12 Best Anniversary Trip Destinations for Every Milestone Year, Ranked

Editor's pick

For a 10th, 25th or later anniversary, nothing on this list matches Tuscany for sheer sense of occasion. Rosewood Castiglion del Bosco sits inside the Val d'Orcia, a UNESCO World Heritage landscape of cypress-lined ridges and medieval hilltop towns, and it is the property I recommend most often for a silver anniversary. The estate spans a 5,000-acre working wine and olive property with the two-Michelin-starred Ristorante Campo del Drago and Italy's only private members' golf club. A frequent promotion offers 'stay three, get the fourth night complimentary,' plus 20% off private villa stays — meaningful at this tier. The experiential depth is what earns the top rank: cooking classes with estate produce, Brunello tastings at the winery, and Val d'Orcia drives that feel cinematic. The honest tradeoff is seasonality — the property closes roughly January 6 to March 21, so peak experience runs May through October, which is also when rates and crowds peak. A more accessible Tuscany entry point is Borgo Santo Pietro, a working-farm wellness resort in western Tuscany. See the official Rosewood property page for current rates and promotions.

Best for

A 25th (silver) anniversary or any landmark milestone that deserves a European estate

Pricing

From ~$1,200/night; villa and multi-night promotions available

Source: Rosewood Hotels & Resorts · Visit Tuscany — Rosewood Castiglion del Bosco

Grace Bay is consistently rated among the world's top three beaches, and for a couple who define an anniversary by turquoise water and effortless access, Turks and Caicos is the clear beach winner — eight direct US city connections, no complex logistics, and a cluster of properties that define the luxury market. Grace Bay Club anchors it with an adults-only hotel zone and 22 reimagined oceanfront suites by AD100 designer Young Huh; it is a Leading Hotels of the World member with rates above $1,500 a night and a recurring 'Fourth Night Free' offer. For maximum seclusion, Amanyara sits within an 18,000-acre nature reserve on North West Point, with private-pool pavilions and reef diving off the property. COMO Parrot Cay takes it further — a private 1,000-acre island reached by a 50-minute boat transfer, with four miles of beach. The tradeoff is that Turks and Caicos is expensive for what is essentially a beach-and-water destination: experiential depth beyond the sand and reef is limited compared with a Tuscany or Japan, so it rewards couples who genuinely want to do very little. See the Grace Bay Club site for current suites and offers.

Best for

A 25th anniversary couple who want a top-tier beach with minimal logistics

Pricing

From ~$1,500/night at Grace Bay Club; higher at Amanyara and COMO Parrot Cay

Source: Grace Bay Club · Visit Turks and Caicos — Grace Bay

Editor's pick

Japan is the destination I recommend most for a 10th anniversary, and it consistently earns the highest satisfaction scores from couples who want experiential depth over pure resort luxury. The classic itinerary pairs three to four nights in Tokyo with a bullet-train transfer to three to four nights in Kyoto, with an optional Hakone or Hiroshima extension. At the ultra-luxury tier, Aman Kyoto — 24 rooms and two villas set in 80 acres of private forest — and Hoshinoya Kyoto, reachable only by private boat along the Ōi River, are the two most-cited milestone properties. Traditional ryokan such as Tawaraya (Kyoto) and Gora Kadan (Hakone) charge roughly ¥60,000–¥150,000 per person per night with kaiseki dinner and breakfast included. A complete 10-night trip runs $7,000–$12,000 for two including premium-economy flights, rising sharply at the Aman tier. The honest weakness is timing pressure: cherry-blossom (late March to mid-April) and autumn-foliage (November) seasons require 4–6 months' advance booking and command peak rates. Aman publishes rooms and seasonal notes on its Aman Kyoto page.

Best for

A 10th anniversary for couples who want culture, food and once-in-a-decade experiences

Pricing

10 nights $7,000–$12,000 for two; ryokan ¥60,000–¥150,000 pp/night

Source: Aman · Visit Japan — Kyoto and Tokyo

The Maldives is the pre-eminent aspirational anniversary destination, and for a couple returning to celebrate — many honeymooned here — an overwater villa upgrade is the natural milestone move. Properties such as JOALI, Soneva Fushi, One&Only Reethi Rah, Four Seasons Landaa Giraavaru and Park Hyatt Maldives sit in the $1,000–$3,500-a-night range. The points angle is strong: World of Hyatt has the best program for the Park Hyatt Maldives, and Chase Ultimate Rewards transfers to Hyatt at 1:1, so couples with accumulated balances can offset overwater villas that otherwise run 150,000–500,000 points a night. Marriott Bonvoy covers the St. Regis Maldives Vommuli and Westin Maldives. The experience is unrivaled for seclusion, house-reef snorkeling off the villa steps and consistent 6:00–6:30 PM sunsets year-round. The honest tradeoffs are real: seaplane transfers add $400–$820 per person, a 27% tax applies, and the Maldives is a destination of profound relaxation rather than variety — days blur together, which is either the point or the problem depending on the couple.

Best for

A 25th anniversary or a return-to-the-honeymoon overwater upgrade

Pricing

$1,000–$3,500/night; overwater villas 150,000–500,000 points/night

Source: Fora Travel — Wedding & Honeymoon Trend Report

For a silver-anniversary couple who want landscape drama and lodge luxury over a beach, New Zealand's South Island is the standout. Rosewood Matakauri near Queenstown overlooks Lake Wakatipu and the Remarkables, with a lakefront bathhouse and hot-cold plunge; rates run NZ$1,950–NZ$3,400 a night (roughly US$1,200–$2,100). Huka Lodge on the Waikato River near Taupō has operated since 1924 and is all-meals-inclusive from around NZ$2,127 a night for two, with NZ$600–$1,200 lodge credits on three-night-plus stays in the 2026 season. Blanket Bay near Glenorchy is the most architecturally dramatic of the three. The appeal is a lodge circuit that combines fine dining, helicopter access to fjords and glaciers, and genuine wilderness. The tradeoffs are distance — it is a long-haul flight from most of the world, best combined into a 10-day-plus trip to justify the journey — and the reverse-hemisphere calendar, so the peak season is the Northern winter (December–February). Scott Dunn publishes lodge details on its Matakauri Lodge page.

Best for

An active 25th-anniversary couple who prefer landscape and lodges to a beach

Pricing

NZ$1,950–NZ$3,400/night (US$1,200–$2,100); lodge credits on 3+ nights

Source: Scott Dunn · Visit New Zealand — South Island Lodges

For a 50th anniversary, the world cruise is the milestone trip that becomes family legend. The Regent Seven Seas 2026 World Cruise, 'Sense of Adventure,' is a 154-night voyage from Miami aboard Seven Seas Mariner across three oceans and six continents, calling at 40-plus countries and 75-plus ports with 16 in-port overnights. Fares run from roughly $95,000 per person in a Deluxe Veranda Suite to $266,500 per person for a Master Suite, taxes and fees included, with an all-inclusive model covering flights, excursions, dining and beverages. Crucially for older couples, Regent offers grand-voyage segment options — a 91-night Arctic leg, a 68-night Cape Horn leg, a 76-night Spice Route leg — so you can join a portion rather than the full circumnavigation. The tradeoff is obvious: the price is extraordinary, and 154 nights is a commitment few can make; the segment options and the more affordable Silversea and Viking alternatives exist precisely for that reason. Regent publishes itineraries and fares on its 2026 World Cruise page.

Best for

A 50th (golden) anniversary couple wanting the ultimate all-inclusive voyage

Pricing

$95,000–$266,500 per person, 154 nights; segments available

Source: Regent Seven Seas Cruises · Visit Regent Seven Seas World Cruise

St. Lucia earns its place on the strength of one of the most photographed rooms on earth: Jade Mountain's open-wall 'sanctuaries,' each with a private infinity pool and a fourth wall entirely absent, framing the twin Piton peaks. It is the destination I steer couples toward for a 10th anniversary when they want beach-and-adventure balance rather than pure resort torpor. Ladera Resort and Sandals Grande St. Lucian round out the reference properties, and the island rewards active couples with volcano hikes, rainforest excursions and the Sulphur Springs drive-in volcano. A five-night Jade Mountain stay runs roughly $7,000–$12,000 for two. The honest weaknesses: the open-wall design that makes the rooms extraordinary also means no air-conditioning and exposure to weather and insects, which suits some couples and unsettles others; and St. Lucia's roads are winding and slow, so airport transfers and excursions eat more time than the map suggests — budget a full 90 minutes from Hewanorra airport to the Soufrière resorts, or book the helicopter transfer to reclaim the afternoon.

Best for

A 10th anniversary balancing beach downtime with active adventure

Pricing

5 nights ~$7,000–$12,000 for two

Source: Fora Travel — Wedding & Honeymoon Trend Report

Santorini is the visual benchmark for a milestone anniversary — whitewashed caldera villages, blue domes and the world's most famous sunset. Adults-only boutique hotels with private plunge pools and caldera views, such as Canvases Epitome and Katikies Garden, anchor a fifth- or tenth-anniversary stay, and a seven-night trip runs $5,500–$9,000 for two. The single most important planning decision is timing: traveling in May or September rather than July–August dramatically improves the experience — fewer crowds, lower rates, the same legendary sunsets. For couples who want the Greek islands without Santorini's crush, Naxos is the under-the-radar alternative, up 450% year-on-year in Fora's 2026 booking data. The honest weakness is overtourism: in peak summer, Santorini's narrow Oia lanes are shoulder-to-shoulder at sunset, and cruise-ship day-trippers can overwhelm the caldera towns, which is exactly why the shoulder-season timing matters so much here. Book a hotel in Imerovigli or Firostefani rather than Oia itself for the same caldera views with far less foot traffic at your doorstep.

Best for

A 5th or 10th anniversary prioritizing scenery, ideally in shoulder season

Pricing

7 nights ~$5,500–$9,000 for two

Source: Fora Travel — Wedding & Honeymoon Trend Report

Best value

Bali is the best value at the luxury tier on this list, and for a fifth or tenth anniversary it delivers a disproportionate experience for the money. Private pool villas in Ubud or Seminyak run $80–$150 a night; a full-day traditional Balinese massage and flower bath for two costs around $60; rooftop dinners with rice-paddy views come in under $30 a head. A complete 10-night trip from the US West Coast, including one business-class leg, can fit within $5,000 in the April–October dry season. At the luxury end, Mandapa, a Ritz-Carlton Reserve in Ubud, sits among rice terraces beside the sacred Ayung River from roughly $750–$1,200 a night — a benchmark 10th-anniversary property. The honest tradeoffs are the long-haul distance from North America and Bali's development pressure: Seminyak and Canggu have grown crowded and trafficky, so I steer anniversary couples toward Ubud's rice-terrace calm or the Uluwatu clifftops rather than the busy southern beaches.

Best for

A 5th or 10th anniversary seeking maximum experience per dollar

Pricing

10 nights within ~$5,000; Mandapa from ~$750–$1,200/night

Source: Fora Travel — Wedding & Honeymoon Trend Report

Iceland is the wild card of the ranking and the right call for a 10th-anniversary couple who find romance in dramatic landscape rather than tropical warmth. Winter (November–March) offers Northern Lights viewing on 40–60% of clear nights, alongside black-sand beaches, geysers, moss-covered lava fields and geothermal lagoons; new luxury lodge properties have expanded romantic programming for 2026. Summer flips the experience to the Midnight Sun, endless daylight and highland access. A seven-night trip runs $6,000–$11,000 for two. What sets Iceland apart is the sheer strangeness of the landscape — few places feel this otherworldly — and the ease of a compact self-drive Golden Circle and South Coast loop. The honest weaknesses are weather volatility, which can cancel Northern Lights tours and close roads with little notice, and Iceland's high cost of living, which makes dining and fuel expensive relative to the accommodation. Build in buffer days and manage aurora expectations.

Best for

A 10th anniversary for couples drawn to dramatic landscape over warmth

Pricing

7 nights ~$6,000–$11,000 for two

Source: Fora Travel — Wedding & Honeymoon Trend Report

For a first anniversary in the $2,000–$5,000 range, a Lisbon-and-Algarve week is the best value in Europe. Five days in Lisbon's tiled hills and miradouros followed by three on the Atlantic cliffs of the Algarve captures genuine European romance without Italy or France pricing. Boutique Lisbon hotels run $150–$220 a night; Algarve cliff-view hotels $180–$300. An eight-night trip for two from the US East Coast totals roughly $5,200–$7,500 including flights and dinners, with the best windows in May–June and September–October. The appeal for a first anniversary is that it recaptures the honeymoon register — a real destination, a sense of discovery — at an achievable price for a couple in their late twenties. The honest weaknesses: the two regions are a 2.5–3 hour drive apart, so you sacrifice some time to transit, and Lisbon's famous hills are punishing on foot for anyone with mobility limits. Pack for both a city and a beach in one bag.

Best for

A first anniversary wanting European romance on a real budget

Pricing

8 nights ~$5,200–$7,500 for two including flights

Source: MonkeyTravel — 2026 Honeymoon Planning Guide

For a first anniversary where budget is the binding constraint but you still want a honeymoon register, Bungalows Key Largo is the smartest domestic pick — one of the very few adults-only, all-inclusive resorts in the continental US. Waterfront bungalows come with private outdoor soaking tubs on the veranda, and because it is reachable by a short flight and drive from most of the East Coast, there are no international logistics, no passports and no time-zone recovery. A seven-night stay runs roughly $3,200–$4,300 all-in for two including domestic flights, with an optional glass-bottom boat excursion around $100. The all-inclusive framing — meals, drinks, activities and non-motorized watersports bundled — is what creates the celebratory register at an accessible price. The honest weaknesses: Key Largo is not the Caribbean, so the water clarity and beach quality trail a true tropical destination, and the resort is compact, so couples wanting variety or exploration will exhaust it quickly. It shines as a two-to-four-night celebratory reset rather than a long stay, and pairs well with a wider Florida Keys road trip down to Key West if you want to extend the escape into a full week without adding much cost.

Best for

A first anniversary on a tight budget wanting an all-inclusive escape

Pricing

7 nights ~$3,200–$4,300 all-in for two

Source: Honeymoons.com — 29 Romantic Anniversary Trip Ideas