Things to Do in Puerto Rico ⎜ San Juan Puerto Rico ⎜ Romantic Things to Do in Old San Juan

Romantic Vacation Ideas - San Juan, Puerto Rico

Always wished to see and experience the romance of a European town?  Come to Old San Juan to experience the romance and charm of European architecture with the added colorful touches and warmth of a tropical paradise without the need to travel far.  As you tour the city, you’ll be walking past couples, of all ages, holding hands, and falling in love all over again. 

San Juan offers romantic hotels and restaurants, but unlike many destinations, the historic district of Old San Juan is romantic all on its own, for the budget-conscious traveler, this is great news, you don’t have to spend much in order to have an utterly romantic getaway in San Juan. 


There are plenty of romantic activities sure to spark romance, many of them are free and very budget-friendly.  Old San Juan is an all-inclusive romantic destination offering something for every type of couple.  Best of all, travel to San Juan is hassle-free with many direct flights from the U.S., Canada, and Europe with no passport required for US Citizens.

Choose to stay at one of the hotels in Old San Juan, as you step outside the door you’ll have easy access to a variety of romantic activities and world-class attractions.  Some suggestions we make may seem simple, but once you get here, you’ll realize that something as ordinary as walking becomes an extraordinary romantic experience.

A Romantic Morning Walk in Old San Juan

San Juan, Puerto Rico

You both have a lot to see, so start off your day with a great breakfast in Old San Juan.

Casa Cortes ChocoBar (210 Calle San Francisco, opens at 8 am) –Who said you can’t have chocolate for breakfast?  Chocolate is often synonymous with romance, for a real decadent treat, head over to Casa Cortes where chocolate is deliciously integrated on every drink and plate.  No calorie counting, you deserve some indulgence, the morning walk should burn most of the calories effortlessly.

For a hearty low-cost breakfast, head to Café Manolin on Calle San Justo, a diner-style restaurant loved by locals for its traditional food at great prices.

Walk along Paseo de la Princesa

Start your walking tour along Paseo de la Princesa.  Local artists display their art along the walk, buy your loved a unique piece of art or jewelry to remember the moment.

Paseo de la Princesa - Old San Juan Puerto Rico

Midway through the walk, you’ll pass a beautiful fountain perfect for a selfie-worthy of many “likes”.  Your walk will become beautifully scenic as you walk along the historic city walls and the inspiring views of San Juan Bay.  Pause, sit down at a bench, and enjoy the views sure to inspire a stare and a kiss.

Paseo de la Princesa - Romantic Places in Old San Juanj

Enter the Gate & Renew Your Vows

At the end of the walkway, you can enter through the historic San Juan Gate .   As soon as you pass the gate you’ll walk up one of the prettiest streets in Old San Juan.

San Juan Gate - Romantic Places to Visit in Old San Juan, Puerto Rico

At the end of the street, you’ll be facing the San Juan Cathedral where thousands of weddings, including celebrities, have promised each other eternal love.  The elegant church is always open and you’re welcome to walk in.  If you’re already married, what about surprising your loved one by going up to the altar and renewing your vows?  Continue your walk up Calle Cristo, your next stop is one of the most beloved landmarks in Puerto Rico.

San Juan Cathedral - Old San Juan, Puerto Rico

Tour Fort of El Morro for Romantic Views, Hideaways & Play

Explore El Morro - Romantic Things to do in San Juan, Puerto Rico

Tour Castilo San Felipe del Morro (El Morro)– This must-see attraction is much more than a historic place.  El Morro is a very interesting place to explore with your loved one and the views are magnificent.  Even on the hottest day, you’ll be cooled and kissed by the trade winds.  It’s become a tradition for couples in love to walk into a Garita to hideaway and kiss on the place that soldiers once stood in order to protect the bay.

Play Together – The grounds of El Morro are not only fun for children, it’s a place where young and old are free to run, play and be kids again.  Vendors around the grounds sell kites for a few dollars.  Grab a kite and surprise your loved one by being playful…run together…laugh.  At the end of El Morro’s walkway buy a piragua or some delicious coconut ice cream for a quick and delicious refreshment.

Re-Energize with a Relaxing Lunch

Across the street from El Morro, you can walk into Cuartel de Ballaja, which houses the Museum of the Americas and Café Don Ruiz, a relaxing coffee shop serving great coffee, sandwiches, muffins, cakes, and crepes.  Skip the air-conditioned seating and sit outside on the courtyard to enjoy the sights of the stunning architecture.

If you need a heavier meal, keep walking towards Calle San Sebastian, where around the Plaza San José on the corner you’ll find many great restaurants serving food from your All-American Burger to our delicious traditional Puerto Rican foods.

Prefer a guided tour or not do much walking?

For couples that prefer to have a guided tour, there are various options tours available for small groups, what about a fun segway tour or seeing Old San Juan and Condado on a sidecar?  See top-rated tours below.

Romantic & Relaxed Afternoon in Old San Juan

San Juan, Puerto Rico

Go for a Romantic Beach Walk & Sea Glass Treasure Hunt

Grab a few bottles of water from a street vendor, then hop on the free trolley at nearby stop #25 along Calle Norzagaray.  Relax and enjoy a 15-30 minute ride through the city.  Your next stop is Playa Peña, the only beach in Old San Juan typically free of crowds (trolley stop #18a at Plaza San Juan Bautista – across from the Capitol Building).  

San Juan Bautista - Old San Juan, Puerto Rico

Walk down the steps through Plaza San Juan Bautista to Peña Beach – a rugged beach along the Atlantic, next to the city walls with waves crashing into rocks creating a romantic melody as you walk holding hands.  Search for sea glass, a souvenir created by nature, sure to remind you of the trip long after your return home.  This beach is rarely crowded, so you may get that perfect shot of 2 pairs of footsteps on the sand.

Playa Pena - Old San Juan, Puerto Rico

Playa Pena - Old San Juan, Puerto Rico

Siesta Time

Head back to your room, you spent time looking for the perfect romantic hotel, so enjoy it.  Take a few hours to relax, embrace each other, and get ready to enjoy a relaxing afternoon and an exciting night in Old San Juan.

Hotel El Convento - Old San Juan, Puerto Rico

A Romantic Evening in Old San Juan

San Juan, Puerto Rico

Romantic Dinner Prelude Ideas

If you wish to spark even more romance before dinner, there are some wonderful activities you can fit in before dinner and night out in Old San Juan.

Sunset Sail along the San Juan Bay

Cruise along the San Juan Bay - Best things to do in San Juan, Puerto Rico

Surprise your loved one with sailing around San Juan Bay at sunset, you’ll get to admire the walled city the way sailors saw it five centuries ago when they arrived at the city illuminated by the golden sun tones.  The views of El Morro Fort and Governor’s Mansion are amazing adding the most beautiful photos to your romantic vacation album.  Sailing tours are among the best-rated tours in San Juan (see below).

Top Rated Sunset Sailing & Boat Tours - San Juan Bay

Watch the Sunset

San Juan Puerto Rico Sunset

For a free activity, the simplicity of watching the sunset with a warm embrace will be the perfect prelude to a romantic dinner in the old city.  Great spots to watch the sunset are the small square overlooking the San Juan Bay at the end of Calle San Jose & Calle Tetuan, Paseo de la Princesa, and the grounds of El Morro by the water.

Have a Professional Photographer Capture Memories

As we travel extensively around the city, we often see couples forget to embrace each other and enjoy their surroundings fully because they spend a lot of time taking photos as they walk around.  We have forgotten the art of and value of photographers, dedicated to capturing special gazes and moments we simply can’t ourselves.  Old San Juan is a beautiful colorful city with many scenic spots, if your budget allows, let a friendly professional capture memories of your special day.

Helicopter Tours

Go on a helicopter ride to see the city from the air with the added romantic glow of the sun setting, rates start around $150.

Have a Romantic Dinner or Food Tour in Old San Juan

San Juan, Puerto Rico

The dining selection in Old San Juan is excellent.  You can opt to split up your dinner courses between restaurants or have a longer and more relaxed dinner.  The most popular restaurants are on the streets of Fortaleza and Recinto Sur.  A great way to find a restaurant is by walking the streets and checking out the menus and atmosphere before you get seated.

For a very special dinner, treat yourselves to the amazing Marmalade (317 Calle Fortaleza), consistently featured on “best lists”, rightfully earned one of the 10 spots on the coveted list of Traveler’s Choice Best of the Best 2020 – Best Fine Dining Restaurants in the Caribbean, serving a “creative blend of eclectic and nutritionally inspired ingredients”.  Be sure to make a reservation as soon as you have your travel plans finalized. Tel: +1 787-724-3969

For a more relaxed vibe, you’ll find restaurants serving food under the stars with tables right on the cobblestone narrow streets lit by the golden glow of lanterns.  Hotel El Convento, one of the most romantic buildings in Old San Juan offers 3 restaurants.

If you make wish to make the most of your time in San Juan and wish to have a more cultural experience, we recommend you book a dining evening tour.

Top Rated Food Tours in Old San Juan

Do Something New & Exciting Together

San Juan, Puerto Rico

Romantic Things to Do in San Juan, Puerto Rico

Take Salsa Lessons

Music is an integral part of Puerto Rican culture, and Puerto Ricans do Salsa the best… ok Cubans are very good too… The best cultural events take place in Old San Juan and you can always count on the best salsa bands to attend.  Strangers become friends at the squares, as they move to the sultry rhythms of Salsa and sing together to the most beloved songs.  As the sounds reach corners and alleys of the colorful streets, you see hips moving as they walk the streets.

Various restaurants offer live entertainment and free salsa lessons.  Learning a few salsa steps is something you can take home with you and do again and again triggering memories of your romantic escape in Old San Juan… Learning to dance salsa will help you understand how music contributes to the reasons Puerto Ricans are often called the happiest people in the world.

Top Rated Dancing Classes in San Juan

Learn to Enjoy the Pleasures & Fun of the Caribbean Together

You’re in Puerto Rico, completely surrounded by the allure of the Caribbean, you both love the beach, lounging, and relaxing.  For a truly special and memorable experience on the water, nurture a more adventurous spirit together by learning to enjoy some of the favorite pass times in the Caribbean such as scuba diving, snorkeling, and surfing.  These are unforgettable experiences that will keep on building memories in every future vacation you share in the Caribbean.  See top-rated lessons in San Juan below.

Top-Rated Water Activity Lessons in San Juan, Puerto Rico

We hope you enjoy your stay in San Juan and we wish you many years of love and happiness.  Share your romantic experience and inspire other couples to fall in love all over again in San Juan.

Map of Places to Visit for a Romantic Day in Old San Juan

San Juan, Puerto Rico
Things to Do in Puerto Rico ⎜ San Juan Puerto Rico ⎜ Romantic Things to Do in Old San Juan