Tailor-made Holiday
Shikoku & Naoshima Tour – Art, Hot Springs & Rural Japan
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At a glance
This is a Japan trip for travelers who want to spend most of their time away from the Tokyo-Kyoto axis. The appeal is not one famous sight after another, but the way the trip moves between places with very different identities: an art island in the Seto Inland Sea, a self-drive through the mountains of Shikoku, old onsen towns and small regional cities that most international itineraries pass straight by.
Naoshima is a major reason to come. The island has become one of Japan’s most important contemporary art destinations, with museums and installations set across the coastline and old villages. From there, the trip shifts inland to the Iya Valley, where you pick up a car and spend two days driving through the mountains, crossing vine bridges and staying near hot springs.
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That mix is what makes the itinerary unusual. You can spend one day at Chichu Art Museum and the next in Oboke Gorge, then continue west to Matsuyama for Dogo Onsen and its hilltop castle. The trip keeps changing character without relying on Japan’s usual headline stops.
Osaka gives you an easy starting point and Tokyo appears only at the end. Most of the journey is spent in places many first-time visitors never see, which makes this particularly good for a second trip to Japan, or for anyone who already knows they want something beyond the classic route.
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.
Day 1: Depart for Japan
Your journey to Japan begins today as you board your international outbound flight to Tokyo.
Day 2: Arrival in Osaka
Land in Tokyo and connect onward to Osaka, where you will be met on arrival and assisted with your transfer to the hotel.
The rest of the day is free. After the long journey, you can keep things easy or head out for a first look at Osaka. Food is one of the city’s great pleasures, so even a simple evening wandering between small restaurants and street-food stalls is a good introduction.
Day 3: Journey to Tokushima via Awaji Island
Leave Osaka and travel toward Shikoku, crossing the Akashi Kaikyo Bridge and continuing across Awaji Island before reaching Tokushima.
The journey itself is part of the day, with views across the Seto Inland Sea as you leave Japan’s larger urban centers behind.
Once in Tokushima, the evening is free. The city is best known for Awa Odori, its annual dance festival, and you can also head out for Tokushima ramen or spend some time around the riverside.
Day 4: Traditional Arts & Tokushima’s Cultural Heritage
Spend the day getting to know some of Tokushima’s traditional performing arts.
Visit a Bunraku puppet theater, where large wooden puppets are operated by skilled performers as part of one of Japan’s best-known theatrical traditions.
You can also visit Awa Odori Kaikan to learn more about the dance festival that defines the city each summer. If you would rather spend part of the day outdoors, Mount Bizan offers views across Tokushima and the surrounding area.
Day 5: Scenic Rail Journey to Takamatsu
Travel by train along the coast to Takamatsu, on the northern edge of Shikoku.
The main stop today is Ritsurin Garden, a large landscaped garden developed over several centuries. Give yourself time here rather than treating it as a quick sightseeing stop. Its ponds, bridges, pines and teahouses are best seen at walking pace.
Later, explore Takamatsu itself. Sanuki udon is the local specialty and one of the easiest ways to get a sense of the region through its food.
Day 6: A Day of Art on Naoshima Island
Take the ferry from Takamatsu to Naoshima for a full day devoted to contemporary art.
The island is home to several major museums and installations, including Chichu Art Museum, where works by Claude Monet, James Turrell and Walter De Maria are integrated into the building and surrounding landscape.
Art is spread across different parts of the island rather than contained in a single museum district, so the day involves moving between galleries, installations and coastal areas. Yayoi Kusama’s pumpkin sculptures are among Naoshima’s best-known works.
Return to Takamatsu after your visit.
Day 7: Into the Remote Iya Valley
Pick up your rental car and drive inland into the Iya Valley.
This is where the trip leaves the cities behind properly. Mountain roads lead through steep valleys and small settlements, with the Kazurabashi vine bridge one of the best-known stops along the way.
Having a car gives you the freedom to stop as you go rather than follow a fixed sightseeing circuit.
Spend the night at a traditional onsen hotel, with time to use the hot spring baths after the drive.
Day 8: Adventure in the Oboke Gorge
Spend another day in the mountains, this time around Oboke Gorge.
The main activity is white-water rafting through the gorge, giving you a very different view of the landscape from the roads above.
Afterward, there is time to explore more of the surrounding area. Walking trails follow parts of the gorge, while the local yokai museum introduces some of the folklore associated with this part of Shikoku.
Return to your onsen hotel for a second night.
Day 9: Drive to Kannonji & Travel to Matsuyama
Leave the Iya Valley and drive toward Kannonji, where you return the rental car before continuing west by train to Matsuyama.
Matsuyama is Shikoku’s largest city, but it still feels very different from Osaka or Tokyo. It is best known for its castle and for Dogo Onsen, the historic hot spring district on the eastern side of the city.
The evening is free, giving you time to wander around Dogo or use the baths before the following day’s sightseeing.
Day 10: Castles, Gardens & Hot Springs
Begin at Matsuyama Castle, which sits above the city and gives you wide views across Matsuyama and toward the Seto Inland Sea.
After exploring the castle, head back toward Dogo Onsen. The district has long been associated with hot spring bathing and remains one of the best-known onsen areas in Japan.
The rest of the afternoon is deliberately open. You can spend more time around Dogo, return to the baths or simply leave part of the day unstructured after several days of moving around Shikoku.
Day 11: Journey to Tokyo via Okayama
Travel east across Shikoku to Okayama.
Stop here to visit Korakuen, one of Japan’s most celebrated landscape gardens, before continuing to Tokyo.
Arriving in the capital at the end of the trip gives you a striking change of scale after Shikoku. Spend the evening however you like, whether that means heading into Shinjuku, booking dinner or simply having a quiet final night before your flight.
Day 12: Departure from Japan
Depending on your flight time, you may have a final morning in Tokyo before transferring to the airport for your journey home.
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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.
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