8-Day Atlantic Crossing: Halifax To Bermuda & Puerto Rico

Surrounded by natural treasures and glorious seascapes, Halifax is an attractive and vibrant hub with noteworthy historic and modern architecture, great dining and shopping, and a lively nightlife and festival scene. The old city manages to feel both hip and historic. Previous generations had the foresight to preserve the cultural and architectural integrity of the city, yet students from five local universities keep it lively and current. It's a perfect starting point to any tour of the Atlantic provinces, but even if you don't venture beyond its boundaries, you will get a real taste of the region.It was Halifax’s natural harbor—the second largest in the world after Sydney, Australia’s—that first drew the British here in 1749, and today most major sites are conveniently located either along it or on the Citadel-crowned hill overlooking it. That’s good news for visitors because this city actually covers quite a bit of ground.Since amalgamating with Dartmouth (directly across the harbor) and several suburbs in 1996, Halifax has been absorbed into the Halifax Regional Municipality, and the HRM, as it is known, has around 415,000 residents. That may not sound like a lot by U.S. standards, but it makes Nova Scotia’s capital the most significant Canadian urban center east of Montréal.There's easy access to the water, and despite being the focal point of a busy commercial port, Halifax Harbour doubles as a playground, with one of the world's longest downtown boardwalks. It's a place where container ships, commuter ferries, cruise ships, and tour boats compete for space, and where workaday tugs and fishing vessels tie up beside glitzy yachts. Like Halifax as a whole, the harbor represents a blend of the traditional and the contemporary.

With a permanent resident population of 1,500 households, Hamilton doesn't qualify as a major metropolis. Yet it has enough stores, restaurants, and offices to amp up the island’s energy level. Moreover, it has a thriving international business community (centered on financial and investment services, insurance, telecommunications, global management of intellectual property, shipping, and aircraft and ship registration), which lends it a degree of sophistication seldom found in so small a center. The central parishes cover the large area of Paget, Warwick, and Devonshire. These parishes are much sleepier than Hamilton and provide great nature and beach respites when you tire of city life. Convenient bus and ferry connections connect the parishes, so trips outside of Hamilton are easy and a fun way to get off the tourist track.

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port").Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.

Aruba, known as “One Happy Island,” is a sun-soaked paradise in the southern Caribbean, famous for its pristine white-sand beaches and crystal-clear turquoise waters. Visitors flock to Palm Beach and Eagle Beach for swimming, sunbathing, and water sports, while adventurous travelers can explore the island’s rugged interior at Arikok National Park, home to unique rock formations, caves, and native wildlife. The capital, Oranjestad, charms with its colorful Dutch colonial architecture, lively markets, and waterfront dining. Aruba’s warm, dry climate and steady trade winds make it perfect for sailing, windsurfing, and kiteboarding year-round. The island also boasts vibrant local culture, with a mix of Caribbean, Dutch, African, and indigenous influences celebrated in music, festivals, and cuisine. Friendly locals, luxury resorts, and a variety of attractions—from snorkeling and scuba diving to casinos and nightlife—ensure every traveler finds something to enjoy. Aruba truly offers a blend of relaxation, adventure, and cultural experiences.