Complete Guide 2026-2028

Regent Caribbean Cruises

Experience the Caribbean Without Compromise

The Ultimate Luxury Caribbean Cruise

Imagine waking each morning to turquoise waters, white-sand beaches, and a new Caribbean paradise waiting just beyond your private balcony. On a Regent Seven Seas Caribbean cruise, every detail—from spacious suites and personalized service to unlimited shore excursions and gourmet dining—is designed to create a seamless luxury vacation.

Unlike traditional cruise vacations where costs quickly add up, Regent's all-inclusive approach lets you focus on the journey rather than the bill. Fine wines, premium spirits, specialty dining, gratuities, Wi-Fi, and immersive shore excursions are included, creating one of the most comprehensive luxury cruise experiences available.

Find Your Itinerary

What is your Caribbean Vibe?

Choosing the right Caribbean cruise isn't simply about selecting a ship—it's about matching your travel style with the destinations.

Eastern Caribbean

Perfect for luxury travelers seeking picture-perfect beaches, crystal-clear waters, and elegant island experiences. Discover the yacht-filled harbors of St. Thomas and the boutique shopping of St. Maarten.

Highlight Ports:

St. ThomasSt. MaartenAntiguaTortola

Regent Caribbean Experience

Explore the Caribbean Regions

Discover which slice of paradise suits your travel style.

What's Included in Your Caribbean Fare

Unlimited Shore Excursions in every port

Specialty dining at all venues

Premium spirits, wine, and champagne

Unlimited Wi-Fi for all devices

Pre-paid gratuities

Valet laundry service

Roundtrip airfare (on select voyages)

* Certain premium experiences may require additional reservations or costs.

When comparing the cost of a luxury beach resort, fine dining, and daily activities, Regent's all-inclusive model provides extraordinary value.

Unrivaled Value in the Caribbean

All-Inclusive Luxury

No Hidden Costs

Leave your wallet in your suite. Your fare covers almost everything, providing incredible peace of mind while you sail the Caribbean.

Unlimited premium spirits and fine wines
Specialty dining with no surcharge
Pre-paid gratuities for all staff
Unlimited shore excursions

Private Sanctuaries

Spacious Suites

Enjoy some of the largest balconies at sea, perfect for tropical lounging and taking in the panoramic views of the Caribbean.

Expansive private balconies
Marble-appointed bathrooms
Spacious sitting areas
Walk-in closets

Anticipatory Service

Personalized Service

With a high staff-to-guest ratio, your favorite drink is always waiting and every detail of your vacation is seamlessly managed.

One of the highest staff-to-guest ratios at sea
Butler service in Penthouse Suites and above
Personalized attention to dietary needs
Unobtrusive, friendly hospitality

Common Caribbean Cruising Mistakes

Booking Too Late

Peak winter holiday sailings sell out nearly a year in advance.

Assuming All Islands Are the Same

The difference between Eastern, Western, and Southern Caribbean is significant.

Missing Out on Excursions

Since they are included, book your top choices early so they don't fill up.

Overpacking

Regent includes valet laundry, so you can pack lighter than you think.

✦ LUXURY TRAVEL EXPERTISE ✦

Angela Hughes Authority & Credentials

CEO, Trips & Ships Luxury Travel

40+ YEARS EXPERTISE

Angela Hughes

Angela Hughes INSIGHTS & LEADERSHIPTrusted Greece Luxury Travel Authority

Angela Hughes has explored over 121 countries and spent more than four decades designing luxury travel experiences. She is widely recognized across the travel industry as a leading travel authority and active travel advocate.

KEY QUALIFICATIONS & ACHIEVEMENTS

Over 4 Decades Designing Luxury Travel Experiences
Explored 121+ Countries Across Seven Continents
Recognized Industry Leader & River Cruise Specialist
CEO & Founder of Trips & Ships Luxury Travel
Specialist in Active River Cruising & Multi-Generational Travel
Personal Relationships with AmaWaterways Executives & Staff

Direct consultation & VIP cruise amenities with Angela Hughes.Ready to Plan Your Dream Voyage?

The Regent Experience

Frequently Asked Questions

Expert Answers for Caribbean Cruisers

Regent includes unlimited shore excursions, specialty dining, premium beverages, unlimited Wi-Fi, gratuities, and luxury suite accommodations. Select voyages also include airfare and pre-cruise hotel packages.

It depends on your preference. Grandeur offers the newest, most contemporary luxury, Explorer offers lavish elegance, and Mariner offers classic luxury with a relaxed atmosphere.

Late November through April offers the best weather, avoiding the peak of hurricane season. However, holidays (Christmas, New Year) are the most expensive times to sail.

Yes, Regent is one of the most all-inclusive luxury cruise lines, meaning you can leave your wallet in your suite safe.

When you factor in the cost of a luxury beach resort, fine dining, premium drinks, and daily excursions, Regent's all-inclusive fare often provides exceptional value.

Regent visits destinations across the Eastern, Western, and Southern Caribbean, including St. Thomas, St. Maarten, Cozumel, Belize, Aruba, Curaçao, and Barbados.

Regent includes unlimited standard shore excursions in every port, such as island tours, snorkeling trips, catamaran sails, and historical walking tours.

Fares typically range from $6,000 to $12,000+ per person for a 7- to 10-night sailing, depending on the season, suite category, and ship.

Pack lightweight resort wear, swimsuits, sun protection, and comfortable walking shoes for the day. Evenings require 'Elegant Casual' attire (no shorts or t-shirts in dining rooms).

Regent is ideal for luxury travelers, couples, and those who want an effortless, all-inclusive vacation without crowds or hidden fees.