San Francisco and Hawaii: City to Island Escape

San Francisco

Spend five nights in San Francisco, staying right on Union Square with the city’s best known areas within easy reach. Ride the cable cars, wander through Chinatown and North Beach, and spend time along the waterfront at Fisherman’s Wharf and the Embarcadero. You can cross the bay by ferry, walk neighbourhood to neighbourhood, or simply spend an afternoon café hopping and people watching. It’s a city that rewards curiosity and works perfectly as a first stop before heading west.

Kauai

From San Francisco, fly on to Kauai, often described as Hawaii’s most scenic island.  Stay in Poipu, close to beaches and coastal walks, with easy access to Waimea Canyon and viewpoints along the Na Pali Coast. Days here are about getting outside, whether that’s swimming, walking coastal paths or stopping at lookouts and quiet beaches you stumble across along the way. Evenings are relaxed, with local restaurants and sunset walks close by.

Maui

Finish the journey in Maui, starting in Kaanapali before moving south to Wailea. In Kaanapali, long sandy beaches and snorkelling spots are right on your doorstep, with lively beachfront areas for sunset drinks and dinners. One evening includes a guided trip to the summit of Haleakala for sunset, a standout experience without the stress of navigating mountain roads yourself. 

Later, a guided Hana Rainforest experience takes you along one of Hawaii’s most talked about routes, passing waterfalls, rainforest and dramatic coastline. The final nights in Wailea are ideal for slowing things down, with calm beaches and coastal paths perfect for an easy end to the trip.