Villas for sailing holidays

  1. Koh Phangan, Thailand

    Anaia Villa

    • Rampantly green estate
    • Sleek contemporary style
    • Earth-kind hideaway

    Price per night from $997.62

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A two-hour spa treatment each, which includes a welcome drink, Thai herbal steam, floral foot ritual and oil massage; plus, sunset cocktails on… more
  2. Cape Town, South Africa

    Cape Kadu

    • Very important views
    • Adventures on your doorstep
    • Elegant indoor-outdoor living

    Price per night from $1,267.95

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    Welcome drinks and canapés on arrival
  3. Cartagena, Colombia

    Casa Ceiba

    • Unmanicured but magical location
    • Cosseting staff
    • Beach all to yourself

    Price per night from $3,605.00

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A reception with drinks and canapés on arrival
  4. Douro Valley, Portugal

    Zannier Private Estates - Quinta do Pessegueiro

    • Wine, glorious wine
    • Intoxicating views
    • Classically beautiful digs

    Price per night from $466.78

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A bottle of wine on arrival