The Best Luxury Anniversary Trips for Couples

It depends on the couple, but the most requested luxury anniversary destinations are the Maldives, Bora Bora, the Amalfi Coast, Santorini, private African safaris and Japan — each designed privately around the milestone.

Beyond the hotel, advisors add private moments — a beach dinner, a sunset sail, in-room celebrations, private guides and surprises — tailored to the couple’s story.

Forest Travel designs bespoke couples’ journeys from approximately US$10,000, scaling with destination, length and experiences. Pricing is confirmed after a no-obligation consultation.

For peak-season or long-haul milestone trips, begin 6–12 months ahead to secure the best villas and experiences; your advisor will advise on timing.

A luxury travel advisory like Forest Travel plans milestone celebration trips and pairs you with vetted private guides at each destination. Since 1986 we have arranged anniversaries, big birthdays and vow renewals privately, so a local expert handles the villa, the driver, the after-hours access and the dinner reserved for two. You travel with someone who knows the place, never a group. Plan from US$1,500 per day for two.

For a 35th anniversary, fly to a destination that matches the milestone: overwater villas in the Maldives or Bora Bora, the cliffside Amalfi Coast and Greek islands, a private African safari, or Japan in blossom season. Each is a straightforward flight from most U.S. gateways, and we arrange private transfers on arrival so the journey stays effortless from wheels-up to the first evening for two.

Yes. Every anniversary we plan includes private guides and, where possible, after-hours or before-opening access arranged just for two. That means a museum or ruin visited privately, a vineyard opened after closing, or a chef cooking a single table. As a Virtuoso member since 2004, Forest Travel holds the relationships that turn a destination into moments no online booking can reach.

The 35th is the coral anniversary, which points naturally toward the sea. Many couples mark it with an overwater villa in the Maldives or Bora Bora, private sailing in the Greek islands, or a quiet cruise on Silversea, Regent Seven Seas or Seabourn. We build the trip around your 35 years together, folding in a private dinner and a surprise timed to the exact date.

Yes. For a landmark anniversary, some couples travel with children, grandchildren or close friends, and we plan the trip so everyone is together yet the couple still has private moments. Think a villa large enough for all, shared excursions by day with private guides, and a dinner arranged just for two on the anniversary itself. We coordinate flights and rooming so nothing falls to you.