A Romantic Day in Old San Juan, Puerto Rico

Top Rated Walking Tours in Old San Juan

+ Tours in Old San Juan

Enter the Gate & Renew Your Love

At the end of Paseo de La Princesa promenade, we invite you to 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.

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.

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

This must-see attraction is much more than a historic place.  El Morro is a fascinating place to explore with your loved one; 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 hide away and kiss where soldiers once stood in order to protect the bay.

Play Together on the Grounds of El Morro

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… running together…laugh.  At the end of El Morro’s walkway buy a piragua or some delicious coconut ice cream for a quick and delightful 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 in the courtyard to enjoy the sights of the stunning architecture.

Go for a Romantic Beach Walk & Sea Glass Treasure Hunt

Your next stop is Playa Peña, the closest beach to Old San Juan typically free of crowds.

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.

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 an exciting afternoon and night in Old San Juan.

See Top Rated Hotels and Small Inns in Old San Juan

Begin a Romantic Evening at Sunset

Watch the 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.

Sunset Sail along the Historic San Juan Bay – A World Class Experience

Surprise your loved one by 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 the UNESCO site of La Fortaleza are amazing additions to your vacation photo memories.  Sailing tours are among the best-rated tours in San Juan (see below).

Have a Romantic Dinner or Food Tour in Old San Juan

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 & 2021 – 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.