2027 San Juan to Barbados – Azamara Cruise

Another cruise vacation—with extras! When choosing a cruise, we first look for an itinerary with embarkation and disembarkation ports where we’d like to spend a few days. We enjoy combining a land-based vacation with a ship-based one. The pre-cruise stay is especially helpful when jet lag is a concern, giving us time to settle in before the ship sets sail.

For this trip, our embarkation port is San Juan, Puerto Rico. We’ve visited Puerto Rico several times and have always enjoyed Old San Juan, so it was an easy choice for our pre-cruise stay.

We’ve booked The Decanter, right in Old San Juan. The hotel offers Wi-Fi, a rooftop bar, a smoke-free environment, and coffee in the lobby. We reserved a room with a terrace that’s advertised as having “breathtaking views of the historic San Juan Cathedral and the vibrant Luna and San José streets.” Sounds fabulous—and just what the doctor ordered after the usual airports, flights, and travel-day hassles.

San Juan isn’t a particularly long journey from home, so we may have little—or no—jet lag to recover from. We’re allowing ourselves four days before the cruise, with a very low-key plan: walk around Old San Juan, enjoy the views, and find good places to eat.

Our walking will have a purpose: finding our next lunch or dinner! Old San Juan has plenty of highly rated restaurants, so we can simply see what sounds good when hunger strikes. No rigid schedule required.

On the map, our hotel is marked with the large red “D.” The two terminals at the bottom are possible places to board the ship; we’ll confirm which one we need closer to departure. The other red circles with the white fork and knife mark potential dining spots—and they’re only a small sample of what Old San Juan has to offer. All in all, it looks like a great place to start the trip.

Then It’s Time to Cruise!

After four days in San Juan, it’s time for the main event: our cruise aboard the Azamara Quest. This nine-calendar-day itinerary, including embarkation and disembarkation days, visits several islands in the eastern Caribbean. We leave San Juan for Virgin Gorda, then head back to St. Thomas before continuing south through the islands to Barbados.

With no sea days, this is going to be a port-packed, go-go cruise! That’s another reason we’re allowing time in San Juan beforehand: we want to be rested and ready for all those ports, evenings, shows, and onboard fun.

We cruised the Caribbean frequently in the 1990s, so we’ve visited many of these ports before. Azamara’s ships are smaller than the large cruise ships we’re used to, though, and we’re curious to see whether that means easier access to the port towns. We’ll find out firsthand—and report back!

All Aboard the Azamara Quest!

This will be our first Azamara cruise. We’ve taken quite a few Princess cruises and enjoyed them all. In 2025, we tried Celebrity because Princess didn’t offer the itinerary we wanted. Let’s just say that experience did not win us over—we’ve decided we won’t be booking another Celebrity cruise. That experience has made us a little cautious about trying a different cruise line.

So why Azamara? We found what looks like a fabulous 2028 Asia itinerary, from Hong Kong to Singapore, and Azamara is the line offering the cruise we want. We decided that a trial run was the sensible approach. If we discover anything about Azamara that doesn’t suit us, we can hopefully plan around it—or make a better-informed decision—before committing to the longer Asia trip. The goal is to improve our chances of having a wonderful 2028 adventure.

As we always do, we started by taking a detailed look at the ship’s public areas. Here’s our deck-by-deck guide to the Azamara Quest, with the venues listed roughly from front to back.

The Quest has public areas on four decks: 5, 9, 10, and 12. Here’s what we found on the ship plans.

Deck 5

• Cabaret Lounge — Full bar and live entertainment, including solo performers and bands.
• The Den — A lounge focused on destination-themed experiences.
• The Quest Shop — Apparel, sundries, handbags, candy, souvenirs, and more.
• Indulgences — Fine jewelry, watches, and other luxury items.
• Mosaic Café — Coffee bar with morning pastries and afternoon light bites.
• Discoveries Bar — A possible favorite for pre-dinner and after-dinner drinks.
• Discoveries Restaurant — The main restaurant, with open seating.

Deck 9 — Pool Deck

• Salon
• The Sanctum Spa
• Fitness Center — Includes treadmills.
• Pool and Pool Bar — A place for a swim and a refreshing drink.
• Swirl & Top — Self-serve frozen yogurt station.
• The Patio — Pool grill during the day and open-air sit-down dining in the evening.
• Windows Café — Buffet with outdoor tables and a menu that changes daily.
• Sunset Bar — Open-air seating next to Windows Café.

Deck 10

• The Living Room — Conversation, games, speakers, coffee, drinks, and tapas.
• The Card Room — A place for card games.
• In Touch — A small computer and internet station.
• Jogging Track
• The Drawing Room — The ship’s library.
• Aqualina Specialty Dining — Italian cuisine.
• Prime C Specialty Dining — Steak and seafood.

Deck 12

• Shuffleboard - A classic cruise-ship favorite. Let the competition begin!
• Sun Deck - An open-air spot to relax and soak up the sunshine.

Our Day-by-Day Cruise Schedule

Here’s our current schedule, including the planned arrival and departure times. We’ll use our booking documents as the final authority if the cruise line changes anything before sailing.

Cruise Ports:

Virgin Gorda, BVI(day #2): is the third-largest and second-most populous island in the British Virgin Islands (BVI), spanning about 8 square miles with a population of nearly 3,500 people. Christopher Columbus named the island "Fat Virgin" in 1493. Virgin Gorda is famous for its unusual geologic formation known as "The Baths", located on the southern end of the island. At the Baths, huge granite boulders lie in piles on the beach, forming scenic grottoes that are open to the sea.

Charlotte Amalie, St. Thomas, USVI(day #3): Charlotte Amalie is the capital and largest town of the U.S. Virgin Islands, located on the southern shore of Saint Thomas. Established as a Danish colony in 1672 and named after the Danish queen. Purchased by the United States from Denmark in 1917 during World War I due to the harbor's strategic military value.

St. John’s, Antigua(day #4): Saint John's is the capital and largest city of Antigua and Barbuda, located on the northwest coast of the island of Antigua. It functions as the nation's commercial, administrative, and cultural heart, featuring a deep-water harbor that welcomes major cruise ships. Vibrant waterfront commercial districts offering duty-free shopping, local boutiques, art galleries, and restaurants right by the cruise terminals.

Saint-Pierre, Martinique(day #5): An historic coastal town and commune in Martinique, located at the foot of Mount Pelée. Founded in 1635 by Pierre Belain d'Esnambuc, it was once the cultural and economic capital of the island, famously known as the "Paris of the Caribbean". Before 1902, Saint-Pierre was Martinique's most vibrant and important city, boasting grand architecture, a theater, and bustling commerce. On May 8, 1902, Mount Pelée erupted catastrophically, unleashing a superheated pyroclastic flow that destroyed the town and killed nearly all of its 30,000 residents in mere minutes. Only a couple of people survived the initial blast, most famously Louis-Auguste Cyparis, a prisoner confined in a thick underground solitary confinement cell.

Port Elizabeth, Bequia, St. Vincent and the Grenadines(day #6): Bequia is the gateway to the 32 islands and cays that comprise the Grenadines. Port Elizabeth is the capital town of the Grenadines Parish, located on the island of Bequia in Saint Vincent and the Grenadines. Named in 1937 after Princess Elizabeth (later Queen Elizabeth II) to commemorate her parents' coronation. Port Elizabeth is an authentic, laid-back Caribbean port town featuring colourful wooden buildings, boutique shops, and a lively waterfront. It serves as a major hub and favorite stop for sailors, yachts, and cruise tenders

St. George’s, Grenada(day #7): Saint George's is the capital and main port of Grenada, located on a horseshoe-shaped natural harbor on the island's southwestern coast. Founded by the French in 1650, the city is renowned for its pastel-colored colonial buildings, steep volcanic hillsides, and rich maritime heritage. The historic, horseshoe-shaped inner harbor and waterfront promenade lined with shops, cafes, and seafood restaurants. Fort George is a hilltop fortress built by the French in 1705 that offers panoramic views of the town and harbor.

Scarborough, Tobago, Trinidad and Tobago(day #8): Trinidad and Tobago is an island country in the southeastern West Indies. It consists of two main islands—Trinidad and Tobago—and several smaller islands. Scarborough is the economic, cultural, and administrative capital of the island of Tobago. Located on Rockly Bay in southwestern Tobago with a population of about 17,500. Home to Fort King George, an 18th-century British fortification overlooking the coastline that features original cannons, barracks, and the Tobago Historical Museum. Scarborough Botanical Garden is a lush 10-acre green space with exotic tropical plants and vibrant birdlife.

Barbados — After the Cruise

Our cruise ends in Bridgetown, Barbados. Our lodging is more than four miles outside town, so we plan to explore a few highlights in Bridgetown before taking a taxi to our hotel.

Possibilities include the historic Parliament Buildings, the Careenage harbor, the Nidhe Israel Synagogue, and the shipwrecks of Carlisle Bay. We haven’t booked any Bridgetown activities yet; we’re still researching and will decide what appeals most as the trip gets closer.

We’ll spend three nights at the Coral Mist Beach Hotel. Rooms feature private balconies overlooking the Caribbean Sea, air conditioning, flat-screen TVs, Wi-Fi, and kitchenettes with a microwave, refrigerator, and coffee maker. The hotel also has an on-site restaurant and bar/lounge, room service, a fitness room, and an airport shuttle for the end of our stay.

After four days exploring Old San Juan, nine days aboard the Azamara Quest, and three nights in Barbados, we’ll have sampled both shipboard life and two Caribbean destinations on land. We’re looking forward to the trip—and especially to finding out whether Azamara is the right fit for our 2028 Asia adventure!