Vamos Puerto Rico: A 4-Day Itinerary

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Advisor - Celine Serrao
Curated By

Celine Serrao

  • Puerto Rico

  • San Juan

  • Beaches

  • Food & Wine

  • Nature Escapes

  • Island

  • Relaxation

  • Long Weekend

Puerto Rico is a vibrant island paradise.
Curator’s statement

Puerto Rico is a perfect island getaway for families, couples and friends. Whether you are adding some days to a vacation before or after a cruise or looking for a long weekend escape, four days here is the perfect amount of time to relax and explore all the island has to offer.

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Where to stay

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Day 1: Let’s go to the beach, beach!

Flamenco Beach is a postcard-perfect setting.

What better way to start your Caribbean vacation than at the beach? The island of Puerto Rico is wrapped by beautiful shores and its variety of beaches can suit any type of vacationer.

Flamenco Beach is like a postcard. It is perfect for sandy days with the family. Here you can enjoy crystal blue waters, build castles and create cherished memories with your loved ones.

Traveling for a bachelor or bachelorette party or are you with a group that just likes to have a good time? Head to Crash Boat Beach. The scene here is lively and it offers a variety of water activities. Here you will have a great day dancing to the bustling music and the sound of the waves.

Playa El Combate is a local favorite. It has less facilities, but the clear and calm waters are unmatched. You can try some authentic Puerto Rican cuisine nearby.
After your day at the beach, retreat to your resort to freshen up before heading to Old San Juan for some shopping, strolling, supper and salsa. Clothing, art, jewelry and cigars are among the top retail therapy finds. Cristo Street and Fortaleza Street have the most shops. Fortaleza also offers a great photo op with a colorful umbrella canopy.

Old San Juan is a beautiful historic area to just roam aimlessly. (It is mostly cobblestone, so, ladies, plan your shoes accordingly). Once you are finished marveling at the quaint little town, sit down for a relaxing dinner. here are many places to choose from, some I would suggest are Marmalade, Princesa - Cocina Cultura and Barrachina (birthplace of the Piña Colada). Finish your night dancing and drinking at La Factoría.

Day 2: Saddle, spa or swing? Your pick.

Royal Isabela is the premiere golf resort in Puerto Rico.

Start your day with a hearty breakfast before heading out for a horseback ride through the rainforest, a day at the spa or tee time at one of Puerto Rico’s breathtaking golf courses.

Both skilled and amateur equestrians can enjoy trotting through the lush green rainforest with knowledgeable guides from La Vista Rides. They will lead you through magnificent trails and take you for a dip in a stream before picking fruits right off the trees for you to enjoy.

If you prefer a less active day and enjoy more relaxation, treat yourself to a day at a spa. Aside from some of the beautiful hotel spas, Cloud Spa and Nouvelle D’Spa have some amazing treatments and experiences to help you unwind.

Would you rather skip the horses and spa and go for a loop? Rio Mar Country Club, TPC Dorado Beach and The Links at Royal Isabela are stunning golf courses. They are well maintained, competitive and offer some unbelievable views.

Finish the day with dinner at Piñones. This neighborhood (or “barrio”) is known for its strip of street food kiosks and is one the best locations to get some authentic Puerto Rican cuisine. I would suggest having dinner on the early side and hopping from stall to stall trying different foods. Then pick one bar to settle and enjoy drinks for the night. If sit-down meals are more your vacation style, I suggest El Nuevo Acuario. El Nuevo Acuario is more casual beach bar, but the food, service and drinks are great.

Day 3: Pool then paddle

La Parguera is a bioluminescent bay.

One day at the beach on a Caribbean vacation is certainly not enough, so on Day 3 I suggest trying another beach or chilling at the resort pool.

You will need to conserve some energy before kayaking in the beautifully glowing waters of Puerto Rico’s bioluminescent bays. There are three different bay areas that offer these unique boating experiences, but I suggest La Parguera since it is the only one that allows you to swim in the magical waters. The experience lasts about two hours and tours start around 7-9pm. There are many different tour operators that guide these adventures. Make sure you plan your transportation ahead of time since cars can be difficult to order in the evening.

Moons Bar and Tapas or Brújula are great restaurants for dinner in the area.

Day 4: Fish and farewells

Santaella is a Puerto Rican restaurant with a tropical vibe.

Spend your last day out atop the majestic waters on a luxurious catamaran ride. Make a splash and snorkel with the colorful tropical fish and if you are lucky enough you may spot some sea turtles. Most tours provide snacks and drinks as you sail around with the salty breeze in your hair. Some make stops at Puerto Rico’s more deserted yet stunning islands where you can bask in the sun.

Bid farewell to Puerto Rico by enjoying the arts, fine dining and drinks in Santurce. Santurce is known for its vibrant murals and has a plethora of live music venues, dance halls and spirited restaurants. Vianda, Santaella (try the mofongo!) and Asere are chic restaurants with delicious food and a variety of cocktails and wine. Continue the party at the fun bars around La Placita de Santurce.

Need to Know

Looking for more travel inspiration? Check out my guide, Scottsdale Before the Veil.

Advisor - Celine Serrao

Travel Advisor

Celine Serrao

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This guide is part of our ongoing series on travel to Puerto Rico.