- I worked for two cruise lines in six years, so I’ve been to some amazing warm-weather ports.
- San Juan, Key West, and Cozumel are gorgeous places to explore.
- I also enjoy Nassau, Bahamas, which is a common port on Caribbean cruises.
As a former crew member on cruise ships who spent six years working for two different cruise lines, I’ve seen my fair share of beachside ports.
Here are my five favorites, based on the variety and quality of experiences I had during my visits.
San Juan, Puerto Rico, has a historic district that sets it apart from other ports
San Juan’s cobblestone streets and colonial architecture draw tourists to the Puerto Rican capital. It’s also home to historical forts, beautiful beaches, and a vibrant culture.
If you’re interested in learning how to surf, you’ll probably have an opportunity to do so in San Juan, whereas some other Caribbean ports don’t have enough waves. But for me, the historical and cultural attractions outweigh the pull of the beaches and other water sports.
I recommend taking a historical walking tour of Old San Juan or signing up for a culinary tour. The Santa Maria Magdalena de Pazzis Cemetery is remarkable and one of the most impressive cemeteries I’ve ever visited.
Get a taste of everyday life by purchasing a kite and flying it on the rolling green lawns by the fort of San Felipe del Morro Castle. Then, take a walk along a gorgeous promenade called the Paseo de la Princesa, watch people dance in the street, and sample food from the local market.
Just be aware that if you head to the popular Fortaleza Street in Old San Juan, you’ll run into Instagrammers posing underneath the umbrellas that are suspended above the street.
Cozumel, Mexico, offers incredible marine life, archaeology, and beaches
Cozumel, an island off the coast of the Yucatán Peninsula, is a very popular cruise destination.
People come here for the incredible beaches, marine biodiversity, and water sports. There are also plenty of shops, restaurants, and beach bars.
Cozumel isn’t far from mainland Mexico, so many cruises offer tours of the Mayan ruins in Tulum or Chichén-Itzá. I’ve never had the opportunity to visit the latter, but the ruins in Tulum are incredible.
The island is a great place to try snorkeling, scuba diving, or other marine sports. Affordable dive schools offer snorkel and scuba lessons for all levels. The marine life is beautiful, and the instructors teach you everything you need to know.
You also can’t go wrong with getting a day pass to a beach resort or checking out the low-key beachside bars along the coast.
Just think twice before renting a scooter unless you have extensive experience riding them. I’ve heard many stories about people who rented scooters in port and have yet to hear one with a happy ending.
Key West, Florida, is a blast to explore by bike
Key West’s architecture, quaint shops, restaurants, and entertainment venues make the scenic, vibrant town a great holiday destination.
The beaches here aren’t the best, in my opinion, but Key West is still a good place for catamaran rides, snorkeling, parasailing, or glass-bottom boat excursions. If you’ve never ridden a jet ski or wave runner before, Key West is a great place to do it.
Of course, you can do these activities in other ports, but it’s the Old Town, the historic district, that makes Key West special.
Guided tours enable you to experience Old Town’s history, architecture, and culture. You can take the Conch Tour Train or the Old Town Trolley Tour, but I’d personally opt for a bicycle tour. I believe the best way to experience Key West is to rent a bike and explore the Old Town on your own. If you’re traveling with another person, you can even rent a tandem bike.
There’s so much to do and see in Key West. The Key West Butterfly and Nature Conservatory is one of the better butterfly gardens I’ve visited. However, I don’t think it’s worth waiting in the long line of people waiting to take photos in front of the Southernmost Point Buoy, which marks the southernmost point of the continental US.
Nassau, Bahamas, attracts a lot of tourists, but there’s also plenty to do away from the crowds
Although the Bahamas are technically part of the North Atlantic Ocean and not the Caribbean, this nation’s ports are often included in Caribbean cruise itineraries.
Nassau, probably the most well-known Bahamian port, is a great place for snorkeling, a catamaran experience, or a day at the beach. It has Atlantis, which has a casino, aquarium, and fun water park.
If you’re looking to cut costs during your trip, head to Cabbage Beach on Paradise Island, just a short drive from Nassau. It’s a beautiful public beach with no entry fees or pass requirements. Just bear in mind that it offers no facilities or public bathrooms.
To avoid the Atlantis crowds, consider visiting the Graycliff Hotel. It doesn’t seem to get as many visitors, is located right by the ocean, and has a beautiful pool and a cigar factory. Built in the 18th century, Graycliff has a rich history involving pirates, royalty, and celebrities.
Philipsburg, Sint Maarten, is packed with adventure — from plane-watching to horseback riding
This Caribbean island is split into two sides: Sint Maarten, a Dutch territory, and Saint Martin, a French territory. So if you’re trying to experience as many cultures as possible on your trip, this island can help you kill two birds with one stone.
Cruise ships usually dock in Philipsburg, the capital of the Dutch side. It’s known for its cobblestone streets, brightly colored buildings, and expansive beaches.
One of the island’s most visited attractions is Maho Beach. It’s located right by the Princess Juliana International Airport, so people line up to watch the planes fly close to the ground right before they land. And while you’re in Sint Maarten, horseback riding in the ocean is another experience worth having.
If you’re a “Star Wars” fan, you’ll get a kick out of The “Yoda Guy” movie exhibit, a small museum started by Nick Maley, a special-effects makeup artist who helped bring Yoda to the screen.
Tourists looking for some healthy competition shouldn’t miss an excursion with 12 Metre Regatta aboard America’s Cup race yachts. You learn to sail as you race against another team of novices around the course. It ended up being more fun than I expected, which might be due to the fact that my team won.
Honestly, I can’t think of any experiences that I wouldn’t redo here.