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Planning a short trip to San Juan? You’re in the right place!
This colorful capital blends centuries-old history with vibrant coastal energy, making it the perfect place to spend a few days. Between strolling the cobblestone streets of Old San Juan, snorkeling with sea turtles, and venturing into the lush El Yunque Rainforest, you’ll get a taste of Puerto Rico’s rich culture and stunning natural beauty.
After countless trips here, we know exactly how to make the most of a few days in the city. That’s why we’ve put together this 3-day itinerary that balances sightseeing, food, and unforgettable experiences, all without the need to rent a car. With affordable rideshares and plenty of walkable areas, exploring San Juan is as easy as it is exciting.
Ready to dive in? Let’s go!
Don’t Miss Out On Our Top Choice!
The tour we loved the most and suggest booking ASAP is this one!
Our personal FAVORITE thing we did was this guided snorkeling tour. We swam with sea turtles, spotted tropical fish weaving through the coral, and soaked up San Juan’s coastal beauty. It was absolutely incredible!
Check out the 11,000+ 5-star reviews and book this tour here!
Itinerary Overview
Over three days, you’ll experience some of San Juan’s most captivating areas, from the pastel-colored streets and historic forts of Old San Juan to the golden sands of Condado Beach and the tranquil waters of Condado Lagoon. You’ll also have time to explore the lush landscapes just beyond the city, including the world-famous El Yunque Rainforest.
The best part is that getting around is simple. Old San Juan is compact and very walkable, making it easy to explore on foot. For anything farther afield, Uber is affordable, reliable, and widely available. That means you can skip renting a car and still reach all your must-see spots with ease.
Day 1: Enjoy coffee at Café Cuatro Sombras, explore Old San Juan on a walking tour, have lunch at Chocobar Cortés, snorkel with sea turtles, take a sunset harbor cruise, and dine at Los Pinos Café.
Day 2: Savor an Old San Juan food tour, relax on the beach, enjoy dinner at Semilla Kitchen & Bar, and paddle through Condado Lagoon on a nighttime LED kayak excursion.
Day 3: Discover El Yunque Rainforest on a full-day guided tour, then return for dinner at Princesa Cocina Cultura and an evening stroll through Old San Juan.
Day 1
Breakfast – Café Cuatro Sombras
We couldn’t think of a better way to start the day than with a strong, velvety coffee at Café Cuatro Sombras. Puerto Rico’s coffee has a well-earned reputation, and this place truly lives up to the hype—we loved the smooth, rich flavor and the warm, laid-back vibe inside.
It’s also perfectly located in Old San Juan, just a short stroll (less than five minutes!) from the meeting point for our morning walking tour. We’d suggest packing your swimsuit before heading out, since you’ll be swapping cobblestone streets for the sea on a snorkeling trip later in the day.
Morning – Discover San Juan’s best sights on a walking tour
After finishing our coffee, we walked just a few minutes to join this 9 am Old San Juan walking tour (which ended around 11:15 am), and we couldn’t have asked for a better start to the day!
Exploring with a local guide is hands-down the best way to get your bearings here, uncovering the stories behind the cobblestone streets, colorful Spanish colonial buildings, and centuries-old forts. On top of that, we left feeling like we stepped right into San Juan’s history and culture.
This 2-hour tour takes you through the city’s most iconic landmarks, all while weaving in fascinating tales about pirates, politics, and everyday life on the island. We loved the small-group format, but if you’d prefer something more tailored, you can easily upgrade to a private tour here.
From scenic plazas to hidden alleyways, every turn revealed something new, and don’t even get us started on the incredible photo spots! The relaxed pace made it easy to soak it all in without feeling rushed, and the guides are full of tips for places to eat, drink, and explore later. By the time we wrapped up, we felt like we had the perfect introduction to the city!
Read over 1,000 five-star reviews and book this tour here!
Early lunch – Chocobar Cortés
After wrapping up the walking tour, we took a short seven-minute stroll to Chocobar Cortés, a brunch spot we’d been hearing about since we arrived. Known for weaving chocolate into both sweet and savory dishes, it’s the kind of place that feels a little indulgent in the best way. We lingered over a leisurely lunch, knowing the afternoon would be more active. From rich hot chocolate to inventive mains, every bite felt like a little celebration.
It’s also perfectly located for the next leg of the day, with the snorkeling tour meeting point just a quick 10-minute Uber ride away. You’ll leave feeling recharged and ready for an afternoon in the water!
Afternoon – Go snorkeling with sea turtles
Just a short ride from Old San Juan is Escambrón Beach, one of the most beautiful spots in the city, and the starting point for today’s guided snorkeling adventure. We recommend booking the 1 pm tour, which will wrap up around 2:30 pm.
We met our friendly guide right on the sand, and from the moment we arrived, we knew this was going to be special. The turquoise water was warm and inviting, and after a quick safety briefing, we were slipping on our masks and fins, ready to explore.
Within minutes, we spotted our first sea turtle gliding effortlessly through the water. Over the course of the tour, we saw four or five of them, along with schools of tropical fish darting in and out of the coral. Our guide pointed out hidden details we would have easily missed and even captured GoPro footage of the whole experience for us to keep, such a great souvenir.
This was easily one of the most memorable things we’ve ever done in San Juan, and we’d happily do it again tomorrow. Whether you’re an experienced snorkeler or it’s your very first time, you’ll feel right at home in the calm waters here!
Book your spot on this unforgettable sea turtle snorkeling tour here!
Evening – Sunset harbor cruise
After your afternoon snorkel session, freshen up back at your hotel before heading over to the San Juan Bay Marina for this sunset harbor cruise. It runs from 5:30 pm to 7 pm and is the absolute perfect way to start winding down a day in San Juan.
While pickup is offered for this tour, it usually runs between 3 and 5 pm, which can feel a bit tight after snorkeling. If you’re able to arrange a later pickup closer to 5 pm, it could work, but heading to the marina on your own is often the more relaxed option.
From the moment we stepped aboard, the crew’s warm welcome set the tone for a relaxed, cheerful evening on the water. As we pulled away from the dock, the sky was already turning gold, and the city walls looked stunning in the soft evening light. Seeing Old San Juan from the water gave us a whole new perspective on how beautiful this place is.
And the sunset itself was pure magic! Shades of orange melted into pinks and purples, the music was upbeat but mellow, and the rum punch kept flowing. We couldn’t resist snapping photo after photo as we glided across the calm waters.
For us, it was a romantic way to end the day, but we could easily see it being just as special for friends, families, or even solo travelers. If you want to fall completely in love with San Juan, this is the tour for you!
Book this incredible sunset cruise with FREE 24-hour cancellation here!
Dinner – Los Pinos Café
After a full day exploring Old San Juan and the coast, we were craving something casual and local, and Los Pinos Café hit the spot. Located about a 10-minute drive from the San Juan Bay Marina, this neighborhood favorite has a laid-back, diner-style vibe and is known for hearty Puerto Rican comfort food served late into the night.
From mofongo and churrasco to generous platters of rice and beans, the portions are big, flavorful, and reasonably priced. It’s the kind of place where you’ll likely be the only tourists in the room, surrounded instead by locals stopping in for a satisfying meal. It’s the perfect way to end the day—simple, satisfying, and full of local flavor that made us feel right at home in San Juan!
Related Read: Still need a hotel? Our where to stay in San Juan guide breaks down the best areas and hotels so you don’t have to guess!
Day 2
Morning – Taste your way around San Juan
We’re big fans of food tours, but this 3-hour food tasting experience took us on a flavorful journey through Puerto Rican history and culture that we’ll never forget. We couldn’t think of a better way to start our second day in San Juan!
We met our guide, Pablo, in the heart of Old San Juan at 10 am, and his warmth and enthusiasm set the tone right from the start. The tour began with a cup of Puerto Rican coffee, the kind that makes you slow down and savor, before we started wandering the cobblestone streets in search of our next bite.
Each stop brought something new to the table, from street food stands serving crispy bacalaítos to a cozy café where we tried mofongo, a delicious mash of plantains, garlic, and pork cracklings. Pablo had a story for every dish, weaving history, culture, and food into something far richer than just a tasting. There was even a tropical drink break, where Dan sipped something minty and refreshing while I treated myself to a creamy coconut concoction!
By the time the tour wrapped up at 1 pm, we felt like we’d eaten our way into the heart of San Juan. If you book this early in your trip, you’ll walk away with not only a full stomach but also a list of local spots and must-try dishes that will make the rest of your stay even more delicious!
With over 4,300 5-star reviews, you can book this popular food here!
Afternoon – Relax on a beach
After a morning of eating and exploring, we were more than ready to slow the pace and soak up the sunshine. San Juan has no shortage of beautiful beaches, and each one offers its own unique vibe.
- Condado Beach is ideal if you want to be right in the heart of the action. Lined with luxury hotels and plenty of restaurants, it’s one of the most popular spots in the city. The atmosphere is lively, so it’s a great choice if you like having amenities and people-watching at your fingertips.
- Isla Verde Beach is your picture-perfect postcard beach, with soft white sand and turquoise waters. You’ll find water sports rentals, lounge chairs, umbrellas, and plenty of space to swim. It’s a great choice if you want that classic Caribbean beach day.
- Playa Ocean Park offers a slightly more laid-back feel while still being popular. It’s a local favorite for its wide stretch of sand and relaxed vibe, making it perfect if you want a beach that’s social without feeling crowded.
Wherever you choose, give yourself time to unwind, dip your toes in the water, and let that Caribbean sun work its magic.
Dinner – Semilla Kitchen & Bar
After a leisurely afternoon on the sand, we headed back to freshen up before making our way to Semilla Kitchen & Bar in Condado. The location couldn’t be more convenient, especially if you’ve spent the day at Condado Beach, and it’s just a five-minute walk from the starting point of our evening tour. Just note they’re closed on Mondays and Tuesdays.
We loved the warm, modern atmosphere here. It felt upscale but still relaxed, perfect for winding down after a sunny day. The menu features fresh, seasonal dishes with creative twists, and everything we tried was full of flavor. Whether you go for seafood, steak, or one of their inventive vegetarian options, you’re in for a delicious meal that sets the tone for the night ahead.
Evening – Explore Condado Lagoon on a nighttime kayak excursion
With dinner wrapped up, we made our way just five minutes down the road for our 8 pm start time on this Condado Lagoon nighttime kayak tour. Start times run every half hour from 6:30 to 10 pm, so you can easily choose one that works around your evening plans.
From the moment we arrived, the atmosphere was fun and lighthearted. The guides greeted us with glow paint and glow sticks so we could really get into the spirit before climbing into our clear-bottomed kayaks. Once on the water, the colorful LED lights beneath us transformed the lagoon into a glowing, otherworldly scene. We could spot fish darting below while the city lights shimmered on the surface.
Paddling was easy thanks to the calm water, and our guides kept the energy high, mixing local history and wildlife facts with plenty of laughs. They even snapped photos for us throughout the trip, which made for great keepsakes. The panoramic nighttime views of San Juan from the water were spectacular, the kind of perspective you just can’t get from land.
This tour was vibrant, colorful, and such a fun way to end the day, and we’re sure you’ll love it too. Just scroll through THOUSANDS of five-star reviews here that rave about the guides, the energy, and the unforgettable experience!
You can read their glowing reviews and book your nighttime kayak tour here!
Why We Book Tours with Viator
Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:
- Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
- Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
- Lowest price guarantee – If you happen to find the same tour at a lower price elsewhere, Viator will refund you the price difference.
- Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
- Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.
Check out the Viator website here! Or, for more info, read our detailed review about Viator here.
Day 3
Full day – Visit El Yunque Rainforest
We had the best day exploring El Yunque Rainforest on this full-day guided tour! This world-famous natural wonder is truly one of the most incredible ways to experience the wild beauty and lush landscapes Puerto Rico is famous for.
We booked the 10:30 am start time (pickups begin about 90 minutes beforehand), though there’s also a 12:30 pm option if you’d prefer a slower start to the morning.
Eduardo, our friendly driver and guide, picked us up right on time, and the day unfolded seamlessly from there. We made a quick stop for smoothies and empanadas to fuel up, then drove deep into the heart of El Yunque National Forest.
Being surrounded by dense jungle was breathtaking, and hiking to Las Paylas’ natural waterslides was a definite highlight. The hike wasn’t too challenging, and cooling off by sliding down smooth rocks into crystal-clear pools was the perfect reward.
After our jungle adventure, we headed to Luquillo Beach for some well-earned relaxation. We had time to lounge on the golden sand, splash in the gentle waves, browse for souvenirs, and enjoy drinks from the local kiosks. The laid-back atmosphere made it an ideal way to end such an active day!
Don’t miss out—book this full-day El Yunque Rainforest tour here!
Dinner – Princesa – Cocina Cultura
After a full day of exploring El Yunque and relaxing on the beach, we were ready for a memorable final dinner in San Juan, and Princesa Cocina Cultura was the perfect choice. Set in a lush, garden-like space in Old San Juan, this popular restaurant celebrates Puerto Rican flavors with a creative twist. We loved the romantic atmosphere, complete with twinkling lights and the sound of live music drifting through the air.
The menu is inspired by traditional recipes, but each dish has its own modern flair. From fresh seafood to rich, slow-cooked meats, everything was beautifully presented and full of flavor. It’s the kind of place where you’ll want to linger, sipping a signature drink while soaking in your last evening on the island. Just keep in mind the restaurant is closed on Sundays and Mondays.
Evening – Old San Juan
For our final evening, we couldn’t resist one last wander through the colorful, cobblestone streets of Old San Juan. The city feels even more magical at night, with the warm glow from the street lamps, the hum of live music spilling from open doors, and locals and travelers alike filling the plazas. We strolled past historic buildings, pausing to peek into inviting bars and cafés, just soaking in the atmosphere.
We ended the night at Don Collins Coffee Cocktails, a cozy spot known for its creative coffee-inspired theme. Sipping a drink here felt like the perfect send-off, a little buzz of caffeine, a little sweetness, and a lot of Puerto Rican charm. It was the ideal final note to our adventure—here’s to an incredible three days in San Juan!
Related Read: Looking for even more ideas? Check out our full guide to the 10 best things to do in San Juan here for can’t-miss experiences beyond this 3-day itinerary.
Where to Stay in San Juan
Now that you’ve got your San Juan itinerary all sorted, the next step is finding the right place to stay. Your hotel can really shape how relaxing and enjoyable your trip feels, so we’ve pulled together our top picks for every budget—from affordable comfort to mid-range charm to luxury indulgence. These spots tend to book up quickly, so if you find availability for your travel dates, be sure to lock in your stay before it’s too late.
Luxury – $$$
For a luxurious stay in San Juan, La Concha Renaissance San Juan Resort is our top choice! This stunning beachfront resort offers three swimming pools, a private beach, a 24-hour casino, a spa, and several fine-dining restaurants. The rooms are bright and modern, featuring floor-to-ceiling windows and private balconies with breathtaking views. It’s the perfect setting for an unforgettable Caribbean escape!
Prices vary by season and room selection but start around $500 USD per night. Check availability and book this stay on Booking.com.
Mid-range – $$
During our last visit to San Juan, we stayed at the Embassy Suites by Hilton San Juan – and we loved it! The location is unbeatable, just two blocks from the stunning Isla Verde Beach and within easy reach of top attractions like Old San Juan, the San Juan cruise port, Plaza Las Americas Mall, and the Mall of San Juan. It also has great amenities, including two swimming pools, a playground, an onsite casino, made-to-order daily breakfast, and 4 restaurants!
Pricing depends on the room category you choose and the time of year, but often ranges between $250 – $400 USD per night. Check pricing and availability for your travel dates on Booking.com.
Budget – $
Nomada Beach Hostel is a charming and budget-friendly spot just steps from the beautiful Isla Verde Beach. This laid-back hostel has everything you need for a comfortable stay, including an outdoor swimming pool, a spacious lounge area, and a shared kitchen where you can whip up your own meals. Guests also enjoy free Wi-Fi and the convenience of an on-site restaurant and bar for tasty bites and drinks!
The rooms are well priced and range from around $60 to $170 USD per night, depending on whether you want a dorm bed or a private room. Check dates and book this stay on Booking.com.
For even more great options, check out all of San Juan’s hotels listed here!
Renting a Car in the Caribbean
Renting a car in the Caribbean gives you the freedom to explore beyond the resorts—think secluded beaches, remote viewpoints, and vibrant local towns that buses don’t reach. As long as you are prepared for the road conditions and informed about local driving rules, renting a car can be a great addition to your trip!
We always book through Discover Cars and can’t recommend them enough. It’s easy to compare providers, filter for exactly what you need (like an automatic or 4×4), and add affordable full coverage insurance. If you want all the details, check out our full Discover Cars review here.
Tips for Renting a Car in the Caribbean
- Know the driving side: Some Caribbean islands drive on the left, while others stick to the right. It really varies island to island, so double-check before you go—and make sure you’re comfortable driving on that side of the road, especially if it’s different from home.
- Know the local driving rules: Road laws and signage can differ between islands, so it’s worth doing a quick check before pickup. Seatbelts are usually mandatory, texting and driving is typically illegal, and honking is often just a friendly heads-up. Expect low speed limits and shared roads—think scooters, pedestrians, and even the occasional animal—so stay alert and take your time!
- Add full insurance: Roads can be unpredictable, with potholes, hills, and narrow lanes—especially outside resort areas. For that reason, we always recommend adding on full coverage insurance to your rental. Discover Cars makes this super easy (and affordable!) to add on, so you can drive with peace of mind.
- Choose the right car: For beach tracks or hilly inland roads, a compact SUV or 4×4 might be your best bet. Discover Cars makes it easy to filter by vehicle type, transmission, or even luggage space to suit your needs.
- Watch for extra fees: Some rental companies charge sand cleaning fees, airport pickup surcharges, or require you to return the car spotless. It’s nothing to stress over—just check the fine print so you’re not caught off guard.
What You Need to Rent a Car in the Caribbean
- A valid driver’s license from your home country.
- On some islands, a temporary/visitor’s driving permit may be required. These are normally issued by the rental agency for a fee. Check with your company in advance, so you’re not surprised by extra costs at pickup!
- An IDP (International Driving Permit) may be required depending on your destination and the language of your license. Always check the country’s requirements beforehand so you’re prepared.
- A credit card in the driver’s name is typically required for the security deposit.
- Most rental companies require drivers to be at least 21 years old, with a young driver surcharge applicable for those under 25. Some companies may have higher age requirements, so make sure you double-check.
Ready to hit the road? Book your car with Discover Cars here and discover the freedom of exploring the Caribbean Islands on your own terms!
Don’t Forget Travel Insurance!
If you’re looking to save money on travel insurance, we currently use and recommend SafetyWing. We’ve been using their coverage since 2018 and they’ve had our backs when we needed emergency flights and got sick overseas.
SafetyWing is one of the cheapest providers out there and covers everything from medical costs to lost luggage, travel delays, and emergency flights. A huge difference we’ve found between them and other companies is that they let you take out a policy AFTER leaving your home country. We’ve also found it handy that it’s a monthly payment rather than a lump sum, and you can get a refund for unused time.
SafetyWing has helped us out in some scary situations before and their affordable coverage has given us peace of mind. You can read our honest review of SafetyWing for all the pros and cons.
Thanks for reading!
We hope this 3-day San Juan itinerary helps you plan the perfect trip! From the cobblestone streets of Old San Juan to snorkeling with sea turtles and exploring the world-famous El Yunque Rainforest, we loved every moment of our time here. Whether you’re visiting for history, food, beaches, or just the island vibes, San Juan delivers it all.
If you’re planning more adventures in the region, don’t miss our other Caribbean blogs here—we’ve spent countless trips exploring this part of the world and have shared our favorite experiences to help you plan. Or here are some of our most popular guides below to keep the inspiration going:
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