Chapter 6: Add a Caribbean Cruise to Your Bucket List

A bucket list could not be complete without a Caribbean cruise, could it? The words “tropical paradise” seem to naturally belong on a bucket list. As we’ve covered some of the most gorgeous places to hike, bike, stroll, eat, shop, fall in love and, of course, cruise, we could never leave out a part of the earth that is embraced by beautiful weather year-round.

The Caribbean is a vast archipelago in the Caribbean Sea and includes over 7,000 islands, 25 independent countries and a relaxed lifestyle many of us wish we could enjoy every day. This unique region of the planet offers a mix of African and European culture for a fascinating blend of music, food, art and traditions.

People flock to the Caribbean to enjoy soothing music, relax on white sandy beaches, swim in turquoise waters, sip festive cocktails and dine on fresh seafood. The Caribbean is an escape many fantasize about, but few get to experience.

Temperatures average between 75 and 85 degrees Fahrenheit all year. Besides the rainy season in August and the hurricane season, which spans from June to November, there’s never a bad time to visit. However, for some, it might always be the right time. The Caribbean is an ideal location for nature-lovers wanting to spot tropical wildlife or for those looking for the ultimate tropical escape.

If you want a vibrant culture, laid-back lifestyle, sugary-white beaches and seemingly endless wildlife viewing opportunities, plus a comfortable climate, make sure to add a Caribbean cruise to your bucket list.

Examples of Windstar Caribbean Cruises

Get ready to sail towards carefree days and electrifying evenings, upon water that looks like liquid jewels. Grab your best hiking gear and prepare to plunge into the lush depths of rainforests, or put on comfortable shoes to spend hours shopping brightly colored markets for stress-free indulgence. We offer cruises that take you from bustling cities to secluded islands, so you have your pick of dream Caribbean destinations. Here’s a sample of what to expect with Windstar.

1. Classic Caribbean

Our Classic Caribbean cruise lasts seven days and starts at $1,799 per person. This round-trip cruise begins in St. Maarten and takes you to Barbuda, Roseau, Pigeon Island, Les Saintes, Basseterre and Gustavia before sailing back.

You’ll get to explore the majesty of the Caribbean islands at your leisure and even take part in a beach party with Windstar to let go of inhibitions Caribbean-style. Shop a stylish boutique or visit a casino in St. Maarten on day one, then get ready to sail to Barbuda.

You’re a lucky traveler when you sail with Windstar because large cruise ships cannot dock in Barbuda. Otherwise, visitors can only reach Barbuda by plane, ferry or cargo freight. Fortunately, our yacht is small enough to gain access yet large enough to give you privacy and comfort while aboard.

While in Barbuda, enjoy searching for rare and endangered wildlife or visit the Frigate Bird Sanctuary in Codrington Lagoon. The bird sanctuary is home to an estimated 100,000 birds.

Stroll unspoiled pink beaches or explore deep seaside caves. Indian Cave, in the Two Foot Bay National Park, features Arawak petroglyphs which you can view inside the cave. Or visit Dark Cave, home to several species of bats and the blind eye shrimp.

Keep your eyes open for dolphins, whales and salt ponds that shimmer with sea salt at Spanish Point. Or simply do nothing but relax all day in Barbuda, where the act of doing nothing is an art — it’s called liming.

On the third day, you’ll head to Roseau, Dominica, where you’ll get the chance to snorkel alongside parrot fish. Day four takes you to St. Lucia to visit Pigeon Island National Park and archaeological relics. Before heading back to St. Maarten you’ll also stop in Les Saintes, Basseterre and Gustavia for more opportunities to explore breathtaking nature, shop for treasures and surrender to a lifestyle you’ll forever cherish.

While in Roseau, take our open-air 4×4 Waterfall and Rainforest excursion where you’ll drive to Morne Bruce for stunning views and amazing photo opportunities. You’ll then ride through mountains to Wotten Waven Sulphur Springs followed by a trip to Titou Gorge — one of the few crater lakes in the Caribbean where you can take a swim.

For a different type of natural spa experience, take our Trafalgar Falls and Hot Springs excursion. This trip invites you to take a dip in hot therapeutic sulfur water tubs, surrounded by fruit trees, birdsong and fragrant blooms. Experience rejuvenation as you cool your skin in flowing streams.

2. San Juan and the Virgin Islands

Our San Juan and the Virgin Islands cruise is a round-trip cruise that last seven days and starts at $1,599 per person. You’ll begin your adventure in historic San Juan, a place where Spanish colonial architecture meets sand and sea. Take in the sights, shop chic boutiques or hike in El Yunque National Forest.

On day two you’ll visit Vieques, a small island six miles east of mainland Puerto Rico. It’s the perfect place to get away and enjoy nature’s treasures without crowds or the hustle and bustle of big cities. In Vieques, you will not find commercial shopping centers or fast food chains, but you will find horses roaming freely and the chance to experience magical bursts of blue light in Mosquito Bay — the brightest bioluminescent bay in the world.

On the fourth day, you’ll visit Little Bay, Montserrat, or the “Pompeii of the Caribbean” where half the island is a lush green paradise and the rest is buried beneath volcanic ash.

Before heading back to San Juan, you’ll get the chance to dine at your choice of creole restaurants in Philipsburg, St. Maarten, and sail your own boat around Sir Francis Drake Waterway in Jost Van Dyke. In Virgin Gorda, you can explore underground pools and caverns or go snorkeling among colorful coral reef.

Is swimming with dolphins on your bucket list? Join the Swim with the Dolphins excursion in Jost Van Dyke to get acquainted with an aquatic companion. You’ll first board a boat and head to the island of Tortola. There you will be given brief instructions and time to change into your swimsuit before entering a dolphin pool. You’ll get to swim alongside a dolphin and give your swimming pal a tummy rub to show your friendship.

3. Secrets of the Southern Caribbean

Experience the Caribbean in a way the conventional cruise can’t allow with our Secrets of the Southern Caribbean cruise. For those who want to go off the beaten path and visit less frequented spots, you’ll want to put this cruise on your bucket list.

The Secrets of the Southern Caribbean cruise lasts seven days and starts at $2,199 per person. You’ll embark on your journey in Colon, Panama, and end in Oranjestad, Aruba. You’ll visit colorful Caribbean ports that have maintained a charming colonial aesthetic next to pristine beaches.

After the first day in Colon, you’ll spend two days in Colombia to stand in the shadows of colonial churches, mansions and fortresses and walk the grounds where pirates and Spanish explorers once roamed with dreams of gold and treasure.

Next, you’ll head to Willemstad, Curacao, where you’ll get the option to venture through Hato Caves or stroll the streets surrounded by pastel-colored buildings.

You’ll continue your journey to the capital city of Bonaire, Kralendijk, which is Dutch for “coral reef.” A cultural and commercial hub only a few blocks in size, Kralendijk may be small, but it’s larger than life in spirit. You might catch traditional music or a dance performance during your visit, and you’ll have plenty of opportunities to shop for souvenirs. Or, simply sit back and enjoy the relaxed Caribbean vibe.

The trip ends in Oranjestad for more relaxing in a Caribbean way. With structures painted in the colors of cupcake frosting, a wide range of boutiques to browse, numerous dining options and fun casinos, you’ll have plenty to do and see to pass the time. However, if you wish to continue savoring the slow moments, kicking back under the Caribbean sun, no one will stop you. In fact, they might join you.

Coffee lovers should take advantage of our Columbian Coffee Experience excursion where they can enjoy pure, fresh Colombian coffee and learn the history behind the cup. You’ll get an overview of the coffee-making process and then taste three different coffees through alternative coffee rituals.

Caribbean Cruise Bucket List Ideas

Chances are, you already have a few items on your bucket list that you can accomplish in the Caribbean. The Caribbean has a magnetic pull that beckons us to visit, slow down and stay as long as we can. It’s a way of life that just feels natural.

How do you make the most out of your Caribbean adventure without overwhelming your schedule? Choose bucket list items that hold the most meaning to you, and make sure to leave plenty of room in your itinerary for the art of doing nothing. Here are a few ideas:

  • Swim in a waterfall: Imagine showering in a cool crystal-clear waterfall in the heart of a dense rainforest. It’s a dream come true, right? It can be a reality. When the currents are not strong, you can take a dip in the cascade of Concord Falls in Grenada. Swim in La Mina Falls in Puerto Rico to take a break from hiking in El Yunque National Forest.
  • Go on an island safari: A guided safari tour can take you through difficult-to-walk areas, get you safely close to wildlife and teach you interesting information you may have otherwise overlooked.
  • Go snorkeling among stingrays: Stingray City, located in the Cayman Islands, is the most popular spot for swimming with stingrays, but other locations like Antigua also offer stingray tours. Stingrays in the Caribbean can grow as wide as six and a half feet and it is safe to gently pet a silky-skinned stingray.
  • Swim with dolphins: Dolphins are one of the most intelligent creatures on the planet. A chance to connect with a marine companion is priceless.
  • Parasail over the Virgin Islands: What could feel more liberating than gliding like a shorebird over tranquil waters? This may not be the best event for the faint of heart, but others should consider adding parasailing to their bucket list.
  • Tour Old San Juan: Founded in 1519 by Spanish explorer Juan Ponce de Leon, San Juan features gothic, renaissance and baroque architecture. Make sure to tour Old San Juan, the city’s historic core.
  • Do nothing for an entire day: How many times in life have you allowed yourself to spend a day doing absolutely nothing? In the Caribbean, it’s acceptable. However, if you feel you must do something, consider spending a day on the beach sipping colorful drinks. Add to your experience with a pina colada or strawberry daiquiri — Caribbean classics.
  • Kayak in Mosquito Bay: Experience the otherworldly bioluminescent bursts of blue as you kayak through the water at night.
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