Puerto Rico offers a little bit of everything for travelers: vibrant cities with beautifully preserved historic districts, gorgeous off-the-radar beaches, and a rich Afro-Caribbean-Creole culture. As a U.S. territory, Puerto Rico is not only easy for U.S. citizens to visit, but it’s also filled with (sometimes jarring) reminders of life back home – Popeye’s Fried Chicken, anyone?
We spent 14 days in Puerto Rico in early May, a visit that was part city explorations, part road trip, and generous servings of relaxing beach time and island adventures. We started our journey in Old San Juan and then traveled along the northern, eastern, and southern coasts to the historic cities of Rincón and Ponce. From Ponce, we drove back to the regional airport near San Juan and caught a puddle-jump flight to the island of Vieques. From Vieques, we took the ferry back to the “main island” and then another ferry to the nearby island of Culebra.
Here are our trip highlights, with plenty of tips for Puerto Rico travelers. (Usual note: Photos are in galleries – just click through to see bigger versions.)
Old San Juan
Founded by Spanish conquistador Juan Ponce de Leon in 1521, the capital city of San Juan became Spain’s most important stopover port for conquering the “New World.” Over the next three centuries, the Spanish fortified the city heavily to fend off repeated attacks by the English (including Sir Frances Drake in 1595) and the Dutch. San Juan finally became a U.S. territory in 1898 with Spain’s defeat in the Spanish-American War.
Today, visitors flock to Old San Juan to gaze upon the beautifully preserved colonial architecture, enjoy the fantastic restaurants and nightlife, and stand in awe of the massive stone fortifications – now designated National Parks.
Tips: The Old San Juan Free Walking Tour was well worth the time. And be aware that San Juan is a huge destination for cruise ships, so be prepared for crowds when the ships are in. Things calm down a lot when they steam out of town in the late afternoon.
El Yunque National Forest
Sited about an hour’s drive out of San Juan, El Yunque is the only tropical rainforest in the U.S. national forest system. We spent a day hiking there, a refreshing break from the heat and bustle of Old San Juan. Although we were caught in a huge rainstorm that socked in our view from atop El Yunque Peak, we really enjoyed our dose of nature.
Tips: You need a reservation to visit El Yunque, available here. We were able to use our Lifetime Senior Passes issued by the National Park Service to enter El Yunque, as well as the Castillo in Old San Juan. More info here. The Rainforest Cafe inside El Yunque is a nice lunch stop.
The Northern Beaches to Rincón
After four days in San Juan, we drove our rental car west along Puerto Rico’s northern border – stopping to explore the string of pretty beaches along the way. In the late afternoon, we reached the popular beach and surfing town of Rincón, where we spent another four nights.
South and Around to Ponce
From Rincón, we spent another leisurely day driving down and around Puerto Rico’s southwestern corner to the colonial city of Ponce. Puerto Rico’s second-largest city, Ponce is named for Juan Ponce de León y Loayza, the great-grandson of Juan Ponce de León. The city is filled with gorgeous old colonial and post-colonial buildings in various states of repair. Like all of Puerto Rico, Ponce is still struggling to come back from the triple-whammy curse of Covid, the devastating 2020 earthquake, and the disastrous Hurricane Maria in 2017.
Vieques and Culebra
Puerto Rico’s two most-visited nearby islands, Vieques and Culebra, are infamous for one sad reason: They were both used as bombing ranges by the U.S. Navy for many decades. After years of activism and protests by the locals, the Navy pulled out of Culebra in the 1970s – but Navy operations didn’t cease on Vieques until 2003. Today, both islands offer gorgeous beaches, friendly folks, and a laid-back vibe.
Vieques’ Bioluminescent Bay
Mosquito Bay on Vieques deserves its own call-out because it’s spectacular; in fact, it’s easily one of our most memorable travel experiences in recent years. By day Mosquito Bay is nothing special, but at night it comes alive with the glow of countless tiny light-emitting dinoflagellates. These little guys have made Mosquito Bay famous as the world’s brightest bioluminescent bay, dimmed only temporarily by Hurricane Maria in 2017.
The best way to experience Mosquito Bay is with an organized nighttime kayaking tour (we highly recommend the tour outfit we chose, Blackbeard Sports). And try to time your tour with the new moon to make sure conditions are as dark as possible. We got extra lucky with a cloudless night, which complemented the glowing waters with a spectacular display of stars and the Milky Way. It was truly unforgettable.
As the tour guides told us, trying to photograph the bioluminescence is pretty much a waste of time unless you have really sophisticated camera gear. We were too busy paddling our kayak and taking in the wonder of it all to even try. But this video does a great job of capturing the magic:
For our first couple of days in San Juan, we relied on Uber (it’s excellent there). For El Yunque and our trip around the western coast to Ponce, we rented a car from Enterprise and were very pleased with the car and the service. From Ponce, we drove the car back, straight up through the middle of the island, to the San Juan airport. Then we hopped a tiny plane to Vieques, operated by Vieques Air Link. (Note: Another option is to take an Uber or taxi to the ferry terminal and ferry over, but the cost is prohibitive – over $100 one way just for the ground transfer.)
On Vieques, we rented a golf cart, which was not ideal given the hills and the longer distances we wanted to cover. A car or jeep would have been a better choice. There are plenty of options for all three on the island.
Getting from Vieques to Culebra was a little complicated, considering the islands are only 15 miles apart. There’s no longer a ferry service directly connecting the islands, so we had to take a ferry from Vieques to the “main island” and then another one over to Culebra. It was almost a full day of travel, but inexpensive. NOTE: the ferry can book up, so your best bet is to purchase tickets online in advance here.
On Culebra, we rented an almost-new Jeep from Carlos Jeep Rental, a first-class operation. We can’t recommend them enough!
Finally, we hopped an even tinier Cape Air flight from Culebra to the San Juan airport for our flight home.
In Old San Juan, Bacaro serves up beautifully imagined Italian food in an atmosphere that’s best described as “1920s Paris meets 1940s Havana.” But make a reservation; Bacaro is always booked up! We also enjoyed tapas, cocktails, and our balcony view of the street scene below at The Mezzanine, just two doors down from our Airbnb.
In Rincón, check out Bakku Japanese Eatery for yummy and creative sushi, The English Rose for a sumptuous breakfast and a panoramic view, and Taqueria Vatos Locos for decent Mexican food and live mariachi music. Make a stop into Tinto wine shop and chat up the friendly owner.
In Ponce, our favorite dining experience was at Mesa, an elegant restaurant with an eclectic menu and huge wine selection.
On Vieques, we had a great lunch and enjoyed chatting up the friendly bartenders at Duffy’s. Casa Nativo is another nice lunch stop. And check out The Rising Roost for a fantastic breakfast and friendly kitties.
On Culebra, we had a great seafood lunch (and got back in touch with our sailing roots) at The Dinghy Dock. Also, you can pick up a pizza from La Jibera, made to order by two enterprising young guys just outside the ferry landing. Then take it across the street to the Sandbar and enjoy a mojito or two, while chatting with the friendly bartenders there. (This was a great solution for our first night there, when all the other restaurants were closed.)
Of our five different accommodations in Puerto Rico, there’s only two we can recommend wholeheartedly. First is the beautiful Airbnb where we stayed in heart of Old San Juan. Located in a former colonial mansion, this one-bedroom apartment oozes with atmosphere, and it’s priced very reasonably. Second is Ulala, a small apartment complex on Culebra that feels almost brand-new with high-quality furnishings and a panoramic view from the patio. (Note: Most accommodations in Puerto Rico do not include breakfast, so having a full kitchen to make our own was a saving grace in both of these properties.)
Puerto Rico was expensive! Surprisingly so. That said, we enjoyed our trip there, but it left us with mixed feelings. This island has endured so much over the past decades: a devastating U.S. military presence (toxic cleanup is still ongoing on Vieques), corrupt and inefficient government, and the triple disasters of Covid, 2020 earthquake, and Hurricane Maria. We got the sense that Puerto Rico is struggling for identity, with its unique culture under threat (at times we felt like we could have been in any urbanized U.S. setting, with all the strip malls and fast food chains). That’s borne out by the numbers – at latest count, Puerto Ricans were essentially split 50-50 on the question of becoming a U.S. state or remaining a territory, with only 10% in favor of complete independence. Whatever happens, we wish Puerto Ricans all the best and hope that any decisions will help the island be better prepared for the future.