Colorful Dutch-colonial building housing the National Archaeological Museum Aruba in Oranjestad

Aruba Rainy Day Plan: What to Do with Kids When It Doesn’t Cooperate

Aruba markets itself as the dry side of the Caribbean, and largely earns it — but even the driest island gets the occasional squall, and unlike some of its smaller neighbors, Aruba actually…

Baby Beach in Aruba, a calm, shallow lagoon on the island's southern tip

Aruba with a Baby or Toddler: What Parents Need to Know Before They Go

Most Aruba content is written for families with school-age kids — kids’ club minimum ages, snorkeling trips, excursions a toddler can’t really do. Traveling with a baby or a child under two is…

Wallblake House, an 18th-century plantation house in The Valley, Anguilla

Beyond the Beach: Land Activities and Culture in Anguilla for Families

Anguilla is built around its beaches, but the island has a real, walkable stretch of history and culture worth a half-day or more away from the sand — plantation-era architecture, an Indigenous archaeological…

Infinity pool overlooking the coastline at a private villa in Anguilla

Anguilla Multigenerational Trip Guide: Villas That Actually Work

Anguilla’s calm, shallow beaches and short distances between everything make it an easier multigenerational destination than islands with rougher surf or long transfer times — but a trip covering three generations still needs…

Rendezvous Bay beach in Anguilla with calm turquoise water

Anguilla on a Budget with Kids: What It Really Costs

Anguilla has a reputation as one of the pricier Caribbean islands, built largely around its five-star resorts and beach clubs, and that reputation isn’t wrong at the top end. But the beaches themselves…

Rocky point and turquoise water along Meads Bay in Anguilla

Best Time of Year to Visit Anguilla with Kids

Anguilla runs warm and sunny nearly year-round, so “best time to visit” is really a question of trade-offs: dry weather and calm seas versus crowds and peak prices, or quieter beaches and lower…

The covered, porch-style Heritage Collection Museum building in East End, Anguilla

Anguilla in the Rain: Best Backup Plans for Families

Anguilla’s appeal is almost entirely outdoors — beaches, boat trips, snorkeling — which makes a rainy stretch feel like it could derail the whole visit. In practice, most rain on Anguilla comes as…

Blowing Point Ferry Terminal in Anguilla, the arrival point for the St. Maarten ferry

Anguilla Day Trip from St. Maarten with Kids: Making the Ferry Work

Anguilla does have its own airport, Clayton J. Lloyd International Airport (AXA), but most visitors from North America arrive via Princess Juliana International Airport (SXM) on St. Maarten, then continue to Anguilla by…

A scenic overlook of a road winding down to a turquoise bay in Anguilla

Renting a Car or Taking Taxis in Anguilla with Kids: What Families Need to Know

Anguilla has no public bus system and taxis run on fixed zone fares rather than meters, so most families end up choosing between a rental car and taxis for every leg of the…

Road Bay, Anguilla, a calm turquoise beach with a coral reef visible near shore

Anguilla with a Baby or Toddler: What Parents Need to Know

Anguilla’s beaches work beautifully with babies and toddlers โ€” calm water, soft sand, and no rough surf at most family beaches. What the standard guides skip over is the logistics layer that makes…

Little Bay, a secluded cove on Anguilla with turquoise water and limestone cliffs

Getting to Anguilla with Kids: Ferries, Flights & the St. Maarten Connection

Anguilla has no scheduled international jet service from most of the U.S. and Europe, so most families still connect through St. Maarten (SXM) via ferry or a short regional flight. There are exceptions:…

Royalton Splash Punta Cana, a family-friendly stay in Punta Cana

One of the Caribbean’s Largest Water Parks: Royalton Splash Punta Cana Reviewed

The main reason families book Royalton Splash Punta Cana is right there in the name: one of the Caribbean’s largest on-site water parks, with a wave pool and seven slides, sits within the…

RumFish Beach at TradeWinds, a family-friendly stay in Clearwater Beach

Stay at One, Play at Two: RumFish Beach Reviewed

The main draw at RumFish Beach at TradeWinds isn’t what’s on the RumFish property itself โ€” it’s the “stay at one, play at two” arrangement with neighboring Island Grand, which puts a three-story…

Sonesta Maho Beach Resort & Casino, a family-friendly stay in St Martin

Waterslides, a Teen Zone, and Plane-Spotting: Sonesta Maho Reviewed

Few Caribbean resorts can offer kids a waterslide session followed immediately by watching a commercial jet pass overhead at close range โ€” but Sonesta Maho Beach Resort & Casino sits directly on Maho…

The Beach House Roatan, a family-friendly stay in Roatan

Half Moon Bay, No Pool: The Beach House Roatan Reviewed

The Beach House Roatan earns its reputation on one specific asset: direct access to Half Moon Bay, one of Roatan’s calmest stretches of Caribbean shoreline, combined with family suites that include kitchenettes or…

St. George's Club Hotel, a family-friendly stay in Bermuda

Kitchens, Cottages, and Historic St. George’s: A Family Review

Cottage-style accommodations with full kitchens are the central draw at St. George’s Club Hotel โ€” a practical advantage that separates it from Bermuda’s conventional hotel stock and makes it particularly well-suited to families…