San Francisco and Hawaii: City to Island Escape

Start with a few days immersed in San Francisco’s neighbourhoods, food and waterfront, then swap city life for Hawaii, where days revolve around beaches, scenic drives and being outdoors. It’s a journey that builds naturally, moving from iconic sights to wide open landscapes, with enough structure to make it easy and enough freedom to make it feel like your own.

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.

 Sunset over the San Francisco skyline,
Sunset over the San Francisco skyline,
Iconic sea lions at PIER 39 at Fisherman's Wharf
Iconic sea lions at PIER 39 at Fisherman's Wharf
Golden Gate Bridge
Golden Gate Bridge
 San Francisco cable car
San Francisco cable car
Kauai, Hawaii
Kauai, Hawaii

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. 

Secret Cove Beach in Maui
Secret Cove Beach in Maui
 Seven Sacred Pools - Hana Rainforest
Seven Sacred Pools - Hana Rainforest

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.

Included in this Itinerary

Return flights from Dublin to San Francisco and home from Maui with British Airways and Aer Lingus, internal flights between San Francisco and Hawaii and between Hawaiian islands with United Airlines and Alaska Airlines, private airport transfers in Kauai, car hire in Maui for 8 days with inclusive insurance, and accommodation throughout as follows: 5 nights at The Westin St. Francis San Francisco Union Square, 7 nights at Koloa Landing Resort at Poipu Autograph Collection, 4 nights at Hyatt Regency Maui Resort and Spa Kaanapali, and 4 nights at Wailea Beach Marriott Resort and Spa. All accommodation is room only. Included activities: Haleakala sunset tour and Hana Rainforest experience. Based on 2 passengers sharing. Flights depart Dublin on 05 September 2026. Price is correct at the time of posting (30 January 2026). Offers are subject to change.

Price from €8,400 per person

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Villas 1 Awali Background Colour Banana Island 3 (2)

Finding your match...

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