Western Caribbean Holiday Cruise

December 17, 2023 thru December 27, 2023

Celebrate the holiday with Pleasurebent Tours and Princess Cruises!

Ancient Mayan ruins rise up from the jungle floor, breaking the pristine beauty of the rainforest to remind all who cruise the Western Caribbean of its deep cultural heritage. White-sand beaches and pristine azure waters are just the beginning with this region of the Caribbean. With just a little exploration on a Western Caribbean cruise, you can open up a world of jungle adventures, breathtaking barrier reefs and powerful cultural connections unlike any other.

Enjoy sweeping views from one of more than 1,400 balconies on Regal Princess or stroll on the SeaWalk®, a glass-floor walkway extending 28 feet beyond the edge of the ship! From the tranquil Sanctuary, a retreat reserved for adults, to the dazzling Princess WaterColor Fantasy light and water show and more, you’ll find diversions for every mood.

Find out more information about the Regal Princess cruise ship, with a 3560 passenger capacity, by clicking here.




All transfers and roundtrip air included!


10 days, 10 nights

Activity Level 2



All meals aboard ship included!




Roundtrip Door to Door Livery Service Included

Tour Highlights

  • Roundtrip air transportation included
  • Costa Maya
  • Belize City
  • Roatan
  • Grand Cayman
  • Jamaica
  • Plus much much more!


  • Roundtrip air transportation to San Diego
  • 10 Day Cruise
  • All transfers
  • Roundtrip door to door livery service
  • All meals aboard the cruise
  • Baggage handling (for 1 piece)
  • Cruise credits as described
  • Services of a Pleasurebent Tours escort (with 15 or more booked)
  • Port charges, taxes and gratuities for included items

Day 1 - Cruise Departure

We fly from Tucson to Houston, where we transfer to the Port of Galveston to board our cruise ship and sail into the Western Caribbean!


Days 2 & 3 – At Sea

Today is a day at sea. Relax, eat a great meal and enjoy the many cruiseship activities.


Day 4 – Montego Bay, Jamaica

Today we stop in Jamaica. One of the most popular beaches in Jamaica with both locals and travelers, Ocho Rios Bay Beach has everything needed for a relaxing day enjoying the Caribbean weather. Soft sand, crystal-clear water, plentiful loungers and ice-cold beverages. Visit Ocho Rios Bay Beach on a Jamaican cruise!

Many optional excursions ranging in price.


Day 5 – Grand Cayman, Cayman Islands

Cruise to Grand Cayman, once home to pirates and scoundrels striking fear into all who sailed near, now stands as one of the most prosperous islands in the entire Caribbean. Meet sea turtles and stingrays in their natural habitats, snorkel through breathtaking shipwrecks and stroll through the capital of Georgetown for world-class dining, shopping and historic architecture.

( Water Shuttle Required, Wheelchair Access Limited )


Day 6 – Roatan, Honduras

Sitting atop an ancient coral reef system, surrounded by gorgeous crystal blue waters and featuring a lush tropical environment, the island of Roatan looks every bit the Caribbean wonderland. Visit the local iguana farm with over 3,000 iguanas roaming the grounds, snorkel and dive the pristine local reefs or sunken ships and Mayan artifacts, or just sit on the picture-perfect beach and relax without a care in the world.

Many optional excursions ranging in price.


Day 7 – Belize City, Belize

Nestled among lush rainforests teeming with life and situated on the western edge of the Caribbean Sea, Belize City is a paradise for those looking to have an unparalleled eco adventure. Take a relaxing inner tube ride down a river and through ancient caves once used for rituals by the Maya, ride horses through a stunning nature park with hundreds of species, and snorkel through the northern hemisphere’s largest barrier reef on a cruise to Belize!


Day 8 – Costa Maya (Mahahual), Mexico

Located in the south of Quintana Roo, Grand Costa Maya is one of the Mexican Caribbean’s hidden gems. The gateway to the region is Quintana Roo’s capital city of Chetumal, whose name in Maya means “place of the red wood.” You can also reach Chetumal on a four-hour drive from Cancun, passing through Riviera Maya’s destinations and Maya Ka’an along the way.

Many optional excursions ranging in price.


Days 9 & 10 – At Sea

Today is a day at sea. Relax, eat a great meal and enjoy the many cruiseship activities.


Day 11 – Disembark, Fly Home

We arrive into Galveston from a glorious holiday cruise on the Western Caribbean, with vivid memories and new friendships, and fly back home afterwards.


Itinerary subject to change.

Package Pricing

L - Inside


Deposit: 20% holds your space!

BD – Balcony


Deposit: 20% holds your space!

DB - Deluxe Balcony


Deposit: 20% holds your space!

MB - Mini-Suite


Deposit: 20% holds your space!

*Price per person, including air from TUS, double occupancy

Single occupancy upon request, limited availability

Deposit: 20% holds your space!

Final Payment Due:

September 13, 2023

Deposit: n/a

Price Includes

Roundtrip air transportation to Houston
10 Day Cruise
All transfers
Roundtrip door to door livery service
All meals aboard the cruise
Baggage handling (for 1 piece)
Cruise credits as described
Services of a Pleasurebent Tours escort (with 15 or more booked)
Port charges, taxes and gratuities for included items

Booking Policy



  • None – Through September 13, 2023
  • 25%* – September 14, 2023 – October 17, 2023
  • 50%* – October 18, 2023 – November 14, 2023
  • 75%* – November 15, 2023 – November 28, 2023
  • 100% – November 28, 2023

We pride ourselves on great service and an enjoyable experience for all, and will go over our booking policies after you make your request for booking. If you’d like to learn more about our booking policies before your trip, give us a call at (520) 325-8839, or visit our Booking Policies page. Click here for more information on our booking policies.

Travel Insurance

We recommend that all travelers purchase a travel protection plan to help protect themselves and their trip investment. Travel protection plans can provide coverage for trip cancellation, trip interruption, emergency medical expenses and emergency evacuation/repatriation, trip delay, baggage delay, and more. For your convenience, we offer the following plan for this tour:


360° Adult Group Choice Flyer– Provides an overview of benefits and coverage limits

360° Adult Group Choice Policy – Provides the full coverage term details, including exclusions and limitations

Cost varies depending on package price. Cost may be more or less depending on your total trip cost. If you do not wish to purchase now, the plan can be purchased any time prior to final payment.

Contact us to purchase. If you have questions about coverage, please review the policy or contact Travelex Insurance Services at 888.574.7026 or email [email protected]. Travelex Insurance Services, Inc. CA Agency License #0D10209. Travel Insurance is underwritten by Berkshire Hathaway Specialty Insurance Company; NAIC #22276. RWF


For your reference, we send to you a detailed itinerary approximately 3-4 weeks prior to the scheduled tour departure. This has day-by-day times and events, hotel information where you can be reached in case of an emergency, and airline information.

The times listed on the itinerary are all approximate. We cannot be held responsible for schedule changes due to unforeseen circumstances with weather, transportation agents, highway conditions, hotels or contracting agents.


Level 2: Relaxed

Expectations: This tour requires light physical activity combined with shorter travel days. Tour members should expect intermittent walking, with occasional slight inclines and stair climbs, including boarding the cruise ship. Activities may include an occasional city or nature walking tour, stopping along the way. Guests should be able to climb a set of stairs, walk up or down slight slopes and navigate some uneven terrain or cobblestone.

Appropriate for: Travelers who are somewhat physically fit and comfortable with longer days of touring and able to cruise.

Visit our Activity Level Ratings page under Plan Your Tour for full information on the ratings system.


It is always a good idea to carry on your person a list of medications that you are taking and an emergency contact phone number while you are traveling. And we suggest making a copy of the itinerary and provide it to a friend or family member.


The traditional end-of-tour gratuity to your tour director is not included. If you feel your Tour Director helped you enjoy your tour, we suggest you enclose a gratuity in an envelope and present it individually at the end of the tour. Simply as a guideline, one may consider a per person, per day gratuity of $8.00 per tour guide as an average to be modified by one’s own personal experience. All hotel porterage fees are included. We also include the gratuities for the coach/livery drivers. Maid tips are not included.


For your convenience we have a (round-tour) door-to-door pickup service with each multi-day tour. (This service is not available to all clients depending on your location.) Approximately 2 to 3 days prior to the departure date you will receive a call from our office and we will tell you your assigned pickup time. (These times can vary up to 15 minutes depending on traffic.)


If you would like to request special accommodations at the hotel(s) where we are lodging, please call us as soon as possible and we will forward these requests for you. The phone numbers of the hotel(s) where we are staying are listed on the itinerary.

Many hotels around the country have instituted a "reconditioning fee" of $300 or more that is levied upon a guest that smokes in a non-smoking room. If this occurs during our tour you will be responsible for paying this fee to the hotel prior to check-out.


We pay close attention to your requests but please realize that these are merely requests and cannot be guaranteed.


Pleasurebent Tours acts solely as agent in arranging hotels, transportation, sightseeing, baggage-handling and other services and does not assume any liability for injury, damage, loss or delay due to any act or default of any company or person. We, along with our subcontractors, reserve the right to make changes to an itinerary if it is necessary for the proper handling of a tour.

Inquire About This Tour

Submit your inquiry for more information about a tour. We will get back to you with a (human) response as soon as possible. During the week that’s usually within a couple of hours. Evenings and weekends may take us a little bit longer. Please note that this is an inquiry for tour bookings only and does not constitute or confirm a reservation on a tour.

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Call 520.325.8839 to Book Today!

If you aren't ready to inquire by email or would rather call and speak to a team member, we look forward to hearing from you.

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