Beach and the City Break: The Best of Puerto Rico in 4 Days

If you knew you could take in all that a private island and a historical city have to offer in only 4 days, would you pack your bags? Puerto Rico may be a small country, but it is diverse and exciting. There really is something for everyone in this tropical paradise. Check out all that is possible in 4 days in beautiful Puerto Rico.

Spend your first two glorious days at the remote El Conquistador.

Seekers of relaxation and explorers will love it here. This resort encompasses 500 acres that overlook the Caribbean Sea and the Atlantic Ocean from where it rests on top of a 300 foot bluff on the Eastern Tip of Puerto Rico. The resort is made up of five villages with different sizes and styles of accommodations. If you are traveling with family, the family resort at El Conquistador is just right. There is no shortage of choices for dining with 23 different restaurants, bars and lounges. Spend some time taking in all the gorgeous sites from the main resort grounds.

For your first night in Puerto Rico, enjoy dinner at the romantic Chops Steakhouse. This is the signature restaurant at El Conquistador that serves American favorites with a twist. In the morning, take a quick ferry ride to Palomino Island, the private island of El Conquistador. Palomino Island is 100 acres of pure bliss. Of course you will want to take in all the views of the crystal blue Caribbean waters and white sands. The natural landscape is straight off of a postcard.

However, if a quiet stroll isn’t your speed, there is so much to do on the island. Participate in water sports, diving/snorkeling, and games like volleyball and ping pong. For the golfers, the main resort has an 18 hole golf course designed by Arthur Hills. There is also a mini golf course!

If all that action isn’t your speed, spa services are also offered here. So relax with a massage or any of the spa beach servicesWe can’t think of anything more luxurious while on vacation than a spa on a private island. Iguana’s Cafe is a perfect stop for lunch on the island. Take the ferry back to the main resort grounds and get ready for the water park.

The Coqui Water Park must be on your to-do list while visiting El Conquistador. This state of the art water park was inspired by the nearby El Yunque rainforest. Overlooking the Caribbean Sea and the Atlantic Ocean, this is not your average aquatic playground. If you are looking for an adrenaline rush, take on the El Gigante Dormído slide with its 40 foot drop. If a slower pace is more your style, grab a raft and float on the lazy river or swim in the 9,000 square foot infinity pool.

Dry off and get dressed for dinner. We recommend the Stingray Cafe for Caribbean inspired cuisine. After dinner, wind down with s’mores by the campfire or play games in the Ultra Lounge.

Before checking out of El Conquistador, take in a little more of the magic here with breakfast at Casitas Café overlooking the Las Casitas Village pool and bright blue ocean. Breakfast set in such a picture perfect surrounding is divine. You’ve got just enough time to take in a quick spa treatment at the Waldorf Astoria Spa. Like the rest of El Conquistador, the views here are unreal. This spa overlooks the sea. After a little pampering, if you wish, you can fit in a workout with a Family Aqua Parkour Class. This class brings the excitement of a parkour workout to the water. It is unlike anything you have ever experienced before.


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Since you only have 4 days in perfect Puerto Rico, it is time to check into The Condado Plaza Hilton for the second half of your trip.

 Here, you will take in all that the old city of San Juan has to offer. This landmark hotel is in the heart of the city. The Condado was designed in 1963 but has since been revamped by designer Leo Daly. With modern rooms and suites, you can choose the view you desire: ocean, lagoon or city. There are 571 deluxe rooms and suites, some with private balconies. In fact, this is the only hotel that overlooks the Condado Lagoon and the Atlantic Ocean. There are eight restaurants, bars and lounges to choose from. If you are traveling with children, they will love the ScoutAbout Children’s Activity Program. With swimming, tennis, a meeting space and a ballroom, this hotel is the perfect urban retreat in a tropical paradise.

After your first night at the Condado Plaza Hilton, suit up for a guided snorkeling reef tour. The resort has an artificial indigenous reef in cooperation with the Condado Lagoon Reef Restoration Project. You can explore the sights of another world underwater right off the private beach of the resort! Once back on dry land, grab lunch at one of the wonderful restaurants. We recommend the Aqua Bar and Grill. With 4 pools, including the only saltwater pool on the island, you will be missing out if you don’t spend some time swimming or lounging poolside. The activities pool with its slide is so much fun you will feel like a kid again.

Take advantage of the Condado Plaza Hilton’s city location and tour Old San Juan. Founded in 1508 by Juan Ponce de Leon, Old San Juan is the oldest settlement in Puerto Rico. Walk along the famous blue cobblestone streets, surrounded by colorful architecture. For amazing restaurants, check out Fortaleza Street. The Cathedral of San Juan Batista is breathtaking in its architectural splendor. Explore the old forts that tower over the ocean. The fortress of El Morro is massive. You can check out cannons and ramparts that defended the City throughout history. There really is nowhere like this historic city. Do some shopping and grab a drink. Take in all the culture that surrounds you in Old San Juan.


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And just like that, your four days in beautiful Puerto Rico will have flown by. The ocean, sea, rainforest and city views will live on in your mind and in your dreams forever. You will crave the excitement and relaxation that you found in this place, and chances are, you will find a way to return to El Conquistador and the Condado Hilton Plaza again and again.

Want more beautiful sites from Puerto Rico? Check out 18 Beautiful Photos of Puerto Rico that Everyone Should See.

Photo Credits: EveryAvenueGirl




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A Russian by birth, Floridian at heart, Elena's favorite pastimes are traveling, photography, volleyball, reading business, psychology and parenting books and finding cool products. Elena started Daily Mom with a vision to provide quality content and help to busy modern women. Follow her life and adventures with her 7 year old daughter at Every Avenue Life and Our Little Voyages. or on Instagram at: @everyavenuelife @everyavenuegirl @befitandtravel @ourlittlevoyages

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