Set sail on a 50-foot (15-meter) Beneteau Oceanis (featured on the cover of Sail Magazine) for a private or semi-private tour with Serendipity Charters, based in Playa Flamingo. You will spend the afternoon being wined and dined while cruising the afternoon away and into the sunset. This luxurious tour includes an open bar and gourmet appetizers and lunch. Guests also have access to snorkeling and fishing gear. It is likely that you will spot dolphins, whales, sea turtles, and jumping sting rays, on top of having a wide-open view of the pristine and dramatic coastline.
Serendipity Charters, Flamingo Marina, +506 85101691
Antares, based in Playa Tamarindo, offers several different sailing tours, including a daily half-day trip, a full-moon outing once a month, and private overnight sailing trips. Once aboard, you will be treated to top-notch service, an open bar, live music, comfortable beanbag chairs and an intimate setting, as well as a six-plate gourmet spread using organic produce and a variety of superfoods. The 80-foot (24-meter) mono haul leaves from Playa Tamarindo and sets sail to Playa Huevo, where you will have the opportunity to go snorkeling and float in the ocean, before setting off into the sunset with a perfectly crafted cocktail in hand.
Antares, Playa Tamarindo, +506 85873095
The Marlin del Rey operates in both Playa Tamarindo and Playas del Coco. This catamaran is so fun that even the locals book a trip every once in a while! The Marlin del Rey is an all-inclusive half-day sailing tour. The price includes an open bar, snacks, lunch, snorkel equipment, and an afternoon that you won’t soon forget. You will sail out to a protected cove where you will have time to snorkel, paddle board, or kayak to the beach, or just float on a noodle with a drink in hand. After lunch, you will set sail again and stay out until the sun sets. Whale, stingray, and sea turtle sightings are very common.
Marlin del Rey, Playa Tamarindo and Playas del Coco, +506 26531212
The Lazy Lizard is based in Portero, near Playa Flamingo in Guanacaste, and offers morning, sunset, and private sailing tours. The sunset catamaran tour is their most popular trip. All the tours are all-inclusive and include drinks, snacks, a picnic-style lunch, snorkeling equipment, and other water-fun equipment. The morning sailing tour tends to be a bit more kid-friendly, while the sunset tour can be a bit boozy. The private tour is perfect for big groups and celebrations.
Lazy Lizard, Portero +506 26545900
Calypso Island Cruise is the original Tortuga Island cruise that first set off to the island with passengers in 1975. Nearly a million people have enjoyed this island tour since then. Tortuga Island is a jaw-dropping and breathtakingly beautiful island off the coast of the Nicoya Peninsula. Your day will feature a cruise through the Gulf of Nicoya, five hours on the white-sand beaches of Tortuga Island, snorkeling, a banana boat ride, a four-course gourmet lunch, unlimited non-alcoholic beverages, reasonably priced cocktails, live music, and hammocks set up beneath palm trees.
Calypso Island Cruise, Puntarenas, +506 22562727
The Trimaran Sunset Sailing Tour was founded 20 years ago and is a family-operated business that prides itself on providing guests with an exceptional and unforgettable sailing excursion. They offer free transportation to guests staying in Manuel Antonio and Quepos. Your day at sea includes a tour of several islands in the area, a tropical fish snorkeling experience, dolphin watching, snacks and drinks, and a perfect setting for a sunset.
Sunset Sails Tours, Marina Pez Vela, Quepos, +506 84681545
Manuel Antonio Catamaran Adventures offer a full-day tour to Manuel Antonio and transportation for those staying in San Jose, Herradura, Jaco, Dominical, and Esterillos. The tour includes a buffet breakfast on the way to Manuel Antonio, two hours of free play time on Playa Manuel Antonio, lunch at a restaurant with captivating views of Manuel Antonio, and then a four-hour catamaran cruise abroad the Ocean King. Once aboard the boat, there will be unlimited snacks and non-alcoholic beverages and up to eight alcoholic beverages. You will also enjoy a snorkeling tour, a dolphin watching tour, amazing views of the sunset out at sea, and a fantastic dinner before returning to your home base.
Manuel Antonio Catamaran Adventures, Manuel Antonio, +506 71090464