Discover Jake Rosenberg's hotel shortlist

  1. Tuscany, Italy

    Monteverdi

    Style

    Mellow mediaeval village

    Setting

    Colourful Castiglioncello

    Price per night from (ex tax)$1,900.56

    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 glass of prosecco and a selection of local cheeses and meats at Enoteca
  2. St Barths, St. Barthélemy

    Hotel Christopher

    Style

    Haute Caribbean

    Setting

    Ocean-view Pointe Milou

    Price per night from (ex tax)$542.43

    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

    House-made treats from the chef
  3. Santorini, Greece

    Kapari Natural Resort

    Style

    Neutral shades, cool caves

    Setting

    Volcanic viewpoint

    Price per night from (ex tax)$375.02

    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

    Free pick-up from either the airport or seaport and a plate of fresh fruit on arrival
  4. New York, United States

    The Bowery

    Style

    Retro glamour

    Setting

    Post-punk East Village

    Price per night from (ex tax)$355.00

    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 bottle of wine
  5. Toronto, Canada

    The Drake

    Style

    Cool, cultural cutting-edge

    Setting

    Art and Design District of Parkdale

    Price per night from (ex tax)$190.51

    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 Starving Artist house red or white wine in your room on arrival