Positano, Italy
Best month to go: June
Why book it: When you saw Under The Tuscan Sun, you dreamed of heading to this beautiful Italian seaside retreat. You can go for outrageously priced luxury hotels like Le Sirenuse and Il San Pietro di Positano— global standards for style, service and more. Or you can make up some of the difference by traveling in June rather than July, and staying at more budget-friendly hotels.
Cheapest month to go: August
Why book it: In August it will be hot temperatures and some store closures in Madrid—but you’ll also save over a trip in June. For one thing, museums are open, have far fewer crowds (along with plenty of air conditioning). And there’s always plenty of good food, drinks and entertainment for you everywhere.
Cheapest month to go: August
Why book it: Visit the Duomo, eat pasta, drink wine, enjoy the Italian way of life. Spend a few days in this intimate, manageable city before heading on a romantic weekend in the surrounding Tuscan countryside, where wine tastings and hillside picnics make for the best getaways for friends, individuals, couples and families!
Bruges, Belgium
Cheapest month to go: July
Best for: Couples
Why book it: If you want to feel like you are in a real life fairy tale this is the place to be! 13th-century architecture makes Bruges one of the most charming places on earth. For a breath of modernity in a city that’s all about the beautiful history, stay at The Van Cleef. Once home to the legendary Van Cleef family, the 700-year-old estate has been updated as a boutique hotel. For over 700 years it has been dedicated to the pursuit of pleasure and power and has been called home to the various Counts and Dukes of the Van Cleef dynasty.
Cheapest month to go: August
Why book it: Dublin has entertainment, gardens, a zoo, tea parlors, history and so much more. (The city also has a great children’s museum and an aquarium.) You can check out or stay at Ashford Castle, where everyone can feel as pampered as royalty.