Suggested Itinerary for a Day in Old San Juan, the Most Romantic City in the Caribbean
There are plenty of romantic activities sure to spark romance, many of them are free and very budget-friendly. Old San Juan is truly 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 many wonderful activities and unique attractions. Some may seem simple to you, but once you get here, you’ll realize that something as ordinary as walking becomes an extraordinary romantic experience.
No need to travel to Europe to experience the romance and charm of its architecture, because it’s here, right in San Juan, with the added colorful touches and warmth of a tropical paradise like no other place in the Caribbean. As you tour the city, you’ll be walking past hundreds of couples, of all ages, holding hands and falling in love all over again.
A Romantic Morning Walk in Old San Juan
Start the Day with a Good Breakfast – 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 here, after all, you’ll be walking around, so don’t feel so guilty with a little indulgence, every calorie is worth enjoying.
For a hearty low-cost breakfast, head to Café Manolin on Calle San Justo, a diner-style restaurant loved by locals for its hearty traditional food at great prices.
Walk along Paseo de la Princesa
Enter the Gate & Renew Your Vows
Tour the Majestic Fort of El Morro & Play
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.
Time for 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.
Romantic & Relaxed Afternoon in Old San Juan
A Romantic Walk on a Quiet Beach
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. Choose from an open-air tram or an air-conditioned bus.
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).
Go for a walk on the beach and a sea glass treasure hunt – Hop off the trolley in front of the Capitol and 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.
Please note: During high tide it may not be possible for you to walk on the beach. Bring beach walking shoes, as you may have to walk over slippery rocks. There are no lifeguards or facilities at the beach, so use at your own risk.
A Romantic Evening in Old San Juan, Puerto Rico
Go on a sunset sailboat tour or a more exhilirating boat ride for great views of the walled city from another point of view.
Helicopter Tours $$$ – Go on a helicopter ride to see the city from the air with the added romantic glow of the sun setting, the adventure will cost an average of $300 p/p, other packages are also available. Be sure to book it in advance.
Watch the Sunset
Have a Romantic Dinner 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 in Fortaleza and Recinto Sur.
Among the popular restaurants with a romantic ambiance are Marmalade (317 Calle Fortaleza) serving a “creative blend of electic and nutritionally inspired ingredients”; 311 Trois Cent Onze (311 Calle Fortaleza) restaurant with elegant romantic decor specializing in French cuisine; La Mallorquina (207 Calle San Justo), a beautifully restored historic restaurant elegantly serving a authentic Spanish & Puerto Rican cuisine. 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. A great way to find a restaurant is by walking the streets and checking out the menus and atmosphere before you get seated.
If you make wish to make the most of your time in San Juan and wish to have a more cultural romantic experience, we recommend you book an dining evening tour.
Dance Salsa – After dinner, head to Nuyorican Cafe at 312 Calle San Francisco, a small club big on celebrating authentic salsa with gusto. If you’re here on a Friday night, you can jam in just about every other corner and plaza to the sounds of jazz during Adoquin Jamming Nights starting at 7 pm. Many 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 most romantic escape in Old San Juan…
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 couples to fall in love again in San Juan.