ShoreTrips logo Shore Excursions - City Tours - Day Activities


Private for up to 2 (Not a per person rate) $526 USD
Private for up to 4 (Not a per person rate) $578 USD
Private for up to 6 (Not a per person rate) $630 USD
Private for up to 8 (Not a per person rate) $970 USD
Private for up to 10 (Not a per person rate) $1027 USD
Private for up to 12 (Not a per person rate) $1075 USD
*Selections and optional choices will be made during checkout


Share this Trip
Add to Itinerary

There is a magical feeling to the area of Old San Juan and your first thought may be that you are not in the United States. There seems to be nothing that looks as old or has the history on the mainland as you will see in Old San Juan. Founded in 1521, this part of the city of San Juan is a UNESCO World Heritage Site, as well as a U.S. Historic Zone. Your walk begins at the water's edge and follows the city wall, where the view is spectacular and the past comes alive. There are over 400 well-preserved buildings in the old city that date back to its inception. The architecture is incredible and, honestly, you will feel as if you are in Europe, with cobblestone streets and buildings sitting side by side.

Most of the old city will remind you of its history as a military stronghold, but much of this area has now been modified to house attractions for tourism. Cafes, small shops, great gardens, and courtyards abound. The former barracks now house the Museo de Las Americas and has a collection of Latin American Folk Art. Some of the religious structures spread throughout the area, such as the San Juan Cathedral that opened in 1540, seem to be both Gothic and modern in architecture due to constant renovations. You'll have the chance to see the San Juan Gate, San Juan Cathedral, and the town square. And you will learn where to find other points of interest that you can return to and explore in greater detail.

This special itinerary was created to deliver an entertaining adventure in this historical city. Unless you take in old San Juan on foot, you really cannot understand how special it is, but accompanied by a local guide, you will learn about the history of this US territory. The cobblestone path through the narrow streets will bring you to the fort and the artisans that still make and sell bamboo cups, local cigars, tropical candles, and souvenirs made of wood, calabash, and other local materials. Most interesting is hearing the background of this island, which most Americans do not realize is part of the USA.

Now, once finished with your informative walk, you will be connected to our darling water taxi, which will take you around the peninsula so you can see the city and the fortifications from the water. Imagine those who sought to conquer this city long ago and the challenges they faced. Because of its prominence in the Caribbean, this network of fortifications was built to protect the transports of gold and silver from the New World to Europe. And because of these rich cargoes, San Juan became a target of the foreign powers of the time. The British attack in 1797, for instance, during the French Revolutionary War, was led by Sir Ralph Abercromby (who had just conquered Trinidad). His army laid siege to the city, but was forced to withdraw in defeat as the Puerto Rican defenses proved more resilient than those of Trinidad.

At the end of your combination tour, you will have a great understanding of the territory of Puerto Rico and Old San Juan itself.

  • This Tour Includes:
  • Private, guided walking tour of Old San Juan
  • Private boat charter, each boat holds up to 6 people
  • Historical narration and guidance by local captain
  • Complimentary sangria
  • Beautiful views of Old San Juan!

Days of Operation

Mon - yes
Tue - yes
Wed - yes
Thu - yes
Fri - yes
Sat - yes
Sun - yes

Departures (local time)

  • 9:00 AM (3.5 hrs) Length approximate
  • 11:00 AM (3.5 hrs) Length approximate
  • 1:00 PM (3.5 hrs) Length approximate

Transfer / Meeting Instructions

No Taxi Required Specific pick up or taxi instructions will appear on your voucher after you purchase your trip.

Special Instructions

If you're staying at a hotel, you'll need to take a taxi to the meeting location in San Juan. Specific directions will be on your voucher once the booking is confirmed.
• If you arrive by cruise ship, please choose a time that is close to your arrival time in port. All times are flexible and will be adjusted according to your arrival.
• If you have more than 12 people in your party, please contact ShoreTrips for pricing.
• We suggest that you wear comfortable walking shoes for walking up stairs, steep grades, and pavement. If you have special interests for your day, please contact ShoreTrips when making your reservation.
• Late departures are frequently requested. Please be advised that the sun sets around 5:30 p.m. in San Juan (depending on the season) and some public buildings are not open.
• The boat portion is one hour; the walking portion is 2.5 hours.
• The $5 admission to San Cristobal Fort is not included in the price of the tour. It will be collected at the time of the tour, should you decide to visit.


• This tour has a maximum of 6 people per water taxi. If there are more than 6 people on the walking tour, you'll be split up into 2 vessels for the water portion.
• This tour can be booked in the early evening; please call ShoreTrips for availability and rates.