San Juan, Puerto Rico

• San Juan mixes colonial Spanish architecture with Caribbean beach culture. Old San Juan has blue cobblestone streets and pastel buildings from the 1500s, while Condado's beachfront looks more like Miami with high-rise hotels and crowded restaurants. Because Puerto Rico is a US territory, you use US dollars, your phone works normally, and English is common alongside Spanish - this makes logistics easier than most Caribbean destinations.
• There's a strong cafe culture here where sitting alone with coffee is normal. Tourist areas like Old San Juan, Condado, and Isla Verde have police around and stay busy late. The neighborhoods feel completely different - Old San Juan is historic with museums and forts, Condado is beach resorts and luxury hotels, Santurce has street art and the local nightlife scene.
• Catcalling happens regularly on the streets but usually doesn't go beyond verbal comments. The bigger concern is petty theft - pickpocketing in crowded tourist spots and bag snatching on beaches. Don't leave anything unattended. Stay out of La Perla and certain low-income areas like Cantera. The public bus system technically exists but isn't practical for visitors, so you'll end up using Uber.
• It stays warm all year, between 75-85°F (24-29°C). Brief afternoon rain showers are normal, and hurricane season runs June through November - this actually matters and you should check forecasts. Some neighborhoods like Condado and Ocean Park are walkable at night, while La Placita in Santurce turns into a street party on weekends.

English and Spanish are both common. Tourist areas, police, and emergency services have English speakers. Cell service works well throughout San Juan, so you can call for help or use translation apps easily.

• People dress up for restaurants and going out at night, even in the heat. Wear something nicer than beach clothes for dinner - sundresses, nice jeans, decent tops. Save swimwear for the pool or beach.
• English is common in tourist areas and plenty of locals speak both languages, but trying basic Spanish helps. 'Buenos días,' 'gracias,' and 'con permiso' are useful. Language matters to Puerto Rican identity.
• The Catholic Church is important here. Cover your shoulders and knees in churches. There's more formality in greetings than you might expect - handshakes and polite introductions when meeting people.
• Tipping works like the US: 15-20% at restaurants, $1-2 per drink at bars. Check if gratuity is already on your bill. Don't pay taxi drivers upfront, and either negotiate the fare before getting in or make sure the meter runs.

• Uber works well in metro San Juan with waits under 10 minutes usually. It's the easiest option, especially at night. Outside the city you'll need to rent a car since Uber coverage drops off.
• The public AMA bus system costs $0.75 but the routes are confusing, schedules unreliable, and information hard to find online. There's a light rail (Tren Urbano) from Bayamón to Sagrado Corazón but it doesn't go where tourists need to go.
• Old San Juan has a free trolley on weekdays 7am-5pm and weekends 9am-1pm. Walking works well in Old San Juan, Condado, and Ocean Park - they're compact. Don't rent a car for the city itself - parking costs a lot and traffic is terrible. Only get a car if you're going outside San Juan.
• If you're planning day trips outside the city, consider renting a car.
• For peace of mind on arrival, book your airport pickup in advance.

Explore San Juan with local guides and curated experiences.