San Juan, Puerto Rico is full of life, color, and hidden treasures. As passionate travel curators, our one true love is being able to explore a destination in an honest and curious way and uncover its beautiful secrets to share with our tribe. There is no doubt that Puerto Rico is alive and well, and more vibrant than ever! Many of our most fabulous vacations with friends, family, and loved ones have been here on this incredible island. We have spent many magical nights in Dorado Beach and seen the beauty of the Bioluminescent Bay in Vieques, but we are always drawn to the energy and culture of San Juan.

Settled in 1521, San Juan is the second oldest city in the Western hemisphere with a rich history. The island was originally a strategic military location for the Spanish before ultimately becoming a territory of the United States in 1898.  Today, the country’s capital is a major metropolis that is home to colorful streets, Spanish forts, sandy beaches, world-class casinos, and fabulous shopping. There is no shortage of things to do, see and especially eat in San Juan. When we were presented with the amazing opportunity to spend a few days there, we knew it was time to pack our bags with our most flattering island looks and head back to one of our favorite places to give our tribe the scoop.

All good trips begin with where you stay. We took our time researching the many different options San Juan has to offer, and narrowed it down to our top three for you. For the perfect blend of family and fun, San Juan Marriott Resort and Stellaris Casino is a great choice. There, you can fully embrace the laid back lifestyle at La Concha Resort, and if you feel like venturing out of the city for more of a luxe getaway, we recommend, Dorado Beach, a Ritz-Carlton Reserve. With over 60 resorts in 14 destinations across the Caribbean and Latin America, Marriott International has a property to suit any of your vacation needs. For this specific trip, we were looking for the full family resort experience, so naturally we chose San Juan Marriott Resort and Stellaris Casino for our stay.

Now, of course, we are all Marriott Bonvoy members, which is the only way to go when you travel as much as we do! Through Bonvoy, we are able to enjoy the core offerings of the Marriott International brand which include coveted location, elevated food and beverage offerings, and expected resort amenities like fabulous pools and relaxing spas.


Old San Juan: Vibrant culture meets a rich history. In Old San Juan, cobblestone streets, antique shops, and museums sit over picturesque landscapes while music from plazas dance through pastel-colored buildings. Reminiscent of Seville, Cuba, and Naples, Old San Juan is the perfect destination blending together a relaxing beach, breezy weather, and architectural marvels with plenty of history. One of the main attractions to visit while in Old San Juan is El Morro Fort. The massive military structure built in 1539 first stood as a representative of Puerto Rico’s status as the guardian of the New World. Before you take off for another adventure, make sure you have some comfortable shoes to explore each corner of the fortress where you can climb to the top and take in spectacular ocean views. San Juan’s oldest fort, Castillo de San Cristobal, is the largest fortress built by the Spanish in the New World. Take a tour of the multi-layered castle, witness locals flying kites on the fort’s grounds, and hold one of the bayonets in the soldier’s barracks for a true throwback moment. Before leaving Old San Juan, stop by  La Casa Blanca, one of the oldest buildings in Puerto Rico and the home of the famed conquistador and explorer Juan Ponce de LeónThe Amazing Grace Sail Tour: Our outstanding itinerary planned by the team at San Juan Marriott Resort and Stellaris Casino took us to the historic hub of Old San Juan in the early evening where we found ourselves boarding The Amazing Grace for a sunset sail. Yes, it was as fabulous as it sounds. Fun fact: the stunning 81-foot sailboat is a replica of the traditional American sailing crafts used to fight the British in the War of Independence and again in 1812. How cool is that? Once on board,  we were greeted with plenty of smiles, tropical music, and one of our favorite things (and necessities) — a cocktail! Our two-hour sail also included a complimentary open bar and an array of Puerto Rican-inspired bites. It was the perfect way to take in all the history and breathtaking views of Old San Juan. Each crew member was well-versed in fascinating tales of the city which made for a compelling history lesson as we lounged back, cocktail in hand, with perfect Caribbean sunset.



Acapulco Taqueria Mexicana: This has to be one of our favorites! – if margaritas and tacos are your thing, Acapulco Taqueria Mexicana is THE place. Located in Calle Loiza, this hole-in-the-wall taco joint is the most authentic Mexican food available outside of Mexico. You’ll have to do some searching, but once you find it, you need to order one of the special tacos of the day, the Al Pastor, and Carne Asada. The tacos are street style (aka small) so you won’t feel the guilt of indulging in three. Wash them down with a refreshing margarita made with their special house mix of freshly squeezed lemons and limes that will have you saying one tequila, two tequila, three tequila, full. Address: 2021 Calle Loiza, San Juan, PR — 00911 Telephone:  +1 (787) 727-5568Image courtesy of Instagram: @cocinaafondoConcina al Fondo: Hidden in the back room of a community art space is one of San Juan’s best kept secrets, Cocina al Fondo. Blending together the perfect mix of modern and traditional Puerto Rican dishes, Cocina al Fondo delivers quality eats from Chef Natalia Vellejo who incorporates flavors from her travels around the world while embracing her Puerto Rican roots. With dishes like rabbit and rice, corn apreas, and roasted squash pastelillos and tomato aioli, you can’t go wrong with anything on the rotating menu.  Address: 1057 Ave. Ponce de Leon, Santurce, Puerto Rico. Telephone: +1 (787) 469-5527La Lanterna: Nestled in Old San Juan’s charming interior courtyards, La Lanterna by Franco Seccarelli pays homage to Chef Franco Seccarelli’s Italian roots bringing a piece of Italy to the heart of the Caribbean. With a stunning colonial patio, lush vegetation, and a flowing fountain, the intimate restaurant has an elegant feel with the perfect touch of home. While you’re there, try the homemade ravioli of the day with a glass of wine imported from the finest Italian vineyards. Address: 202 Calle del Cristo, San Juan, 00901, Puerto Rico. Telephone: +1(787) 340-8188

La Factoria: Grabbing a spot on The World’s 50 Best Bars List, La Factoria is where you go for unbeatable service, lots of dancing, and most notably, the perfect craft cocktail. Located in Old San Juan, this bar gives all the speakeasy vibes with dim lighting and a sexy atmosphere. Try a spin on a classic with a hand-crafted Spiced Old Fashion or Lavender Mule made fresh with local ingredients.  Address: 148 Calle San Sebastián, San Juan, 00901, Puerto Rico Telephone: +1(787) 412-4251

Gallo Negro: Step inside what looks like an artist’s personal studio for some incredible dishes bursting with flavor.  This gourmet whiskey bar serves up mean whiskey cocktails that pair perfectly with their eclectic menu like the must-have Turkish Eggs and Brutus brussel sprouts, made perfectly crisp and drizzled with balsamic vinaigrette.  Address: 1107 Avenida Juan Ponce de León, San Juan, 00907, Puerto Rico Telephone: +1(787) 554-5445

Santaella: With experience as an international chef, restaurant owner, and cookbook author, Chef Jose Santaella’s Santaella gives travelers a taste of Puerto Rico’s native comida criolla. Step inside the elegant eatery for an upscale dining experience where the star is the local and traditional fare. Savor the flavors of Puerto Rico as you enjoy croquetas of the day or caramelized braised pork shank. Don’t forget to leave room for dessert! There’s a good chance it’ll come with Santaella’s homemade ice cream.  Address: 219 Calle Canals, San Juan, 00907, Puerto Rico Telephone: +1(787) 722-7600


Luca: Founded by Puerto Rican designer Laura Lugo, Luca is home to curated, one-of-a-kind pieces that you’re going to want in your closet. The contemporary shop is filled with emerging and mid-career designers from the native island as well as global destinations like Japan, Spain, Israel, and Italy – all handpicked by Lugo. Browse through racks of timeless and elegant clothing and pair it with a statement piece from Luca’s gorgeous selection of handmade jewelry. Shop now- Luca 

Pure Soul: Located in the heart of Old San Juan, Pure Soul is perfect for all of your vacation needs. Amazing linen staples line the racks of this cozy corner shop that brings sophistication to the casual island vibes of Puerto Rico. We scored some stylish off-the-shoulder summer dresses in vibrant blue hues and straw hats which are always a classic summer staple. Native New Yorker? Pure Soul has a summer out-post on Shelter Island bringing the flair of San Juan to summer out East! Shop now- Pure Soul

Olivia Boutique: If you’re on the hunt for an outfit that is sure to turn heads, look no further than Olivia Boutique. The shop caters to the fashion-conscious female shopper on the hunt for unique and undiscovered designer pieces. With buyers that actively curate the very best in international design from dozens of global markets, you may need an extra suitcase to bring home all the new additions to your closet. Shop now- Olivia Boutique

Olé: Did you really go to Puerto Rico if you didn’t visit Olé? Featured in the New York Times and countless travel blogs, this old-fashioned emporium sells authentic Panama hats, that have been rocked by celebs and royalty like Mick Jagger and the Prince of Morocco. With a lifetime guarantee and custom tailoring, splurge on a classic or make it your own and shop variety of ribbons and hand-painted options. Shop now- Olé 

Playero: For all your island needs, head over to the family-owned and operated Playero. With roots that run deep in surf culture, this shop specializes in high-quality beachwear and accessories to wear on and off the sand. Take home one of their classic Playero designs or shop some of the world’s top surfboard designers and innovators like Eric Arakawa, Maurice Cole, and Malcom Cambell. Shop now-Playero


Step into comfort and elegance as you enter the San Juan Marriott and Stellaris Casino. This amazing beach-front property, located in the coveted neighborhood of Condado Beach, has 513 spacious guest rooms and 12 suites divided between the main tower and the cabanas. The absolute perfect destination for a family getaway, this property has something for all ages to enjoy.

The moment we stepped on property we were met with the warmest hospitality and walking into our cabanas, we knew we had arrived in paradise. Each room is carefully designed with comfort and style in mind and is filled with splashes of Caribbean hues and luxurious amenities. The cabana rooms offered on property include an expansive balcony to take in ocean views and smiling families lounging by the pool.

The San Juan Marriott and Stellaris Casino is our favorite choice for a family or group getaway in San Juan. If you are in search of a more vibrant/nightlife vibe, we suggest La Concha Resort, also located in Condado Beach.


Outdoor Pool

An epic combination of relaxation and fun, the outdoor pool at the San Juan Marriott is not short of a good time. With a winding water slide and swim-up bar, you never need to leave the pool deck to keep the party going.

Condado Beach

Grab a cocktail from the swim-up bar and head down the steps of the pool deck to the white sands of Condado Beach for a change of scenery. Take a dip in the warm island waters or work on your tan. The amazing beach attendant will happily set you up with lounge chairs, a table, and an umbrella.

Ocean Club Spa

A spa treatment is our favorite vacation indulgence. The Ocean Club Spa is perfect for a morning detox after a long night of enjoying San Juan. We were greeted by the talented Eva who educated us on the spa offerings and the products that were used to make our experiences so memorable. We chose the body massage and express facial. The body massage brought us back to life and the express facial was exactly what the doctor ordered. The express facial is perfect for those who want to be pampered, but not spend their entire day inside. If you are not in the mood for a facial, the express exfoliation is our second choice and will have your skin feeling like butter by the end.Yoga

Bring balance to your trip with on-property yoga. The resort offers guided meditation through a calming flow on the sun deck by one of the many expert instructors onsite during your (nama)stay. What better way to get in full vacation mode than by finding your Om to the sounds of the ocean and feel of the tropical breeze?Stellaris Casino

Feeling lucky? Win big at the San Juan Marriott Resort and Stellaris Casino’s in-house James Bond moment. This stunning 13,000-square-foot, 24-hour casino features all the classics like blackjack, craps, mini-baccarat, roulette and state-of-the-art slot machines. If you’re feeling extra lucky, kick your experience up a notch in the “Slot VIP Areas.”



San Juan Marriott and Stellaris Casino’s signature restaurant offers delectable delights using locally sourced ingredients to create authentic Puerto Rican dishes for breakfast, lunch, and dinner. Snag an outdoor table and enjoy Condado Beach views while indulging in their amazing Seafood Ceviche and Grilled Octopus.

Red Coral Lounge

While there are many places to explore in San Juan, you do not need to leave the hotel for dinner and dancing! The Red Coral Lounge, located in the lobby of the San Juan Marriott is one of the most popular restaurants on the island. Choose from an amazing menu of hand-rolled sushi options and then dance the night away to the tunes of a live band every Thursday, Friday and Saturday night.

La Panaderia

This is the perfect place for grab-and-go. From coffee to pastries, everything we had from La Panaderia was outstanding. We confess, we went there multiple times a day during our stay. Located in the hotel’s lobby, La Panaderia is open from 7:30 am to 9:00 pm, so it’s always available for the perfect pick-me-up. TC tip – chat with the barista before ordering, they can recommend something you may have never had, and it will not disappoint!

San Juan is a beautiful city full of vibrant history and culture. If you are itching for a getaway, put San Juan at the top of your list!