Puerto Plata, Dominican Republic, is a vibrant city on the northern coast known for its rich history, stunning beaches, and lush landscapes. Visitors can ride the only cable car in the Caribbean to the top of Pico Isabel de Torres for breathtaking views and explore the botanical gardens. The city is also home to the historic Fort San Felipe, a 16th-century fortress offering a glimpse into the region's colonial past. The Amber Museum showcases exquisite Dominican amber, while the bustling Malecón, a seaside promenade, is perfect for enjoying local cuisine, shopping, and the lively culture of Puerto Plata.

Lovely Samana is an environmental treasure. Untamed, with plenty of coves, bays, mountains, waterfalls and diverse geography zones where nature abounds. The protected natural area known as Los Haitises National Park is home to two endemic mammal species, the Hispaniolan hutia and the Hispaniolan solenodon along with numerous birds including the brown pelican, frigate birds, barn owls, stygian owls and Hispaniolan amazons. Its beaches are famous for body-boarding and wading.

For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.

• The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns.

 
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.

Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away. 

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.