When thinking of the Caribbean, most people envision white sandy beaches, crystal clear oceans and lots of palm trees (which is exactly what the doctor ordered and what we got at the first stop on our cruise…Princess Cays!) So when the Princess Caribbean made its way to the second stop on our Eastern Caribbean cruise, San Juan, Puerto Rico, I was not at all expecting to be greeted by hundreds of colorful Spanish Colonial buildings and cobblestone streets that have stood the test of time, all surrounded by the walls of a a 16th century fortress. It honestly felt as though we had been magically transported to some faraway port in Europe, and I was instantly transfixed. It’s honestly hard to choose which of the four stops on our Eastern Caribbean cruise with Princess Cruises was my favorite because they were all so different and offered such unique experiences, but if I had to choose, I think it would have to be San Juan. The city is incredibly beautiful, with so much to see and do…I only wished we’d had a little more time to explore (Cole and I both decided it’s a place we’d love to come back and visit for a full stay!) Luckily, we did get a full 8 hours in San Juan, and we stayed for the full time (per usual), so I’ve come back with lots of tips on how to make the most of your cruise port day in the beautiful, historical city of San Juan, Puerto Rico. From what to bring to what to do, click through to read my San Juan travel guide.
PS – click here for the latest Princess Cruises Offers!!
San Juan – Overview
During our seven-day Eastern Caribbean cruise, this port was the second stop (after the Bahamas) and the fourth day of our cruise. It was the furthest our ship traveled, so we had a full day at sea before we arrived (it was one of two formal nights on our itinerary), which was perfect timing to rest, reset and enjoy the amazing things our MedallionClass ship offered before our day in San Juan. You’ll definitely want to rest up before this port day, because the best way to explore and see the city is through walking (although there are many other options, too!) You’ll also want to come hungry, because San Juan has incredible food, and is the birthplace of rum, after all, so come thirsty too. When visiting San Juan, you can prepare for a day that’s rich in culture, history, amazing food and lots of eye candy as your explore the picturesque, candy-coated Spanish colonial buildings along centuries-old cobblestone streets. Keep scrolling for my tips on what to bring and suggestions on what to do during your port day at San Juan.
Getting There
One of the things I’ve noticed about cruising with Princess is that if there is more than one ship docking at port, Princess is usually the first to get there, and often arrives earlier than the timeline on your itinerary (which is amaaazing for a girl like me who is always running late!). Being the first ship to arrive at a port, (especially during a busy time for travel!) means you can avoid the crowds and can get to where you’re going much quicker/easier! This was definitely the case when we arrived in San Juan, Puerto Rico, just about 15 minutes before the 10:00am docking time on our itinerary. Unlike Princess Cays in the Bahamas, San Juan is a port where ships will pull right up and dock, so there are no water taxis needed. The walk to the port is less than 5 minutes and if you chose to do an excursion, they will most likely meet you right off the ship at the port.
What To Pack/Wear
I’ll be doing a post at the end of this month with my overall cruising tips and what to pack on a Caribbean cruise, so stay tuned for that, but I also thought it would be helpful to add some tips on what to pack for San Juan if this port happens to be on your itinerary. A great thing to note about San Juan is that because it is a US territory, if you are traveling from the US, your cell phone will work just fine on its original plan (without charging you an insane amount of $$$!) So definitely bring your phone along with you and turn your data on if you’d like to post on social media while traveling or catch up with your fam, but be sure to set an alarm to turn your phone back onto airplane mode when the ship leaves the port. You’ll definitely also want to bring along your camera and GoPro/video camera if you brought one, because there will be lots of beautiful sights you’ll want to capture in this gorgeous city. Also be sure to wear comfortable shoes you can walk in, because you’ll probably be doing lots of walking. Although San Juan is an island and has lots of gorgeous beaches, you most likely won’t spend your day on the beach here because there are so many other things to see and do, so don’t worry about packing or wearing your swimsuit, but do wear something comfortable and breathable because it’s pretty warm and humid in Puerto Rico year-round (it’s usually in the 80’s no matter what time of year). Annnd if you’re a crazy person like me, be sure to pack a backpack full of 5 extra outfit changes (kidding, but yes, it’s what we did…shout out to my husband Cole for being such a trooper!)
**Helpful Tip!! There’s actually a Walgreens located right outside where the ships dock, just in case there’s something from home you forgot to pack and need to buy!
What To Do – History & Culture Tour
When you look at the excursion options for San Juan, you’ll see lots of history and culture tours, which you can either do on foot, on a segway or on a bus/trolley. If it’s your first time to visit San Juan, you simply must include one of the tours in your day, and if you are able, I would definitely recommend one of the walking tours so you can truly take in the beauty and history of San Juan. We chose an excursion which included both a walking historical tour and a culinary experience where we got to make our own mojitos and eat mofongo, a Puerto Rican dish made from plantains that they mash and cook like potatoes and serve with meat and vegetables. It was SO good and it was a really cool experience to learn about how they prepare the dish and about the history of rum and Puerto Rico. Keep scrolling for photos and details on the culinary portion of our excursion in San Juan.
What To Do – Stand Under The Umbrella(s)
…ella ella. (sorry I had to y’all!) In our world of social media and smart phones, photography is important to everyone, not just the crazies like me who have decided to make social media their job. If you’re visiting San Juan, you simply must pay a trip to Fortaleza Street, known more recently for its beautiful display of colorful umbrellas hanging from the sky. This actually wasn’t a stop on our walking tour, but it was the very first place Cole and I visited after our tour ended, and was probably the spot I was most excited to shoot at in San Juan (for obvious reasons). The street is just a short 10-15 minute walk from the ship and is located right in front of the Governor’s Mansion (which is a gorgeous turquoise blue Spanish colonial building!) I was excited to find that the umbrellas had been changed to pink in honor of the Susan G. Komen foundation, so I might have brought the pink maxi dress just to shoot in front of the umbrellas. I think it was worth it! The umbrellas are usually an array of bright rainbow colors (which would have been equally as fun to see and shoot at!)
What To Do – Visit a Castle!
One of the things that makes San Juan so beautiful and unique are the fortresses that surround it. There are two fortresses/castles in San Juan, and you absolutely should make plans to visit at least one during your day at port. Castillo San Felipe El Morro is a six-level fort that was constructed in the 1500’s, rising 140 feet above the sea. Castillo de San Cristobal sits at the entrace of Old San JUan and is one of the largest defenses ever built in the Americas. Both offer up incredible views of the city and the ocean, but we decided to visit the Castillo de San Cristobal since it was closer in walking distance. I’m so glad we did! It was really amazing to see the entire city of Old San Juan from that view.
**Helpful Tip!! It does cost money to tour/visit the castles, so be prepared for that. It’s just $5 at each location for adults 16 and older and free for kids. 
What To Eat & Drink
Since a meal was included in our excursion, we did get to try local food but we actually didn’t get to try any specific restaurants, so I can’t make any recommendations on that note. But if you can, do try some of the local flavors. Puerto Rican food is a multi-cultural event, mixing Spanish, Cuban, Mexican, Africa, Taino and American flavors for cuisine that is uniquely their own! And, of course, you can’t leave the world’s leading rum producer without having a mojito or two.
That’s all for now! Stay tuned for my guides on the last two stops of our Eastern Caribbean Cruise with Princess Cruises. You can see all of my travel content on instagram here and on the blog here!
Fairwell xx,
**Thanks so much to Princess Cruises for sponsoring this post. All opinions are my own.
Rena
May 16, 2019 at 1:48 amThe pictures and the outfits are simply a dream!
xx from Bavaria/Germany, Rena
Lauren Vandiver
May 27, 2019 at 1:24 pmThank you so much Rena!! San Juan definitely made it easy to take photographs because it was so beautiful!
xx,
-Lauren
Benita James
May 16, 2019 at 4:19 amWow!!
Such stunning pictures.
Bernie, xx
The Style Fanatic
Lauren Vandiver
May 27, 2019 at 1:18 pmThank you so much love!! San Juan definitely made our job of capturing photos easy with how incredibly beautiful it was!
xx,
-Lauren
Vanessa
May 16, 2019 at 8:42 amThese pics are amazing!! It’s like pink heaven with the pink umbrellas!!
xoxo, Vanessa
http://www.WhatWouldVWear.com
Lauren Vandiver
May 27, 2019 at 1:07 pmOh thank you so much beauty!! Aren’t the pink umbrellas fun?? I was so excited that they changed them to pink during the time we visited!!
xx,
-Lauren
Jennifer
May 16, 2019 at 1:35 pmSan Juan is on my bucket list!
Jennifer
Effortlessly Sophisticated
Lauren Vandiver
May 27, 2019 at 1:02 pmIt definitely should be! Such a gorgeous place to see with so much to do!! 🙂
xx,
-Lauren
Kara
May 17, 2019 at 6:57 pmI had no idea how cute San Juan was but now I want to visit! You can really see how rich in history it is and the architecture is beautiful, and the street of umbrellas is such a fun photo spot. And I am in love with all of your photos!
x Kara | http://karascloset.net
Lauren Vandiver
May 27, 2019 at 1:02 pmRight?! I didn’t know either! It totally felt like we were somewhere in Europe, not the Caribbean!! And thank you so much – San Juan definitely made it easy to capture pretty content!! 🙂
xx,
-Lauren
Robin
May 20, 2019 at 9:22 amI loved san juan! It was so beautiful and the foods were amazing! I hope to go back and take my husband this time! I think those pink umbrellas are new, because I am sure I would of seen those! They look so beautiful and i love the photos you took there!
-Robin
Runwayteacher.com
Lauren Vandiver
May 27, 2019 at 12:59 pmIsn’t it just beautiful?! I wasn’t expecting it to be as gorgeous and culturally rich as it was! Yes – it’s also a place we want to go back!! Ohh and the pink umbrellas were only that way for a month or so – they are usually a rainbow of colors, but I do think they have been there for a little while and will be there for a while, so hopefully you’ll get to see them and photograph them!! 🙂
xx,
-Lauren
Marina W
May 21, 2019 at 2:02 amThis is such a girly and pretty post 🙂 Love it!
Marina W
http://www.waitmarinawho.com/2019/05/prague-is-for-intellectuals.html
Lauren Vandiver
May 27, 2019 at 12:56 pmThank you so much love!!
xx,
-Lauren
Laura
May 21, 2019 at 7:52 amIt looks so beautiful place to visit and the photos are just gorgeous x
Lauren Vandiver
May 27, 2019 at 12:55 pmThank you so much!! We were just taken away by how beautiful it was! Definitely would love to go back!!
xx,
-Lauren
Molly
May 22, 2019 at 8:42 amDYING to go there now after seeing your photos!!! So colorful and beautiful!!
http://www.mollyonthemoveblog.com
Lauren Vandiver
May 27, 2019 at 12:48 pmYES!! I would love to see the gorgeous photos you get – the city is so photogenic!!
xx,
-Lauren
Annie
May 22, 2019 at 4:30 pmWow, this is so gorgeous, I need to visit PR! Loving your bright looks and the pink umbrella shot 🙂
xo Annie
New England Romance
Lauren Vandiver
May 27, 2019 at 12:43 pmYou absolutely should put it on your list of places to travel – the city is so colorful, gorgeous and has so much rich history and culture!! 😉
xx,
-Lauren
Trendmixblog
May 23, 2019 at 8:18 amThis looks like such an amazing trip! Everything is so beautiful and colorful, so glad you had a great time! 🙂
Lauren Vandiver
May 27, 2019 at 12:39 pmThanks so much love!! Yes – I was so taken away with how lovely and colorful this city was!! We wished we could have staye dlonger!!
xx,
-Lauren
Talyssa
May 24, 2019 at 7:37 amThe photo of you in the umbrella street is simply magical! Absolutely love how colourful the towns are!! I’ve yet to go on a cruise, but the more I hear about them, the more I want to go!!
Lauren Vandiver
May 27, 2019 at 12:38 pmOh thank you so much friend!! I was super excited that they were pink for the time that we were there!! And absolutely!! I’d never been on a cruise until just a few years ago with Princess and now it’s our favorite way to travel!!
xx,
-Lauren
LackaDaisy
May 24, 2019 at 10:01 amWhat a fantastic place!! Wish to visit that side of the world sometime soon, these photos gave me an absolute wonderlust <3
LackaDaisy
Lauren Vandiver
May 27, 2019 at 12:37 pmAww thank you so much for your sweet compliments!! YES! You absolutely must travel to the Caribbean…there are so many beautiful things to see and do!! 🙂
xx,
-Lauren
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