Escape the Canadian winter and join me for a very special boutique Travel With Bradley journey to Costa Rica and Panama aboard the elegant Windstar Star Legend.
This carefully designed small-group experience combines deluxe hotels, tropical scenery, fascinating wildlife and the relaxed luxury of Windstar's intimate yacht-style cruising. Carrying only 312 guests, Windstar offers a far more personal and uncrowded experience than larger cruise ships, with exceptional service, spacious ocean-view suites and access to smaller ports and hidden coastal destinations many larger ships simply cannot reach.
Guests will have the opportunity to enhance their experience with a wonderful selection of optional Windstar shore excursions available for purchase throughout the voyage. Whether you prefer relaxing beach days, nature experiences, wildlife encounters or cultural touring, there will be something for everyone to enjoy.
I truly believe this journey offers the perfect combination of relaxation, adventure and warm tropical hospitality. As this is a special boutique departure with very limited space available, I encourage early booking.
This is truly relaxed luxury at sea.
Warmest Regards,
Bradley Walters
Itinerary
February 7 – 19, 2027
TORONTO – SAN JOSE, COSTA RICA
Due to our late return flight, we are including a one-night post stay at a Toronto Airport Hotel when you return to Toronto on February 18. This afternoon leave your vehicle at the hotel with complimentary parking and enjoy a shuttle ride to Toronto Pearson Airport. I will then greet you to assist with your flight check-in. Afterwards, meet your fellow passengers in the Plaza Premium Lounge for food and beverages — a special Travel With Bradley perk. Upon our late-night arrival in San José, we’ll transfer to an elegant upscale hotel for a good night rest to prepare for the exciting adventure ahead.
Meals Included: Lunch (L)
SAN JOSE & POAS VOLCANO
After breakfast, we’ll enjoy a guided excursion into Costa Rica’s beautiful mountain landscapes including a visit to Poas Volcano, one of the country’s most impressive natural wonders. We’ll also visit the gift store/cafe at Hacienda Alsacia, Starbucks’ renowned coffee farm, where guests may purchase locally grown Costa Rican coffee. Following lunch at a local favourite restaurant, return to the hotel for time to relax before our welcome dinner this evening.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
SAN JOSE – PUERTO CALDERA
After breakfast we'll transfer to Puerto Caldera where our beautiful yacht waits for our first glimpse of the elegant Windstar Star Legend. We will have lunch onboard, then you can settle into your ocean-view suite. Enjoy spacious ocean-view suites, exceptional dining and the kind of warm personalized service Windstar is famous for. With an impressive 1.5-to-1 guest-to-crew ratio, the atmosphere feels relaxed, welcoming and wonderfully uncrowded. Take time this afternoon to become acquainted with the ship, relax on deck and begin enjoying Windstar's wonderfully relaxed atmosphere as our Costa Rican coastal adventure begins.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
PLAYA FLAMINGO, COSTA RICA
Today we arrive at beautiful Playa Flamingo, famous for its stunning white sand beaches, crystal-clear waters and relaxed tropical atmosphere. Guests may wish to spend the day enjoying the beach, exploring the charming coastal area or joining one of Windstar’s optional shore excursions. The region is well known for its beautiful scenery, marine life and laid-back lifestyle, making it a wonderful introduction to Costa Rica’s Pacific coastline.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
PUNTA LEONA, COSTA RICA
Surrounded by lush rainforest and tropical beauty, Punta Leona offers a wonderful opportunity to experience Costa Rica’s incredible natural environment. This area is famous for its rich wildlife and guests may spot colourful scarlet macaws, monkeys and exotic tropical birds throughout the day. Whether relaxing on the beach, enjoying the scenery from the yacht or participating in an optional excursion, today promises another unforgettable Costa Rican experience.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
QUEPOS & MANUEL ANTONIO NATIONAL PARK
We arrive at Quepos the charming gateway to nearby Manuel Antonio National Park, considered one of Costa Rica’s most spectacular national parks. Famous for its lush rainforest, beautiful beaches and abundant wildlife, this region offers excellent opportunities to experience Costa Rica’s remarkable biodiversity. Sloths, monkeys, iguanas and colourful tropical birds are often spotted here. Guests may choose to relax and take in the scenery or participate in one of Windstar’s optional excursions.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
PUERTO JIMENEZ & GOLFO DULCE
Today’s visit to Puerto Jimenez, scenic Golfo Dulce showcases one of the most untouched and biodiverse regions of Costa Rica. Surrounded by rainforest and dramatic coastal scenery, this remote destination offers an authentic glimpse into Costa Rica’s natural beauty. Guests may enjoy relaxing onboard, exploring ashore or joining one of Windstar’s optional nature-focused excursions to further experience the region’s wildlife and tropical landscapes.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
ISLA PARIDA, PANAMA
Enjoy the peaceful tropical beauty of Isla Parida, a stunning island paradise located off Panama’s Pacific coast. Palm-lined beaches, warm turquoise waters and a wonderfully relaxed atmosphere create the perfect setting for a leisurely day. Whether swimming, sunbathing, enjoying water activities or simply relaxing onboard, today offers another memorable experience in paradise.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
DAY AT SEA
The day is yours to simply relax and enjoy the many comforts of the elegant Windstar Star Legend. After a leisurely breakfast, spend time on deck with a tropical drink, take in the beautiful ocean scenery and enjoy the relaxed pace of life aboard this intimate yacht-style ship as we sail toward Panama City.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
PANAMA CITY & THE PANAMA CANAL
Following disembarkation this morning, we’ll meet our local guide for a fascinating day exploring vibrant Panama City. One of the major highlights of our journey will be a special close-up visit to the world-famous Panama Canal where we’ll gain a deeper appreciation for one of the world’s greatest engineering achievements. Following lunch at an excellent local restaurant, we’ll check into our centrally located upscale downtown hotel, ideally located for taking in the Panama City’s modern skyline, restaurants and lively atmosphere.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
PANAMA CITY
Enjoy a leisurely day to relax beside the hotel pool, explore Panama City independently or simply soak up the sunshine and warm tropical atmosphere. This evening we'll gather together for a special farewell dinner celebrating our wonderful journey through Costa Rica and Panama.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
PANAMA CITY – TORONTO POST STAY
After breakfast we’ll enjoy a coffee and chocolate tasting, then a casual luncheon before heading to the airport for our evening direct flight to Toronto. Due to our late arrival, we have included the overnight stay at a Toronto Pearson Airport area hotel.
Meals Included: Breakfast, Lunch (B/L)
HOMEWARD BOUND
This morning, guests will continue homeward following a wonderful Travel With Bradley boutique yacht adventure filled with tropical scenery, unforgettable experiences and new friendships.
**Note: Cruise lines offer a variety of shore excursions. Please review shore excursions closely before booking to ensure you choose based on your ability level for your safety.
You are the best judge of your mobility level, but at "Travel With Bradley" we provide a tour activity level to help you know what to expect. We sometimes run into situations that we cannot predict in advance such as stairs, a hill or a lengthy walk, so please keep this in mind when considering a journey.
Level 3 – Active
This trip is appropriate for travellers who lead an active lifestyle and have a good level of fitness. Walking for 3-4 hours on uneven terrain which could be rugged, or rocky, or other moderate physical activities can be expected on this tour. Travellers must be able to manage their own luggage. Not suitable for someone who requires the use of a cane or walker.
