Anchored in Awe: Oliver’s Favorite Ports Around the World

For those who embrace the rhythm of the sea and the call of adventure, ports are more than mere pit stops—they are gateways to culture, history, flavor, and wonder. Among seasoned seafarers, few have chronicled their maritime journeys with the passion and vividness of Oliver Grant, a lifelong sailor, travel writer, and maritime photographer. Over the course of three decades, Oliver has dropped anchor in more than 100 ports across six continents, each visit woven into the tapestry of his nautical memoirs.

But among this vast array of seafaring experiences, some ports have imprinted themselves more deeply than others. In his latest travel chronicle, “Anchored in Awe”, Oliver reflects on his all-time favorite ports—places where the charm of the harbor, the warmth of the locals, and the thrill of exploration came together in perfect harmony.

Here, we share a curated selection of Oliver’s favorite ports around the world, each a dazzling thread in the global quilt of maritime travel.

1. Portofino, Italy: The Jewel of the Ligurian Coast

To Oliver, Portofino isn’t just a destination—it’s a dream rendered in pastel and framed by emerald waters. Nestled along the Italian Riviera, this tiny fishing village has become synonymous with elegance and tranquility.

“I remember watching the early morning mist lift over the harbor,” Oliver recalls. “The sun turned the water into liquid gold. Locals unloaded the day’s catch, and the scent of espresso floated on the breeze.”

Portofino’s harbor is small, but its impact is vast. With narrow lanes, boutique shops, and the iconic Church of St. George watching over the harbor, Portofino’s appeal lies in its romantic scale. Hike up to Castello Brown for sweeping views, or simply lounge at a café with a Campari Spritz in hand—this is dolce vita at its finest.

2. Cape Town, South Africa: Where Oceans and Cultures Collide

At the foot of Table Mountain, Cape Town’s Victoria & Alfred Waterfront bustles with life. For Oliver, the port’s dramatic setting and multicultural vibe make it unforgettable.

“Cape Town’s harbor has a heartbeat,” Oliver writes. “You feel it in the rhythms of the street performers, the spices in the air, and the cry of seagulls over the Atlantic.”

Cape Town is more than scenic. Its harbor is rich in history, once a key stopover for ships en route to Asia. Today, the waterfront blends maritime tradition with modern flair—fine dining, art galleries, and history museums sit shoulder to shoulder.

Don’t miss a ferry to Robben Island, where Nelson Mandela was imprisoned. “It’s a humbling journey,” Oliver says, “that adds depth to Cape Town’s breathtaking beauty.”

3. Kyoto via Maizuru Port, Japan: Tranquility Meets Tradition

Though Kyoto is inland, ships dock at the Maizuru Port on the Sea of Japan—one of Oliver’s most surprising discoveries.

“Maizuru was a quiet port,” he explains. “But the journey inland to Kyoto was like stepping back into a centuries-old painting.”

The port is serene, surrounded by forested hills. From here, visitors can take scenic trains or drives to Kyoto, where temples, geishas, and Zen gardens await. It’s this juxtaposition—modern docks against the timeless beauty of Kyoto—that left Oliver spellbound.

In his words: “There’s a stillness in Kyoto that lingers in your soul. Every moss-covered stone and sliding paper door whispers the past.”

4. Sydney, Australia: Urban Energy and Ocean Blues

Sydney Harbour may be one of the most photographed in the world, but for Oliver, arriving by sea amplifies its magic tenfold.

“There’s something primal about sailing past the Opera House and under the Harbour Bridge,” he says. “It’s like the city rises to greet you.”

Sydney’s Circular Quay is a vibrant hub where art, culture, and cuisine meet. Ferries buzz across the harbor, while buskers perform for travelers sipping flat whites in the sun. A hike through the nearby Royal Botanic Garden or a climb up the Harbour Bridge offers panoramic views.

But it’s Sydney’s maritime spirit that captivates. “The harbor is alive,” Oliver muses. “Not just with vessels, but with stories.”

5. Havana, Cuba: A Port Lost in Time

For Oliver, few ports evoked as much emotion as Havana.

“Sailing into Havana is like turning the clock back sixty years,” he writes. “Rusting Buicks line the streets, while salsa music echoes from open windows.”

The Port of Havana, once a key hub in Spanish colonial trade, still bears the weight of history. Fortresses guard the harbor entrance, and colonial architecture stands proud despite weather and wear.

Oliver wandered the narrow lanes of Old Havana, chatted with fishermen along the Malecón, and sipped mojitos in smoky bars that once hosted Hemingway. “Every crack in the wall had a story. Every face told a tale of endurance and passion.”

6. Reykjavík, Iceland: Gateway to the Elements

The cold, windswept port of Reykjavík offers stark contrast to the tropical ports of the Caribbean or Mediterranean, but to Oliver, its elemental beauty is unmatched.

“The North Atlantic greets you like a Viking,” he jokes. “But once inside the harbor, Reykjavík reveals a quiet resilience.”

The port is small but efficient, serving as a springboard to Iceland’s geothermal wonders and glacial landscapes. In summer, the sun barely sets, while in winter, the aurora dances across the sky.

“I bathed in the Blue Lagoon after a freezing sail through rough waters,” Oliver remembers. “It was surreal—like the Earth itself was welcoming me back.”

7. Cartagena, Colombia: The Walled Wonder

Few ports blend old and new like Cartagena. Set on the Caribbean coast, the city’s port leads to a UNESCO-listed old town surrounded by thick stone walls and brimming with Spanish colonial charm.

“Cartagena’s harbor is hot, chaotic, and filled with life,” Oliver notes. “And then you walk through the old gates and step into another century.”

Balconies drip with bougainvillea, Afro-Caribbean rhythms echo through the alleys, and street food sizzles on every corner. The port is also an important hub for trade and tourism, with modern cruise terminals that stand in contrast to the old city’s cobblestones.

“It’s a feast for the senses,” Oliver says. “And for me, that’s what makes a port unforgettable.”

8. Valparaíso, Chile: Colorful Chaos by the Sea

Perched on steep hills overlooking the Pacific, Valparaíso is a visual riot of color, murals, and zigzagging funiculars.

“Valparaíso doesn’t try to impress—it just is,” Oliver says. “Raw, honest, and bursting with energy.”

The port was once one of South America's most important before the Panama Canal shifted trade routes. Today, it remains a vital commercial port and a cultural beacon. Street art and poetry thrive here, and every building seems to tell a story.

“Pablo Neruda loved this place, and I can see why,” Oliver writes. “It’s messy in the most beautiful way.”

9. Halifax, Nova Scotia: Where Sea Meets Soul

For maritime heritage, Halifax is tough to beat. Its deep natural harbor has welcomed sailors since the 18th century, and the city proudly wears its seafaring past.

“The people of Halifax live with the sea,” Oliver says. “It’s not a backdrop—it’s a companion.”

He visited the Maritime Museum of the Atlantic, saw artifacts from the Titanic, and wandered along the historic waterfront boardwalk. Lobster rolls, maritime music, and salty air completed the experience.

“There’s an old-soul kindness here,” he writes. “The kind that makes you want to stay a little longer.”

10. Singapore: The Pinnacle of Modern Port Efficiency

Finally, no list of world-class ports would be complete without Singapore, one of the busiest and most efficient harbors on the planet.

But it’s not just about scale for Oliver—it’s about precision.

“Singapore is a symphony,” he says. “Everything works, everyone moves with purpose, and yet there’s time for orchids and hawker food.”

The Marina Bay area dazzles with futuristic architecture, while neighborhoods like Little India and Chinatown hum with tradition. For sailors, the blend of technological prowess and cultural depth is irresistible.

“It’s a glimpse of the future,” Oliver says. “And yet it still feels human.”

Conclusion: Ports as Portals

In “Anchored in Awe”, Oliver reminds us that ports are more than infrastructure. They’re portals—to new lands, new cultures, and new versions of ourselves. Whether it’s the opulence of Portofino, the grit of Valparaíso, or the innovation of Singapore, each harbor offers a different kind of awakening.

“Every time I tie a line to a new dock,” Oliver reflects, “I feel the same thrill I did on my first voyage. It’s not just about where you sail—it’s about what you find when you arrive.”

For travelers, dreamers, and seafarers alike, Oliver’s journey is an invitation: to explore, to connect, and to stay anchored in awe.