Continuing our adventure from Africa towards the entrance to the Mediterranean Sea our first stop is in Funchal, Madeira an island of the country of Portugal. Tucked away in the middle of the Atlantic Ocean, Funchal — the capital of Madeira, Portugal — is one of those rare places that still feels like a hidden gem. A place where misty mountains kiss the clouds, banana groves spill down hillsides, and cobblestone streets lead you to unexpected beauty.
The city Funchal is a tapestry of colonial charm, subtropical gardens, and bold ocean views. It’s small enough to explore on foot, but packed with character. Whitewashed buildings with red-tiled roofs rise up the hillsides, framed by green mountains and the endless Atlantic beyond.
The streets of the Old Town (Zona Velha) are a maze of colorful doors, local art, and tiny bars serving up the island’s famed black scabbard fish and bolo do caco garlic bread.
Funchal feels like it was designed by a botanist. You’ll see why it’s often called the “floating garden of the Atlantic.”
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Monte Palace Tropical Garden is like walking through a dream: koi ponds, tile murals, waterfalls, and plants from all over the world.
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Take the Funchal Cable Car up to Monte for sweeping views of the bay.
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For a thrill, try the iconic toboggan ride down the hill in a wicker sled — yes, it’s touristy, but it’s fun and fast and only found here. Unfortunately because it was Sunday they weren’t running the day of our visit.
Church of Our Lady of Monte (Igreja de Nossa Senhora do Monte)
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A beautiful 18th-century Baroque church with a grand staircase and panoramic views.
The view from the base of the stairs…. After our time at the top of the cable car we decide to take the Hop on- Hop Off Bus tour which will wind us through the mountain areas outside of Funchal and up the coast.
The Hop-On Hop-Off Bus in Madeira is more than just a sightseeing ride — it’s a rolling balcony over one of the most stunning islands in the Atlantic. It lets you move at your own pace, skip the hassle of local transport, and focus on what really matters: soaking in the lush, dramatic beauty of Madeira.
Whether you’re traveling solo, with kids, or just want to take a break from hardcore hiking, this bus tour is a relaxed, scenic, and surprisingly fun way to see the island.
The Madeira HOHO… 
Next up was a stop at Camera De Lobos. Stepping off the bus the feeling began to shift immediately. This a a very picturesque cute fishing village. The harbor and water is always visible from the rows of whitewashed houses and cliffs peppered lush vegetation. Small fishing boats — painted in sun-faded blues, reds, and yellows — bobbed gently in the water which is nearly like classic New England. It almost is a tranquil moment that communicates a simpler lifestyle rather than another traditional tourist stop.
Getting back on the HOHO for our trip back to the pier/port in Funchal we continued an “Ooh N Ahh” Tour of the sites of Funchal, Madeira. The city is a busy place, built on many steep hills, but the lush vegetation and plants coupled with the location adjacent to the coastline make a spectacular place hence why it is often referred to as the Island of Eternal Spring due to its mild, year-round climate and abundant flora. It’s also called the “Pearl of the Atlantic” for its natural beauty and attractiveness. Additionally, Madeira has been nicknamed the “Hawaii of Europe” for its dramatic landscapes, including volcanic peaks and lush, green terrain.
The evening we left Madeira we had a great meal in MDR (Main Dining Room) reflecting on our time in Madeira. It is such a beautiful Island in the country of Portugal. Afterwards we headed to the Princess Theatre and we are so thankful we did. Performing tonight was a a Trio called “The Trawler men”… An truly outstanding performance!
With one day of sea on Monday 3/24/25 to rest up before our arrival in Gibraltar and the entrance to the Great Mediterranean Sea!
Tuesday 3/25/25: The Famous Rock of Gibraltar…
Sailing into Gibraltar is an unforgettable experience. As your cruise ship approaches the port, the iconic Rock of Gibraltar dominates the skyline, offering a dramatic welcome to this unique British territory at the southern tip of Spain. The port is conveniently located within walking distance of the city center, making it easy to explore right off the ship. From duty-free shopping and charming streets to the famous Barbary macaques and stunning views from the Upper Rock, Gibraltar is a compact yet fascinating destination perfect for a day’s adventure.
One of the must-do experiences is taking the cable car to the top of the Rock. Departing from the base station near the city center, the ride takes just six minutes and offers stunning panoramic views along the way. At the summit, you’re treated to breathtaking vistas stretching across the Mediterranean, Spain, and even the coast of Africa on a clear day.
Up top, you’ll encounter Gibraltar’s famous Barbary macaques, Europe’s only wild monkey population — curious, cheeky, and always a highlight for visitors. There’s also plenty to explore, from historical sites like the Siege Tunnels to scenic walking paths along the Upper Rock Nature Reserve.
Our next stop was a walk up to O’Hara’s Battery which was an important strategic position to protect entrance into the Mediterranean Sea….
Our next tourist stop up on top of Gibraltar is the famous St. Michael’s Cave… This cave is a wet cave with spectacular rock formations and with unbelievably dramatic lighting that really brings this wonder of nature to life…
We decided to walk most of the way down from the top of Gibraltar. Yes it is a ways but many opportunities for great pics below…
While the views and the macaques are major highlights, Gibraltar’s military history is equally compelling — and much of it is literally carved into the Rock itself. One of the most fascinating areas to explore at the top is the network of Great Siege Tunnels, an impressive system of military caves and tunnels dug by hand during the late 18th century.
These tunnels were originally created during the Great Siege of Gibraltar (1779–1783), when British forces were defending the territory against Spanish and French troops. Engineers carved through the solid limestone to build strategic lookout points and gun positions, allowing them to defend the north face of the Rock. The ingenuity and effort involved are astonishing, especially when you consider the primitive tools used at the time.
Later, during World War II, the tunnel system was expanded dramatically. Over 30 miles of tunnels were dug to create underground barracks, hospitals, storage areas, and command centers — effectively turning the Rock into a fortress city that could support thousands of troops. Today, parts of these World War II tunnels are also open to the public, offering a glimpse into the wartime history that shaped Gibraltar’s strategic importance.
Walking through the tunnels, with displays and audio guides bringing history to life, gives visitors a powerful sense of the challenges and resilience of those who lived and served here. It’s a must-see for history buffs, military enthusiasts, or anyone curious about how this small outpost played a big role in global conflicts.
Whether you’re drawn by the unique blend of British and Mediterranean culture, the rich military history, or simply the unbeatable views, Gibraltar makes for a fascinating and easy-to-navigate port of call that we both will never forget…
Friday 3/28/25 : Siracusa, Italy
Siracusa, on the southeastern coast of Sicily, offers a perfect blend of ancient history, Mediterranean beauty, and relaxed Italian charm — all within easy reach of the cruise port. Once one of the most powerful cities in the ancient Greek world, Siracusa is now a captivating destination with layers of history and culture waiting to be explored.
Most cruise ships dock near the heart of the city, just a short distance from Ortigia Island, the historic center of Siracusa. Easily walkable and incredibly atmospheric, Ortigia is a maze of narrow alleys, elegant piazzas, seaside promenades, and baroque architecture. Here, you can wander through Piazza Duomo, visit the stunning Cathedral of Syracuse — built atop a 5th-century BC Greek temple — and enjoy a leisurely espresso with views of the sea.
For history lovers, a visit to the Parco Archeologico della Neapolis is a must. Just a short taxi or shuttle ride from the port, this vast archaeological park is home to some of the most impressive ancient Greek and Roman ruins in Sicily. Highlights include the Greek Theatre, still used today for performances, the Ear of Dionysius, a mysterious limestone cave with incredible acoustics, and the Roman Amphitheatre.
Between sightseeing, there’s plenty of time to enjoy the local Sicilian flavors. Whether it’s a scoop of pistachio gelato, a fresh seafood lunch by the harbor, or a glass of chilled local wine, Siracusa invites you to slow down and savor the moment.
With its stunning coastal views, deep historical roots, and relaxed island atmosphere, Siracusa is a gem of a port stop — easy to explore in a day, but sure to leave a lasting impression.
Well we have only started our time in the Mediterranean Sea and each stop has already been exhilarating and unique. We are just getting started here. From Sicily we continue to sail East with the Greek Islands up next . We have wanted to visit Greece since our daughter studied abroad there back in 2008. We have few travel regrets on our ongoing Revolutionary Journey aside from not getting over to Greece when she was there. We can ‘t wait to see in person the many memories she has shared with us from her college time there….
