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Anniversary Trips

Island trips for a milestone anniversary, from private dinners and villas with pools to places that reward a few extra nights together.

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How to plan an anniversary trip

An anniversary trip is shaped by the milestone and by how much time you can take. A first or fifth anniversary often fits into a long weekend; a tenth, twenty-fifth or fortieth deserves the kind of week you would have booked as a honeymoon. Decide which one this is, then choose the island, and leave the hotel until last.

Short celebration or big milestone

From Europe, three to five nights works best on a short-haul island. Santorini gives you a caldera terrace and dinner in the village with very little transfer time, and Mallorca suits couples who want to walk, drive the mountain roads and eat well. For a landmark year, a week or more in the Indian Ocean makes more sense: the Maldives for total stillness, Seychelles for scenery and remoteness, Mauritius for a mix of beach time and evenings out.

What to check before booking

  • The weather on your actual date: an anniversary cannot move, so check rain and wind for that month. Santorini and Mallorca are strongest from late spring to early autumn; Mauritius is gentlest from May to early December.
  • Quiet or lively: some couples want silence; others want a bar, a dress-up dinner and other people around. Pick the island to match.
  • The celebration itself: ask in advance what the hotel can arrange on the night, such as a private dinner on the beach or terrace, and what it costs.
  • Travel fatigue: if either of you dislikes long flights, a short-haul island with a quick transfer beats a far-flung atoll.
  • Opening dates: several Mediterranean hotels close in winter, so a November or February anniversary points to the tropics.

Budget signals

Caldera suites in Santorini start from around US$400 to US$700 a night in season, and the leading Mallorca estates from around €550 to €700. A full Indian Ocean week for two runs from around US$5,000 in Mauritius to US$16,000 and up for a comfortable stay in the Maldives, before flights. Mention the anniversary when you book: an upgrade is never guaranteed, but hotels note it.

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