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Fall 2023 Eastern Caribbean Sailing

November 12 - 19, 2023


aboard Princess Cruises'




departing Fort Lauderdale for Princess Cays,

San Juan, Amber Cove, and Grand Turk

This sailing is now SOLD OUT!
Please consider joining us in 2024

Sun Nov 12:  


Mon Nov 13:  


Tues Nov 14:  


Weds Nov 15:     


Thurs Nov 16:  


Fri Nov 17:   

Sat Nov 18:   

Sun Nov 19:    

Fort Lauderdale, FL (depart 3pm)


Princess Cays, Bahamas  (9am - 4pm) 


Day at Sea


San Juan, Puerto Rico  (7am - 4pm)


Amber Cove, Dominican Republic  (9am - 6pm)


Grand Turk, Turks & Caicos  (8am - 5pm)

Day at Sea

Fort Lauderdale, FL  (arrive 7:00am)


7-Day Eastern Caribbean, featuring San Juan

The 'Best of the Best' Eastern Caribbean Itinerary
Picture the Caribbean; soft sandy beaches, warm winds blowing through palm trees and crystal-clear waters stretching as far as the eye can see. That’s the Eastern Caribbean cruise experience. Enjoy the calm waters around the islands, and snorkel, swim and sail your way through engaging activities. Relax on world-famous beaches, cool drink in hand, for a day of rejuvenation topped off by luxurious shopping. Dive in; the Caribbean is waiting!

Fort Lauderdale, Florida


One of the most gay-friendly cities in Florida and a perfect destination for any visitor, Fort Lauderdale is home to beautiful sandy beaches and an exciting gay scene. Known as 'America's Venice' due to its extensive canal system it draws boaters as well as beach-goers, attracting more than 10 million visitors annually. Fort Lauderdale boasts world-class theaters, museums, sightseeing, and shopping. The hub of the city’s gay community is Wilton Manors, the residential neighborhood of Fort Lauderdale that is iconic for its high concentration of gay bars, restaurants and clubs.

  •    More about Fort Lauderdale here

Princess Cays, Bahamas


Possibly your most relaxing port of call, Princess Cays is where you'll enjoy your private beach party on the island of Eleuthera in the Bahamas. One hundred miles long and only two miles wide, Eleuthera offers unspoiled beaches. The Princess Cruise Line's private resort at Princess Cays is situated on more than 40 acres and features over a half-mile of white-sand shoreline, all at the southern tip of the island. The resort boasts outstanding amenities while carefully preserving this natural paradise. Take in the views from the observation tower. Enjoy a complimentary beach barbecue. Sip a cool drink or browse the shops and the local craft market. All of Princess Cays' facilities are linked by walkways. Recreational activities abound. Enjoy volleyball and a full range of water sports, or simply relax on the beach.   

  •    More about Princess Cays here

San Juan, Puerto Rico


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.

  •    More about San Juan here

Amber Cove, Dominican Republic


Tucked on the north coast of the Dominican Republic, Amber Cove, named for the translucent gemstone found on its shores, sits just seven miles from the town Puerto Plata, a cinematic locale used as the backdrop for the first Jurassic Park film. Just steps from the dock take in the sparkling beach, which offers a plethora of water activities, and the serene, natural beauty from the comfort of a private bungalow. Or venture off the property to take to the high seas on a luxury catamaran snorkeling expedition or explore the 450-year-old San Felipe Fortress. For high-flying adventure, swing through the trees on a zip line or ride a cable car 2,500 feet to the top of Mount Isabel de Torres for a look at its massive statue of Christ the Redeemer. And for those with a forward-thinking approach to social activism, delve into the culture and traditions of the friendly Dominican people while giving back to the community and making an impact on their lives. The experience will leave you feeling as warm as the glow from the amber sun.

  •    More about Amber Cove here

Grand Turk, Turks & Caicos


Grand Turk, the capital of the Turks and Caicos Islands, is a small island bursting with turn-of-the-century Caribbean charm, retaining the look and feel of the Caribbean 40 years ago. Grand Turk was founded by Bermudan salt rakers some three centuries ago and its Bermudan-British-colonial architecture surrounded by colorful local dwellings make the island a treasure to visit. It is recognized as being one of the first places in the New World where Christopher Columbus landed and also gained worldwide attention when John Glenn splashed down near Grand Turk on his historic first mission to space. Grand Turk is six miles long and just over a mile wide with a population of only 6,000. It is blessed with miles of uncrowded, beautiful beaches and is close to several uninhabited cays such as Gibb's Cay, home of the stingray encounter. While there are many landside attractions to explore such as the Old Prison, Lighthouse Park, and the re-created salt salina, the real beauty of the island lies underwater. Grand Turk is world-famous for its healthy and beautiful coral reefs that surround the island, stretching almost from the coastline to the 7,000-foot vertical wall just offshore.

  •    More about Grand Turk here

One of our favorite ships, CARIBBEAN PRINCESS



Exciting adventures await aboard Caribbean Princess, particularly since her multi-million-dollar array of luxurious enhancements. From staterooms that offer a more restful sleep, to endless tempting new dining options plus many other upgrades, you’ll find Caribbean Princess herself has come back new.


Make the most of your vacation time aboard Caribbean Princess,

with the Princess MedallionClass vacations experience; a personalized and hassle-free vacation, so you can do more of what you love.


Plus, stay connected while at sea with fast and affordable MedallionNet Wi-Fi.

For more details about the MedallionClass experience, click here

Cabin Options and Pricing

Obstructed OceanView Cabin         from $1,169 per person, double occupancy 

OceanView Cabin                             from $1,199 per person, double occupancy 

Balcony Cabin                                   from $1,369 per person, double occupancy 

Please complete and submit Registration Form below so we can contact you with cabin pricing and availabilty!

Mini-Suite Balcony Cabin                 from $1,559 per person, double occupancy

Inside Cabin                                      from $1,029 per person, double occupancy 



Inside Cabin                                      from $1,618 per person, single occupancy 

Obstructed OceanView Cabin         from $1,898 per person, single occupancy 

OceanView Cabin                             from $1,958 per person, single occupancy 

Balcony Cabin                                   from $2,298 per person, single occupancy 

Please complete and submit Registration Form below so we can contact you with cabin pricing and availabilty!

Mini-Suite Balcony Cabin                 from $2,678 per person, single occupancy



Add an additional $193.64 per person for taxes, cruise fees & port-related expenses to the above rates. (taxes subject to change). 


Princess Cruises reserves the right to reinstate fuel supplements if the price of light sweet crude oil according to the NYMEX, should it increase to above $65 per barrel.  Note: In the unlikely event that we do not reach a minimum number of participants to offer the full experience of activities and events as presented, this Chumley's BearCruise group may be cancelled prior to final payments becoming due.

Your Chumley’s PLUS Group Rate (shown above) also includes:


  • Princess Cruise Line's Plus Beverage Package (click for details)

  • WiFi for one device per guest

  • Gratuities for your Dining Room Staff and Cabin Stewards

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This package valued at $667!

Chumley's BearCruise Package Pricing: 


Note:  Pricing above reflects original contracted rates between our agency and cruise line.  Other promotional rates may apply.  Rates may be lower or higher than those listed above based on current promotions and availability of cabins at the time of booking.  An agent of Connie George Travel Associates will apprise you of any changes, available pricing promotions and cabin options specific to your interests before moving forward with any booking or charging of your credit card.


Your Chumley’s BearCruise package rate includes

  • 7 nights’ accommodations

  • All shipboard meals with coffee, tea and iced tea included

  • All cruise line's shipboard entertainment 

  • Private CBC Facebook group access to get to know others and to keep up with important trip details

  • Access to negotiated pricing at the official CBC host hotel ($)

  • Access to all exclusive pre-cruise and shipboard private CBC dances, parties and events

  • Access to private group dining area

  • Access to optional private CBC shore excursions ($)

  • Exclusive gifts for CBC guests

  • Unlimited Beverage Package

  • WiFi

  • Gratuities

Additional package pricing available for triple or quad occupancy as well as for Full Suite Cabins, please ask.

Please select the link to our registration form at the bottom of this page (click on the green bar) so

we may accurately provide a no-obligation quote for the best price based on your criteria and interests. 

Contact Carlos at should you have questions.

Your Travel Agents for this sailing


Connie George, owner of Connie George Travel Assoc., LLC.

has been a travel counselor for more than 35 years. Long ago

she decided to have her agency specialize in cruise vacations

with particular interest in group cruises and cruising for people

who have disabilities, making her very familiar with special needs, requests and attention to detail!

     Contact Connie at or

Carlos Estela, Group Specialist at Connie George Travel Assoc., LLC.  

     Contact Carlos at or


Seeking a Cabin Mate?

Interested in sailing with us, but looking for a cabin mate? Just post on our Chumley's BearCruise Facebook page, and remember to include questions like 'are you a late night party guy or early riser?', 'snorer or not?', and of course 'what type of cabin are you interested in?' in order to find your perfect fit! 

Click here to go to our Facebook page and post your message now.

Click on the logo to visit our Chumley's BearCruise Facebook page and post your message!

All set?  Let's get started...

Just click the green button below to access the Registration Form for this sailing... it will
show you details on cabin
selection and pricing, and once completed and submitted will allow
our travel
experts to contact you to discuss the best price and availability for your specific needs. 
Remember that there is no obligation for you to submit the Registration Form,
will have the opportunity to decide whether or not you'd like to join us once contacted.  

Click here for CBC Fall 2023 Registration Form

This sailing is now SOLD OUT!
Please consider joining us in 2024

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