Luxury Anniversary Trips

The best anniversary trips

Some milestones deserve more than a dinner reservation. Whether you’re marking five years or fifty, an anniversary is an opportunity to step away from the everyday: to reconnect, reflect, and rediscover what you love most, both about the world and about each other.

Whatever your anniversary means to you (and whoever you want to share it with) we’ll design an experience that honours it. Explore some of our most remarkable anniversary destinations below, or get in touch to start planning something entirely tailor-made.

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What makes a Black Tomato anniversary trip?

Multigenerational Anniversary Celebrations

An anniversary isn’t always just a couple’s occasion. Many of our clients choose to mark their milestone by bringing the whole family together – children, grandchildren, and everyone in between – for a shared adventure that creates memories across generations. From a private villa on Lake Como to a family safari in the Serengeti, we handle every detail so you can focus entirely on each other. Multigenerational group itineraries available on request.

Our Multi-gen Trips

Landmark Anniversary Trips for Couples

For couples celebrating a significant milestone – a 10th, 25th, or 50th – a luxury anniversary trip offers the chance to mark the occasion in genuinely unforgettable style. From a private ryokan in Kyoto to a candlelit dinner on the Amalfi Coast, we design tailor-made itineraries that feel as significant as the years they celebrate.

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Places to Travel for Your Anniversary

Italy

Few places on earth are more naturally suited to celebration than Lake Como. Arrive to find waters framed by the Alps, and a pace of life that tells you this is somewhere special. From here, head south through the vine-covered hills of Tuscany, where lunches at centuries-old estates and private wine tastings make the perfect backdrop for reflection and romance. The grand finale is the Amalfi Coast, where couples can slip away on a private boat and families can explore cliff-top villages together.
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Greece

Greece has been the backdrop for love stories for millennia, and it remains one of the world's most compelling destinations. Ancient temples, shimmering seas, and tavernas create an atmosphere that resonates with travellers of every age. Begin your anniversary journey in storied Athens, where private after-hours access to the Acropolis turns a sightseeing stop into something genuinely special. Sail through the glittering Cyclades uncovering quiet coves, harborside villages, and clifftop churches, before ending in iconic Santorini, where sunsets paint the whitewashed hillsides gold. Whether it's just the two of you or the whole family gathered to celebrate, Greece has a way of making every moment feel timeless.
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New Zealand

New Zealand is the kind of place that makes you feel alive - ideal for an anniversary trip. The landscapes here are unlike anywhere else on earth: glaciers calving into fjords, volcanic plateaus steaming in the morning light, vineyards rolling down to surf-beaten coasts. Couples will find deep romance in the remoteness of it all, while families and multigenerational groups will enjoy New Zealand's spirit of adventure. Try white-water rafting in Queenstown, a Māori cultural experience in Rotorua, or simply driving a spectacular coastal road with nowhere urgent to be. New Zealand doesn't ask you to slow down. It simply makes you want to.
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Borneo

For an anniversary trip that takes your breath away, few destinations compare to Borneo. This is one of the world's last great wildernesses, where ancient rainforests, mist-covered mountains, and rivers wind through landscapes virtually unchanged for millions of years. Celebrate your milestone by tracking orangutans through the jungle canopy at Sepilok, drifting by riverboat through the remote Kinabatangan corridor, and diving into some of the planet's most biodiverse waters off the coast of Sipadan. For couples, there's an intimacy to experiencing raw, undisturbed nature together.
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Turkey

Turkey rewards every kind of traveller, which makes it a natural fit for anniversary groups of all shapes and sizes. Begin in Istanbul where Byzantine domes and Ottoman minarets rise above the Bosphorus. A private guide will take you beyond the tourist trail to the city's most compelling neighborhoods and hidden culinary gems. From there, travel to the otherworldly landscapes of Cappadocia, where hot air balloon rides at dawn rank among the most romantic experiences on the planet. End your journey on the Turquoise Coast, where clear waters lap against ancient ruins and a private gulet charter offers the freedom to explore at your own pace. Turkey rewards slowness, and for an anniversary trip, that's exactly the point.
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Japan

Japan moves you, and in ways you don't always expect. For an anniversary trip, it offers something genuinely rare: the sense that you're witnessing something remarkable, and that experiencing it together makes it more meaningful still. Begin in Tokyo, where the energy of one of the world's great cities gives way to extraordinary food, design, and culture. Travel the bullet train to Kyoto, where temple gardens, tea ceremonies, and the soft glow of lantern-lit streets create an atmosphere of deep romance. Find private ryokan stays and kaiseki dinners designed for two or more. Add cherry blossom season for a trip that is, quite literally, unforgettable.
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Tanzania

Tanzania is where the natural world performs for you on your anniversary safari. The silence of a private game drive at dawn, coffee in hand, is a kind of intimacy that's hard to find anywhere else. After the safari, the spice-scented streets and powder-white beaches of Zanzibar offer the perfect counterpoint - a chance to slow down, and mark your milestone over seafood dinners on the sand. For families looking to celebrate together, Tanzania delivers at every turn. For couples seeking something transformative, it delivers that too.
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Hawaii

Hawaii occupies a unique place in the world's imagination. In person, it more than lives up to it. An anniversary trip here can be as active or as indulgent as you choose, which makes it equally well-suited to couples seeking romance and families looking to share an adventure. Island-hop between Maui's golden beaches and the lush valleys of Kauai, stand at the edge of an active volcano on the Big Island, and snorkel through waters so clear you'll question whether they're real. The archipelago's spirit of aloha - warm, generous, and genuinely welcoming - means you'll feel at home from the moment you arrive.
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France

France has long been synonymous with romance, but for much more than candlelit dinners and champagne toasts - which is what makes it such a compelling anniversary destination. Begin in Paris, where private after-hours access to the Louvre and morning walks along the Seine set an elegant tone. Travel south to the lavender-covered wine regions of the Luberon, before old-world glamour and Michelin-starred terraces on the French Riviera provide a fitting final act. For those celebrating, few things mark a milestone quite like uncorking champagne in the region where it was made.
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South Africa

South Africa tops more bucket lists than almost anywhere else on earth. When you arrive, you understand exactly why. For anniversary couples, few experiences compare to a sunrise game drive in a private wildlife concession, followed by breakfast in the bush as elephants graze nearby. Toast your milestone over a multi-course tasting menu in Franschhoek, explore the tidal pools and beaches of the Cape Peninsula together, and end your journey with sundowners on a private deck as the African sky turns every shade of amber.
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Plan Your Anniversary Trip

Every anniversary trip we create is entirely tailor-made. Get in touch with our travel experts to start planning yours — whether you’re celebrating as a couple, with family, or across generations.