EMBARKING ON AN EASTERN CARIBBEAN CRUISE: A PERSONAL GUIDE
With the sea as my second home and over 50 cruises to reminisce about, I’m more at home on water than on land. For seasoned sailors and landlubbers alike, I’ve gathered a treasure trove of tips for an Eastern Caribbean cruise—a region where turquoise waters meet diverse ports, from Amber Cove to the storied streets of San Juan.
Sailing Through Seasons: Picking the Perfect Time
Cruising knows no off-season, with the sun-kissed decks welcoming travelers year-round. There are now even waiting lists for many US ports. The fall and winter seasons promise tempting deals and breezy weather—the perfect backdrop for your sea adventure, but remember that hurricane season looms through October.
Choosing Your Nautical Steed
From the grandeur of Holland America to the family-friendly vibe of Carnival, I’ve walked the gangways of the crème de la crème on many an Eastern Caribbean cruise—including Costa, NCL, Royal Caribbean, Windstar, Disney, and Celebrity. Each brand holds fast to its unique charm and sets sail to meet a mariner’s every need.
Once your voyage is charted, the quest to curate your land excursions begins. Perhaps the serenity or fun of the ship is all you seek—a floating sanctuary where time is measured in sunsets and meals you don’t have to cook or clean up after. But for adventurers yearning to tread less familiar paths, allow me to be your compass as you wander ashore.
Amber Cove: A Dominican Delight
In the heart of the Dominican Republic lies Amber Cove, a port that dazzles without a single step beyond its bounds. Yet, beyond the gates lie the island’s true wonders. Shop to your heart’s content, dine in savory splendor at modestly priced eateries, or plunge into a pool complex where the fee is included in your cruise vacation.
Zip, Swim, or Hammock in the Cove
Be bold and zipline over the crystalline waters, claim a beach hut painted with vivid colors or sway in a hammock’s gentle embrace. If exploration beckons, the DR’s cultural landscape awaits—from touring the iconic Amber Museum to visiting the historic churches or spending the afternoon at a five-star resort soaking up its amenities.
There’s Cabaret Beach for the sunseekers—with plenty of waves and golden sands. Or perhaps the thrill of natural rock water slides at Rio de Damajagua calls to you.
In Puerto Plata, step into the local rhythm at Independence Square, where the town comes to life in a lovely juxtaposition of old and new. There are many souvenir opportunities here, including excellent street vendors’ artworks.
Bahamas Bliss: Half Moon Cay and Beyond
The Bahamas are a constellation of island retreats, each shining with its own light on your Eastern Caribbean cruise. On Eleuthera, Princess Cruises offers a secluded slice of paradise; at Half Moon Cay, Holland America invites you to a private cruise ship sanctuary.
Seize the day with outdoor escapades, refueling with a beachside feast of sizzling grills and extraordinary delights—all on the house. What’s included? A typical beach lunch features jerk or BBQ meats, vegetables, ice cream, fruit, burgers, and hot dogs.
Another option is to stroll the shores with a drink in hand or paddle through azure waves. Have you ever wanted your hair braided? This is the place to do so.
A Private Paradise
On these private sands, choose your adventure—go cycling, rent a dune buggy, seek sun shelter in a clamshell, or go paddling among the shimmering shoals. I love renting the foam mats to float in the ocean, allowing maximum sun. Be cautious and reapply sunscreen quite often to avoid burning.
Lounge chairs are provided free of charge. And there are designated swimming areas. Drink in the sun or indulge in a cabana’s luxury, flanked by soft white sands, before picking up some authentic souvenirs at one of the island kiosks.
Castaway Cay: Disney’s Caribbean Crown
Castaway Cay is more than a port—it’s a splash of Disney magic amid the Caribbean blues. Every detail is steeped in enchantment, from island 5Ks to Christmas decorations that rival Santa’s workshop.
Beyond providing all the island indulgences, Disney’s jewel outshines the rest with a signature blend of joy and creativity that only the masters of imagination can deliver. In other words, Disney’s private island is the best. It’s even more fun to visit when it is decorated for Christmas.
Pro Tip: Remember to pick up exclusive trading pins at this port of call.
Grand Turk’s Barefoot Bliss
Imagine the perfect day when ocean waves kiss white sandy shores and nature’s palette comes to life—a reality in Grand Turk. Though it spans just seven square miles, this gem offers more than meets the eye. I’ve visited multiple times on cruises and land trips, and it is a vacation destination I’d recommend repeatedly.
Grand Turk’s Margaritaville (the largest in the Caribbean) awaits with its inviting pool and upbeat rhythms. It’s a place to unwind or mingle to your heart’s content—all at no cost. It’s a haven where chill tropical cocktails, more fun served at the swim-up bar, and leisure reading under the warm sun are daily norms.
Adventure beckons with dune buggy thrills and wildlife encounters—wild horses and donkeys may stroll by as you trek towards the island’s historic weathered lighthouse or on the opposite side of the island. Two other adventures I always enjoy are the Gibbs Cay stingray encounter and visiting the Salt House Museum.
Indulge in underwater escapades like scuba and snorkeling or reel in the excitement with a fishing expedition; Grand Turk is all about the vibe of island life.
Puerto Rico’s Colonial Charm
Over fifteen years, I’ve watched San Juan, Puerto Rico, transform its streetscape, enhancing the past’s splendor with the present’s touches. Wander this gorgeous city, where a local café invites you to savor tapas and sip refreshing mojitos at places like Rosa de Triano.
Experience a tapestry of taste and history through the ‘Flavors of Old San Juan Food Tour.’ For the memory-makers, the monumental forts stand tall, safeguarding stories and stamper’s delight for National Park Passport bearers.
From skies reflecting in glass-bottom kayaks to trails best seen from horseback, San Juan is where past and present dance harmoniously on your Eastern Caribbean cruise.
St. Kitts: Nature’s Masterpiece
Nestled in the Lesser Antilles, St. Kitts, paired with Nevis, paints a portrait of natural majesty. Lush mountains backdrop historic fortresses and the sugarcane heritage stretching under clear blue skies. Walk through time in the museum dedicated to Alexander Hamilton and marvel at the unmatched colonial architecture setting St. Kitts apart.
St. Maarten/St. Martin’s Dual Delight
A unique twofold nation island, St. Maarten/St. Martin mesmerizes with its blend of culture and beachside allure. Philipsburg reflects the Dutch spirit through its charming buildings and sandy retreats like the famous Orient Beach, with its eclectic mix of sunbathers—an invisible border’s subtle reminder of the distinct experience awaiting on either side.
The town of Marigot shifts the mood to French chic, where designer labels and award-winning dining become the day’s focus. I adore both sides, but the pulse of tourists tends to favor St. Maarten’s shores.
St. Thomas: The Pinnacle of Paradise
St. Thomas, with its notorious pledge to pirate tales and luxurious hotels, consistently captures the heart of the Caribbean seeker. Ascend the famous Mountain Top for its iconic banana daiquiri and panorama that’s beyond Instagrammable. This would mark the spot of one of the best photo op coordinates in the world.
Magen’s Bay, lauded globally, boasts a shoreline that could rival any artist’s canvas. The ocean calls for exploration here via catamaran, scuba, or snorkeling.
I’ve been to the island so often that I like to walk into town (Charlotte Amalie), browse the shops, have a tasty lunch at the Greenhouse Restaurant & Bar, and check out the open-air markets with beautiful jewelry. Larimar is a stone abundant in the USVI and makes an excellent purchase for you or your loved one.
St. John offers a quieter excursion. Less-trodden paths lead to stellar waterfront mansions and the allure of ivory sands that beckon travelers back time and again. It used to be my favorite of the three US Virgin Islands, but I have not been there since Hurricane Irma devastated it in 2017.
Set Sail with Confidence all new
An Eastern Caribbean cruise is a voyage through cultures, flavors, and thrills—a canvas where your story is painted in ocean shades. My journeys are shared to recount and inspire your travels over horizons near and far.
Bon Voyage!
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