Beyond the Port - Eat, Explore, Escape: A 7 day Southern Caribbean Cruise Itinerary

1) Port of Departure: Old San Juan, Puerto Rico

Old San Juan is a vibrant blend of history, culture and charm, perfect for a short but unforgettable getaway and the starting point of your cruise. Cobblestone streets lined with colorful colonial buildings create the backdrop for this centuries-old city, where every corner tells a story.
I highly recommend staying at Fortaleza Suites if you’re looking for a small, boutique and affordable option. It places you right in the heart of it all — just steps from the iconic blue brick streets and within easy reach of Old San Juan’s most treasured sites. The property offers warm, comfortable accommodations that reflect the local style, with colorful decor and a relaxed, homey atmosphere. It’s also a great choice for groups, with multiple apartment-style rooms that can comfortably host larger parties. Fortaleza Suites is also just a short walk or cab ride from the cruise ports, making it an especially convenient stay for cruise travelers.

Dinner at The Cave is a must to experience authentic Cuban cuisine. Their take on mofongo, a traditional dish made from mashed plantains and filled with tender meats or veggies, is rich, savory and unforgettable. The menu also offers a variety of Cuban favorites, like ropa vieja and lechón, that will satisfy any craving for bold, flavorful food. The restaurant’s unique ambiance, tucked into a dimly lit, stone-lined space, gives off an intimate, almost hidden-gem vibe — perfect for a relaxed, flavorful evening. Afterward, head to Café El Guirénex, a laid-back local with excellent mojitos and empanadas. It's a great spot to unwind with a drink in hand, enjoy the casual vibe, and mingle with locals and fellow travelers alike.

Before you leave, tour the old fort — Castillo San Felipe del Morro. This impressive 16th-century citadel overlooks the Atlantic Ocean and offers sweeping views, historic tunnels and massive stone walls that once protected the island. A walk through El Morro connects you to Puerto Rico’s colonial past and adds a sense of awe to your stay in Old San Juan.

Whether you're into food, history or just wandering beautiful streets, this quick trip delivers a memorable slice of Puerto Rico.

Balcony View from Fortaleza Suites

2) Day trip from Old San Juan: El Yunque National Forest - Natural Waterslide Hike

A day trip to El Yunque National Forest in Fajardo is an unforgettable adventure and a must-do before getting on the ship. Start your day by driving from Old San Juan to the forest, where you'll meet your guide from Paradise Tours for a private tour to one of the park’s most exciting features: the natural waterslide. The tour is led by passionate, knowledgeable guides who share fascinating details about the park’s diverse ecosystem, including the elusive coquí frog, whose calls echo throughout the rainforest.
The hike itself is best suited for those in good physical condition, as it involves walking through the river and navigating up muddy hillsides. While the terrain can be challenging, the effort is absolutely worth it when you reach the stunning swimming hole and natural waterslide.

El Yunque National Forest Natural Waterslide

3) Bridgetown, Barbados

A port stop in Barbados offers the perfect opportunity for a more personalized and authentic experience by skipping the typical ship excursions and opting for a local taxi driver. Once you disembark, simply ask one of the taxi drivers at the port to take you on a customized day tour. This approach allows you to get insider recommendations and experience Barbados from a local perspective, all while enjoying the flexibility of tailoring your itinerary to suit your interests.

Start your adventure with a tour of Bridgetown, the vibrant capital city. Explore the historic sites and take in the lively atmosphere that blends colonial charm with modern energy.

Afterward, head to the Nicholas Abbey Plantation House and Rum Distillery, where you can enjoy a fascinating tour of the plantation’s rich history followed by a rum tasting. This experience gives you a glimpse into the island’s heritage while savoring some of the finest rum produced on the island.

For lunch, make your way to Saavey Beach, where you’ll find an array of food trucks offering authentic, local Barbadian cuisine. From fresh fish to savory rotis and sweet treats, the food trucks provide a delicious and casual way to experience the island's flavors.

Nicholas Abbey Plantation House, Barbados

4) Port of Spain, Trinidad

A port stop in Port of Spain, Trinidad offers an exciting opportunity to explore the island, though it’s best to leave the city for a more scenic and safe journey across the island. While Port of Spain has a rich history as the capital, featuring historical sites like the Magnificent Seven (a row of beautiful colonial-style mansions) and Queen's Park Savannah, it’s generally not considered the safest area for tourists to explore on foot. Instead, your local driver can give you a more personalized and secure experience, taking you to the other side of the island, where the true beauty of Trinidad shines.

The drive over the mountains to Maracas Beach is an adventure in itself. The journey takes about an hour along narrow, winding roads that climb through lush tropical forests, offering breathtaking views of the island. The drive can be a bit nerve-wracking as you navigate the steep roads, especially since the locals drive on the left side of the road. But the stunning panoramas and the chance to see more of the island make it worth the trip. Once you arrive at Maracas Beach, you'll be greeted by golden sands and clear blue waters, the perfect spot to relax and unwind.

While at Maracas Beach, make sure to try the local bake n' shark — a popular Trinidadian dish. It consists of freshly fried shark meat served in a soft, fluffy bread roll (called a “bake”), often topped with a variety of condiments like lettuce, tomatoes, peppers and the signature hot sauce. It’s a must-try dish that offers a true taste of local culture. After enjoying your meal, spend the rest of the day soaking up the sun, swimming, or simply relaxing by the water.

Trinidad mountain views

5) Scarborough, Tobago

Upon arrival, take a taxi to Mt Irvine Beach, a hidden gem away from the usual tourist spots. This small, secluded beach is ideal for those looking to enjoy some peace and quiet. While it’s not the best spot for snorkeling, it provides a serene atmosphere to unwind, with food and drinks available at a small, local bar where you can grab a refreshing drink or a quick bite. After leaving Mt Irvine, head over to Store Bay for lunch, a lively spot with numerous local food options. Here, you can enjoy traditional dishes, including the delicious crab and dumplings, a Tobago specialty. Just be prepared: there are no shell crackers provided, so be ready for a bit of a curry mess as you dive into your meal, but it’s absolutely worth the effort. The flavors are rich and satisfying, making it a must-try during your visit. If you have some time left after your meal, you can take a dip in the beach here — primarily frequented by locals — before heading back to the ship. Store Bay offers a great spot to experience local life and enjoy the laid-back vibe of Tobago.

Mt. Irvine Beach

6) Castries, St. Lucia

The catamaran and snorkeling trip to the base of the Grand Pitons in St. Lucia is a must-do experience that will take up the entire day. The journey along the island’s rugged coastline offers breathtaking views of the iconic Grand Pitons, towering volcanic peaks that rise dramatically from the sea. While the snorkeling might not be the most vibrant, the stunning scenery and crystal-clear waters make it a memorable experience.

Onboard, you can relax with a refreshing rum punch while soaking in the sun and marveling at the landscapes. The trip is so captivating that it will leave you wanting to return to St. Lucia to discover more of the island’s natural beauty and hidden gems.

St. Lucia snorkel/swim site

7) St. Maarten,

St. Maarten offers a mix of adventure, stunning views and local charm. One of the top excursions is a horseback riding tour with Lucky Stables, which offers a unique experience of exploring the island on horseback. Lucky Stables is known for its friendly, professional staff and well-trained horses, ensuring a safe and enjoyable ride. The tour takes you through a tropical yet desert-like trail, offering panoramic views of the island's landscape. The highlight of the ride is a refreshing dip in the water at the end, where you can ride your horse into the crystal-clear sea for an unforgettable experience.

After the ride, head over to Maho Beach, just a short distance away, where you can watch planes fly overhead as they approach Princess Juliana International Airport. The planes fly incredibly low, making it a thrilling and unique experience.

For lunch, make your way to the Sunset Bar and Grill, a popular spot with an amazing view of the planes landing. Their fish tacos are a must-try — fresh, flavorful, and a perfect beachside meal to enjoy while taking in the sights and sounds of St. Maarten.

St. Maarten horseback riding trail

Maho Beach

During your cruise stops, you'll find that most places you visit accept credit cards, so cash is only needed for taxi drivers and tips. US dollars are widely accepted so, whether you're exploring local attractions or enjoying a beachside meal, you’ll be able to pay without worrying about exchanging currency.

One of the best ways to experience these destinations is by using local taxi drivers rather than booking everything through the cruise ship. This approach not only gives you a more personal experience, allowing you to connect with locals and get insider tips, but it’s also cost-effective. It’s a great way to support the local economy directly, while getting a local’s perspective on the area. Plus, without the rigid schedules of large tours, you can tailor your day to your interests and truly soak in the culture and charm of each place you visit.

For more inspiration and insider recommendations, visit our Cruises page.