Windstar Cruises: Costa Rica & The Panama Canal Sailing Review

Recently, I was able to check off a journey that has held a permanent place at the top of my personal travel bucket list for quite some time: cruising through the historic Panama Canal aboard a true sailing yacht.

I sailed aboard Windstar Cruises’ Wind Star on a classic seven-night itinerary from Puerto Caldera, Costa Rica, to Colón, Panama. It was an exceptionally relaxing and rejuvenating voyage where my travel companion and I had to be responsible for very little. We booked a pre-cruise hotel night in San José and all private transfers directly with Windstar Cruises — and from the moment we cleared Costa Rican customs, we were expertly and flawlessly taken care of.

Pre-Cruise Luxury: Marriott Hacienda Belén

After an easy 20-minute private transfer from Juan Santamaría International Airport (SJO), we arrived at the Marriott Hacienda Belén in San José. Since our morning flight landed early, we began our day with an al fresco breakfast at the Hacienda Kitchen before checking in.

The garden patio features sweeping views across manicured grounds toward the rolling hills framing San José. We spent a peaceful afternoon unwinding beside the swimming pools before an early dinner. The dedicated Windstar hospitality desk in the lobby issued our ship luggage tags and provided our morning departure timetable, ensuring our transfer to the pier was completely stress-free.

Embarkation & Life Aboard the 148-Guest Wind Star

The following morning, after a restful sleep and breakfast, our private shuttle carried us west to the Pacific port of Puerto Caldera. Check-in was swift, security was seamless, and our luggage was delivered directly into our stateroom while we were welcomed aboard with champagne.

For an intimate 148-passenger sailing yacht, our oceanview stateroom felt remarkably spacious and thoughtfully laid out. There was generous wardrobe space, a comfortable queen bed with Egyptian cotton linens, a well-appointed marble bathroom, and clever under-bed storage that easily swallowed our luggage. Throughout the cruise, we continued to discover intuitive, hidden cubbies and shelves.

Each evening before dinner, guests gathered in the main lounge for live music and a “Port Talk” with the Destinations Manager and expedition naturalist, Diego. He detailed the schedule for the next day, highlighted hidden coves and walking routes for independent wanderers, and shared fascinating context on local biodiversity and Central American history. It became the natural social hub where lifelong friendships were forged.

Dining aboard Windstar is a standout highlight. Most evenings, we dined at Amphora, the yacht’s elegant main restaurant. There are no assigned tables or rigid dining times; you can choose an intimate table for two or join fellow travelers at larger tables. The menu changes nightly with inventive fresh seafood, handmade pastas, and prime cuts. Portions are thoughtfully sized so you never leave feeling overly full — although the homemade lasagna was so exceptional it tempted an encore!

Quepos & Dolphin Encounters in Golfo Dulce

Our first port of call along Costa Rica’s Pacific coastline was Quepos, the gateway to Manuel Antonio National Park. Because our visit fell on a quiet Sunday, we elected to spend the morning taking full advantage of the ship’s iconic Marina Watersports Platform.

The marina platform lowers directly from the ship’s stern into the Pacific. The water was crystalline and warm, making for ideal swimming and paddleboarding. That evening, we dined al fresco under the stars at Candles — Windstar’s complimentary reservation-only deck grill, accompanied by gentle ocean breezes and grilled sea bass.

In Puerto Jiménez, nestled within the pristine waters of Golfo Dulce, we joined the Dolphin Watching expedition. A wonderful convenience of small-ship sailing: the local excursion launch pulled directly up alongside the Wind Star’s gangway to pick us up, eliminating the need to tender into a commercial dock first.

Wildlife in nature operates on its own terms, but Golfo Dulce delivered absolute magic. Within twenty minutes, our boat was surrounded by a resident pod of 40 to 50 pantropical spotted dolphins, including mothers leaping synchronically with tiny newborn calves! The dolphins rode our bow wake and leaped through the air for nearly an hour — an unforgettable encounter before we spotted several large bottlenose dolphins nearby.

Windstar Signature Beach Day: Isla Parida, Panama

Windstar is world-renowned for its private Beach Days, and our day on Isla Parida in Panama’s Gulf of Chiriquí National Marine Park was pure tropical bliss.

The crew shuttled everything ashore onto an uninhabited, palm-lined beach with powdery white sands and turquoise water. Chaise lounges were positioned beneath shady palms, a full open bar was poured, ocean kayaks and stand-up paddleboards were lined up along the surf, and a sumptuous beach barbecue lunch was prepared over open coals. For ultimate relaxation, spa therapists even offered open-air beachside massages.

Following a restorative day at sea under full sails, our final port before the canal was Balboa, Panama. After strolling the marina promenade, I returned to the ship for a rejuvenating deep-tissue treatment at the World Spa with therapist Fe — a modest spa in footprint, but extraordinary in technique. That evening concluded with Windstar’s legendary Top Deck Barbecue, where the pool deck was transformed into a lavish open-air feast with whole roasted pig, fresh paella, grilled jumbo shrimp, and dessert buffets under a canopy of stars.

Transiting the Panama Canal: Pacific to Caribbean

The centerpiece of our voyage began in the pre-dawn darkness just off Panama City. The logistical choreography executed by the Panama Canal Authority (ACP) is awe-inspiring to watch firsthand from the open decks of a sailing yacht.

Because our four masts rise over 200 feet above the waterline, our northbound transit had to be timed precisely for dead low tide to pass beneath the iconic Bridge of the Americas. As we glided beneath the massive steel arch, there were barely five feet of clearance between the bridge girder and the top of our mainmast — a breathtaking start to the day.

From the Pacific entrance, electric locomotives known as “mules” guided the Wind Star into the dual chambers of the Miraflores Locks. The massive steel miter gates closed behind us, and without mechanical pumps — relying entirely on gravity from upstream lakes — millions of gallons of freshwater lifted the ship up toward Miraflores Lake.

A single lift through the Pedro Miguel Lock raised us to the summit level of Gatun Lake, sitting 85 feet above sea level. From there, we navigated the narrow canyon of the Culebra Cut (Gaillard Cut), blasted through the Continental Divide by tens of thousands of workers over a century ago.

Cruising across Gatun Lake was mesmerizing. The five miles of rainforest bordering either side of the canal are federally protected conservation reserves, alive with toucans, howler monkeys, and lush jungle canopies.

Finally, in the afternoon, we entered the triple-flight Gatun Locks, stepping down 85 feet in three continuous stages before slipping into the Caribbean Sea. The entire transit spanned nearly nine hours — every minute narrated with expert historical commentary from our guest canal pilot.

Disembarkation & Smooth Homeward Transit

Our journey concluded at the port of Colón on the Atlantic coast. Disembarkation was as smooth as embarkation: our luggage was waiting in the customs terminal, and within minutes we were aboard our comfortable air-conditioned coach for the 90-minute highway transfer across the Isthmus to Tocumen International Airport (PTY) in Panama City.

PTY is modern, air-conditioned, and remarkably easy to navigate, with extensive food courts, airline lounges, and device-charging stations before our nonstop flight home.

Frequently Asked Questions: Cruising Costa Rica & Panama