Forget Hawaii, Retire To Puerto Rico's Coastal City With Crystal-Clear Waters, Tasty Eats, And Warm Winters

Aguadilla is on Puerto Rico's northwest coast and is known for all things water-related, with a name that translates to "the place of the water" in English. Not only is Aguadilla among Puerto Rico's five best cities for a vibrant, warm winter vacation, but after visiting, you may want to live here permanently. For those approaching retirement, Hawaii is often on their wishlist when comparing islands. However, Puerto Rico, a U.S. territory, is also home to top-tier beaches and coastal communities, including some that are just a few miles from Aguadilla.

Not only is Puerto Rico relatively affordable for homeownership, but its day-to-day living expenses are also significantly lower than other islands like Hawaii. Forget the freezing temperatures of the states, and move to Puerto Rico, where average temperatures are in the 70s and 80 (Fahrenheit) year-round. Aguadilla shares a coast with about a dozen clear-water beaches, golf courses to fill your time, an art museum, delicious restaurants, and historic landmarks that are perfect for retirees to balance relaxation and an active lifestyle.

Aguadilla also has its own international airport, called Rafael Hernández International Airport, which is only about 6 miles from the city center — easily accessible by car or taxi. Plus, flights to Puerto Rico tend to be much cheaper than long-haul flights to Hawaii. With lower everyday costs, cheaper flights to the continental U.S., affordable housing, and beautiful beaches on the horizon, Aguadilla is an exceptional choice to spend your golden years.

One of the biggest advantages of settling in Aquadilla is that you don't need a passport to retire to this Caribbean island, where the dollar goes a long way. A study conducted by Realtor.com in 2025 reported that Hawaii placed among the least affordable housing markets in the country, with a median home listing price of over $800,000. Meanwhile, in Aguadilla, the median home value is $150,800, according to the U.S. Census Bureau.

Puerto Rico tends to be substantially more affordable than Hawaii across the board. According to the website MyLifeElsewhere.com, the Aloha State is 82.5% more expensive than Puerto Rico (as of this writing). Going out to eat is about 43% cheaper in Puerto Rico, buying groceries is about 41% less, and other cost-of-living expenses are easier to manage on a fixed income.

Put your saved money to good use in Aguadilla. Play a round of golf at the Punta Borinquen Golf Course, which is open to the public, and while you are in the area, check out the ruins of a lighthouse. Built in the 1700s by the Spanish, Punta Borinquen Lighthouse is one of the most historically significant sites in the town. For an indoor activity, check out the Museo de Arte de Aguadilla y del Caribe, which exhibits artwork from Puerto Rican and Caribbean artists. To practice your Spanish, head to the Aguadilla Farmers Market for fresh fruit and produce. Or walk along the waterfront promenade called Paseo La Real Marina for sunset views and people-watching.

The city is home to many incredible beaches, including Puerto Rico's tropical beach with rainbow fish and a sunken pier that looks like a postcard come to life. Located just 4 miles from town, Crash Boat Beach was ranked the second-best beach in the territory by U.S. News & World Report in 2025. The city is home to over 10 beaches, where you can dive, snorkel, and swim in turquoise, almost-transparent waters. Surfer's Beach is great for experienced surfers who can handle the swells. To rent a surfboard, head to the Surf Zone near the beach. Farther north of town, Las Cascadas Water Park is one of the most fun water parks to check out in the Caribbean, according to reviews.

There's a variety of restaurants to try that serve up American comfort food, Thai dishes, steak, Chinese food, Italian, sushi, and seafood. But the Puerto Rican restaurants arguably outshine the rest. Local favorites like Desecheo feature Caribbean fare and Latin American cuisine. As Aguadilla's No. 1 restaurant on Tripadvisor, the menu includes chuleta kan-kan, a popular bone-in pork chop that's popular on the island, with the chicharrón-like, crispy skin still attached.

One reviewer, Eden A., on Yelp said, "If you're looking for a good home cooked Puerto Rican meal, this place is it. I had the chuleta kan-kan which was sensational with a side of white rice, beans and sweet plantains. The majority of the people had mofongos which were also delicious. The alcapurrias were good as well for appetizers." Other appetizers include lightly battered shrimp, plantain chips, queso frito (fried cheese), breaded fish bites, and crispy chicken strips. A great way to end your night is by enjoying a homemade brew at Boxlab Brewing Company, such as the Sonera, a blonde ale with notes of cherry and lime.