San Juan Puerto RicoThings to Do in San JuanOld San Juan ⎮ Old San Juan Tours 

Old San Juan offers some of the best walking experiences in the Caribbean, with world-class UNESCO sites, scenic walkways, fun cultural experiences, and much more.  Visitors such as cruisers with a limited time in Old San Juan may wish to book a tour to make the most of your time in Old San Juan.  There are a number of tours sure to satisfy your wanderlust, travel preferences, and vacation budget starting at just $35 per person.

The historic district of San Juan can certainly be explored on your own, but there are a number of reasons for booking a tour.

After the tour, you’ll have a good overview of Old San Juan, perhaps wishing to see more, take more vacation photos, and see more places on your own.  We recommend you visit one of the forts on your own at a relaxed pace, shop, relax at a square, and perhaps join locals flying kites on the grounds of Castillo San Felipe del Morro.

Benefits of Exploring Old San Juan with a Professional Tour Guide

  • Cruisers with a short time in Old San Juan will make the most of their time without worrying about logistics.
  • There are a number of interesting places that you may miss on your own.
  • History comes to life with the knowledge, interesting stories of the past, and humor Puerto Ricans are known for.
  • After the tour, you’ll have a better understanding of the city, sparking interest to go back in order to explore more.
  • Having a local tour guide is a great way to get to know the culture of Puerto Rico, they’re happy to answer your questions and share valuable tips for the rest of your visit.
  • You may wish to choose a private or driving tour to meet your special needs, and interests. 

Featured Old San Juan Tour

Winner of Traveler’s Choice Best of the Best 2020 – #3 on Top 10 Experiences in the Caribbean

General & Budget Friendly Walking Tours

Old San Juan Puerto Rico - Walking Tours

The following walking tours focus on the main landmarks, historical gems of the city, scenic walkways, with the added knowledge of an experienced tour guide sharing interesting facts, and stories.

Following are three walking tours of Old San Juan liked by travelers like you.

Top Rated Tours to

Food & Walking Tours - Old San Juan

One of the pleasures of traveling is giving your taste buds new flavors, San Juan is the perfect place to experience the island’s gastronomy in some of the most romantic settings, historic colonial buildings, and relaxed cafes.  Whether you’re short on time or spending a week in San Juan, a food-tasting walking tour is a perfect start, so you get the best of Old San Juan and have more time to further explore, if you’re a cruiser you’ll have additional time to explore the forts.

A food tasting walking tour in Old San Juan will take you to the most interesting places, accompanied by passionate guides telling interesting stories, historical facts, and sharing the cultural food traditions of Puerto Rico.

Top Rated Old San Juan & Food Tours

Old San Juan & Around the Island

Perhaps you don’t have much time in San Juan but wish to see the natural wonders and interesting places of Puerto Rico, no worries, there are a few tours with glowing reviews that have put together great itineraries taking care of all the details so you get the most of your time in San Juan.

Top Rated Tours - Old San Juan & Around the Island

Sunset Old San Juan Walking Tours

Sunset lovers, romantics, those that may wish to spend the sunshine at the beach or explore the forts earlier in the day, can choose to explore the historic city at the most magical time of the day.  The city walls are accentuated by the golden glow of the sunset and the colorful streets become more subdued.

After the tour, you’ll be ready for a great dinner, be sure to ask your tour guide for recommendations.

Top Rated Old San Juan Sunset Tours

Cocktail Tours in Old San Juan

Puerto Rico is referred to as the rum capital of the Caribbean, San Juan is the best destination to experience great Puerto Rican rum and amazing cocktail creations uniquely found in the city.  Spend the daylight hours at the beach, then head to Old San Juan for a cocktail tasting and walking tour, a nice prelude to dinner in town. You’ll be exploring the city with stops at some of the best bars to savor the most delicious concoctions with Puerto Rican rum.

Top Rated Old San Juan Cocktail Tours

Old San Juan, Art & Culture Tours

Puerto Rican culture is festive, colorful, with rhythms from Taino natives and African roots, as you’ve probably read in our guide, Old San Juan is a great place to experience it.  You’ll get many stories and understanding of the Puerto Rican through the works of art you’ll find by simply walking around Old San Juan, driving through the more metro area of the city and nearby towns… and you’ll get great Instagram-worthy sharing photos of your vacation.

See tours below to choose what most appeals to you.  In addition to Old San Juan, the following tours include:

  • a visit to the village of Loiza which is the best village to learn about the African roots, and how it is embedded in Puerto Rican music, food, and traditions. You’ll learn about hand-made masks featured in some of the greater cultural events celebrated around the island and even join a Bomba class with local musicians and dancers.   You’ll also see famous art murals around Santurce.  See tour
  • One tour offers sightseeing around the New City area to observe the best art murals and a visit to La Placita in Santurce, known for its local produce and kiosks.  See tour

Top Rated San Juan & Cultural Arts Tours

Bike Tours of Old San Juan

Bicycling is a fun and romantic way to explore Old San Juan and the New City.   In the past few years, much was spent on infrastructure in order to make the city more walking and bicycle-friendly.   Ride surrounded by the colorful colonial buildings, scenic pathways with sweeping views of the historic city, commanding city walls with breathtaking views along the San Juan Bay & Atlantic Ocean.

Top Rated Bike Tours in Old San Juan

Old San Juan & Photography Session

Old San Juan Vacation Photography Sessions

Segway Tours of Old San Juan

Old San Juan, Puerto Rico - Segway Tours - Things to Do

See more in less time with a segway tour in Old San Juan.  Never rode a segway? No worries, they’ll teach you how before you hop on to explore the city.  This tour is only offered as a small group of 8 or less, so if you’re traveling with friends, co-workers and wish to take the whole family, be sure to book well in advance to secure your preferred date and time.

Top Rated Segway Tours in Old San Juan, Puerto Rico

Private Walking Tours

Private Tours in Old San Juan

Driving Tours

Top Rated Driving Tours - Old San Juan

Historical Tours

Unique Tours