4 Days of Romance and Fun in Puerto Rico

Day 1: Fall in love with the city

Are you ready to shower your sweetheart with love and some pampering? That is what awaits you on your first day in Puerto Rico. Kick off your Caribbean adventure by checking in the Condado Vanderbilt. Give in to the luxury of this stunning, historic property and let your eyes feast on the incredible ocean views from the hotel's veranda. If you're looking for a more central location, Condado Palm Inn San Juan, Tapestry Collection by Hilton is just one block from the beach and a short stroll away from numerous restaurants, shopping outlets, museums, and entertainment venues in the area. Another option away from resorts is O:LV Fifty Five, an adults-only boutique hotel nestled between the Condado Lagoon – steps away from the beach.  

Drop off your bags, get refreshed, and head out to explore the city. If shopping is on your to-do list in Puerto Rico, then Condado is the perfect opportunity for you to cross it off. So stroll down Ashford Avenue – the Puerto Rican "Fifth Avenue" – where you can find anything from Louis Vuitton, Cartier, and Gucci, as well as local designers like Nono Maldonado, Lisa Thon, and Harry Robles.    

Are you feeling hungry? Pass by Cocina Abierta, a perfect spot for a date! With an eclectic menu and open-kitchen concept, this establishment fusion different cultures into one dish. If you're looking for a more local experience, try the food at Cayo Caribe, whose specialty seafood dishes won't disappoint.     

Tips for exploring the Condado Neighborhood

Day 2: Meet love on the eastside

Say bye to city life and head east to a quieter and laid-back time!  

Since you're going at your own pace and are in good company, choose the road less traveled from San Juan to Río Grande. Roll down your car's windows so you can best enjoy the scenic view of the beach and enjoy the ocean breeze as you cruise through Piñones. You're not in a hurry, so stop for some alcapurrias or bacalaítos (or both) and a couple of ice-cold beers at local's favorites Nana's Place, Donde Olga, or El Boricua. For a nice brunch atmosphere, head on over to Coffee at the View just overlooking El Yunque rainforest 

Once in Río Grande, you'll have plenty of options to spend the night. If you want to keep the upscale- luxurious theme for your vacation, you can opt to stay at St. Regis Bahía Beach Resort, the Hyatt Regency Grand Reserve, or at the Wyndham Grand Rio Mar, three oceanfront paradises for couples looking to spoil you during vacation. You can find a more intimate setting at Dos Aguas Bed and Breakfast, a quintessential yet modern choice nestled in the foothills of the rainforest.  

After settling in your hotel, it is time for some beach bumming. Head out to Luquillo's beach La Monserrate, where you can spend a few hours relaxing under the sun and refreshing in the soft blue waves. You can rent long chairs and umbrellas there, kick back and enjoy piña coladas, coco frío (cold coconut water), helados (sorbets), and some fritters from local businesses.  

If you're not feeling full of all the snacking on the beach, set out to the Kioskos de Luquillo, a strip of restaurants, bars, and souvenir shops right outside La Monserrate. From homemade burgers at Burger Shack to Peruvian cuisine at Ceviche Hut to comida criolla at El Terruño or La Parrilla, you can find anything your heart – and stomach – desires.   

Once you've had your late lunch, spend some time wandering around the shops. If you're not too beat, you can arrange for a couple's sunset horseback riding tour at Hacienda Carabalí or a surreal glow-in-the-dark experience at Laguna Grande bioluminescent bay in Fajardo. Plan for dinner at Paros, the onsite restaurant at St. Regis. Other nearby restaurants like Don Pepe, W Sushi Bar, or Dos Panza's Mexican restaurant provide a more relaxed ambiance.  

Find other things to do on the east coast of the Island

Day 3: Sail your troubles away!

Yes, you've spent time at the beach, but is there such a thing as too much Vitamin Sea?  

Your partner – and a towel – are all you need to embark on a romantic catamaran trip to Icacos and its surrounding cays, right off the coast of Fajardo (15 minutes away from your stay in Río Grande). One of the most pristine beaches on the east side sits at a nature reserve, where you can hike around the cay, snorkel, explore the amazing marine life, or relax on the boat and enjoy the view. But let's be honest, once you see the turquoise waters crashing into the white sand shore, you'll splash around in no time. Book a VIP Luxury experience with private certified charters like Caribe Bliss.  

Going to Fajardo and not passing by Las Croabas is almost unforgivable. You can arrange a picnic at the small park or walk around el malecón for a romantic sunset stroll.  

For your last dinner in Puerto Rico, find passion and fire at chef Myrta's kitchen at Pasión por el Fogón, a mesón gastronómico with offerings like shrimp-stuffed lobsters, stuffed mofongo, mamposteao' with skirt steak, and much more. Other great dining options are La Estación, Sal y Pimienta, and El Bohío; all packed with rich creole food.  

After dinner, head back to your hotel and relax. Then, kick it by the pool with a few cocktails or explore a bit more of Luquillo's relaxed energy, where you can catch a live band or go karaoke-ing at Boardrider's Surf Bar, sip a few drinks, or walk under the moonlight at La Pared.  

Discover other beaches nearby