Looking for a 4-day weekend getaway to a tropical, beautiful island? Rich in history, miles of waterfront, and a quick flight from the States, San Juan, Puerto Rico is one of the best places for a vacation or weekend getaway.
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We visited Puerto Rico in early January as the American Farm Bureau Federation (AFBF) annual convention was being hosted there. I had the opportunity to speak on a panel for work, and Jack and I decided to turn it into a 4-day weekend getaway. Whether you're looking to explore the oceanfront, indulge in the rich history, hike into the rainforest, or park it on the beach, Puerto Rico is for you!
After sharing our weekend pictures on Instagram, y'all asked me to share my recommendations on the best things to do in San Juan, where to eat, what to do, and the best part —it's all wrapped in this complete travel guide.
Things to know before going
- Ease of Travel: Puerto Rico is a US territory, therefore United States citizens do not need a passport to enter the country. There are several direct flights from the States a day which makes it an easy get away. The country's currency is USD which makes using cash and credit card seamless (we love that)!
- Transportation: We ubered to and from the airport. Lyft is not available in the country yet; but Ubers were incredibly affordable ($10/ride to the airport!). There are also plenty of taxi's around, but we felt safer using Uber.
- Communication: The official language is Spanish. However, everyone we encountered in San Juan also spoke English. As always, it's nice when you can try to use their native language, so learning the basics wouldn't hurt! Cell phone providers work the same in PR. We both have Verizon and had no issues with connectivity.
- Other good things to know: Unlike countries in Europe, it's important to tip at restaurants, hotels, and ride services. The weather is warm and enjoyable. The rainy season is from April - November (December to March have the sunniest days)! The outlets are the same as in the United States.
Where to stay on the island
The three most popular places to stay in San Juan are Old San Juan (where we stayed), Isla Verde, and Condado (beach-front). All of them sparkle in their own way and offer different attractions near them.
Old San Juan reminds me of the coast of Spain, but everything is in USD and a lot of people speak English. Colorful buildings line cobblestone streets, there's a breeze from the water, and packed with charm. We walked by Hotel El Convento and it's a gem!
- Pros of Old San Juan: Best location for restaurants and bars, the whole area is walkable, great night-life and charm
- Cons of Old San Juan: No public beach access, no large resorts (other than the Sheraton on the water), and the cruise port brings in a lot of people every day
From what I've read of Condado, it's centrally located and is less than a 10-minute ride to Old San Juan. It is miles of beachfront, resorts, and restaurants and bars. It is a popular tourist area so some things are higher priced here. I've heard the Condado Vanderbilt Hotel is stunning!
As for Isla Verde, it offers gorgeous beachfronts. It's a 15-20 minute Uber ride to Old San Juan and close to the airport.
Things to do in Old San Juan, Puerto Rico
There is something for everyone of all ages in San Juan- that's what makes it such an ideal destination! There are tours in-and-around the city, explorations in the rainforest just a quick ride away, and everything in between. San Juan is rich in history, dating back to the 1500s.
- Explore the city: The best way to explore this city is on foot. The roads are cobblestone and tight. It's much easier to walk. While you could book a walking tour, I prefer to explore on my own. Be sure to walk by Fortaleza Street, it's the most Instagrammable/TikTok street in Old San Juan. The art installation changes often so you'll see different installs depending on when you go!
- Rich in History: Old San Juan is home to two forts, the large one being The Castillo San Felipe del Morro. It was built over the course of 300 years and used a protection against island attackers. Puerto Rico literally means 'Rich Port'. It's less than a half mile walk from the furthest point of the island. Be sure to bring payment; it's $10/admission for an adult. If you keep your receipt, you can take it to the other fort and explore it at no additional charge.
- Spend a day on the beach: While you do have to take a short uber, head to the beach at Condado, its the best place to spend an afternoon. Local pina coladas and salty waves, the vibes are unmatched.
- Looking for more: Try taking a Puerto Rican Cooking Class (I like to book through Airbnb Experience), even buy a ticket to explore the Bacardi Tour, or hike in El Yunque National Forest (You'll need transportation lined up for this). Other popular day trips: head to an island like Vieques or check out the popular waterfall, San Sebastian.
Getting around the Island
Regardless of where you are staying, walking or Ubering will be the easiest way to get around the Island. Ubers are relatively inexpensive and there are SO many.
In our opinion, renting a car would be more of a hassle than a convenience. Hotels will charge a fee to park it. Unless you're renting a car for the day to get to an excursion, lining up a ride service is the best bet. Check with your hotel and see if they offer a shuttle service for different areas/excursions of the island!
Favorite places to eat
If you're touring a new city for its food, then you and I would be great friends. It makes up a large part of the trip if you ask me. One thing Jack and I love to do is ask our waitstaff for recommendations. It's easy to see what Trip Advisor, Instagram/TikTok is recommending, but some gems come from the locals themselves!
Above all, make reservations on open table if you can. The places we went did fill up or were booked when we arrived. It's easy to squeeze two people in, but try to lock in reservations. While we didn't have a bad meal while we were in Puerto Rico, here are a few of our must-eat recommendations:
Breakfast & Lunch
- La Carreta: A quaint and delicious brunch restaurant located just a few blocks north of the cruise port. The food was phenomenal. We ordered the Umami Toast, Turkey Avocado Sandwich, and Pina Coladas. 12/10 recommend. Try to arrive before 10:30am on the weekend, otherwise it gets crowded and it's a slow wait.
- Bien Papaya: If you're like me and love a quick smoothie with protein, check out Bien Papaya for a refueling smoothie. Simple ingredients, wonderful staff, and healthy breakfast! Perfect for on the go, too!
- Spiga: A recommendation from TikTok for gourmet coffee, delicious baked goods and breakfast sandwiches. It's a quaint shop and everything is homemade. Easy on the go food!
- Lote 23: A handful of restaurants that have opened food trucks in a cozy outdoor space. Grab a bite, brew or just hang out in this cute area.
- Pio Pio Champagne Bar: And before you tell me champagne isn't dinner, this is actually a dinner restaurant and recommended by our waiter at brunch one day. Great food and great vibes!
- El Asador: We ventured here on our first night in and had a lovely, relaxing 2 hour dinner. Equal mix between locals and visitors, the food was delicious. Order the Penne alla Shrimp and you'll be amazed.
- Azalea: Upscale sushi restaurant. We didn't have reservations, but sat at the bar. The drinks and vibe are incredible! Totally recommend this as one of your dinners in PR.
- El Viejo Almacen: A beautiful, Argentinian restaurant we walked by. Stunning interior and aesthetic, would be a delicious for dinner!
- Epicuro Culinary Center: Another recommendation from our waiter. You can book this experience dinner on Open Table, but it books a few weeks out. A husband and wife, farm-to-table cooking experience immersed around one kitchen table.
- La Factoria: If you're looking for an award-winning cocktail, this is the place to be. Music flows from their open windows, the saltwater breeze catches you at the bar, and the ambiance of the overall bar is unmatched. It says 'welcome to Old San Juan, stay awhile' when you enter the abode. Drink recommendation: Old Cuban.
- The Mezzanine: Another fabulous bar recommendation (thank you TikTok). Right in the heart of the island, it was a perfect place to grab a drink before dinner.
- Arya: This roof-top bar is located near Condado Beach and an easy uber away. Looking for views while you sip a fabulous cocktail, this is the place to be!
- Anita Gelato Puerto Rico: Essentially the only gelato place in Old San Juan and you can tell based off of the consistent line of customers. It looked fabulous; the line detoured us from stopping in.
- Senor Paleta: Gourmet popsicles with delicious flavors and toppings. We settled for the pops when we saw the gelato line. Tastier than I thought they would be and a good night cap!
I’d love to hear your thoughts in the comments below. It’s my passion to share about traveling that can aid your experience or be shared with others. Let me know if you have any questions; happy to answer them below! Safe travels XO Courtney Paige