Caribbean Cruise from San Juan

  • 5 ports of call: Tortola, St. Kitts, Antigua, Dominica, and Barbados!
  • 7 nights on the Grand Princess, February 1- 8, 2026
  • From $805 including port charges!

For our 20th anniversary Cruise Retreat, we’ll set sail from San Juan to visit Tortola, St. Kitts, Antigua, Dominica, and Barbados.

Experience History, Beautiful Beaches, and Unique Flavors along with Diverse Cultures, Hidden Island Gems and more on this fabulous and unique itinerary.

Join Private Group Shore Excursions to Dense Rainforests, Visit Jagged Volcanoes soaring above azure and turquoise seas, and see Rare Birds, and Waterfalls too!

Add in some great food and entertainment, private events and dance parties in the company of some of the nicest and most fun people you’ll ever want to know, and you’ve got a vacation that just can’t be beat!!

BOOK NOW TO ADD SPECIAL PERKS:

  • Just $60/day for Drinks, WiFi, and Gratuities
  • $90/day for all this, specialty dining and more!
  • Solo Rooms Available
Book Now
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Details and Itinerary for HIV Cruise Retreat #20

Ports of Call

Puerto Rico

San Juan

The oldest city under the American flag, San Juan vibrates to a lively salsa beat. There’s an unmistakable zest in the air here. Perhaps it’s the stunning natural setting: the verdant peaks, tropical forests, and gleaming white-sand beaches. Or maybe it’s Puerto Rico’s mix of cultures, the blend and occasional clash of four centuries of Spanish heritage overlaid with a century spent as America’s only Commonwealth. Whatever the reason, San Juan is one of the most enticing ports in the Caribbean, and it only gets lovelier with age.
Tortola

Tortola

Once known as a hideaway for pirates and freebooters, the British Virgin Islands (BVI) are today a lure for sun worshippers and yachtsmen alike. Constant trade winds along the Sir Francis Drake Channel make for ideal sailing conditions, while the secluded beaches, incredible vistas, and friendly inhabitants make the islands a wonderful place to visit. Tortola, the largest island in the BVI, is home to Road Town, the islands’ capital. Browse the many small shops, enjoy a drink at a harbor café, or simply relax on the spectacular beach at Cane Garden Bay. The island’s mountainous terrain makes for fabulous views. For a real treat, take a ferry across the channel to Virgin Gorda, home of the famous Baths. At this unique beach, gigantic boulders create secluded coves and form picturesque grottos.
St. Kitts

St. Kitts

Jagged volcanoes soaring above azure and turquoise seas, dense rainforests in myriad shades of green, rolling fields of sugarcane–welcome to St. Kitts. St. Kitts presents an exotic landscape more common to Polynesia than the Caribbean. The islands’ terrain, rich soil, and climate made them ideal locations for raising sugarcane. In fact, St. Kitts was once the crown jewel of the Caribbean. During the 17th and 18th centuries, Spain, France and England vied for control of the island, with the English finally winning out in 1787. Today, British and French heritage is evident. Basseterre, the capital of St. Kitts, boasts fine, restored colonial buildings. Impressive Brimstone Hill Fortress, called the “Gibraltar of the West Indies,” is one of the most impressive fortresses in the Caribbean.
Antigua

Antigua

The largest of the British Leeward Islands, Antigua (pronounced an-tee-ga) boasts one of the Caribbean’s most spectacular coastlines with secluded coves and sun drenched beaches. The island’s rolling hills are dotted with stone sugar mills, relics from the bygone era when sugar was king. Historic Nelson’s Dockyard, where Admiral Horatio Nelson quartered his fleet in 1784, attests to Antigua’s long and colorful nautical history during colonial times. And St. John’s, the island’s bustling capital, offers visitors a wealth of boutiques, restaurants and pubs.
Dominica

Dominica

Dominica is an unspoiled Caribbean paradise. The vibrant, rich rainforest is home to rare birds, including Sisserou and Jacquot parrots. Streams tumble down mountain slopes and thread fertile valleys on their short route to the sea. Dominica is also home to the last Carib Indians. When Columbus made landfall on his second voyage of discovery, this fierce tribe managed to keep the explorer at bay. And while the island proved a lure for both British and French planters, Dominica somehow managed to escape the trammels of civilization. This former British possession, independent since 1978, today lures visitors from around the world with its unspoiled beauty. As the islanders fondly say, “Apres Bondi, c’est la terre” (After God, it is the land).
Barbados

Barbados

Barbados is one of the few Caribbean islands solely colonized by one nation. It’s no wonder Bajans describe their country as being “more English than England sheself,” surnames like Worthing and Hastings abound. But look around and you know you’re not in England: rich and fertile tropical fields meet a glistening, azure sea. The soft pastels of old chattel houses blend with the vibrant reds, oranges, and greens of roadside fruit stands. In short, Barbados exudes a charm all its own. Perhaps it is due to Bajan culture, that celebrated blend of English tradition and the African heritage brought to the island by slaves imported to work the sugar plantations. The potent brew which results flavors every aspect of island life, from music, dance and art, to religion, language and food.

Pre- or Post-Cruise Hotel Stay

You can start your vacation off right by adding a few nights before or after the cruise at our host hotel (TO BE ADVISED). We will have a special group rate, you can choose from one king bed or two doubles.  No deposit is required and you will only incur charges to your credit card upon checkout.

Ship and Cabin Details

ABOUT THE SHIP

With an atmosphere of comfortable elegance, tantalizing dining options and dazzling entertainment, your stay on board the Grand Princess will be anything but ordinary.

  • Refurbished: March 2019
  • Guest Capacity: 2,600 lower berths
  • Number of Crew: 1,150
  • Tonnage: 107,517

Rates begin at only $805.00 per person for an inside cabin (including port charge and taxes). Your Cruise Retreat rate includes all your meals, basic beverages and entertainment.  For $60/day more, you can add a drink package, free WiFi and cruise gratuities.  For $90/day more, you will also receive specialty dining and lots of other perks. Our shipboard events and excursions are all private.

Inside Cabin...From $805
Ocean View...From $875
Balcony...From $1185
Mini Suite...From $1635

The rates reflected were in effect as of March 2025. When you reserve we will find you the very lowest fare available.

  • All rates are per person based upon two sharing a cabin.
  • Single occupancy is two times the stated rates.  Triple and quad rates as well as suites or any other category are available upon request.  ** See additional details for Cruise Designs match program.

In order to participate in group activities or dine with our group, all reservations must be made through us (there are no exceptions).

Additional Details

With 200 anticipated guests in our group, you will feel at home right from your very first day. Our collection of amazing men and women are all-embracing. Included are private events such as cocktail parties and exclusive shore excursions. PLUS, on our days “at sea” we plan several fun shipboard events and activities. In the dining room we will have our own block of tables, which is always a great way to get to know people. Feel free to table-hop each night so you can meet as many people as possible. Our mission has always been, and continues to be, welcoming. You will feel at ease from the get-go as our members really look forward and take care of each other.

Although a predominantly gay group, we welcome everyone of all sexual persuasions. A contingent of heteros come every year and always have a blast and add tremendous energy to the entire group. We welcome your family, partners and friends regardless of serostatus.

Traveling solo? Fear not, as our cruises attract a large number of single travelers. We offer a cabinmate matching program to help keep your costs down, as a single occupancy cabin is up to double the normal rates.

It is most gratifying to see the large number of long lasting friendships that develop each year. Your new community awaits you. We are privileged to have many, many cruisers join us for three, five and even ten sailings. Some never miss a year! These repeat guests give you an inkling of a new extended family waiting to meet you.

Add These Special Perks as Part of Your Cabin Fare!

Drink Package

Enjoy a Beverage Package, which includes cocktails, wine, beer, fountain soda, bottled water, specialty coffees, teas and more.

Free Wifi

Stay connected with family and friends – posting, video chatting, sharing – thanks to the best Wi-Fi at sea.

Crew Tips Included

The cruise ship pays crew appreciation on your behalf, so the crew who takes such good care of you is taken care of too.

Specialty Dining & More

Buy our Premium Perks and receive unlimited Specialty Dining, Premium Liquor, Photos & more!
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