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Bermuda Bliss

Summary

Embark on a voyage from the East Coast to San Juan with an overnight in St. George’s, Bermuda. Indulge in the luxury of multiple sea days, where you’ll have uninterrupted relaxation. Explore the UNESCO World Heritage Site of St. George’s, Bermuda. Take in the charming streets lined with colonial buildings, visit the iconic St. Peter's Church, one of the oldest Anglican churches in the Western Hemisphere, and discover the fascinating history at the Bermuda National Trust Museum. For nature enthusiasts, St. George's offers stunning coastal views, and Tobacco Bay provides an opportunity for snorkeling in crystal-clear waters teeming with marine life. Arrive in the historic and vibrant city of San Juan, Puerto Rico. Traverse the cobblestone streets of Old San Juan, visit ancient forts, and immerse yourself in the rich local culture. From colonial charm to lively markets, San Juan welcomes you with a blend of history and Caribbean flair.

Cruise line Windstar Cruises

Ship Star Pride

Duration 10 nights

Type Ocean Cruise

Regions Caribbean,
Americas,
South America

Itinerary & Map

Boston, Massachusetts → San Juan (Puerto Rico) 11 days · 6 ports · 1 sea day
Day 1 Boston, Massachusetts Embark

There’s history and culture around every bend in Boston—skyscrapers nestle next to historic hotels while modern marketplaces line the antique cobblestone street...

Full description
Day 4 Hamilton Overnight

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...

Full description
Day 5 Hamilton and Saint George

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...

Full description
Day 6 Saint George
Day 9 Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in...

Full description
Day 10 At Sea
Day 11 San Juan (Puerto Rico) Disembark

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, radiat...

Full description
Scroll for all 11 days
Route overview map
Day 1 Boston, Massachusetts Embark

There’s history and culture around every bend in Boston—skyscrapers nestle next to historic hotels while modern marketplaces line the antique cobblestone street...

Full description
Day 4 Hamilton Overnight

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...

Full description
Day 5 Hamilton and Saint George

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...

Full description
Day 6 Saint George
Day 9 Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in...

Full description
Day 10 At Sea
Day 11 San Juan (Puerto Rico) Disembark

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, radiat...

Full description

Boston, Massachusetts

There’s history and culture around every bend in Boston—skyscrapers nestle next to historic hotels while modern marketplaces line the antique cobblestone streets. But to Bostonians, living in a city that blends yesterday and today is just another day in beloved Beantown.

Hamilton

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.

Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

San Juan (Puerto Rico)

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.

Date & price

Departs

Fri 22 Oct 2027

from £3,056 pp

Enquire now Call 020 7590 0610

Per person, based on two sharing, cruise only. Updated daily and confirmed when you book.

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Fri 22 Oct 2027
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