Tiffany Costa

Travel Guide

2026 Edit

United States

The short list of US cities and states I keep returning to — what to do, where to stay, and the one thing I never skip in each.

New York

Things to do, neighborhoods, food & nightlife

A long weekend in NYC works best with one neighborhood as your base — I pick the West Village or SoHo and walk everything else.

Florida

Palm Beach to Miami — towns, food & nightlife

Miami for the food and the boat days, Palm Beach for slower mornings, and a string of beach towns in between. Tap a city to open its full list.

Colorado

Mountains, towns & alpine adventures

Aspen in winter for ski weekends, Telluride in summer for the hikes and zero crowds. Fly into Denver only if you want the road trip.

California

LA, San Diego & San Francisco

I split California trips between LA and the coast — three nights in Santa Monica, then drive up to Santa Barbara or Big Sur. Tap a city to open its full list.

Chicago

Things to do, neighborhoods & food

Underrated for a long weekend in summer — architecture boat tour, lakefront runs, and the best deep-dish-versus-tavern-style debate of your life.

Nashville

Nightlife, line dancing, daytime & food

Stay in The Gulch or 12 South. Two nights is plenty — one for live music, one for the food and a slower morning.

Hawaii — Oahu

Beaches, activities & experiences

Oahu has every version of Hawaii on one island — the North Shore for surf and slow days, Waikiki for the city, and Kailua for the prettiest water. Rent a car for the full week — Waikiki is walkable, but the best beaches and hikes are spread across the island.

Boston

Things to do, neighborhoods & food

Best in fall. Two nights to walk the Freedom Trail, eat in the North End, and day-trip out to Cape Cod or Newport if the weather holds.