San Juan, the capital of Puerto Rico, is rich in Spanish heritage, whether you’re wondering the cobblestone streets and plazas of the Old Town, or exploring the nearby beaches or lush rainforests, you’ll soon realise why this Caribbean island is one of the most popular departure ports for cruise passengers from around the world.
When is the best time to cruise from Puerto Rico?
Cruises from Puerto Rico are seasonal, with most ships operating from the island between the months of November through to April. Escaping on a Caribbean cruise during the cold British winter months is the perfect antidote to cure those winter blues. If you’re looking to celebrate the festive season in style why not cruise over the Christmas and New Year period, swapping the cold weather for warm Caribbean sunshine.

Which cruise lines sail from Puerto Rico?
Two of the newest ships at sea will call Puerto Rico home in the coming months. Norwegian Cruise Line‘s newest ship, the Norwegian Viva, will spend her maiden winter season in the Caribbean sailing 7-night port-intensive itineraries from San Juan. Another brand new vessel will make her debut in Puerto Rico, Virgin Voyages‘ Brilliant Lady will kick start her first sailings with a winter season exploring the Southern Caribbean on 7-night itineraries.
Royal Caribbean‘s family-friendly ship Jewel of the Seas will also sail out of San Juan from November 2023 through to March 2024 whilst those looking for a more luxurious adult cruising experience can opt for select sailings with Regent Seven Seas, Viking and Ritz Carlton.
Where do cruises from Puerto Rico go to?
From Puerto Rico, you’ll be able to explore some of the Southern and Eastern Caribbean’s most beautiful islands. Whereas cruises from the mainland USA tend to need a few days at sea before they reach the Caribbean, cruising from Puerto Rico allows you to experience a more port-intensive itinerary.
From the beautiful beaches of Barbados to the tropical vibes of Trinidad and Tobago, you’ll be sure to wake up on a different slice of paradise each day of your cruise. Some itineraries even call into the stunning ABC islands, the group of Aruba, Bonaire, and Curaçao, the three westernmost islands of the Leeward Antilles in the Caribbean Sea.
What should you do whilst you’re in Puerto Rico?
Welcome to San Juan, the capital of Puerto Rico and one of the most beautiful cities in the Caribbean, rich in Spanish heritage with its 17th-century architecture and historic buildings. You’ll have the opportunity to stroll around the grounds of one of the biggest fortifications built by the Spaniards in the New World, Fort San Cristobal. Explore its Main Plaza, “Garitas” watchtowers and authentic mortor balls.
A trip to Puerto Rico wouldn’t be complete without indulging in one of the island’s most popular exports. Catch a ferry across the bay from Old San Juan and join a guided tour of the distillery that produces most of the Bacardí rum consumed worldwide (which is A LOT considering it’s the number one rum in the world). You’ll be greeted with a Welcome Cocktail at the bat-winged Pavillion and can choose between three tour options: Historic Tour, Rum Tasting, or a Mixology Class. In the gift shop, you can even bottle your own premium rum directly from the barrel.
Cocktail lovers will want to make sure they head to the Caribe Hilton Hotel, which is the setting for two of the origin stories of the piña colada. The Caribe Hilton insisted that the recipe was crafted by Ramón “Monchito” Marrero, a bartender who worked at the hotel’s Beachcomber Bar and was commissioned to create a signature cocktail back in 1954. But, Ricardo García, another bartender at the Caribe Hilton at the time, alleged that he came up with the refreshing recipe that same year as a result of a coconut shortage that forced him to improvise. Either way, what better excuse to sip on a cocktail or two?
If you’re wanting to keep the drinks flowing and celebrate late into the night you should definitely head for Santurce’s market, La Placita, which is recognised as the centre of San Juan’s nightlife scene. The historic market plaza and its neighbouring roads host what becomes a bustling street party, particularly busy on Thursday and Friday nights. Alternatively, you could visit one of “The World’s 50 Best Bars,” La Factoria is a must for cocktails and salsa dancing. Located in the heart of Old San Juan, this lively speakeasy features craft drink variations and was even featured in the video to Luis Fonsi’s hit song “Despacito”.

Extend your stay?
Looking to explore further afield from Puerto Rico’s capital San Juan? Why not spend a few days exploring the Eastern side of the island. For energetic travellers, it doesn’t get much better than a hike through El Yunque – the only tropical rainforest in the U.S. – followed by a refreshing swim in a cool waterfall pool. There are also options to go rock climbing, abseiling etc.
Meanwhile, the northwest corner of the island is home to numerous beaches, offering a range of activity options. If you’re looking to relax why not spend a day on one of the island’s beautiful beaches, whilst for those looking to stay active you could always try your hand at surfing at María’s Beach. Then there’s Steps Beach for snorkelling and diving and the nearby Tres Palmas Marine Reserve for the best spot to look out for colourful marine life.