Experience world-class entertainment, luxury hotels, and fine dining as you explore the dynamic city of San Francisco and the tropical paradise of Hawaii. Unwind in Hawaii’s natural beauty, from pristine beaches to breathtaking volcanoes, as you enjoy the best of Oahu, Maui, The Big Island & Kauai. Get in touch with our team to create your perfect itinerary. Whether you want to soak up the culture of San Francisco, explore the breathtaking beauty of Hawaii, or even add an exciting stop in Las Vegas, we’ll ensure your trip is unforgettable.
San Francisco – A City of Iconic Landmarks and Coastal Charm
San Francisco is a world-famous destination known for its breathtaking scenery, historic landmarks, and vibrant culture. Whether you're a first-time visitor or a returning traveler, this city has something for everyone. Stroll down Fisherman’s Wharf, dine at world-renowned restaurants, and take in some of the most spectacular coastal views in the world. With direct flights from the UK and onward to Hawaii, San Francisco is the perfect starting point for your dream holiday.
Top Things to Do in San Francisco:
- Golden Gate Bridge – Walk or cycle across this world-famous landmark for unbeatable views.
- Alcatraz Island – Take a ferry to the legendary former prison and explore its eerie history.
- Fisherman’s Wharf & Pier 39 – Enjoy fresh seafood, visit the sea lions, and shop for unique souvenirs.
- Ride a Cable Car – Experience a piece of history while taking in stunning city views.
- Chinatown – Discover the largest Chinatown outside Asia, full of fantastic dining options.
- Wine Country Day Trip – Visit Napa Valley or Sonoma for world-class wine tasting.
Recommended Hotels in San Francisco:
- Hotel Zephyr – A stylish, waterfront hotel at Fisherman’s Wharf with a quirky, modern design.
- Argonaut Hotel – A boutique hotel with nautical-themed decor, offering stunning bay views.
- Fairmont San Francisco – A historic luxury hotel located atop Nob Hill, perfect for a high-end stay.
Hawaii – Four Islands, Amazing Adventure
Hawaii is a dream destination for so many travellers seeking a mix of relaxation, adventure, and natural beauty. Each island offers something unique, from beachfront luxury resorts to cascading waterfalls! Whether you're looking to explore volcanic landscapes, experience Hawaiian culture, or simply unwind on sun-drenched beaches, there's an island for you, and our Hawaii Specialists at TailorMade Hawaii are here to help you plan your dream Hawaii and San Francisco holiday!
Oahu – The Heart of Hawaii
Oahu is the most famous island of Hawaii, home to the infamous Waikiki Beach, the historic Pearl Harbor, and the iconic Diamond Head Crater. Whether you want to immerse yourself in the local culture, explore lush rainforests, or simply relax on stunning beaches, Oahu has it all.
Things to Do on Oahu:
- Visit the famous Waikiki Beach — you can try your hand at surfing like the locals or simply relax on the golden sands!
- Explore Pearl Harbor National Memorial— this historic site is not to be missed and is home to the USS Arizona Memorial
- Hike Diamond Head — feeling adventurous? Why not hike to the top of Diamond Head for stunning views over Waikiki Beach and Honolulu
Oahu Hotel Options:
- Hilton Hawaiian Village Waikiki Beach Resort – Expansive beachfront resort with lush gardens, multiple pools, and family-friendly amenities.
- Turtle Bay Resort – Secluded North Shore retreat offering stunning ocean views, world-class golf, and outdoor adventures.
- Hyatt Regency Waikiki Beach Resort and Spa – Contemporary stay in the heart of Waikiki, featuring modern comforts and easy beach access.
Big Island – Volcanic Wonders & Diverse Landscapes
The Big Island is known for its dramatic landscapes, including active volcanoes (Kīlauea), black sand beaches, and lush rainforests. If you're seeking adventure and breathtaking scenery, this is the place to be.
Things to Do on Big Island:
- Witness Active Volcanoes at Hawai‘i Volcanoes National Park – Experience the power of nature as you explore lava fields, steam vents, and the awe-inspiring Kīlauea and Mauna Loa volcanoes. Learn about the island’s geological history through scenic drives and hiking trails.
- Explore Lush Rainforests – Immerse yourself in Hawaii’s tropical beauty by hiking through verdant forests filled with cascading waterfalls, exotic wildlife, and vibrant plant life. Popular spots include Akaka Falls State Park and the Hamakua Coast.
- Snorkel with Manta Rays – Dive into the ocean at night for a thrilling experience as graceful manta rays glide around you. The Kona Coast is one of the best places in the world for this unforgettable, up-close encounter with these gentle giants.
Hotel Options on Big Island:
- Four Seasons Resort Hualalai – A luxurious oceanfront retreat offering world-class service, stunning beachfront accommodations, and exclusive amenities, including championship golf and a serene spa.
- Mauna Kea Beach Hotel, Autograph Collection – Classic Hawaiian elegance set on a pristine white-sand beach, featuring timeless architecture, fine dining, and a renowned golf course.
- Fairmont Orchid, Hawaii – A tropical paradise on the Kohala Coast, boasting a world-class spa, lush gardens, a private lagoon, and exceptional dining experiences.
Maui – The Ultimate Tropical Escape
Maui is often ranked among the world's best islands, offering everything from pristine beaches to breathtaking scenic drives. If you want a mix of adventure and relaxation, Maui is an excellent choice.
Things to Do on Maui:
- Drive the Scenic Road to Hana – Drive the unforgettable Hana Highway, a winding coastal road with breathtaking ocean views, lush rainforests, cascading waterfalls, and hidden beaches. Stop at local fruit stands and explore charming small towns along the way.
- Watch the Sunrise at Haleakalā – Experience a once-in-a-lifetime moment as the sun rises above the clouds from the summit of Haleakalā, Maui’s majestic 10,000-foot volcano.
- Relax on World-Famous Beaches – Unwind on Maui’s pristine shores, from the golden sands of Kaanapali Beach to the unique black sand of Waiʻānapanapa State Park. Whether you’re sunbathing, snorkeling, or catching waves, Maui’s beaches offer something for everyone.
Maui Hotel Options:
- The Ritz-Carlton Maui, Kapalua – A refined oceanfront resort nestled along Maui’s stunning northwest coast, offering breathtaking coastal views, world-class dining, championship golf courses, and an immersive cultural experience.
- Wailea Beach Resort – Marriott, Maui – A luxurious oceanfront retreat featuring elegantly designed rooms, stunning infinity pools, a serene spa, and direct access to the golden sands of Wailea Beach.
- Hyatt Regency Maui Resort and Spa – A tropical paradise set on Ka‘anapali Beach, boasting a sprawling lagoon-style pool, vibrant cultural activities, award-winning dining, and an unforgettable rooftop stargazing experience.
Kauai – The Garden Isle
Kauai is Hawaii’s most lush and picturesque island, known for its incredible cliffs, waterfalls, and serene beaches. If you're looking for natural beauty and tranquility, Kauai is the perfect destination.
Things to Do on Kauai:
- Explore the Breathtaking Nā Pali Coast – Discover one of Hawaii’s most stunning natural wonders by hiking the rugged Kalalau Trail or taking a scenic boat tour along the dramatic sea cliffs. Enjoy secluded beaches, cascading waterfalls, and sea caves while spotting dolphins, sea turtles, and other marine life.
- Cruise the Wailua River – Embark on a peaceful boat tour along Hawaii’s only navigable river, surrounded by lush rainforest and ancient Hawaiian temples. Stop at the famous Fern Grotto, a hidden lava rock cave draped in tropical greenery, for a magical experience.
- Visit Waimea Canyon – The "Grand Canyon of the Pacific" – Marvel at the vibrant red and green cliffs of Waimea Canyon, stretching over 10 miles long and 3,000 feet deep. Drive to scenic viewpoints, hike picturesque trails, and take in panoramic vistas of waterfalls and lush valleys.
Kauai Hotel Options:
- Grand Hyatt Kauai Resort & Spa – A tropical oasis set on the south shore of Kauai, featuring lush gardens, sparkling lagoons, and stunning pools. This luxurious resort offers a tranquil ambiance with world-class amenities, including an award-winning spa, championship golf course, and a variety of fine dining options, all with breathtaking views of the ocean and surrounding landscape.
- Hanalei Bay Resort – A hidden gem nestled on the north shore of Kauai, offering spectacular ocean views, serene surroundings, and easy access to the iconic Hanalei Bay. With spacious, well-appointed suites, lush tropical gardens, and a peaceful atmosphere.
- Sheraton Kauai Resort – Set on the pristine sands of Poipu Beach, this relaxed beachfront resort offers a perfect blend of island charm and modern luxury. Guests can enjoy spacious oceanfront rooms, two ocean-view pools, a variety of dining options.
Popular Hawaii and San Francisco Holiday Options
We offer a variety of Hawaii and San Francisco itineraries to suit your preferences. Here are some of our most popular combinations:
- San Francisco & Oahu – The perfect mix of vibrant city life and stunning beaches. Explore the iconic landmarks of San Francisco, including the Golden Gate Bridge and Alcatraz Island, then head to Oahu for world-famous beaches like Waikiki and cultural experiences such as visiting Pearl Harbor. Enjoy surfing, snorkelling, or simply relaxing along the island's pristine shores.
- San Francisco & Big Island – Adventure seekers will love this option, with volcanoes and rugged landscapes. In San Francisco, enjoy the city’s eclectic neighborhoods, museums, and world-class dining. Then, head to the Big Island to explore Hawaii Volcanoes National Park, hike to waterfalls in Waipi’o Valley, and visit the Kona Coast for snorkelling with manta rays or stargazing at Mauna Kea.
- San Francisco & Maui – Ideal for honeymooners or those seeking a luxurious escape. After soaking in the vibrant energy of San Francisco, head to Maui for its breathtaking beaches, luxury resorts, and scenic drives. Experience the sunrise at Haleakalā, relax on the sands of Wailea Beach, and take a scenic drive along the famous Road to Hana, stopping to explore waterfalls, tropical rainforests, and secluded beaches.
- San Francisco & Kauai – A dream trip for nature lovers and those looking for serenity. After exploring the cultural and culinary delights of San Francisco, head to Kauai, known as the “Garden Isle,” for lush rainforests, the stunning Na Pali Coast, and dramatic Waimea Canyon.
- San Francisco, Hawaii & Las Vegas – Add some excitement with a stop in Las Vegas after enjoying Hawaii. Begin in San Francisco, take in the city's iconic sights, then head to the neon lights and entertainment of Las Vegas for world-class shows, dining, and nightlife. Afterward, choose from one, two, or three Hawaiian islands for the ultimate relaxation and adventure. Visit Oahu’s beaches, the volcanic landscapes of the Big Island, or the luxurious resorts of Maui.
- San Francisco, Maui & Oahu – A perfect blend of culture, relaxation, and adventure. Start in San Francisco, where you can explore the Golden Gate Bridge and Fisherman’s Wharf. Then head to Maui, known for its luxurious resorts, scenic drives like the Road to Hana, and iconic Haleakalā sunrise. Finally, experience the energy of Oahu with world-famous beaches, infamous landmarks like Diamond Head, and snorkelling at Hanauma Bay.
- San Francisco, Oahu & LA – A dynamic trio, perfect for beach and city lovers! Begin in San Francisco with its iconic landmarks, diverse food scene, and rich culture. Then, head to Oahu for a blend of surf, history, and natural beauty, including Waikiki Beach, Pearl Harbor, and lush hiking trails. Finish in Los Angeles, where you can explore Hollywood, enjoy upscale shopping in Beverly Hills, relax on Santa Monica’s beaches, and discover art at the Getty Museum.
Start Planning Your Dream Hawaii & San Francisco Holiday Today! Get in touch with our team to create your perfect itinerary. Whether you want to soak up the culture of San Francisco, explore the breathtaking beauty of Hawaii, or add an exciting stop in Las Vegas, we’ll ensure your trip is unforgettable.
