Annual Thanksgiving Cruise

12-Day Eastern Caribbean

November 16 - 28, 2025

Itinerary       Pricing       Inclusions

Roseborough Travel has been hosting an Annual Thanksgiving Cruise for over 30 years for a reason... be it no cooking or cleaning of dishes, the opportunity to visit amazing ports of call, or the fun of getting together with a group of like-minded traveling companions. Whatever your reason is, you will not want to miss out on our tradition.

Travel roundtrip from DeLand via deluxe motorcoach with Roseborough Travel down to Fort Lauderdale, where we’ll set sail on Holland America Line's Rotterdam and discover a vacation like no other. The Rotterdam delivers the best of everything Holland America does: exquisite cuisine, award-winning service, superbly appointed staterooms and suites, and world-class entertainment. Dance the night away at B.B. King’s Blues Club or relive your favorite rock classics at Rolling Stone Lounge. Experience Rotterdam’s Pinnacle Class luxury and find a mastery of the details that keep our guests returning again and again.

November 16: Fort Lauderdale, Florida, US - Embark

Bright and early, we'll head down to the cruise port in Fort Lauderdale to embark on our exciting Thanksgiving Cruise! 

November 17: Half Moon Cay, Bahamas

In a region renowned for tropical wonders, one island rises to the top—ours. We’re not the only ones enamored with our slice of paradise—Half Moon Cay is the highest-rated Bahamas private island. It has won Porthole Cruise Magazine’s Best Private Island award consecutively for 20 years. We’ve spent a quarter of a century perfecting the experience. When you feel the sugar-white sand on your toes or kayak its crystal lagoon, you’ll understand why cruise travelers love Half Moon Cay, a highlight of our Bahamas cruises.

November 18 - 19: Days at Sea

November 20: Philipsburg, St. Maarten

Philipsburg, the bustling capital of the Dutch side of Sint Maarten, offers visitors a fascinating mix of cultures, scenic beaches, and excellent shopping opportunities. From the historic Fort Amsterdam to the vibrant Boardwalk, Philipsburg invites travelers to immerse in its lively atmosphere and Dutch heritage, while just a short trip away, the French side of the island offers its own distinct charm and culinary delights.

November 21: Castries, St. Lucia

In Castries, the essence of Saint Lucia comes alive with its bustling markets, historical sites, and scenic views. It’s a gateway to adventure, from hiking to the Pitons to immersive cultural experiences like learning about banana farming. Holland America Line excursions offer a blend of exploration and relaxation, ensuring a memorable journey through this Caribbean paradise.

Roseborough Exclusive Group Excursion: Soufriere Island Delight

Discover the delightful island of St. Lucia as you wind your way through the banana and coconut plantations and the rich tropical vegetation that carpets the mountains.

You'll drive through two traditional fishing villages and skirt the fringes of the rain forest before arriving at Soufriere. Take in the breathtaking views of the spectacular twin Pitons Mountains as you descend into the town of Soufriere.

Once in Soufriere, you'll visit the Sulphur Springs at the drive-in volcano. The smell in the air will tell you when you've arrived at the steaming, bubbling holes of the sulphuric waters, said to have medicinal and rejuvenating properties.

After the smell of sulfur, your nose will appreciate the sweet scents at the Diamond Botanical Gardens. It is located on land still owned by a lovely woman who is the descendant of the original owners. You'll have time to wander the grounds and enjoy the lushness and beauty of the gardens.

As you return to Castries, you'll still be savoring the sites you just experienced.

November 22: Scarborough, Trinidad & Tobago

Scarborough, the cultural center of Tobago, is home to historic treasures and surrounded by natural beauty. From crystal clear lagoons to the local delicacy of curried crab and dumplings, Scarborough offers an authentic Caribbean experience. Relax on tranquil beaches, tour an archaeological museum, and enjoy an in-depth exploration of this island port with Holland America Line.

November 23: Bridgetown, Barbados

Bridgetown, the vibrant capital of Barbados, offers a rich cultural heritage and stunning natural beauty. With a UNESCO-listed historic center and as the birthplace of Rihanna, Bridgetown delights visitors with its intriguing history, music, and cuisine. Holland America Line excursions provide a comprehensive experience of Barbados' lively culture and breathtaking landscapes.

November 24: Point-a-Pitre, Guadeloupe

Point-a-Pitre, the cultural hub of the Guadeloupe Islands, overlooks the Caribbean Sea. Stunning landscapes, lively markets, and colorful architecture define this French Caribbean jewel. Holland America Line curated shore excursions offer an engaging, immersive experience with the island’s exquisite nature and culinary offerings.

November 25: San Juan, Puerto Rico

San Juan, Puerto Rico, is a treasure trove of culture, history, and natural beauty. On a Holland America Line cruise, discover the cobblestone streets of Old San Juan, a UNESCO World Heritage Site, taste local culinary delights like fried plantains, or unwind on the sun-soaked shores of Condado Beach. Adventure awaits with excursions to El Yunque National Forest and the glowing waters of the bioluminescent bay.

Roseborough Exclusive Group Excursion: Old San Juan: The Walk for Foodies

While meandering to a great local restaurant, you'll get acquainted with a little bit of Puerto Rican history and become familiar with important details of Puerto Rican culture. You'll also have a feel of the unique shopping district that these ancient streets provide. This portion of the tour will be about 2 hours of walking through many years of history.

Next up is an introduction to your chef and his local cuisine. This location is a find. Its a unique colonial atmosphere in a convenient spot with an excellent chef. You'll be interacting with the chef and have a hands-on lesson in preparing this dish. Take a load off your feet as the next 2 hours you can prepare and enjoy time with your new friends while learning a new skill.

Mofongo is a must try for first-time visitors who want to truly sample the local fare and, for locals, its simply something to satisfy a craving. Mofongo is a mashed mound of plantains or cassava into which a combination of meat, or vegetables is added. Become a chef for a day and find out how this incredible Puerto Rican meal is made, and then, at the end, enjoy the fruits of your own delicious creation!

Your menu consists of:

Appetizers
Plantain or Cassava Mofongo filled with chicken
Rum cocktail
Soft drink
Delicious dessert

November 26 - 27: Days at Sea (Happy Thanksgiving on November 27th!)

November 28: Fort Lauderdale, FL - Disembark

The time has come to disembark and make our way back home with all the wonderful memories made on our trip.