Captain Jose and his first mate Tiago welcomed us to the LisbonByBoat sunset cruise at the shiny, slick Belem Marina. There were six other customers along for the ride on a lovely, warm evening aboard a luxury 65-foot sailing yacht, and we all had big fun taking in the sights and learning about the region. Seeing a city from the water is always a hoot.
We sailed around the mouth of the Tagus River, which starts in Spain and journeys 625 miles to the ocean in Lisbon. It resembled a bay more than a river. There were quite a few tour boats cashing in on sunset, just like every other big city on the water. There were also cruise ships, small ferry boats, and recreational fishermen. In some spots, it resembled a boat parade.
The sail lasted about two hours, and we cruised past and under the Tagus’s captivating attractions. We raised the main sail but didn’t actually sail because the wind was light and there was heavy traffic. We motored slowly north along the Lisbon waterfront for a few miles, then headed back the way we had come while the hits just kept on coming.
The Discoveries Monument, a sculpted block of white limestone resembling a sailboat, with the carved heads of all the great Portuguese sailing discoverers, sits on the Lisbon waterfront like it’s about to set sail for parts unknown. At the prow of the boat stands Henry the Navigator, holding a tiny ship in his hands. Henry had the best PR machine in the world working for him. To this day, he gets credit for being a great discoverer, hence the navigator moniker, but in truth, he didn’t really know how to sail very well and rarely knew where he was. The Portuguese actually discovered Brazil by accident. They were trying to reach India, which was in the opposite direction.
Belem Tower is the fort that guarded Lisbon Harbor, even though it was only big enough to house a few cannons, making it the puniest fort I ever saw. The Tower of Saint Vincent is a 16th-century global symbol of the Age of Discovery. Built between 1514 and 1520 under King Manuel I, it acted as both a defensive fortress at the mouth of the Tagus River and a ceremonial gateway for returning explorers. Listed as a UNESCO World Heritage Site since 1983, it is widely celebrated for its striking Manueline (Portuguese Late Gothic) architecture, which weaves together Moorish watchtowers, carved ropes, and ancient astronomical instruments and spheres. The interior of the tower is temporarily closed for structural restoration as part of Portugal’s national recovery and heritage preservation plan. While visitors cannot climb the internal levels or the rooftop terrace right now, the exterior remains fully accessible from the riverfront promenade. It remains one of Lisbon’s most popular spots for photography and coastal walks.
The Fairey III-D Biplane Seaplane is a life-sized stainless steel replica of the plane that made the first aerial crossing of the South Atlantic. It marks the exact spot from which the aviators, Gago Coutinho and Sacadura Cabral, took off on March 30, 1922, to celebrate the 100th anniversary of Brazil’s independence. The 5,210-mile trip from Lisbon to Rio de Janeiro took 79 days. The mission actually used three different biplanes because the first two — Lusitânia and Pátria — were lost at sea in accidents during the journey. While the riverside biplane is a replica, the actual third plane that finished the flight, the Santa Cruz, is meticulously preserved and on display at the nearby Maritime Museum (Museu de Marinha). The flight was a major milestone not just for its distance, but also for its use of the artificial horizon sextant, an invention by Gago Coutinho that enabled precise aerial navigation without a physical horizon.
The 25th April Bridge (Salazar Bridge) is the iconic suspension bridge connecting Lisbon with the municipality of Almada across the Tagus River. A spitting image of the San Francisco/Oakland Bridge, it features the same “International Orange” color and a similar steel truss design. They claim it’s even earthquake-proof. Let’s hope.
King Christ, the gleaming white Jesus with outstretched arms, stands atop a basalt ridge above the river and resembles its father, Christ the Redeemer, in Rio. Christ the King stands 108 feet tall on its own, representing one meter for each year of Jesus’s life. The addition of a 3-meter crown and a 16.5-meter stone brings its total height to 172 feet. The Christ the Redeemer Art Deco statue stands 98 feet tall on its own, resting on a 26-foot pedestal. The total height is 125 feet. This is a big deal to the people of Portugal. Brazil was a former colony, and even though they came up with the first arms-stretched statue on a hill, the Portuguese were bound and determined to build one even bigger. There’s even a church inside.
The Vasco da Gama Bridge is the longest bridge in Europe (10.7 miles). Spanning the widest section of the Tagus River estuary (known as the Mar de Palha), it links northern Lisbon with the south bank municipalities of Montijo and Alcochete. Opened on March 29, 1998, the bridge was built to alleviate severe traffic congestion on the city’s iconic 25 de Abril Bridge and was timed perfectly for the Lisbon World Exposition (Expo ’98), celebrating the 500th anniversary of Vasco da Gama’s maritime discovery of India.
The Lisbon Cathedral, known as the Sé de Lisboa, stands out along the Lisbon waterfront. It is a very special place. It is the oldest church in the city, founded in 1147, and the fortress-like Romanesque structure has survived numerous earthquakes. Its imposing, thick-walled design originally served as both a church and a defensive stronghold, symbolizing the Christian Reconquista, with significant Gothic additions later. It was built on the site of a former mosque immediately after Lisbon was reconquered from the Moors in 1147. The cathedral is believed to have a baptismal font where Saint Anthony of Padua was baptized. He’s the patron saint of lost things.
As we cruised along the shoreline, our eyes were drawn to Commerce Square (Praça do Comércio), Lisbon’s largest and most important square. In a city where you can’t swing a cat without hitting a square, Commerce Square stands out. It was built on the site of the old Royal Palace, which was destroyed by the 1755 earthquake. When the square was first built, commercial ships would unload their goods directly onto it, as it was considered the doorway to Lisbon and crucial for its maritime trade. These days, the Triumphal Arch is the main draw. The southern end of the plaza is an open expanse overlooking the Tagus River. The other three sides have yellow buildings with arches along their façades. On the riverbank, near the square, is the Cais de Sodré ferry terminal, from which several ferries depart down the Tagus River. Tourists are drawn to the square from all directions like lemmings to the sea, and most know nothing of its grand history. It’s a grand photo op.
On 1 February 1908, King Carlos I of Portugal was assassinated in Commerce Square (then known as Terreiro do Paço) in an event famously known as the Lisbon Regicide. King Carlos I was killed instantly after being shot in the neck and face by assassins. His eldest son and heir-apparent, Prince Luís Filipe, was also fatally wounded in the same attack and died approximately 20 minutes later. Technically, he was King Manuel I for twenty minutes.
The primary assassins were Manuel Buíça and Alfredo Luís da Costa, members of the Carbonária, a radical, anti-clerical secret society that operated primarily in Portugal and was modeled after the early 19th-century Italian Carbonari movement. They ambushed the royal family’s open carriage as they returned from the Ducal Palace of Vila Viçosa.
Queen Amélie famously attempted to defend her family by striking one of the assassins with a bouquet of flowers. Their younger son, Manuel, survived with a wound to his arm and subsequently became King Manuel II, the last King of Portugal.
The regicide was a turning point that severely weakened the Portuguese monarchy. Just two years later, the 1910 Revolution broke out, leading to the abolition of the monarchy and the establishment of the Portuguese First Republic.
Today, a bronze plaque on the pavement on the eastern side of Commerce Square marks the exact location where the assassination took place. Most folks don’t know it’s there and flock instead to the big statue of the king riding his horse.
Surrounding the square stands an impressive array of yellow government buildings that resemble grand warehouses, which is what they were when the Commercial ships anchored at the edge of the square and unloaded their cargo directly into the plaza. Over the centuries, these symmetrical structures served several critical institutional purposes:
- Trade and Customs Admin: The primary function was managing the heavy inflow of goods from Portugal’s global trading empire.
- Government Ministries: From the 19th century onward, they housed core departments including the Ministries of Finance, Internal Administration, Agriculture, and Maritime Affairs.
- Military Headquarters: Before the ministries were unified, the old War and Navy Ministries operated out of these wings.
- The Supreme Court: The complex also housed Portugal’s highest judicial branch.
According to our skipper, the Tagus waterfront used to be a polluted mess, and in 1998, coinciding with the European Expo, it was finally cleaned up. Lisbon transformed a 50-hectare derelict industrial wasteland on its eastern riverfront into the thriving Parque das Nações district. Cleanup efforts included remediating heavily polluted brownfields, relocating massive oil and chemical tank farms, and pioneering advanced infrastructure.
There is still some industry along the water, mostly agricultural and oil storage. The old red-and-white stone wedding cake power plant is now a handsome museum. And a few brightly-colored cranes were loading some rustbucket ships that appeared to be leaking oil.
A fleet of large and small ferry boats runs between cities and suburban hubs along both sides of the Tagus. Some are for transporting locals back and forth across the busy river, while others lead tours. There’s never a dull moment on the Tagus.
The 1755 Earthquake changed the flow of the Tagus, and all the shoreline was underwater, including the former Royal Ribeira Palace. Folks talk about it like it happened yesterday. Natural disasters have a very long shelf life.
Given that the Tagus isn’t far from the Atlantic Ocean (10 miles), Lisbon’s fishery is a vibrant mix of recreational angling, deeply rooted in centuries of maritime tradition. The local maritime landscape offers everything from action-packed deep-sea sportfishing to historic seafood-tasting trails. In summer, all hell breaks loose when dolphins come up the river to feed and frolic.
Stranger still, there is the ongoing and increasingly unnerving phenomenon of Iberian orcas (killer whales) attacking and sometimes sinking sailing vessels off the coast of Portugal and Spain.
The behavior, which began in 2020, has continued into 2026 with numerous disturbing incidents.
On September 13, 2025, a pod of orcas sank a tourist sailboat, the Oceanview, off Fonte da Telha (near Lisbon). All five people on board were rescued.
October 10, 2025, the French yacht Ti’fare sank 50 nautical miles off the coast of Peniche after orcas breached its hull.
In March 2026, multiple “attacks” were reported, including incidents south of Sesimbra and near Cabo da Roca.
The stats are unsettling: Over 750 events have been recorded since 2020, with over 70 incidents already reported in early 2026. The good news is the whales aren’t hunting people. They are just killing the boats. Theories abound. The most popular guess is that the whales have declared war after seeing their buddies run over by ships.
In times of trouble like these, many people turn to the church. And the church will be more than happy to offer you a Portuguese custard tart, known as Pastel de Nata (or Pastéis de Belém), which was invented by monks at the Jerónimos Monastery (Mosteiro dos Jerónimos) in the Belém district of Lisbon, across the train tracks from the marina where our tour boat was docked.
Before the 18th century, monks in monasteries, including Jerónimos, used large quantities of egg whites to starch their religious habits. To avoid wasting leftover egg yolks, they developed a recipe for a sweet custard tart. Essentially, laundry led to Portugal’s national sweet.
Following the monastery’s 1834 closure, the monks began selling pastries at a nearby sugar refinery to earn money. In 1837, this sugar refinery opened as Fábrica de Pastéis de Belém, which still operates today and is considered the only place producing the original recipe. The monastery is now a UNESCO World Heritage Site in Belém.
Unlike any other major European city, Lisbon’s airport is located in the middle of town. So, there are big jets flying low over the city at all hours of the day and night. It looks like Lisbon is constantly under aerial attack.
Lisbon’s harbor area is quite attractive and world-renowned. I felt a special connection to it because it shares some common history with my hometown of Annapolis, Maryland, which calls itself the “Sailing Capital of the World”.
Lisbon is often called the “Sailing Capital of Europe” because of its strategic position where the Tagus River meets the Atlantic. It has hosted several prestigious international regattas and round-the-world races.
The very first Tall Ships Race took place in 1956 between Torquay (UK) and Lisbon. Since 1956, Lisbon has hosted the fleet on several occasions, including major celebrations for the 50th anniversary (2006) and, most recently, for the Magellan-Elcano edition (2023). During these events, the docks of Alcântara host over 100 historic vessels, including the Portuguese Navy’s own famous tall ship, the NRP Sagres, which has visited the Chesapeake several times.
The Ocean Race (formerly the Volvo Ocean Race, which stopped in Annapolis several times) made Lisbon a central hub for this premier round-the-world offshore race, hosting major stopovers in three consecutive editions. Lisbon staged stopovers in 2011–12, 2014–15, and 2017–18.
Because of its ideal training conditions, Lisbon was also chosen as the permanent home of The Boatyard, the facility where the race’s high-performance Volvo Ocean 65 sailboats were refitted and maintained. The Tagus River also hosted the intense “In-Port” sprint races, offering spectators on shore a spectacular close-up view of the world’s greatest sailors in high-speed action.
Seeing Lisbon from the water — at sunset, no less — offered us a unique perspective, and one we will long treasure.
