, or impact?
- What insurance coverage is appropriate at this tier?
Advisors play a unique role in helping you align travel aspirations with your overall plan, whether that means structuring an international rental properly or planning liquidity for a luxury family reunion.
Tax-Savvy Travel: Avoiding Common Pitfalls
High-spending travelers are often surprised to learn how travel can affect their tax situation. Some key considerations are:
- Business travel must be “ordinary and necessary” to be deductible. Proper documentation is critical.
- Executives who travel for work should ensure their employer uses an accountable reimbursement plan, which allows for business-related travel expenses, such as flights, hotels, and meals, to be reimbursed tax-free when properly documented. Having an accountable plan in place is often the only way to preserve the tax efficiency of business travel. Without it, high-cost travel related to board meetings, client visits, or conferences may become non-deductible out-of-pocket expenses, even if they’re clearly tied to work. Advisors can help clients navigate these rules and, if needed, collaborate with corporate HR to structure reimbursements correctly.
- Many families fall in love with a destination during summer travel and eventually decide to purchase a vacation home abroad. If you go down that path, and especially if you later rent the property out when you’re not using it, it’s important to know that the Foreign Earned Income Exclusion (FEIE) does not apply to rental income. Even if you’re living overseas part-time, U.S. citizens are still taxed on foreign rental income and must follow strict reporting rules for both income and foreign bank accounts (e.g., FBAR and FATCA). Owning and enjoying a property abroad can absolutely be part of a long-term plan, but it requires careful coordination to avoid unexpected tax burdens.
- Residency triggers from digital nomad visas or prolonged international stays can lead to unexpected filing obligations under FBAR and FATCA.
The bottom line? Casual vacation planning doesn’t cut it at this level. Strategic preparation can save thousands and protect against costly IRS scrutiny.
Multi-Generational Travel: Memory-Making with Intention
Virtuoso calls it the #1 travel trend, and for good reason. Families are seizing the moment to gather across generations, with travel serving as the glue that holds them together. From estate planning to family governance, multi-generational trips have surprising depth. Advisors can help:
- Plan cash flow and gifting to cover group travel
- Structure ownership or rental of large, shared villas
- Integrate philanthropic travel with Donor Advised Fund planning
- Bridge generational gaps in preference, from eco-adventure to cultural immersion
When well-planned, these trips become an investment in family connection, one that pays dividends for decades.
Exclusive Destinations and Evolving Travel Trends
Summer 2025 is all about exclusivity, personalization, and climate-aware choices. Emerging themes to watch include:
- Coolcations: Demand is soaring for destinations like Iceland, Norway, and Slovenia where luxury meets cooler temps. 6 Summer Travel Trends for Luxury Travelers | TravelAge West
- Set-jetting: Sicily saw a 400%+ spike in travel after The White Lotus. The intersection of media and travel planning is real and fast-moving. Luxury Summer Travel Trends 2025 | DreamArt Photography
- Superyachts & river cruising: Discerning families are trading mega-ships for intimate, custom-crafted experiences on water. 7 Big Summer Travel Trends in 2025, Says Samantha Brown - Parade
- Privacy-focused properties: Private islands and secluded villas continue to top wish lists for clients seeking discretion. Ranking of the Top 10 Destinations Chosen by Millionaires for Summer Vacations in August | LUXONOMY
We help clients evaluate these opportunities through a planning lens – logistics, insurance, cost, and value alignment.
Don’t Skimp on Protection: Insurance for High-Stakes Travel
The average cost of a luxury summer getaway now exceeds $10,000, and many are far above that. Traditional travel insurance often falls short for high-net-worth families. Luxury policies offer:
- Cancel-for-any-reason protection
- Coverage for business equipment or pre-existing medical conditions
- Concierge services and global evacuation coverage
- Reimbursement for lost deposits on premium bookings
Policies typically run between 3–8% of the total trip cost, far less than the exposure you’d face without one.
Owning (or Renting) Abroad: Wealth Strategy in Disguise
International real estate is as much a lifestyle decision as it is a portfolio diversification play. But it also means:
- Complying with FBAR and FATCA for accounts or assets abroad
- Navigating different depreciation rules (30 years abroad vs. 27.5 in U.S.)
- Understanding how foreign income, currency gains, and residency-by-investment programs intersect with U.S. tax law
Whether you’re buying a Tuscan farmhouse or renting a St. Barts villa for the season, these transactions carry consequences. We help coordinate with your legal and tax team to ensure no detail is overlooked.
Travel Well, With Purpose
At its best, luxury travel does more than deliver comfort, it creates clarity. It gives families space to reconnect, reflect, and reimagine. It fosters legacy, models values, and celebrates what wealth can do when wielded with intention. But to travel well at this level is to plan well. If your summer calendar includes a major trip or if you’re thinking about property abroad, multi-generational experiences, or a work-from-anywhere arrangement, we’d love to help you navigate the financial components that come along with those dreams.
Next Step: Let’s Plan a Summer Travel Check-In
Before you pack your bags, let’s review:
- Tax exposure from travel plans
- Insurance adequacy
- Gifting and liquidity for family travel
- Foreign asset or residency issues
- Business and remote work considerations
Let’s ensure this season of exploration supports the broader vision you’ve built and protects what matters most. Schedule a summer travel review now.
Wealthspire Advisors LLC and its subsidiaries are separately registered investment advisers and subsidiary companies of NFP, an Aon company. © 2025 Wealthspire Advisors
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