Puerto Rico’s drinking tours pack maximum cultural value into your evening hours. The best options center around Old San Juan, where expert guides connect visitors with authentic local bars while sharing cultural insights. Small-group walking tours work particularly well here – you’ll dodge the tourist traps and discover family-run spots serving perfectly mixed piña coladas and mojitos.
We especially like the Old San Juan Sunset Walk & Taste Tour – it combines history, architecture, and bar visits in a manageable 3-hour format. For those seeking something more upscale, the Sunset Sailing & Cocktails cruise delivers stunning views along with premium drinks and appetizers.
Let’s explore our favorite drinking tours across the island.
Key Points
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The Old San Juan Bar Crawl offers a 90% recommendation rate, complimentary drinks, and a concluding tapas-style dining experience showcasing Puerto Rican cuisine.
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Private Sailing and Snorkeling Tours provide an open bar with local beer, premium rum, and appetizers, along with equipment for snorkeling and water activities.
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The Private Sunset Sail Tour offers a 3-hour experience with an open bar, charcuterie board, and additional activities like snorkeling and paddle boarding.
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The Old San Juan – Bar Hopping Private Tour is led by a knowledgeable guide and includes two alcoholic drinks and a shot, focusing on local bars and Puerto Rican libations.
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The Party Island Beach Adventure & Bacardi Bar tour provides a full day of activities, including tubing and lunch, with unlimited alcoholic beverages included.
Old San Juan Bar Crawl: Experience Local Hotspots
The Old San Juan Bar Crawl offers travelers an exhilarating exploration of the unique pub scene in Puerto Rico’s historic capital.
This lively tour boasts a 90% recommendation rate from over 396 reviews and a Badge of Excellence. Guests will experience the city’s rich 500-year history while enjoying complimentary drinks, including a mojito and house shot at each bar.
The tour concludes with tapas-style dining, allowing visitors to sample Puerto Rican cuisine.
Though some reviewers noted organizational and drink variety issues, the experience is praised for its fun atmosphere, friendly hosts, and opportunities to meet fellow travelers.
Comfortable shoes are recommended due to the uneven streets of Old San Juan.
Read our full review: Old San Juan Bar Crawl: Experience Local Hotspots Review
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Puerto Rico Private Sail and Snorkel, Open Bar & Appetizers
This private sailing and snorkeling excursion in Puerto Rico offers a truly immersive experience for adventurous travelers.
With a 5.0 rating from 13 reviews, the tour boasts a 100% traveler recommendation. Guests will enjoy an open bar featuring local beer, premium rum, and more, as well as a spread of delectable appetizers.
Snorkeling gear, paddleboards, and safety equipment are provided, along with brief instruction.
The tour departs from the Safe Harbor Puerto Del Rey marina in Fajardo, with detailed directions given upon booking.
While not wheelchair accessible, the activity is suitable for most travelers in moderate physical condition, though those with certain medical conditions should avoid it.
Read our full review: Puerto Rico Private Sail and Snorkel, Open Bar & Appetizers Review
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Private Puerto Rico Sail and Snorkel Tour With Open Bar
Seeking a more personalized and immersive Puerto Rico adventure? The Private Puerto Rico Sail and Snorkel Tour With Open Bar promises just that.
This private day trip takes you to the eastern islands of Palominos, Lobos, and/or Icacos, where you’ll paddle, snorkel, swim, and soak up the sun. You’ll have your own boat, avoiding the crowds, and discover local marine life like turtles and colorful fish.
The tour includes an open bar, water, coffee/tea, pastries, and a gourmet snack spread. Snorkeling gear, paddleboards, and safety equipment are provided, along with brief instruction.
While not suitable for those with medical conditions or young children, this tour offers a unique way to explore Puerto Rico’s hidden gems and create lasting memories.
Read our full review: Private Puerto Rico Sail and Snorkel Tour With Open Bar Review
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Private Sailing & Snorkeling Tour With Bar & Food in Fajardo, PR
Setting out on a private sailing and snorkeling adventure in the idyllic waters of Fajardo, Puerto Rico, offers guests an unforgettable day of sun, sea, and exploration.
With a capacity of up to 6 travelers, this full-day tour provides a personalized experience tailored to the group’s interests. Travelers can enjoy a private boat with a USCG captain and crew, as well as a delightful spread of charcuterie, fresh fruit, and dips, complemented by a full bar and non-alcoholic drinks.
Snorkeling gear, paddleboards, and floaties are provided, and guests can even bring their own lunch. The knowledgeable captain shares insights about the local wildlife and sailing, ensuring a truly immersive Puerto Rican experience.
Read our full review: Private Sailing & Snorkeling Tour With Bar & Food in Fajardo, PR Review
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Old San Juan – Bar Hopping Private Tour
For travelers in Puerto Rico seeking to enjoy the vibrant nightlife of Old San Juan, the Old San Juan – Bar Hopping Private Tour offers a personalized journey through the city’s lively drinking establishments.
This 4.5-star rated tour provides guests with two alcoholic drinks or cocktails, plus a shot or non-alcoholic beverage, as they explore local bars and sample the best of Puerto Rican libations.
Led by the knowledgeable guide Jan Carlos, the tour allows participants to discover unique spots and experience the welcoming atmosphere of San Juan’s nightlife.
While some guests have wished for more drinks, the tour’s host has acknowledged the feedback and emphasized additional options during the experience.
Read our full review: Old San Juan – Bar Hopping Private Tour Review
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Private Sunset Sail Tour in Fajardo With Open Bar and Appetizers
This private sunset sail tour in Fajardo, Puerto Rico, allows guests to experience the stunning natural beauty of the area from the comfort of a USCG-certified vessel.
During the 3-hour excursion, guests can enjoy an open bar featuring a variety of alcoholic and non-alcoholic beverages, along with a delectable charcuterie board, fresh fruit platter, and assorted dips.
The tour also provides snorkeling gear, paddle boards, and floaties for those who want to get in the water.
With a maximum group size of 6, this tour offers an intimate and personalized experience that’s perfect for anyone seeking a relaxing and indulgent way to enjoy the Caribbean sunset.
Read our full review: Private Sunset Sail Tour in Fajardo With Open Bar and Appetizers Review
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Party Island Beach Adventure & Bacardi Bar
The Party Island Beach Adventure & Bacardi Bar takes guests on an exhilarating journey to explore the vibrant culture and natural beauty of Puerto Rico.
This 5-star rated tour offers a full day of fun, including tubing, a delicious lunch, and unlimited alcoholic beverages.
Pickup is at the San Juan Ferry Terminal, and the tour guide will be easily identifiable.
While the tour isn’t recommended for those with certain medical conditions, most travelers can participate.
With a maximum of 7 guests, this intimate experience allows you to learn about Puerto Rico’s stunning scenery and lively atmosphere.
Booking confirmation and additional details are provided upon request.
Read our full review: Party Island Beach Adventure & Bacardi Bar Review
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Chinchorreo Bar Hopping Tour From San Juan
Explore Puerto Rico’s vibrant bar scene on the Chinchorreo Bar Hopping Tour from San Juan. This activity, operated by DUHU, takes you on a bar-hopping adventure in the heart of Old San Juan.
For $100 per person, you’ll travel in an air-conditioned vehicle and enjoy lunch and alcoholic beverages. The tour starts at 9 AM from Pier #3, across from Walgreens Pharmacy, and returns to the same meeting point.
With a maximum of 25 travelers, this tour offers a personalized experience. However, children and individuals under 18 aren’t permitted. Guests can take advantage of the Reserve Now and Pay Later option.
Just be aware that the tour isn’t wheelchair accessible.
Read our full review: Chinchorreo Bar Hopping Tour From San Juan Review
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Sum Up
Puerto Rico’s drinking tours offer a diverse array of experiences, from exploring the local bars and nightlife in Old San Juan to sailing and snorkeling adventures with open bars. Whether you’re looking for a lively bar crawl, a scenic sunset sail, or a beach party, there’s a drinking tour that’ll suit your tastes and make your trip to Puerto Rico even more memorable.