Winter Cruise to Paradise - Eastern Caribbean 2026

Day 1

Day 1: Tuesday, January 20, 2026
Your winter escape kicks off in comfort and style as you board a luxury Burlington Trailways motorcoach, complete with a friendly onboard host and professional driver, from the available departure location of your choice. Sit back, relax, and enjoy the scenic ride as we head south toward warmer days ahead. Tonight, we’ll stay at the welcoming Drury Inn & Suites in Paducah, Kentucky, where hospitality is top-notch. We will arrive with time to enjoy the 5:30 Kickback reception, featuring a rotating menu of hearty hot food, fresh salads, snacks, and complimentary beverages—including beer, wine, and mixed drinks. If you’d prefer to venture out on your own, the hotel is conveniently located near other restaurants, giving you another choice for dining options just steps away.

Day 2

Day 2: Wednesday, January 21, 2026
Enjoy a hearty breakfast at the hotel before we continue our comfortable journey southward. Sit back, unwind, and take in the changing scenery as we make our way toward the Sunshine State. This evening, we’ll settle in at the Drury Inn Atlanta Marietta in Georgia, another trusted and traveler-friendly stop. Once again, you’re invited to take part in the included 5:30 Kickback reception, featuring a rotating selection of hot foods, fresh salads, and complimentary beverages. It’s the perfect opportunity to relax, recharge, and enjoy some conversation and camaraderie with your fellow Trailways travelers as we look forward to the cruise adventure ahead.

Day 3

Day 3: Thursday, January 22, 2026
After another restful night and a delicious breakfast, we hit the road once more for the final stretch of our scenic journey to Florida. By late afternoon, we’ll arrive in sunny Orlando for an overnight stay at the Drury Inn & Suites near Universal Orlando Resort. This well-located resort hotel offers all the comforts of home and the warm hospitality you’ve come to expect. Once again, you can take advantage of the 5:30 Kickback reception, featuring satisfying hot foods and complimentary beverages. If you’re in the mood for something different, there’s a Wendy’s conveniently located right next door and a Chick-fil-A just a short stroll away—giving you easy options for a quick bite before settling in for the evening.

Day 4

Day 4: Friday, January 23, 2026
The day we’ve been waiting for has finally arrived! After a short and easy drive from Orlando, we’ll arrive at Port Canaveral, where the impressive Adventure of the Seas awaits. Once we’re checked in and settled aboard, it’s time to officially begin our 9-day, 8-night cruise to paradise! Spend the afternoon getting acquainted with the ship—grab lunch at the Windjammer Café, explore the pools and hot tubs, or check out the daily activity schedule filled with live music, trivia games, and dance classes. As the ship sets sail, head to the upper decks for the festive sail away celebration, complete with music, dancing, and tropical drinks as we wave goodbye to the mainland. The ocean breeze, the excitement in the air, and the promise of adventure ahead make this the perfect start to your Caribbean escape.

Day 5

Day 5: Saturday, January 24, 2026
Today is all about enjoying life at sea aboard Adventure of the Seas! With no port stop, you have the entire day to explore, unwind, and make the most of everything this incredible ship has to offer. Start your morning with breakfast overlooking the ocean, then take your pick from a variety of activities—join a fitness class, attend an enrichment seminar, try your luck in the casino, or simply lounge by the pool with a good book and a cool drink. Feeling adventurous? Tackle the rock-climbing wall, take a spin on the ice skating rink, or catch one of the ship’s exciting live shows or movie screenings. Enjoy a leisurely lunch, indulge in some duty-free shopping, or book a relaxing spa treatment. As the sun sets, get dressed up for dinner, then enjoy live music, dancing, or a Broadway-style performance. However you choose to spend your day, it’s all leading up to tomorrow’s exciting arrival in Puerto Plata, Dominican Republic!

Day 6

Day 6: Sunday, January 25, 2026
We dock today in the vibrant coastal city of Puerto Plata from 9:00 a.m. to 6:00 p.m.—giving you a full day to explore the beauty and culture of the Dominican Republic! Whether you choose to venture out on your own or book a Royal Caribbean shore excursion, there’s something for everyone to enjoy. Stroll through the charming historic district and visit the colorful Umbrella Street, shop for local crafts and amber jewelry, or take a cable car ride up Mount Isabel de Torres for stunning panoramic views. For beach lovers, nearby Playa Dorada offers golden sand and warm, turquoise waters perfect for relaxing or swimming. Adventurous travelers might enjoy excursions such as snorkeling in Sosa Bay, exploring waterfalls and lush jungle trails, or visiting a rum distillery to sample local flavors. However you spend your day, Puerto Plata offers a rich mix of culture, nature, and relaxation—just be sure to be back aboard by sail away for another night of fun at sea!

Day 7

Day 7: Monday, January 26, 2026
Today we arrive in the enchanting city of San Juan, Puerto Rico, docking from 11:00 a.m. to 10:00 p.m.—giving you plenty of time to soak in the island’s rich history, vibrant culture, and tropical charm. A fantastic (and free!) way to explore is by hopping on one of the open-air trolleys that loop through Old San Juan, making stops at the city’s top sights like the iconic El Morro Fortress, San Cristbal Castle, and beautiful plazas lined with colorful colonial architecture. Be sure to wear comfortable shoes, as the cobblestone streets can be steep and uneven—but they’re also part of what makes this historic city so magical. Spend time browsing local boutiques, sampling authentic Puerto Rican cuisine, or sipping a pia colada in the city where it was born! If you’d prefer something more structured, there are a variety of shore excursions available—from guided walking tours and rainforest adventures to salsa dancing experiences and culinary tastings. However you choose to spend your day, San Juan is sure to be a highlight of the journey.

Day 8

Day 8: Tuesday, January 27, 2026
We arrive bright and early today in Charlotte Amalie, St. Thomas, docking at 7:00 a.m. and remaining in port until 6:00 p.m.—giving you a full day to explore this Caribbean gem. As you venture out, remember to look both ways when crossing the street—locals drive on the left here, unlike the mainland U.S.! St. Thomas offers the lively energy of a bustling port city blended perfectly with the laid-back allure of a secluded island escape. Spend your day strolling through the historic downtown district, where open-air markets and duty-free shops offer everything from handmade crafts to fine jewelry. For those craving a beach day, few spots compare to the breathtaking beauty of Magen’s Bay—a perfect place to unwind on powdery white sand or take a dip in the calm, crystal-clear waters. You may also opt to book a shore excursion—perhaps a catamaran sail and snorkel adventure, a scenic island tour, or even a ride up to Paradise Point for stunning views. Whether you’re seeking shopping, sunbathing, or sightseeing, St. Thomas delivers a truly memorable day in paradise.

Day 9

Today we arrive in beautiful St. Croix, the largest of the U.S. Virgin Islands, docking from 7:00 a.m. to 6:00 p.m. This is our final port of call before we enjoy two relaxing days at sea on our journey back to the mainland—so make the most of your time in this Caribbean treasure! St. Croix offers a wonderful blend of natural beauty, cultural charm, and laid-back island vibes. On your own, you can explore the quaint streets of Christiansted or Frederiksted, browse local artisan shops, or relax at one of the island’s stunning beaches. History buffs may enjoy a visit to Fort Christiansvaern or a self-guided walking tour through colonial landmarks. For those looking for adventure, consider a purchased excursion—perhaps snorkeling at the Buck Island Reef National Monument, kayaking through a bioluminescent bay, or visiting a rum distillery for a taste of the island’s spirited culture. And if you stop into a café or restaurant, be aware that most include a 10–15% service charge as a gratuity, so there’s usually no need to tip extra unless you feel moved to. Whether you spend the day exploring or unwinding, St. Croix is the perfect sendoff from island life.

Day 10

Today is the first of two relaxing days at sea as we begin our journey back to the mainland—giving you even more time to unwind and enjoy the many amenities aboard Adventure of the Seas. Start your day with a leisurely breakfast and ocean views, then dive into whatever suits your mood—whether that’s lounging by the pool, indulging in a spa treatment, trying your hand at trivia, or exploring the ship’s many onboard activities. Take a yoga class, catch a movie, or browse the shops for duty-free treasures. If you’re feeling adventurous, ride the FlowRider, scale the rock-climbing wall, or glide across the ice skating rink. As evening approaches, enjoy a fabulous dinner, catch a live show or musical performance, and toast to new friends and great memories. With two full days at sea ahead, there’s no rush—just the perfect opportunity to soak up the serenity and splendor of cruising life.

Day 11

It’s our final full day at sea, and your last chance to take full advantage of everything Adventure of the Seas has to offer before we return to port tomorrow. Whether you’ve already fallen into a relaxing cruise rhythm or still have a few onboard experiences on your list, today is the perfect time to enjoy them. Maybe you’ve been meaning to try a specialty restaurant, treat yourself to a luxurious spa service, or catch one of the dazzling evening shows. Take a dip in the pool, challenge a friend to mini golf, or join in one of the many fun activities scheduled throughout the day—from dance classes to games and workshops. For those looking to slow things down, find a quiet lounge with a view, enjoy a drink under the sun, or simply stroll the deck and soak in the sea breeze. However you choose to spend your last day aboard, make it one to remember—savor the moments, the memories, and the magic of life at sea.

Day 12

We bid farewell to the sea as we arrive back at Port Canaveral and begin the disembarkation process after a memorable 9-day Caribbean cruise. With hearts full of sunshine, suitcases full of souvenirs, and maybe an extra pound or two, we’ll reboard our comfortable Burlington Trailways motorcoach and begin our journey back to the Midwest. As we travel north, reflect on the unforgettable experiences, beautiful ports of call, and new friendships made along the way. Tonight, we’ll overnight at the Drury Inn & Suites Atlanta Morrow in Georgia, where you can once again enjoy the 5:30 Kickback reception. It’s a great time to unwind, relax, and reminisce with fellow travelers—maybe swap stories about your favorite cruise meals or that perfect beach day in paradise.

Day 13

Fuel up with a hearty breakfast this morning as we welcome the start of February and continue our comfortable motorcoach journey northward. After days of tropical sunshine, we gradually return to the familiar chill of Midwest winter—but with warm memories to carry us through. This evening, we’ll overnight one final time at the Drury Inn & Suites in Paducah, Kentucky. Join your fellow travelers for one last 5:30 Kickback reception, or, if you’re in the mood to dine out, take your pick from the many nearby restaurants including Cheddar’s Scratch Kitchen, Buffalo Wild Wings, Texas Roadhouse, or Panera Bread. It’s the perfect evening to relax, share laughs, and reflect on all the highlights of our unforgettable Caribbean escape. Tomorrow, we return home—ready to slip into our own cozy beds, refreshed and recharged by the adventures behind us.

Day 14

Welcome back home, travelers! It’s February 2nd—Groundhog Day—and while we wait to hear whether spring is just around the corner, one thing’s for sure: you’ve created fabulous memories, experienced the island vibes, and maybe even are now sporting a tropical tan to carry

you through the rest of winter. As you settle back into your routine, we hope you’re already dreaming of your next adventure. Whether it’s another sun-soaked cruise, a scenic mountain escape, or an exciting mystery tour, we will have something in store for you! Thanks for joining us on this unforgettable journey—until next time, happy trails and stay warm out there!