You have a few hours in San Juan and one question: what should you actually bring? The answer is simpler than you think. San Juan is warm, sunny, and walkable, so the right shoes, a little sun protection, and a few small essentials will keep you comfortable all day. Here is what to wear and pack, from someone who spends every day on these streets.
Start With the Weather
Puerto Rico is warm all year. The island’s official tourism site describes winter temperatures in the 70s and 80s Fahrenheit, and summer is only a little warmer. The rainy season runs roughly from May to October, so showers are more likely then, and hurricane season officially runs June 1 to November 30. Whatever month you visit, check the forecast the morning you land.
The practical takeaway is to dress light. Breathable cotton or linen, shorts or a flowy skirt, and a hat will do far more for you than a jacket ever will. Even on a cloudier day, the humidity makes it feel warm once you start walking.
Shoes Matter More Than Anything Else
If you only get one thing right, make it your footwear. Old San Juan is built on historic cobblestone streets and sloping sidewalks, and the stones can be uneven and slick after a rain shower. Flip-flops and high heels are a recipe for sore feet.
Comfortable sneakers or sturdy walking sandals with a good grip are the best choice. If you plan to visit a beach later in the day, bring flip-flops or water shoes in your bag and switch when you get there.
Sun Protection Is Not Optional
The Caribbean sun is strong, and the old city has more open stone and sea wall than shade. Wear sunscreen, put on sunglasses, and bring a hat. A lightweight long-sleeve shirt can actually feel cooler than bare skin on a bright afternoon.
Reapply sunscreen if you swim or sweat, and take shade breaks along the way. The walls, the plazas, and the small cafes are all good places to cool off for a few minutes.
The Small Essentials Worth Packing
A refillable water bottle is at the top of the list. You will drink more than you expect, and it saves money compared with buying bottles at the pier. According to Discover Puerto Rico, the tap water is safe to drink because it is filtered and treated at the source, though if you prefer bottled water, our main tour includes a cooler with water.
Bring a small bag or backpack for your phone, sunscreen, and a light rain layer. Skip the heavy carry-all, because you will feel it by lunchtime.
On money, Puerto Rico uses the U.S. dollar, and cards are widely accepted. Discover Puerto Rico still suggests carrying a bit of cash for small vendors, and that is good advice for a coffee, a snack, or a tip. Your phone charger also works here, since Puerto Rico uses standard U.S. outlets.
What to Wear for Photos
San Juan is one of the most photogenic cities in the Caribbean. The colorful buildings, blue ocean, and stone walls look great with simple, bright clothing. Solid colors and light fabrics tend to photograph well in strong sun, while very busy patterns can compete with the background.
If photos are the main goal and your time is short, our 2-hour city photo tour is a great fit. It is a private, driven tour with hop-off and hop-on photo stops around Old San Juan, for $200 total for up to 4 guests. It is scheduled on request based on availability, so contact us to set a time. Larger groups can call for availability.
Dressing for a Full Day With Beach Time
If you are joining our private tour, think layers you can change easily. Our main tour lasts about 5 hours. It covers Old San Juan’s major points of interest, then two local beaches. The beaches are chosen by guest preference and the day’s weather, so pack with flexibility in mind.
Wear your swimsuit under a light outfit, and bring a towel and a change of clothes in a small bag. Our private Jeep tour is $474 per tour for 2 to 4 guests, and pickup is at your hotel or cruise ship. Traveling with a larger group of 5 to 11 guests? We use a passenger van at $100 per person. You can see the details on our cruise tours page. Tours run in English or Spanish, and cancellations are accepted up to 24 hours before.
A Quick Packing Checklist for Cruise Passengers
Before you leave the ship, check that you have your ship card and ID, your phone, a hat, sunglasses, and sunscreen. Add a water bottle, a little cash, comfortable shoes, and a light rain layer. Know your all-aboard time, and keep a screenshot of it on your phone.
Our free cruise day guide walks you through the whole day, hour by hour. We also stay flexible around ship times, so you do not have to rush.
Flying In Instead?
If you are flying to the island, pack the same way, then add a swimsuit and a casual outfit for dinner. For help comparing options, see our flights to San Juan page. U.S. citizens do not need a passport to travel to Puerto Rico, but it is smart to check ID rules for your state before you go.
Ready to Explore San Juan?
Pack light, wear good shoes, and leave the planning to us. Book online here, or call or text us at (787) 222-4184. And if you want a souvenir that says you were here, take a look at our 2SantosPR shirts.
