In the Caribbean, the best ports are the ones you’ve never heard of — until now

The Caribbean is a sensory feast: impossibly blue water, vibrant reefs teeming with life, landscapes that shift from lush rainforest to sun-bleached desert within a single island chain. But the real magic happens at the harbors themselves — the intimate coves and storied ports where the islands reveal their character up close.

This is where Windstar’s small ships have the advantage. Rather than crowding into the same mega-ports as the big cruise lines, our yachts slip into harbors too small, too shallow, or simply too special for larger vessels.

Before diving into these picturesque harbors, it’s worth noting that the Caribbean can be tricky to parse, since it’s made up of three main archipelagos (sometimes called the West Indies collectively):

• The Greater Antilles — the big islands: Cuba, Jamaica, Hispaniola (Haiti/Dominican Republic), and Puerto Rico. These aren’t referred to as Leeward or Windward at all. Aside from Puerto Rico, where San Juan is a hub for some Leeward Islands itineraries, Windstar doesn’t currently visit this group.
• The Lesser Antilles — the best-known group, running from the Virgin Islands to Grenada, split into two sub-groups. The Leewards arc down from the north: the Virgin Islands through Anguilla, St. Maarten/St. Martin, St. Barts, St. Kitts, Nevis, Antigua, and Guadeloupe. The Windwards lie further south: Dominica down through Martinique, St. Lucia, St. Vincent and the Grenadines, and Grenada.
• The Leeward Antilles — a separate, often-confused third group: islands off Venezuela’s coast like Aruba, Curaçao, and Bonaire, plus Venezuela’s own island territories.

Windstar itineraries may focus on just one region or mix and match across overlapping areas. And it’s important to note that most of Windstar’s best off-the-path yacht harbor ports are located in either the Greater Antilles or Lesser Antilles. These are places that transport travelers’ experiences beyond the usual big ship ports in the region.

Here’s a look at some of the most scenic harbors along Windstar’s Caribbean routes.

The Leeward Islands

Anguilla:

Known for its pristine, sugar-white beaches and laid-back glamour, Anguilla offers the ultimate Caribbean retreat. It’s a destination reserved largely for small ship cruise lines, which anchor in the intimate Road Bay, its low-key harbor lined with beach shacks and cafés. Snorkeling at Little Bay offers calm, clear waters, and the beaches throughout the island are soft and pristine.

Here’s a tip: it’s no longer a secret that Anguilla is one of the Caribbean’s culinary magnets. This tiny island has roughly 100 restaurants, including acclaimed spots like Blanchards — now celebrating more than 30 years on the island and widely credited with kickstarting its culinary reputation — the newer L’Étoile at Manoah Boutique Hotel, and Celeste by Kerth Gumbs at the Malliouhana Resort. Just as central to Anguilla’s food-lover reputation are its casual beach shack eateries (Blanchard’s, in fact, operates a fine-dining restaurant and a casual spot side by side).

Planning tip: Anguilla is included on Windstar itineraries such as:

• Beach, Fun and Sun
• San Juan and the Virgin Islands

Antigua:

Antigua is a little more than 100 square miles — about the size of Shreveport, Louisiana — yet it boasts 365 beaches. Its coastline is exquisite, thanks to an abundance of coral that keeps the water clear.

St. John’s, Antigua’s capital, is the usual port for big-ship visitors, but Windstar anchors in Falmouth Harbour, a world away, alongside other yachts and sailing vessels. The tender dock is within walking distance of Nelson’s Dockyard, a charming Georgian-era village also known as Antigua Naval Dockyard and Related Archaeological Sites.

Another option on this more pastoral side of the island: Antigua’s Rainforest Canopy Zipline, with 13 ziplines and two suspension bridges. For a gourmet afternoon on the beach, take a short taxi ride to Catherine’s Café on Pigeon Point Beach. And because Windstar’s yachts anchor in the harbor itself, its marinas are often open for swimming, sunbathing, and water sports.

Planning tip: Antigua is a highlight of several Caribbean itineraries, including:

• Beach, Fun and Sun
• Masterpieces at Sea: Gems of the Leeward Islands
• Star Collector: Caribbean Explorations

British Virgin Islands:

The British Virgin Islands of Tortola, Jost Van Dyke, and Virgin Gorda are a mainstay of Windstar’s intimate Caribbean voyages and are among the most laid-back places any small cruise ship visits.

Soper’s Hole, Tortola

Tortola is one of the only British Virgin Islands to accept larger cruise ships (at Road Town, its main city), but, as with Anguilla, Windstar docks instead at Soper’s Hole, a tiny harbor with a restaurant, a bar, and colorful West Indian buildings. This stop is a low-key jumping-off point for beach adventures at spots like Long Bay Beach or Smuggler’s Cove.

Prickly Pear Cay, Virgin Gorda

In Virgin Gorda’s North Sound, Prickly Pear Cay is an uninhabited national park island — and, on Windstar’s itineraries, typically the site of its famous beach barbecues. Travelers usually spend the morning exploring Virgin Gorda by shore excursion (unless spending the whole day at the beach, since there’s no independent transportation on the cay). The must-see experience is a trip to Virgin Gorda’s The Baths: massive granite boulders spread across Devil’s Bay on the island’s north shore, threaded by a series of steps and ropes that guide adventurers through grottos from beach to bay. It’s also an excellent spot for snorkeling.

As BVI Insider explains, these boulders — found along the shoreline from Devil’s Bay to Spring Bay — were formed by volcanic uplift. Roughly 45 million years ago, an intrusion of hot liquid magma (a batholith) pushed ancient seafloor sediments above sea level.

Jost Van Dyke

At just three-square miles, Jost Van Dyke is the smallest of the BVI’s main islands. For visitors, there are two main destinations. Great Harbour holds Jost’s small town — government offices, a church, and the famous Foxy’s Tamarind Bar. Foxy’s is far more than a beach bar; it’s set right on the sand, with a barbecue, hammocks, and live music.

On the other side of the hill is White Bay, entirely pleasure-oriented, lined with beach bars and cafés such as the Soggy Dollar Bar, birthplace of the beloved Painkiller cocktail.

Framing both waterfronts is a mountain ridge that tops out around 1,000 feet.

Because ships anchor in Great Harbour alongside sailboats and yachts, its marinas are often open to guests.

Planning tips: Numerous ports here find their way into Windstar’s itineraries. They include:

• Beach Fun and Sun (Jost van Dyke, Soper’s Hole and Virgin Gorda/Prickly Pear Cay)
• San Juan and the Virgin Islands (Jost van Dyke and Virgin Gorda/Prickly Pear Cay)
• Star Collector: Caribbean Explorations (Jost van Dyke, Soper’s Hole, Virgin Gorda/Prickly Pear Cay)
• Star Collector: Caribbean Collection: ABC, BVI & the Windwards (Jost van Dyke, Virgin Gorda)
• Star Collector: Atlantic Crossing to the British Virgin Islands (Jost Van Dyke, Virgin Gorda)
• Star Collector: Windward Islands, ABC Islands, and the Virgin Islands (Jost Van Dyke, Virgin Gorda)

United States Virgin Islands: St. John

St. John, a far more intimate island than the USVI’s St. Thomas, offers smaller cruise ships an anchorage that’s more working harbor than postcard bay. Even so, views of the surrounding mountainous islands, an abundance of gorgeous beaches and bays, and a vibrant downtown known for distinctive eateries and boutiques make it a lovely — and rare — port of call for small ships.

Planning tip: Cruz Bay is a port of call on a handful of Windstar’s itineraries, such as:

• San Juan and the Virgin Islands
• Windstar’s Star Collector: Atlantic Crossing to the Virgin Islands

St. Barts: Gustavia

Like every island in the Lesser Antilles, St. Barts (full name Saint-Barthélémy) has plenty of gorgeous bays and beaches, and it’s a great destination for snorkeling and diving. But that’s the least of this swanky, French-flavored isle’s appeal — it’s known just as much as the preeminent Caribbean playground for the rich and famous. Cruise travelers arrive by tender (only small ships are welcome, and all must anchor out in Gustavia Bay), and the main town of Gustavia is packed with pricey boutiques from Louis Vuitton, Prada, Cartier, and Hermès. Its restaurants — aside from the rather touristy Le Select — are equally elegant.

Gustavia is a destination in itself, but you’ll miss much of St. Bart’s charm if you don’t explore further. St. Jean Beach, near Eden Rock, is another wonderful spot for a day out, with tranquil seas alongside numerous boutiques and restaurants. For something more rustic, head to Saline Beach, home to a handful of salt ponds once used to harvest the mineral.

Planning tips: St. Bart’s appears on the following Caribbean itineraries:

• Classic Caribbean
• Star Collector: Caribbean Explorations
• Masterpieces at Sea: Gems of the Leeward Islands
• Star Collector: Atlantic Crossing to the Virgin Islands
• Star Collector: Windward Islands, ABC Islands, and the Virgin Islands

St. Martin: Marigot

Planning tips: If the adjacent island of St. Maarten is the more common port for this two-nation island — particularly as an embarkation/debarkation stop — Marigot itself appears on a few itineraries, including:

• San Juan and the Virgin Islands
• Star Collector: Windward Islands, ABC Islands, and the Virgin Islands

Guadeloupe’s Les Saintes

Small ships skip Guadeloupe’s bustling capital of Pointe-à-Pitre. Instead, they anchor at Les Saintes, an archipelago serving Terre-de-Haut. Its picturesque bay is framed by red-roofed houses, volcanic mountains, and an old fort.

There’s otherwise little to see in this fishing village unless you head out on the water — kayaking, snorkeling, and sailing are the main draws, and Windstar’s marinas are often open here. One sightseeing exception: the Habitation Bellevue Distillery, which has made rum since 1821, offers self-guided tours and tastings; visit between February and April to watch its workers in action.

Planning tip: Guadeloupe appears on the following Windstar itineraries:

• Masterpieces at Sea: Gems of the Leeward Islands
• Classic Caribbean
• Beach, Fun and Sun

The Windward Islands

Bequia, Saint Vincent and the Grenadines: Port Elizabeth

St. Vincent and the Grenadines is an island nation, of which Bequia is one of the larger islands. The official language is English, and the main industry is agriculture, including the harvest of arrowroot — used as a gluten-free thickener.

Bequia — meaning “island of the cloud,” pronounced “beck-way” — is a seven-square-mile speck. Ships can only anchor in Admiralty Bay, since Bequia has no cruise ship pier and only smaller vessels can access the island. From there, you’ll tender into Port Elizabeth, the island’s walkable, low-key capital, full of local color and free of Caribbean crowds.

The star attractions are Bequia’s beaches, including Hope Beach on the island’s windward side — your reward for a lengthy taxi ride from Port Elizabeth and a mile-long hike down to the shore is a real sense of seclusion. Another option is Friendship Bay, a quiet spot on the opposite side of the island from Port Elizabeth; again, plan to bring your own refreshments. As with any unfamiliar beach, ask locals what swimming conditions and skill level are appropriate before taking the plunge.

Another option is Bar One, a floating watering hole in Admiralty Bay. After tendering to the jetty at Port Elizabeth, call ahead to request water taxi pickup (about 5–10 EC dollars). Phone: 1-784-530-8123.

Planning tip: Bequia is a stop on the following Windstar itineraries:

• Windward Ways and Tobago Cays
• Windward Islands Surf and Sunsets

Care to share your own favorite yacht harbor in the Caribbean? Tell us all about it in our comments section.

The post Best Caribbean Harbors for Small Ship Cruises appeared first on Windstar Cruises Travel Blog.

I was told my borrowed horse Luther had just two speeds as we headed out for our sunset ride through El Salobre on the island of Gran Canaria: “slow and super slow.” This, on my second to last day of touring the Canary Islands on Windstar Cruises’ Wind Star, felt like provenance, a gift. I had tasked myself every day of this inaugural 10-day Canary Idyll itinerary aboard Wind Star to look at the world with Luther-level languor, a last hurrah of quiet before the holidays. It was my moment to be quiet within myself not only onboard but also at these extraordinarily charming ports.

Luther, that gentle, molasses-slow giant, was my spirit animal.

Feeling fortunate in the Canaries

Our cruise with Wind Star, which carries up to 148 guests as well as 101 staff members, began at Santa Cruz de Tenerife and stopped at San Sebastián de La Gomera, Santa Cruz de la Palma, Madeira, Lanzarote, and Las Palmas de Gran Canaria before debarking at Santa Cruz de Tenerife. While not a vastly experienced cruiser, I had already been to bustling ports like Valencia and Palma de Mallorca, and a part of me was expecting something similar.

What I was not expecting was the topography of this island. Like the Hawaii of Europe. All lush green mountains and ocean breezes, black sand beaches and palm trees. The Canary Islands, I quickly learned, might be a part of Spain but also something else entirely. There’s a reason this archipelago, just 60 miles off the northwest coast of Africa, were once called the “fortunate islands.” The people I met at these ports of call, the food I ate, the wine I drank, the black sand beaches where I floated under the sun, left me drunk with my own good fortune to be here.

I am at a crossroads in my own life that is both fortunate and unusual. My four sons have gone off to live their own lives, and I am searching for my next stage after raising them on my own for the last 25 years. Trying to tell myself that now is the time to slow down, to notice, to find peace, after a lifetime of running kids around and sitting on the sidelines.

I could not have chosen a better place than the Canary Islands.

On arrival, a late night wander through Santa Cruz de Tenerife

My flight didn’t arrive until evening in Santa Cruz de Tenerife, which meant I had just enough time to check into the hotel Windstar had chosen for me right in the middle of the old town, the Iberostar Heritage Mencey, wash my face. Eventually, I headed out for that most important of Spanish traditions, late night tapas at a local restaurant, dining around 10 p.m. in a restaurant crowded with locals. I feasted on fresh local bread with salted butter and warm crab potato salad and ham croquettes with a glass of local wine. My wander home took me through the surprisingly quiet, balmy streets of old town Tenerife. A perfect introduction to the Canary Islands, as it set me up for a different pace. A slower pace, an unfamiliar pace so quintessential to Spain itself.

Unveiling the cruise experience on Wind Star

Before boarding the Wind Star on Santa Cruz de Tenerife, I took the 6 1/2 hour flight from Toronto to Dublin. My flight arrived in the morning and I connected in the afternoon for the four hour flight to Santa Cruz de Tenerife. The layover was long but easy, with enough time to leave the airport and take the bus to the little town of Swords for a classic Irish breakfast.

For faster flights, the Madrid layover on my way home was excellent.

Seeing Wind Star at port, a jewel of a sailing ship, was a treat. As our captain noted on our first night, “You will feel like you are on an adventure in this ship.”

Indeed. That first night, I was rocked to sleep in my stateroom by waves as though I were in a hammock. Especially on sea days, when everyone on the ship found their corners to tuck under a blanket in the bright sunshine to enjoy a coffee or a signature cocktail. And we were always inspired by the ports of call we visited.

Whistling a happy tune in San Sebastián de La Gomera

Our first port of call was San Sebastián de La Gomera, a place so specific and unusual that Christopher Columbus couldn’t even tear himself away back in the 15th century. No small thing considering his agenda. Rumor has it that his extended stay had a little something to do with a little affair he was having with the female ruler of the island at the time, Beatriz de Bobadilla. I suspect it had more to do with the black sand beaches, the lush green hills and sweeping vistas from Benchijigua Nature Reserve. Or perhaps he was entranced by the unique whistle language, Silbo Gomero, unique to the island. In fact, I was lucky enough to take a walking tour of the charming port town and hear this UNESCO-protected language being taught to some local students. We stopped and rested, listened to the children’s musical whistling. Their giddy laughter when they got it right. Their easy joy.

Before leaving port, I spontaneously threw on my swimsuit and took the quick walk from our ship to the beach for an evening swim at my travel partner Eddy’s suggestion. Eddy and I met on a Windstar cruise circumnavigating Iceland just two years ago and instantly knew we would be simpatico travel pals. He is a travel agent, a thinker, a planner of epic proportions. I am happy to say yes to just about anything, especially my very first swim on a black sand beach. We joined locals for a sunset dip just before our ship left port, floating on our backs in the cool sea and wishing we had spent more time just being on this quiet stretch of beach. This, of course, is the true benefit of this type of small ship cruise. Small ports, fewer people, easy to shift plans on a dime. Or, as I discovered in our next port, to make new plans as we went along.

Old-world charm and wild winds on Santa Cruz de la Palma

We awoke to wild winds when we docked in Santa Cruz de la Palma. I had been toying with the idea of an excursion, but decided I wanted to focus two desires. I wanted to sample a decadent dessert and a coffee and I wanted to see the Canarian balconies, renowned for their ornate, wooden designs that marry form and function. What’s intriguing is that they are beautiful but also practical, as they offer ventilation on hot summer days. The colorful, covered balconies decorated for the holidays with greenery and flowers were easy to find, and Santa Cruz de la Palma was easy to navigate.

Lots of cafes and locally owned shops dotted the historic city center, and I found what has become, for me, the dessert to beat all desserts, the Principe Alberto. A chocolate tart/sponge cake with crushed almonds grown right on the islands, decadently drenched in strong coffee. “There’s no such thing as bad food in the Canaries,” a British woman said to me in line at the cafe while I was deliberating on my options.

Road trip of natural pools, hiking in the clouds, and charming villages in Madeira

Two days in Madeira, our only stop in Portugal, felt like a good time to rent a car. Fortunately, my pal Eddy relished the hair pin turns and long drives through dark tunnels, because this was by far the best way to get a real taste of Madeira.  To think I might have missed out on a walk through the quaint fishing village of Camara de Lobos, just a quick drive out of the thriving capital city of Funchal, or had missed a chance to swim in the famous natural pools of Porto Moniz! I don’t think I spent more than 15 minutes indoors during my time in Madeira.

We hiked the TikTok famous hike through Stairway to Heaven, a section of the Pico do Arieiro trail, as the sun went down. The sunset’s power made me feel wordless and liquid.

That car gave me the chance to slow down, to notice everything, to take my time. From the thatched roof cottages of Santana to the laid back surfing village of Porto da Cruz, I got the full culture hug of Madeira without feeling rushed. While we went our own way, there were some tempting excursions on offer from Wind Star. A toboggan ride from Monte, at the tip of Funchal, down the steep streets of the city was a hit with other cruisers, as was the panoramic drive and Tuk Tuk ride in Funchal.

Life on Board

Wind Star’s size, carrying just 148 passengers, was perfect for me. Small enough to feel intimate and cozy, to get to know the staff and fellow travelers, but not so small that I felt pressure to engage if I wanted a moment to myself. A highlight was the onboard barbecue, where we danced the night away under the stars after a feast that took over one entire deck. We met a mom and daughter spending time together after a tough year, a couple on their 50th wedding anniversary and a pair of newlyweds.

And, as ever, it was the staff who really made everything special. How they manage to remember not just names but also preferences, little details like how I like my coffee or sending a piece of chocolate cake to my room after I mentioned it in the dining room one evening, is heartwarming. They became friends, so much so that I felt quite sad to leave them behind.

Volcanic wine and walking in volcanoes on Lanzarote

Lanzarote doesn’t look like anywhere else. It is stark and rocky and wild. A tough place to grow anything and yet life thrives on this island. Most importantly, its wine industry continues to thrive. Especially the Malvasia Volcanica grape endemic to the island’s volcanic soil, producing a crisp, cold white wine with mineral and citrus notes unlike anything I’ve ever sipped.

Every view in Lanzarote was otherworldly, almost impossibly different, almost like being on the moon. From the Green Lake to walking inside a volcano at Caldero Blanca, and from camels lounging outside Timanfaya National Park to quiet seaside villages perched on volcanic rock, it’s all unique. And best enjoyed at a slow easy pace, preferably sipping a glass of wine.

Coffee, oranges, and Luther on Gran Canaria

Our final two days were spent in Gran Canaria, which felt like five different islands in one. At first blush, Gran Canaria was industrial, busy, hectic. A culture shock after the peace and quiet of Lanzarote. A trip to the north sent me to verdant greenery and massive rocky cliffs. A trip south featured sand dunes to rival the African desert, so close and yet so far. Everywhere I looked felt like a different island entirely. Especially when our excursion, a horseback riding experience, took us a quick drive away from Las Palmas and we slowed right down. Just in time for my fateful meeting with Luther, that gentle giant. Eddy is a comfortable rider with years of experience, and I was determined not to let my anxiety get the better of me though Luther’s size did not help.

But the peaceful surroundings, the sun setting over the southern foothills of Gran Canaria from the peak of Pico de las Nieves to the Maspalomas dunes, the cactus flowers blooming all around us, brought me back to myself. Reminded me of where I was, and how far I’d come, and why I was here. To try new things. To get out of my own head. To slow down and breathe.

And so on my last day, I joined an excursion out to the other side of the island, the Agaete region. We stopped at the little town of Puerto de las Nieves, where I hung out with some locals going for a morning dip. Watched stray cats and dogs sunning themselves. Wondered if it would be strange if I just moved here for awhile. There was something about the sea and the cliffs and the tranquility that appealed to me.

Then back on the bus to visit a farm in the hills. Bodega Los Berrazales is far from the tourists and the beaches and the shopping. We took a road that felt like putting on jeans two sizes too small. Squeezing past little tables of men playing cards, clothes lines of colorful t-shirts, rows of houses that looked like they were hugging each other.

Here I wandered through the orange groves. I ate some cheese and honey, not just delicious but vital to the local economy and the cultural identity of the island. The sale of goat cheese and honey supports small, sustainable farms like this one, which also incidentally produces the only coffee in Europe. I wanted to lie down in the tall grass afterwards for a little nap.

Ultimately, the greatest gift of my Canary Islands cruise on Wind Star was that I had learned to slow down. Learned to be present. Learned to drift from island to island with ease and joy. Now I have two speeds myself. Slow and super slow.

If you Go: The Canary Islands

• Our Passport Guide is a great resource for facts and tips about a Canary Islands cruise.
• Canary Islands voyages, which have been hosted aboard Wind Star and will soon take place on Wind Spirit, her identical 148-passenger sister ship, are a perfect antidote to winter in the Northern Hemisphere. Itineraries run from mid-autumn to late winter.
• The 10-day Hidden Gems of the Canary Islands and Madeira is a great option for your first visit. And if you want a longer getaway, Windstar offers 18 and 20 day trips via Spain’s southern coast and Morocco.

The post What It’s Like: Cruising Around Spain’s Canary Islands appeared first on Windstar Cruises Travel Blog.