Welcome to Your Ultimate Guidebook for a Memorable Stay!

We extend our warmest welcome to your cozy haven away from home! As you step into our meticulously designed short-term rental nestled in the heart of San Juan, Puerto Rico, you’re not just booking a place to stay; you’re embarking on an unforgettable experience.

Our Guidebook is your key to unlocking the secrets of our vibrant city and discovering the hidden gems that make it unique. Whether you’re a food enthusiast, a history buff, an adventure seeker, or someone who just loves to unwind in a serene environment, we have curated a comprehensive collection of recommendations to cater to every traveler’s taste. 

Concierge Service

For the most stress free experience booking trips, activities, transportation, charter boats, and private chefs, I highly recommend contacting the Lucky Penny’s preferred concierge service run by Sergio Lopez:
https://fixatrippuertorico.com
+1 787-630-3684
info@fixatrippuertorico.com

This service just happens to be local to my neighborhood (and they are very familiar with the Lucky Penny), but is one of the most highly recommended on the island. Oftentimes in Puerto Rico it can be very difficult making arrangements because businesses and services are very slow to respond, if they answer the phone or reply to emails at all.

Sergio can arrange almost any type of activity whether it’s hiking, snorkeling, charter boats, deep sea fishing, food tours, Zipline, ATVs or horseback riding. On top of that, he has relationships with many of the vendors and can get better rates than what you will find online. Trips to El Yunque and the Bio Bay are especially popular and they will make everything easy and fun. Just tell them you’re staying at the Lucky Penny, they are very familiar with the house.

Private Chefs

Many guests have enjoyed having a private chef come to the house and prepare a special meal. If you have trouble getting timely responses, you might just contact Sergio and let him do the negotiation for you.

Chef Philip M Reilly
chefphilipmreilly@gmail.com
787.378.6618
https://www.instagram.com/chef_philipmreilly

Chef Nivia Villaneuva (Also does cooking classes)
939.293.9062
cookingwithnivia@gmail.com
https://linktr.ee/cookingwithnivia

Mirepua Catering Joan Hernandez
787.366.2420
cateringmirepua@gmail.com
https://mirepuacatering.wordpress.com/

TU Chef PR Dario Tani
786.287.7046
https://www.tuchefpr.com/

Chef José de Cordova
305.917.3100
chefsinspiration@gmail.com

In House Chef
This chef does more catering style from my experience, but a very professional setup.
https://www.inhousechefpr.com/
inhousechef.pr@gmail.com
787.941.7330

Old San Juan

There are a lot of good shops/restaurants/ bars in Old San Juan, definitely spend some time there. I recommend Al Fresco for a rooftop wine bar, and Marmalade for the best dining experience on the island (the only restaurant here I would consider Michelin star worthy). Chocobar Cortes in OSJ is an authentic PR confectionary dating to the 1920s, and they have developed an excellent restaurant around chocolate themed dishes.

If you enjoy cigars, check out Cigar House which has a large selection, plus a smoking lounge/bar in the back. For made in PR souvenirs, try Puerto Rican Arts and Crafts. They have a lot of artwork, figurines, and masks all made locally. Certainly visit the historic fort, El Morro (500 years old!) You may also consider doing a food tour:https://sanjuanfoodtours.com/. Finally, check out the place made famous by Despacito, La Factoria, (which is actually four bars in one), as well as Barrachina (birthplace of the Pina Colada).

San Juan Restaurants

For restaurants in San Juan, I highly recommend Santaella in La Placita for an upscale take on Puerto Rican cuisine. Other popular spots with excellent food are Eter Rooftop in the Miramar area, Mario Pagan in Condado and Jose Enrique on Ashford Ave. Breakfast options include Bistro Isla Verde (very close to the house), Tostado on Calle Loiza (also a great street with many authentic PR options), and Pinky’s on Ashford Ave. All these places are 5-15 minutes from the house.

More recommended options:

  • Sophia’s OSJ: outdoor seating in OSJ with elevated local food.
  • Cocina Abierta: Puertorican dishes tapas style.
  • San Juan Smokehouse: small open air restaurant in La Placita, great local area for drinks afterward as well.
  • La Alcapurria Quemá: empanadas/alcapurrias/drinks in La Placita.
  • La Casita Blanca: off the beaten path, but you won’t find classic local dishes done better.
  • Casita Miramar: traditional restaurant with new takes on local cuisine.
  • Vianda: excellent upscale option just outside the main tourist area.

Quick spots near the house (within 5 minutes drive or walking distance) or while waiting to check in:

  • Numero Uno beach bar: a few blocks from the house in Ocean Park, drinks and food right on the sand.
  • Pirlio Ocean Park: best pizza around as well as other options (try the Margarepa made with Quenepa!).
  • Cayo Caribe Ashford Ave: seafood/mofongo and casual outdoor seating.
  • Barbacoa: a few blocks from the house with the best local butcher shop (CUT) attached.
  • Acapulco: great tacos and drinks.
  • Tresbe Calle Loiza: actually a cluster of three restaurants, casual with all outdoor seating.
  • Pa’ Pical Isla Verde: hole in the wall with strong drinks, and the best empanadas.

Around the island: Salitre Arecibo: oceanside restaurant with beautiful views and great food. La Estación Fajardo: well worth the drive, open air restaurant with some of the best BBQ I’ve had anywhere.

Grocery Stores

Closest large grocery store is SuperMax de Diego (5 mins), which also has a very good wine/liquor store above it called The House. This grocery store tends to be very busy, so I prefer Pueblo Ciudadela which is a couple minutes further, but much nicer and quieter. Walking distance from the house is Plaza Loiza, it’s a local grocery store and while it doesn’t look great, it has all the essentials plus alcohol (and usually better prices). Large chains like Walmart, Costco and Sam’s Club are also available. 

Charter Boats

I certainly recommend doing a charter boat trip if you have time. If you prefer to set up a charter boat yourself to some of the small islands surrounding PR ( the beaches are amazing!), I have several suggestions:

The most popular: https://www.eastislandpr.com/
They are the biggest and also tend to do larger group outings…but usually also the most cost effective.

These others are smaller and can also do smaller boat private excursions:
https://www.pureadventurepr.com/
http://culebravipeastpr.com
https://www.jimboattrips.com/

There are many options all leaving from the Fajardo marina, really most are probably good, it just depends on exactly what you want to do and spend. It’s definitely worth the time and expense however, the beaches and waters of Culebra and Vieques are really beautiful, and there are several smaller islands including Icacos, Culebrita, and Palominos to which they can also take you. These are the areas where you will truly find the postcard worthy beaches in PR. 

Activities

Many tour companies here typically can arrange transportation, so you may find it easier just to have them pick you up. Although it’s not too difficult to find your way around, if you choose to drive yourself. You might also consider Carabali Rainforest Park, and Toro Verde Adventure Park, all great activities including ATVs, horseback riding and ziplines.

https://carabalirainforestpark.com/
http://toroverdepr.com/

The closest Jet Skis are in Isla Verde (also the best beach in the metro area), near the El San Juan hotel.
https://www.wwsurfingschool.com/

Sightseeing Around the Island

An excellent website developed by PR tourism may give you additional ideas:
https://www.discoverpuertorico.com/

If you have time there are some spots around the island not to be missed:
El Yunque Rainforest
https://tinyurl.com/du29pz9p
Bioluminescent Bays:
https://tinyurl.com/nntysjvx
Flamenco Beach (Culebra, one of the top beaches in the world):
https://tinyurl.com/t4mn8zxm
Cabo Rojo (west side of Island, beautiful beaches, lighthouse and pink salt flats)
https://tinyurl.com/ycrkvnp8
Luquillo Kiosks and nearby Balneario La Monserrate (try La Parrilla, the grilled lobster is amazing!)
https://tinyurl.com/4w94cxv3