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Your Ultimate Puerto Rico Travel Guide?
Nope! This is Not Your Ultimate Puerto Rico Travel guide. Why are we even in Puerto Rico? San Juan, Puerto Rico is where our Windstar cruise starts and ends. The island was never the “entree” but it did become the “appetizer” for a return trip.
We have three days before the ship sails. Three days in a city with 500 years of history on every corner, a rainforest an hour away, and islands off the coast that people fly across the world to see. We did what three days allows before we head for our cruise. Mainly, we plan what to do on a return trip.
Here’s what we found. Let’s start with your travel insurance first, then move on to where we stayed. If you need a packing list right away. jump to it here.
Our Home Base: The San Juan Marriott Resort & Stellaris Casino
The San Juan Marriott Resort & Stellaris Casino sits right on Condado Beach in the heart of the Condado neighborhood — San Juan’s most upscale district, about five miles from Old Town and ten minutes from the airport.
Start your morning at La Panaderia, the coffee shop right inside the resort. Locally sourced Puerto Rican coffee and fresh pastries. Plus, they make killer cappuccinos, frappes and other coffee specialties. Do not skip this.
We had an ocean view unit. Private balcony. Coffee out there every morning watching the Atlantic. I didn’t need anything else to justify the trip, but Puerto Rico kept adding to the argument.
The resort has two pools, a casino that runs 24 hours, (not our thing but you may love it) a spa (we just didn’t have time for this), and more dining options than three days can cover. Beach chairs are set up every morning. Walk out the lobby, down a short path, and you’re on the sand. And if you’re lucky, you can grab one of the few hammocks and sway your worries away!
The staff knows the island. Ask them. They’ll point you in the right direction faster than any app. We walked the beach both directions to the very end. Twice. Because you can.
Other Hotels We’d Consider for our next Puerto Rico Visit
We loved our oceanfront room at the San Juan Marriott Resort & Stellaris Casino, especially sitting on our balcony and watching the world go by. But if you’re like me, you like choices, so I researched some other highly rated properties that are similar to the Marriott. We haven’t stayed at any of these hotels, but they are on our shortlist. Let us know if you stay at one of these resorts and we’ll update the list as needed.
1. La Concha Resort, Autograph Collection
Best for: Couples, nightlife, and a lively beachfront atmosphere
La Concha is right on Condado Beach with a lively, beachy energy. This resort has something for everyone: three outdoor pools, one of which is an adults-only ocean pool, six restaurants, and a casino, all steps away from vibrant city nightlife, plus adventure sports — kayaking, surfing, snorkeling are all bookable on site. Rated 8.8 on Expedia and consistently praised for its beachfront dining and poolside scene. Guests consistently rave about its energy, ocean views, and the convenience of walking to dozens of restaurants and shops.
2. Condado Vanderbilt Hotel
Best for: Luxury travelers who appreciate classic elegance
If old-world glamour is more your style, the Condado Vanderbilt delivers. Built in 1919, it feels like stepping into a 1920s Caribbean dream; so elegant and polished. The Vanderbilt provides impeccable service, spacious rooms, beautiful pools, outstanding dining, and a quieter, more refined atmosphere than some of the larger resorts nearby. Multiple pools, a full-service spa with Turkish bath, direct beach access, and dining with ocean views. Guests who stay here tend to come back. Rated 9.0 on Expedia.
3. Fairmont El San Juan Hotel
Best for: Resort amenities and one of Puerto Rico’s best beaches
Located on Isla Verde Beach, about 15 minutes from Old San Juan, this beautifully restored resort blends classic Puerto Rican charm with modern luxury. Guests love the expansive pools, lush tropical grounds, lively entertainment, and one of the widest stretches of beach in the San Juan area.
4. Dorado Beach, a Ritz-Carlton Reserve
Best for: A once-in-a-lifetime splurge
If you’re celebrating something special, Dorado Beach is hard to beat. This stunning resort, envisioned by Laurance S. Rockefeller in the 1950’s, is an ultra-luxury, eco-friendly Caribbean getaway at its best. The 50 acre sanctuary sits inside a larger 1,400-acre gated residential estate and offers private beaches, a five-acre spa, and championship golf. Guests describe it as peaceful, intimate, and exceptionally luxurious, with stunning beachfront accommodations, world-class service, and beautifully landscaped grounds. About 40 minutes west of San Juan, this isn’t the former Ritz-Carlton you may remember. It’s an entirely different experience.
5. Las Casitas Village, Fajardo
Best for: Snorkeling, island hopping, and exploring Puerto Rico’s east coast
If your dream vacation revolves around Culebra, Vieques, or snorkeling excursions (that’s us, for sure) I’d seriously consider staying in Fajardo instead of San Juan. Las Casitas Village is an exclusive, luxury villa community located on a 300-foot cliffside within the larger El Conquistador Resort. Guests enjoy a private enclave with personalized butler service, access to the resort’s private island and are much closer to the ferries and catamaran departures, leaving you with more time on the water. Guests especially appreciate the spacious villas, sweeping ocean views, and easy access to the islands.
A Word About the Sun in Puerto Rico
If the sun seems hotter to you in Puerto Rico, it’s because San Juan is much closer to the equator than the continental US, resulting in more direct sunlight and consistently high UV index levels. At 18° N latitude, the sun passes more directly overhead, which means that the sun’s rays pass through less of the atmosphere to reach your skin.
I always pack a hiking hat with a neck flap, but for some reason, when we set out on foot from the hotel that morning, I didn’t put it on. We wanted to check out Ashford Avenue, which is right outside the Marriott’s front door. Wide sidewalks. Well-lit. Safe day and night — but it was SO hot.
It’s also exposed. In the heat of the day, it is no joke. My LifeWave energy patch kept me going — but I still ducked into a resort along the avenue and bought a hat on the spot. Pack and WEAR the hat. Learn from my mistake.
3 Experiences in One Day
We stayed in San Juan because we only had three days before our cruise departed. Old San Juan, which was on our short list, was a short Uber ride away. What we didn’t realize, is that two famous forts are within easy walking distance of Old San Juan. We visited not one but three tourist attractions in one afternoon! Plus, we walked down to the cruise docks just for fun. Old San Juan, Castillo San Felipe del Morro and Castillo San Cristóbal are our first three recommendations.
Old San Juan: Five Centuries in Six Square Miles
Some places are worth seeing. Old San Juan is worth wandering.
Forget the map and let the blue cobblestone streets decide where to go. Around every corner, we found even more colorful buildings. Balconies overflowing with flowers. Doors painted turquoise, sunshine yellow, and coral. Best of all were the tiny cafés spilling onto the sidewalks. So many unique and interesting shops, you can easily spend several days here.
Even though the city is more than 500 years old, it feels so alive. Street musicians play in the plazas. Locals gather on benches to chat. Cruise passengers, photographers, and families all somehow share the same narrow streets without anyone seeming to be in much of a hurry.
Take an Uber and wear comfortable shoes. Those beautiful blue cobblestones were laid centuries ago, and while they’re part of Old San Juan’s charm, they can be uneven underfoot. Make sure to stop for lunch at one of the many outdoor cafes. There is nothing better than watching the world go by while you sit at your umbrella shaded table, enjoying local fare. We loved it!
The Iguana
Did I mention the iguana in Old Town? I love to hold the local critters; Jack, not so much. When I spotted what looked like a tiny dinosaur “for hire” in the middle of the plaza, I made a beeline for him. The young man stood casually off to the side of the plaza with this enormous green iguana thrown over his shoulder, as if it were a sleepy house cat.
A few dollars later, this prehistoric-looking fellow is mine for the moment. His claws wrapped gently around my hand as he stared off into the distance. He gave me one slow blink that seemed to say, “You’re not the first human to think this is exciting.” Tourists smiled as they walked by. Jack took pictures and is even persuaded to join the photo session. The iguana never flinched.
The Forts: Two of Them, Both Worth Your Time
Most people know about El Morro. Fewer know there are two forts. Both are included on the same $10 ticket.
Castillo San Felipe del Morro (El Morro)
El Morro sits at the very tip of Old San Juan on the northwestern edge of the islet. Commissioned by Spain in 1539, it took 250 years to complete and stands six levels high. With walls up to 25 feet thick, El Morro rises 140 feet above the Atlantic shoreline.
Sir Francis Drake attacked in 1595. The Dutch attacked in 1625. The U.S. Navy shelled it in 1898. It held everytime and is still standing.
A World Heritage Site
UNESCO declared it a World Heritage Site in 1983. It is now run by the National Park Service, where Rangers lead free tours, or you can walk it yourself with a map from the entrance. (This is what we did.)
The views from the top are worth the climb. Ocean on one side. The colored rooftops of Old San Juan on the other. Bay below. Atlantic ahead. Awesome.
The grassy esplanade in front is a different kind of beautiful. Locals fly kites out there every weekend. You’ll find kids, adults, couples, singles, all enjoying the esplanade. It’s one of those scenes that makes you slow down.
Castillo San Cristóbal
San Cristóbal sits at the opposite end of Old San Juan on the northeastern edge. Completed in 1783, it is the largest fortification the Spanish ever built in the New World. While El Morro protected the city from the sea, San Cristóbal protected it from land.
San Cristóbal has deep moats, an intricate tunnel system, and a sentry box called La Garita del Diablo — the Devil’s Sentry Box. Built in 1634, the “Sentry Box” sits alone on the ocean-facing wall, battered by waves and cut off from the rest of the fort.
The Legend of La Garita del Diable
The legend begins with a guard who simply…vanished.
Each night, the soldiers called out to one another in the darkness, confirming they were awake and standing watch. Then one voice stopped answering.
When the others reached his post, his uniform was there. His weapon was there. The guard, Sánchez, was not. No sign of a struggle. No explanation. Just an empty post overlooking the sea.
Some say the devil claimed him. Others insist he slipped away under the cover of darkness to elope with his sweetheart, Dina. Centuries later, no one knows for certain.
Today, it’s one of the most photographed spots inside the fort. Whether you’re drawn by the ghost story or the love story, it’s hard to stand there without wondering what really happened on that long-ago night.
Both forts are part of the San Juan National Historic Site, and one admission ticket covers them both. They’re about a 15-minute walk apart along the old city walls, where sweeping ocean views make the stroll every bit as memorable as the destination.
We only had three days. These two didn’t make the cut. They’re leading the return trip.
Still on Our List: 3 More Experiences You Shouldn’t Miss in San Juan, Puerto Rico
El Yunque National Rainforest
We didn’t get to visit El Yunque this trip, but reading about it made it a “must do” next time around.
Located about an hour from San Juan, the city quietly gives way to a world where the air feels softer, the greens seem impossibly greener, and waterfalls hide around the next bend. El Yunque is the only tropical rainforest in the U.S. National Forest System, but labels don’t really capture it. This is a place to slow down.
Trails seem to disappear beneath towering palms and giant ferns. Water tumbles over ancient rocks into cool pools where it’s hard to resist dangling your feet or climbing in for a swim. La Mina Falls is the best known; Juan Diego Falls invites you to sit on rocks in the middle of the creek while the water rushes past, and La Coca Falls spills dramatically down an 85-foot rock face, reminding you that not every beautiful place needs to be touched to be appreciated. (We are definitely going here!)
If you go, go early. Once the tour buses arrive, the rainforest begins to wake to a different soundtrack. But in those first quiet hours, when the only voices belong to birds, tree frogs, and rushing water, it’s easy to understand why so many people leave El Yunque feeling like they’ve wandered into another world.
Getting to El Yunque
El Yunque is about an hour from San Juan. Unless you’re renting a car, the easiest option is a guided tour. Most tours pick up at hotels in Condado and Isla Verde (including the Marriott Stellaris), cost about $45 to $90 per person, and include transportation, a guide, and several hours to explore the rainforest. It’s an easy, stress-free way to visit one of Puerto Rico’s most magical places. Taxis are not recommended as it may be difficult to get one to return.
Culebra Island: A Snorkeling Paradise
Culebra sits about 20 miles off Puerto Rico’s east coast. It’s the island people mean when they talk about snorkeling in Puerto Rico.
The water is that shade of Caribbean blue that looks fake in photographs and doesn’t look real until you’re standing in it.
Tamarindo Beach — known as Turtle Beach by locals — is where you swim alongside sea turtles and rays. Not near them. With them. Carlos Rosario Beach requires a short hike from Flamenco Beach and delivers pristine coral reefs with fish in colors that have no business existing.
Some places ask you to slow down. Culebra doesn’t ask. It simply makes you forget what time it is.
Getting to Culebra Island
Getting to Culebra is part of the adventure.
You can catch the public ferry from Ceiba, about an hour’s drive from San Juan, or hop aboard a small plane if you’d rather trade highway miles for a bird’s-eye view of the Caribbean.
But if you’re staying in San Juan and only have a day, I’d choose a catamaran excursion from Fajardo. They typically include lunch, snorkeling gear, and, yes, unlimited drinks.
The boat does the work. You do the snorkeling.
Vieques: The World’s Brightest Bioluminescent Bay
The big attraction on Vieques is Mosquito Bay, which is considered the brightest bioluminescent bay on Earth. Tiny microorganisms called dinoflagellates light up the water whenever it’s disturbed. Every paddle stroke, every fish, even your fingertips leave a trail of electric blue light. Go on a moonless night if you can. The darker the sky, the brighter the glow.
In addition to Mosquito Bay, Vieques has more than 40 beaches, many of them nearly deserted. A few of the more popular are:
Playa Negra: One of Puerto Rico’s few black sand beaches, reached by a short walk through a mangrove.
Sun Bay: Long crescent of golden sand with calm swimming.
Blue Beach (Bahía de la Chiva): Crystal-clear water and excellent snorkeling.
Caracas Beach (Red Beach): Powdery white sand and brilliant turquoise water.
Green Beach: Also excellent for snorkeling.
Wild Horses
One of the island’s signatures is its free-roaming horses. You’ll see them grazing beside roads, wandering beaches, and sometimes standing beneath palm trees as though they’ve posed for every visitor’s camera.
Getting There
You can reach Vieques by:
- Ferry from Ceiba (about a 30 to 45 minute crossing)
- Small plane from San Juan or Ceiba (roughly 20 to 30 minutes)
Once you’re there, renting a Jeep, golf cart, or car is almost essential because taxis are limited and the island’s best beaches are spread out.
A Comparison of Culebra and Vieques
Choose Culebra if you want:
- The Caribbean’s famous turquoise water
- World-class snorkeling
- Flamenco Beach
- An easy day trip
Choose Vieques if you want:
- The magical glow of Mosquito Bay
- Wild horses wandering freely
- Quiet, uncrowded beaches
- A more relaxed, off-the-beaten-path experience
For most visitors staying at the Marriott Stellaris in San Juan, Culebra is the better one-day excursion because it’s built around snorkeling and iconic beaches.
But if you have two or three extra days, I’d head to Vieques. Watching your kayak carve glowing blue ribbons through the water in Mosquito Bay is the kind of experience that stays with you long after you’ve unpacked your suitcase. Now that you know what to do, keep reading for what to pack.
What to Pack for Puerto Rico (or any tropical climate)
We each travel with one carry-on and a backpack. Always. If you want to know exactly what we pack to keep us comfortable on a long flight, that’s all in our “San Juan Airport Hotel post.”
As for clothing, the goal is easy-care, lightweight, and multi-purpose clothing. Things that work on a fort tour, a beach walk, and dinner, without needing a second bag.
We wrote an entire post on Packing for Puerto Rico. (Good for any tropical area.)
We’ll Definitely Be Back!
San Juan surprised us in the best of ways.
We came for a cruise. We left with a list of reasons to go back. The forts alone are worth the trip. Old Town alone is worth the trip. The beach at the Marriott, the coffee at La Panaderia, the iguana on the plaza — all of it adds up to something that doesn’t fit in three days.
Give it more time than we did. You won’t regret it.
We hope you found this post about planning for YOUR Puerto Rico adventure helpful! If you did, please follow us on FB, IG and continue to follow our blog, Seniors with Latitude. Happy Travels!
Elaine Schaefer is a travel advisor and coach at Seniors with Latitude. She travels with her husband, Jack and writes about finding adventure, well-being and fitness after 60 and well beyond.
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