Boulevards & Byways

Take a Sailing Excursion in Puerto Rico

Sail the Amazing Grace in San Juan Bay – Puerto Rico

A  Relaxing, Fun, and Informative Tour Not to be Missed

This is the 83 foot top sail schooner, the Amazing Grace.

This beauty is the 83 foot top sail schooner, the Amazing Grace.

On Puerto Rico’s northern coast, an 83 foot topsail schooner, the Amazing Grace, sails in San Juan Bay and lures its passengers into the history and culture of Old San Juan. Although walking the city is something many, including myself, thoroughly enjoy, I was able to experience the city from another perspective – the water – during this sailing journey.

This beautiful vessel flies seven sails used in different combinations to suit the wind. The ship is representative of the ones used by the British in the War of Independence and again in 1812, both as ships of the U.S. Navy and as privateers.  The pirates captured many of the privateer vessels. You won’t however, find pirates here today, but a pirate flag flutters from its stern, reminding us of gnarly tales associated with the schooner’s history.

A pirate flag flutters in the breeze.

A pirate flag flutters in the breeze.

Shortly after boarding the vessel for a sunset cruise, the crew hoisted the sails and we embarked on our journey.  We passed candy-colored, century’s old buildings peeking from behind an imposing stone wall. The staff informed us that the wall, 42 feet tall, is in some places 45 feet thick at the base. As we lazily sailed upon the bay, listening to a historical narrative, we were offered soft drinks, beer, water, and mixed drinks by the charismatic crew.  I sipped my refreshing mojito and reflecting on what life must have been like back in that time, and it’s only from the water’s view do you realize how commanding the wall was to invaders and how pirates were dissuaded from entering the city.

Marvel at the beauty, join the adventure, and be part of history

The red gate guards the entrance to the city of Old San Juan.

Further down the bay we passed a stunningly large red gate built in 1520. The crew went on to explain how it provided dignitary’s access to the city as is the only remaining gate of the 5 built. As the sun began to set and the shadows illuminated the vibrant Fort Morro prominently standing guard to the entrance to the San Juan Bay, we were given a fun opportunity to fire a small cannon towards the fort. The echo of the blast rang in our ears, as the real cannons did so many years ago. The attentive crew then passed around delicious tapas consisting of cheese, sliders, and empanadas to quell our hunger as we headed back to shore.

Fort Morro stands majestically with it's high walls and imposing structure.

Fort Morro stands majestically with it’s high walls and imposing structure.

Put sailing aboard the Amazing Grace schooner on your list of things to do. Day sails and sunset trips can be booked through East Island Excursions,, and leaves from Old San Juan cruise port. This has been one of my top travel highlights of Puerto Rico and I have no doubt it will be yours also. It’s a relaxing and fun opportunity to explore the history and culture of the bay and the city of Old San Juan in a very unique way.

You can charter the Amazing Grace for your next special event – small weddings & rehearsals, theme birthdays, anniversaries, family reunions, and memorials.

During a sunset cruise, this beautiful view can be yours.

During a sunset cruise, this beautiful view can be yours.

East Island Excursions





Day Tour Times:
The sails come down at we head back to shore.

The sails come down at we head back to shore.

9:30 am – 11:00 am (Check in 9:00 am)
12:00 pm – 1:30 pm (Check in 11:30 am)
2:30 pm – 4:00 pm (Check In 2:00 pm)

Day Tour Includes:
Refreshments: Regular and diet sodas, juices and
beer, Piña Colada.

Day Tour pricing:

Adults ……………….$79.00*


(4 to 11 years old)

Sunset Sail Tour times:
The view is beautiful in San Juan Bay.

The view is beautiful in San Juan Bay.

5:00 pm – 7:00 pm (Check in 4:30 pm)
5:30 pm – 7:30 pm Summer Time (Check in 5:00 pm)

Sunset Sail Includes:
Beverages: Puerto Rican Rum, White Wine, Piña Colada, regular and diet sodas, Iced Tea, Orange and Cranberry juice, Club Soda and Medulla beers.

Sunset Sail Pricing:
Adults ……………….$95.00*

Children ……………$85.00*

(4 to 11 years old)

*(Plus taxes 11.5%)


Disclosure details: Boulevards and Byways attended the tour as a guest of East Island Excursions.  All opinions are my own.


7 Amazing Things to do in Old San Juan Puerto Rico


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