Save a Spot - Most Popular Walking Tour

We created this easy guide to help you find the perfect tour in Old San Juan.  From interesting history tours and romantic sunset walks to private driving tours, there’s something for everyone to enjoy the magic of Old San Juan. 

Old San Juan provides unparalleled walking experiences in the Caribbean, featuring world-class UNESCO sites, scenic walkways, immersive cultural encounters, and much more.  

For visitors, especially cruisers with limited time, booking a tour is a great way to maximize your Old San Juan experience.  Various tours are available to cater to your wanderlust, travel preferences, and vacation budget, starting at just $35 per person.

Tour Categories

Old San Juan, Puerto Rico

Do you Need a Tour to See Old San Juan?

While exploring the historic district of San Juan on your own is certainly an option, there are compelling reasons to consider booking a tour. A guided tour provides a comprehensive overview of Old San Juan, leaving you eager to delve deeper, capture more vacation photos, and explore additional locations at your own pace. We suggest venturing to one of the forts independently for a leisurely experience, indulging in shopping, unwinding at a charming square, and even joining locals flying kites on the grounds of Castillo San Felipe del Morro.

+ Benefits of Exploring Old San Juan with a Professional Tour Guide

  • Cruise Ship Visitors: Maximize your time in Old San Juan with the benefits of organized tours, eliminating logistical concerns.
  • Personalize your experience with the option of a private or driving tour catering to your specific needs and interests.
  • Uncover hidden gems that might be overlooked when exploring on your own, ensuring you don’t miss out on the most interesting gems in the historic district. 
  • Immerse yourself in the rich history of the city with knowledgeable guides who bring stories of the past to life, infused with the humor for which Puerto Ricans are renowned. 
  • Connect with the local culture by having a guide who happily answers your questions and provides valuable tips for the remainder of your visit.
  • Gain a comprehensive understanding of the city during the tour, igniting a desire to return for further exploration.

Featured Old San Juan Tours

Featured Tours to Explore Old San Juan

Award Winning Tour - Flavors of Old San Juan Food Tour

Winner of  TripAdvisor’s Traveler’s Choice Best of the Best – Top 10 Experiences in the Caribbean – #4 in 2022 & #3 in 2020

Best Old San Juan Tour and Experiences - 2022 TripAdvisor Traveler's Choice

General & Budget Friendly Walking Tours

Old San Juan Budget Friendly / Cheap Tours

Enrich your journey in Old San Juan with the expertise of seasoned tour guides and explore the essence of Old San Juan with captivating walking tours that highlight the city’s main landmarks, historical treasures, architecture, and interesting stories you would otherwise miss.

Following are the top three walking tours in Old San Juan, cherished by fellow travelers like yourself.

Budget Friendly Old San Juan Tours

Food & Walking Tours - Old San Juan

Old San Juan Food Tours

One of the pleasures of traveling is giving your taste buds new experiences, we invite you to indulge by savoring the island’s rich gastronomy in the charming Old San Juan ambiance.  Set against the backdrop of historic colonial buildings and relaxed cafes, Old San Juan is an ideal destination for a culinary adventure.  Accompanied by passionate guides telling interesting stories and historical facts and sharing the cultural food traditions of Puerto Rico.  Whether you have a limited timeframe or a week to spare in San Juan, kickstart your experience with a food-tasting walking tour, giving you ample time for further exploration.  

Top Rated Old San Juan Food Tours

Accessible Tours of Old San Juan, Puerto Rico

Embark on a memorable journey through Old San Juan tailored to meet your accessibility needs. Our welcoming guides are committed to ensuring that everyone, regardless of mobility challenges, can enjoy this historic city’s rich history and vibrant culture.  Opt for a comfortable golf cart tour, offering a relaxed and accessible way to explore the charming streets, iconic landmarks, and hidden gems of Old San Juan. For a more private and personalized experience, indulge in a private driving tour, where our guides will navigate you through the city’s captivating stories, picturesque sights, and cultural wonders. Discover the beauty of Old San Juan without limitations as we strive to make your visit an inclusive and unforgettable experience.

Accessible Old San Juan Tours

Old San Juan & Around the Island

Old San Juan Tours with Sightseeing Around Puerto Rico

If your time in San Juan is limited, but you’re eager to explore Puerto Rico’s natural wonders and intriguing spots, fret not!  There are highly acclaimed tours with glowing reviews that meticulously curate excellent itineraries, ensuring every detail is taken care of.  With these thoughtfully designed tours, you can maximize your time in San Juan and make the most of your exploration of the captivating sights and wonders of Puerto Rico.

Old San Juan & Sightseeing Tours Around the Island

Sunset Old San Juan Walking Tours

Old San Juan Sunset Tours

For sunset lovers and romantics, consider discovering the historic city during its most magical time – as the sun sets.  The city walls are bathed in a golden glow, and the vibrant streets take on a more serene ambiance.  

Sunset Tours of Old San Juan

Old San Juan, Art & Culture Tours

Old San Juan Art and Cultural Tours

Immerse yourself in the vibrant tapestry of Puerto Rican culture, where festivity and color weave together the rhythms rooted in Taino Natives, African heritage, and Spanish culture.  Old San Juan emerges as an ideal canvas to experience this rich cultural mosaic.  Stroll through the historic streets of Old San Juan, traverse the metro area, and explore nearby towns to encounter captivating works of art that narrate the stories and essence of Puerto Rican life.  Capture unforgettable moments with Instagram-worthy photos that encapsulate the spirit of your vacation.

Art & Culture Tours  ⎮  Dancing Lessons  ⎮ Food & Drink Tours ⎮  Rum Distillery Tours

Top Rated Cultural Tours

Old San Juan & Photography Session

Old San Juan Photography Tours

Part of the vacation experience involves capturing moments through photos to share with friends.  If you take a moment to observe your surroundings as you stroll, you’ll notice the considerable time people invest in taking pictures and attempting to perfect their selfies, often missing the joy of fully immersing themselves in the experiences and beauty unfolding around them.  Old San Juan stands out as one of the most picturesque destinations in the Caribbean, offering vibrant and scenic locations as the ideal backdrop.  We encourage you to let friendly and professional locals provide you with the opportunity to put the camera away, allowing you to relish Old San Juan while they skillfully capture your affectionate gazes and expressions of excitement, guiding you through the most breathtaking spots.

Top Rated Old San Juan & Photography Experiences

Tours for Families with Children

Segway Tours of Old San Juan

Private Driving Tours

If you’re short on time or simply prefer to drive around Old San Juan, there are some wonderful tours available in Old San Juan. Choose from specialized tours that delve into the captivating history of Old San Juan or opt for all-inclusive private tours that extend beyond the city limits to showcase additional intriguing destinations, allowing you to savor a broader experience of Puerto Rico.

Top Rated Driving Tours of Old San Juan

See more driving tours

Maximize your exploration of Old San Juan by opting for a Segway tour – an exhilarating way to see more in less time.  If you’ve never ridden a Segway before, no worries; expert guides will provide thorough instruction before you embark on your city exploration. This exclusive tour is tailored for intimate groups, accommodating eight or fewer participants.  Whether you’re traveling with friends, co-workers, or the whole family, ensure you secure your preferred date and time by booking well in advance.

Private Old San Juan Tours

While group tours have their charm, private tours offer an even more personalized experience, ensuring that you or your group receive undivided attention tailored to your preferences and individual needs. Our friendly tour guides are readily available to cater to your desires. 

Private Walking Tours

Group tours are nice, but private tours are even better.  Local friendly tour guides are available to offer you or your group undivided attention, you’ll be able to ask more questions and walk at a pace that’s comfortable for your group. 

Private Walking Tours of Old San Juan

Walking Tours with Fort Visit

We recommend exploring the forts at your own pace and participating in one of the standard walking tours.  However, if you find yourself pressed for time or interested in alternative activities, the following tours are ideal for maximizing your visit to Old San Juan.

Old San Juan Walking Tours with Fort

Ghost Walking Tours in Old San Juan

Delve into the supernatural side of Old San Juan, where a myriad of tales and reported sightings add an eerie charm to the historic city.  Let a seasoned local guide regale you with ghostly stories and illuminate the paranormal history that intertwines with the city’s beautiful sights.  Explore the mysterious and haunted corners of Old San Juan while gaining insights into the spectral occurrences that have left an indelible mark on this enchanting destination. 

Ghost Walking Tours in Old San Juan