Depending on where you’re going, you want to bring at least three but no more than five pairs of shoes. Wear a comfortable sneaker on the plane for walking tours and light excursions, a heel or elevated sandals for dinners, and a sandal or flip flop for the beach/pool. If there’s room in your luggage, bring a slipper for walking around the hotel. You can bring additional shoes for going out or adventuring, but if you bring more than five pairs, you may as well check another bag filled with shoes (which we fully support, too). Try to pack light when it comes to shoes so you can bring more outfits, which is all you'll see in photos anyway.