On Multigenerational Travel to the Caribbean, Our Family Reconnects

I’m not going to sugarcoat it: When I picked up my parents from the airport in Fort Lauderdale, in order to embark on our multigenerational travel adventure, my dad looked pretty awful. It’s not like the two-hour-long trip from San Juan was particularly grueling, and they had even picked a very reasonable 11 a.m. flight. It turns out he hadn’t slept a wink the night before, though it wasn’t because he was feeling ill, uncomfortable or otherwise indisposed. By his own sheepish admission, my dad was restless with excitement and anticipation at his first experience on a Silversea family cruise. “Just like a child,” my mother quipped, rolling her eyes.

Fortunately, Dad’s semblance began to improve during the short ride to Port Everglades, and the first glimpse of Silver Whisper on Cruise Terminal 19 continued to lift his already high spirits. The hassle-free embarkation and check-in processes were a breeze, and soon enough he was enjoying the bounty of La Terrazza’s buffet-style lunch. As for Mom, she was finally able to relax, a glass of Champagne in hand.

Inside Silver Whisper
All smiles before dinner in The Restaurant aboard Silver Whisper./Jorge Oliver

It was precisely their enjoyment and relaxation that motivated me to plan a two-week voyage around the eastern Caribbean aboard Silver Whisper. I was certain that Silversea’s impeccable service and all-inclusive amenities were just the thing to get away from reality for 14 days. Yet there was also the allure of multigenerational travel — something I hadn’t experienced with my folks in decades. I was curious about how my parents’ differing travel styles and preferences would unfold on this opportunity, and how they would gel with how my wife and I like to travel.

Dad is all about keeping himself busy; he was determined not to miss any arrival or departure, to see as many shows as possible, attend all the lectures and deliver his favorite conversation-starter — “where are you from?” — to every crew member he met. He even made it a point to work out at the gym, something I can honestly say I’ve never seen him do, although I suspect his determination had more to do with not missing out on any of Silver Whisper’s features than creating a new fitness regimen.

Mom, on the other hand, had far simpler plans. This was her opportunity to unwind and enjoy her family without worrying about all the demands and stresses of being the hostess. Sure, she’d check out the trivia, browse the boutiques and enjoy tea time now and then. But her laissez-faire attitude dictated a more play-it-by-ear approach. As for my wife and I, our style combines a bit of both approaches, but is largely defined by a desire to blaze our own trail. Sometimes spontaneously, sometimes through meticulous planning, our goal was to stray as far from the ordinary and delve deep into both our Silversea voyage and this multigenerational travel adventure around the Caribbean.

How Silversea does luxury family travel

From Fort Lauderdale’s Port Everglades, our nine-port roundtrip itinerary was a combination of tried-and-true Caribbean classics including BarbadosAntigua and the British Virgin Islands, as well as some less-visited destinations such as Les Saintes and Nevis. The fact that many of our ports of call were familiar didn’t damper Dad’s desire for discovery one iota. If anything, it elevated his enthusiasm. I witnessed this on the third day of our cruise, as we approached San Juan. Never mind that my parents, who live on the island, were just here 72 hours ago. There was Dad, propped on deck 10, taking in the view and admiring the beauty of the walled city at dusk as though he was laying eyes on it for the first time. Inspired, I can only surmise, by the novelty of being brought here by Silver Whisper, my folks made it a point to explore the city in earnest, following the well-worn trails of cobblestone streets and colonial relics as eagerly as our fellow passengers. I found myself following in their footsteps, sharing their enthusiasm with a mixture of awe, nostalgia and familiarity.

Forested mountains of Martinique
Dad enjoying the wild, lush highlands of Martinique./Jorge Oliver

Beyond this very familiar port, our itinerary was sufficiently broad that it allowed opportunities to satisfy my parents’ often disparate interests. Dad is all about nature while Mom tends to favor creature comforts, and my wife and I sit somewhere in the middle. Thus, our shore visits became a series of delightful dichotomies: in Martinique, we enjoyed the lush highlands of the island’s north and the chic charm of Fort de France. In Barbados, we experienced the soft, sandy beaches of the west coast and the West Indian hustle-and-bustle of Bridgetown. And in Antigua, we searched for the best of the island’s rumored 365 beaches (Ffryes on the southwest coast took the honors) and the traces of the past in Nelson’s Dockyard. In Nevis, we reveled in the bountiful beauty of the botanical gardens and the historical relevance of Alexander Hamilton’s origins.

Even when we decided to forgo our own planning in favor of partaking in a shore excursion organized by Silversea, I was amazed at how well it fit all of our visions of an ideal day ashore. Such was the case of our stop in Road Town, Tortola, where we signed up for the “Escape to Jost Van Dyke” catamaran excursion. The approximately 45-minute ride across the Drake Channel, straddling the limits of the USVI and BVI, led us to White Bay on the southern coast of Jost Van Dyke. It was impossible to argue against the scenic backdrop of the mountainous three-square-mile isle as the crystal-clear waters lapped against the powdery-white sands. A perfect day, we could all agree, made all the better by the strategic location of the Soggy Dollar Bar, the famous birthplace of the Painkiller rum cocktail.

White Bay, Jost Van Dyke
My wife Constanza savoring the arrival to Jost Van Dyke on the catamaran Rebel Yell, during our call in Tortola, British Virgin Islands./Jorge Oliver

Sweet home Silver Whisper

As satisfying as our ports of call were, our time aboard Silver Whisper was just as enjoyable as our onshore adventures. Our itinerary included three days at sea, which gave us ample time to explore all that our ship had to offer.

Dad was always out and about. On his many treks all over the ship, he befriended our guest lecturer, the medic, the shore excursions coordinator, two of the singers, half of the wait staff and what seemed like roughly a third of our fellow passengers. He even became acquainted with our captain, whom he met at the gym and made sure to be one of the first guests to sign up for the bridge tour on day 11 of our Silversea family cruise.

Silver Whisper balcony
Dad enjoying the perks of his suite’s very spacious balcony during one of our days at sea aboard Silver Whisper./Jorge Oliver

Mom preferred pacing herself. She was just as content spending time in her suite reading a good book or enjoying tea time at the ship’s Panorama Lounge. She began to develop routines, such as avidly reading the Daily Chronicles while having her morning macchiato or faithfully participating in trivia every afternoon.

I made it a point to embrace both styles and devote a healthy amount of time indulging in their interests. To my delight, and slight surprise, I found plenty to enjoy. Thanks to Dad and his obsessive need to witness all of our arrivals and departures, I learned more than I thought possible about the technical maneuvers required to dock a cruise ship, the role of the pilot boat and the navigational features of all our ports of call (Dad only knows all of this out of sheer interest and keen observation).

I also got to meet Captain Tomas Kulas, whom my dad came to regard as a friend by the end of our voyage. Mom rekindled my competitive side as we teamed up every afternoon to aim for a top finish on the daily trivia, and she reminded me of the quiet allure of simply catching up with a good book in the comfort of our suite. And I still had plenty of quality time, both on land and sea, to spend with my wife pursuing our interests. Whether it was dinner for two at La Dame, perusing the West Indian market stalls in search of that elusive ornamental accent for our living room or simply getting lost in the spirit of curiosity by hoofing it on each of our destinations, Silversea allowed us to rediscover our passion for travel at our own leisurely pace.

As the voyage came to a close, I asked my parents during our last dinner at The Restaurant what they enjoyed the most from our Silversea family cruise. I expected wildly varying answers, but was surprised when they offered the same response: Silver Whisper.

Their reasons were different, but the charm of the ship suited them equally. In Dad’s case, the size of the ship afforded the opportunity to visit destinations that aren’t typically included in Caribbean itineraries. Mom enjoyed sailing on a cruise that felt like a ship, as opposed to a small city on the high seas. Dad sang praises about the ship’s convivial atmosphere, while Mom appreciated the level of service and attention to detail from crew members.

Silver Suite in Silver Whisper
The folks about to enjoy some in-suite canapes, courtesy of our butler./Jorge Oliver

The following day, while we waited for our turn to disembark, I caught a glimpse of my parents perusing the Silversea itinerary guide, searching for the next adventure. Summer in Alaska? An escape to the Aegean? A foray to the fjords? Dare they try an expedition to Antarctica? Their faces beamed with anticipation and excitement as they studied the seemingly endless options … just like two kids.

Ready to embark on your own multigenerational adventure? Check out these Silversea cruises to the Caribbean and Central AmericaAlaskaNorthern Europe and more—all of which excel at luxury family travel.