Tailor-made Vacation · USA
Luxury Hawaii Adventure
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Embark on an unforgettable Hawaii island-hopping adventure combining the dramatic landscapes of the Big Island with the lush natural beauty of Kauai. Over the course of this journey, you’ll experience two of Hawaii’s most spectacular islands, where volcanic landscapes, tropical rainforests and golden beaches create one of the most diverse destinations in the Pacific.
Begin on the Big Island of Hawaii, home to powerful volcanoes, black sand beaches and world-class marine life.
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Explore the volcanic landscapes of Hawai‘i Volcanoes National Park, soar above lava fields and waterfalls on a scenic helicopter flight, and snorkel along the Kona Coast with the chance to encounter graceful manta rays beneath the Pacific waters.
Continue to the island of Kauai, often known as the “Garden Isle” for its dramatic cliffs, lush valleys and unspoilt coastline.
Sail along the iconic Na Pali Coast, hike through the vast landscapes of Waimea Canyon, and discover hidden beaches and tropical scenery at your own pace.
Combining adventure, natural beauty and relaxed island living, this itinerary offers the perfect introduction to the best of Hawaii.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Days 1-4: Hawaii (Big Island)
Your Hawaii adventure begins on the Big Island, the largest and most diverse island in the Hawaiian archipelago. Known for its dramatic volcanic landscapes, black sand beaches and lush rainforests, this island offers some of the most spectacular scenery in the Pacific.
During your stay, explore Hawai‘i Volcanoes National Park, home to the legendary Kīlauea volcano and vast lava fields shaped by centuries of eruptions. One of the most unforgettable experiences is a helicopter flight over the Big Island – an exclusive experience allowing you to witness waterfalls, volcanic craters and rugged coastline from above.
Along the Kona Coast, snorkelling opportunities abound, including the chance to join a twilight manta ray snorkelling experience, one of Hawaii’s most remarkable marine encounters. With time to relax at your resort or explore scenic coastal drives, the Big Island combines adventure with laid-back island living.
Day 5: Big Island to Kauai
Today you fly from the Big Island to Kauai, often called the “Garden Isle” for its lush valleys, towering cliffs and tropical landscapes. On arrival, collect your rental car and settle into your hotel on the island’s sunny south shore, close to the charming resort area of Poipu.
The afternoon is free to relax after your journey. Take a stroll along golden beaches, explore local restaurants, or simply unwind with sunset views over the Pacific Ocean. Kauai offers a slower pace than many Hawaiian islands, making it the perfect place to reconnect with nature and enjoy the island’s spectacular scenery.
Days 6-8: Kauai
Spend the next few days exploring Kauai, one of Hawaii’s most naturally beautiful islands. A highlight is visiting Waimea Canyon State Park, often described as the “Grand Canyon of the Pacific”. Its vast red cliffs, deep valleys and sweeping viewpoints make it one of the most breathtaking landscapes in Hawaii.
Another unforgettable experience is sailing along the legendary Na Pali Coast, where dramatic emerald cliffs plunge into the ocean. On a boat excursion you’ll discover hidden sea caves, remote beaches and crystal-clear waters ideal for swimming and snorkelling.
Sporting rainforest-covered mountains, scenic drives and secluded beaches, Kauai offers the perfect balance of adventure and relaxation during your Hawaiian island-hopping journey.
Day 9: Depart Kauai
After breakfast, enjoy a final morning soaking up the island atmosphere before transferring to the airport for your onward flight.
Whether you spent your last hours relaxing on Poipu Beach, exploring the coastal scenery or picking up souvenirs in Lihue, your time in Hawaii concludes with unforgettable memories of volcanic landscapes, tropical rainforests and spectacular Pacific coastlines.
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.