For two days only—November 28th and December 1st—you can enjoy the Travelwithkey Black Friday Sale plus an extra 20% off on a variety of Legacy Shop products.

When I think about the perfect Caribbean getaway, I imagine more than just sun and sand. It’s about crafting moments that resonate deeply...

Bringing together multiple generations of family for a reunion is a joyful and memorable experience.

Traveling to the Caribbean with your family is an exciting opportunity to create lasting memories, explore vibrant cultures, and enjoy stunning tropical landscapes. Whether you are planning a trip with grandparents, parents, and children or a reunion with extended family, the Caribbean offers something for everyone.

Traveling with family, especially multigenerational groups, can be a rewarding yet complex experience. Planning a trip that satisfies everyone’s interests, needs, and comfort levels requires time, patience, and expertise.

If you have Caribbean roots or wish to immerse yourself in the rich culture of the region, a legacy trip to the US Virgin Islands could be life-changing.

The U.S. Virgin Islands (USVI) are a hidden gem in the Caribbean, rich in history, culture, and breathtaking landscapes.

The U.S. Virgin Islands (USVI) is a breathtaking archipelago in the Caribbean, teeming with vibrant history and culture.

TravelWithKey was never about tourism. It was about transformation.

After every journey, I find myself craving the rhythm of the Caribbean—the way color dances, the way stories live in fabric and wood.

This guide is part travel gospel, part shopping list—with affiliate links to my favorite budget-friendly finds that make every getaway smoother and smarter.

Every item here has earned its place in my travel toolkit. From organizing chaos to creating comfort, they’re small upgrades that turn travel into transformation.

To travel while Black is to hold dual truths: hypervisibility and erasure.

Part 2: Vetting Tourist Companies & Staying Safe Beyond the Brochure Some places feel safe because they look familiar. After all,...

Malcolm-Jamal Warner’s untimely passing is a call. To know. To honor. To teach each other how to live fully and safely in this world.

The African diaspora didn’t just cross oceans—it stayed, survived, and evolved.

Start by exploring resorts, excursions, and destinations that truly match your family’s vibe—whether that’s tracing your roots, relaxing beachside, or doing a little bit of everything.