Luxury Anniversary Trip Ideas: 12 Escapes by Milestone

First, fifth, tenth, twenty-fifth. The right anniversary trip depends less on the destination and more on which anniversary it is.

The one rule that applies to every anniversary

Do not build an itinerary. The most common mistake we see is compressing three cities into five nights on the grounds that it is a special occasion. Anniversaries reward depth: one or two bases, long mornings, a table booked for the actual date, and enough slack that a delayed flight does not cost you the dinner. Book the restaurant that matters before you book the flights.

First anniversary: short, close and vivid

You want intensity rather than distance. Three nights on the Amalfi Coast at Le Sirenuse or the Caruso; a Lake Como villa suite at Villa d'Este or Passalacqua; or a Paris weekend at Le Bristol with one three-star lunch. From the US east coast, add Bermuda's Rosewood or a Charleston-to-Kiawah weekend for something reachable in under three hours.

Fifth anniversary: the first proper long-haul

Five years is usually the point where a week becomes possible again. Santorini or Mykonos in late May; a Bali villa in Ubud followed by three nights on the Bukit; or Costa Rica's Nayara and Papagayo peninsula for couples who want the trip to include something active. Budget US$8,000-14,000 for a week for two at this level.

Tenth anniversary: somewhere neither of you has been

A decade in, novelty matters more than comfort. Kyoto in late November for the maples, staying at a ryokan with private onsen; a Kenyan or Tanzanian safari with three nights in the Mara and three on Zanzibar; or French Polynesia, where Bora Bora still justifies the hype. These are US$15,000-25,000 trips done properly.

Twenty-fifth and beyond: take the trip you postponed

This is the milestone for the Maldives overwater villa, the two-week Japan itinerary, the private-island week at COMO Parrot Cay or Amanyara, or the Orient Express to Venice followed by a week in Puglia. Silver anniversaries are also the point at which chartering — a yacht in the Aegean or a villa with staff in Tuscany — makes more sense than a hotel.

Timing it against the actual date

If your anniversary falls in a difficult month — August in Europe, September in the Caribbean, January in the South Pacific — move the trip rather than the standard. A December anniversary is better served by the Maldives, Thailand or the Caribbean than by a European city in the rain. A July anniversary is better in the Med by boat than in a heat-bound city.

What to ask the hotel for

Tell the property it is an anniversary at the time of booking rather than at check-in, and be specific: a table with the view rather than a cake, a late checkout rather than champagne. Good hotels will move a room or hold a corner table if given three weeks' notice. Very few will do it on the day.