Recommendations: Best Things To Do in San Juan, Puerto Rico?

One of the craziest dichotomies in travel places me in a conundrum every year. Planning our annual cruise vacation. One of the biggest selling points of cruise vacations is that it is one-stop shopping, everything is handled for you. Sorry, that’s not how the Cole family rolls…

San Juan, Puerto Rico

Any suggestions for great things to do in Puerto Rico? Add a comment below and help promote family harmony
Photo Credit: Josh Bozarth | Flickr

My family has now made it an annual ritual to take a cruise over the winter holidays. It seems this tradition was born soon after our relocation to Milwaukee, Wisconsin. A beautiful area in summer – I highly recommend attending Summerfest, the world’s largest music festival in late June / early July – but not well suited to human habitation in winter.

So as opposed to taking the more pedestrian path of booking excursions through the cruise line, our brood wants to go beyond the typical and encounter unique experiences that will create lasting memories. This approach frequently requires logistical coordination comparable to NASA missions with the additional necessity to maintain family harmony.

Family harmony is a delicate commodity. For some, I am certain it may represent a mythical oxymoron. For us, the key prerequisites are open communication and diligent planning. We have also discovered that we do not need to have the whole family together 24/7 for the whole trip so we share an identical experience. We typically pair up for various activities when diverging interests prefer disparate alternatives.

With the dual purpose of sharing some of the resources we use to research great destination experiences, and hopefully soliciting some suggestions from the all-knowing blogosphere, this is the first of a series of posts showcasing the ports of call on our holiday cruise. We start with Puerto Rico.

The family has been to Puerto Rico before, having spent time at The Rio Mar Beach Resort. Probably our most enjoyable and memorable activity was exploring El Yunque National Rain Forest.

A bit of detail regarding our family composition – My wife and I can both remember The Beatles first tour of America. I like adventure and my wife likes the beach and shopping. Our two daughters are 13 and 20 years old respectively. A personal, yet admittedly unrealistic, goal is to partake of activities that would avoid interaction with teenage or twenty-something boys…

With that in mind, let us know what you think are the best activities for our day in port – Actually we will be in San Juan the day before and day after the cruise since San Juan is its port of embarkation.

Here are the resources I am using to research the best experiences for our day in port for San Juan, Puerto Rico:

Of course, the ports are only one facet of a cruise experience – below is some information on the ship and itinerary:

Celebrity Cruises
Cruiseline: Website
Ship: Celebrity Millennium
Itinerary: 10 Night Southern Caribbean Cruise San Juan, Puerto Rico | St. Maarten, Netherlands Antilles | Castries, Saint Lucia | Bridgetown, Barbados | Saint George’s, Grenada | Scarborough, Trinidad and Tobago | Roseau, Dominica | St. Thomas, Virgin Islands
Videos: YouTube Page
Social Media: Facebook Page

Full disclosure: I am not being compensated in any way by Celebrity Cruises, its parent Royal Caribbean or any other party associated with the planning or experience of this trip. It is a 100% personally funded family holiday.

About Robert Cole

Robert Cole is the founder of RockCheetah, a hotel marketing strategy and travel technology consulting practice. He also authors the Views from a Corner Suite Blog and publishes the Travel Quote of the Day. Robert speaks regularly at major travel industry conferences, authors articles for leading travel industry publications, advises travel-related startups and the equity investment community. He is an evangelist for the global travel industry.