Guys Trips
Bahamas
Exumas
Three generations sailing the Exumas, tracing a route from Staniel Cay to Highbourne Cay through turquoise water and the kind of waterside restaurants worth dropping anchor for.
Best For
Experienced sailors wanting a week of island-hopping through the Exumas.
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Canada
Vancouver & Whistler, BC
A West Coast winter week with friends: three ski days across Whistler and Blackcomb, then a short downtown Vancouver stay with a Canucks game to finish.
Best For
Families looking for a ski week with friends and a short coastal-city stop in one route.
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Canada
Big White, Kelowna, BC
A short ski escape to Big White in the Okanagan, with true ski-in, ski-out ease, tree runs, good snow and dinners in the village between full days on the mountain.
Best For
Skiers after a quick trip with the lifts steps away, on a resort that skews family over nightlife.
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Ireland
Kinsale, Kerry, Dingle, Dromoland, Clare & Connemara
A multigenerational road trip along Ireland's Wild Atlantic Way, designed for a variety of interests, from sea cliffs and castles to Skellig Michael for Star Wars fans.
Best For
Families after big coastal scenery, adventure and room for the detours.
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Italy
Venice, Tuscany, Rome & Amalfi Coast
Cliff jumping and learning to row a gondola, ancient ruins and vineyard happy hours: twelve days in Italy that balanced teenage energy with adult indulgence.
Best For
Those who want four distinct versions of Italy, made for teens and adults alike.
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Italy
Florence
From a garden party at a villa above Fiesole to an e-bike day through the Chianti vineyards and a farewell dinner in one of Florence's oldest churches.
Best For
Couples with a short window for both Florence and the Chianti countryside.
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St. Barts
Vitet
A hilltop villa above the island's quieter east end, with the week built on beach rotations, a private pool and water activities. St. Barts, sized for younger kids.
Best For
Families after a villa base, with kids young enough to live at the beach and dinners out together.
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St. Barts
Lurin
Ten years after a first family visit, St. Barts again at an adult pace: one central base and meals as the main event, with fishing and sailing to complement.
Best For
Families with adult kids after understated chic, where the next meal sets the plan.
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Turks & Caicos Islands
Grace Bay
Grace Bay's long white beach is the base for a four-night girls' getaway, with an adults-only all-inclusive setting a social, easygoing pace from morning tennis to late nights.
Best For
Friends celebrating somewhere warm: early tennis, lazy days on the sand and lively resort evenings.
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U.S.A.
Jackson Hole, WY
A multigenerational ski week in Jackson Hole beneath the Tetons: skiing for every ability, backcountry and wildlife tours and a mountain town with a country cool off the slopes.
Best For
Those who want challenging skiing, with enough for gentler skiers that no one is left behind.
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