10 Best San Jose Multiday Tours in Winter

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Get a customized trip to San Jose in Winter

Plan a multi-country or regional adventure across San Jose in Winter, with help from a local expert.

Jean Carlo IlamaTravel Expert in Costa Rica
Randall Jiménez Moreno
Travel Expert in Costa Rica
Ellen Zoe GoldenTravel Expert in Costa Rica
Olman RomeroTravel Expert in Costa Rica, Nicaragua & Panama
Yuliana ValverdeTravel Expert in Costa Rica, Nicaragua & Panama

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Super Sales

Central and South American Adventure: From Costa Rica to Colombia - Winter tours

No booking fees

Best price guaranteed

Phones charged and playlists queued — this 27-day journey is a full-on adventure through Central and South America that’s packed with wild nature, laid-back beach towns, and buzzing cities. Start in Costa Rica with the surfy chill of Puerto Viejo before heading into Panama’s hidden gems — think island time in Bocas del Toro, misty hikes in Boquete, and the crater village of Valle de Antón. Then go fully off-grid on the San Blas Islands, where Indigenous communities run the show and turquoise water meets white sand. After that, it’s Colombia time. Wander Cartagena’s colourful old town, trek through jungle trails to waterfalls in Minca, kick back in Santa Marta, and finish strong in Medellín with mountaintop views and a nightlife scene to match. From slow travel moments to fast-paced fun, this one’s got it all.

Explorer

Tour Type

Small Group Tour

Accommodation

Guest House, Hostel, Hotel, Hut

Age Range

18-39 yrs

Operated in

english

Destinations

San Jose, Medellin, Valle De Ant

San Jose, Medellin, Valle De Antón, Panama City, San Blas Islands, Cartagena, Puerto Viejo de Talamanca, Minca, Palomino, Tayrona National Park, Santa Marta, Bocas Del Toro, Boquete

Duration27 days

From

USD 3,999

USD 3,879

Saving

USD 120

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Super Sales

Panama: Craters, Coasts & Highland Mountains - Winter tours

No booking fees

Best price guaranteed

Eighteen days of next-level beaches, wild landscapes, and full-on freedom — this is Panama like you’ve never seen it. Start in Costa Rica and cruise into the often-overlooked magic of Panama, where every stop hits different. Catch the surfy vibes in Puerto Viejo, snorkel your heart out in Bocas del Toro, and hike cloud forest trails in lush Boquete. Sleep inside a volcanic crater in the town of Valle de Antón, dance the night away in Panama City, and unplug completely with three off-the-grid nights on the jaw-dropping San Blas Islands. Between waterfalls, reefs, Indigenous culture, and epic new friendships, this trip brings the kind of stories you’ll be telling for years.

Explorer

Tour Type

Small Group Tour

Accommodation

Guest House, Hostel, Hotel, Hut

Age Range

18-39 yrs

Operated in

english

Destinations

Panama City, San Jose, Valle De

Panama City, San Jose, Valle De Antón, San Blas Islands, Puerto Viejo de Talamanca, Bocas Del Toro, Boquete

Duration18 days

From

USD 2,049

USD 1,988

Saving

USD 61

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Super Sales

Costa Rica to Panama: Surf, Treks & Starry Skies - Winter tours

No booking fees

Best price guaranteed

Ready to bounce from beach to jungle to crater town? This 13-day trip kicks off in Costa Rica and cruises into the wild beauty of Panama, where laid-back vibes meet epic adventure. Chill out on the Caribbean coast in Puerto Viejo, snorkel through starfish-studded waters in Bocas del Toro, and hike cloud forest trails to hidden waterfalls in Boquete. You’ll get up close with local culture, learn how chocolate is made from the source, and hang out in Valle de Antón — an actual town inside a volcanic crater. Wrap it up with a night out in Panama City, and you’ve got a Central American escape that’s anything but basic.

Explorer

Tour Type

Small Group Tour

Accommodation

Guest House, Hostel, Hotel

Age Range

18-39 yrs

Operated in

english

Destinations

Panama City, San Jose, Valle De

Panama City, San Jose, Valle De Antón, Puerto Viejo de Talamanca, Bocas Del Toro, Boquete

Duration13 days

From

USD 1,199

USD 1,163

Saving

USD 36

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Super Sales

Total Central America: Two Months of Wild - Winter tours

No booking fees

Best price guaranteed

Two months. Seven countries. One unforgettable ride. This all-out Central American adventure kicks off in Mexico City with tacos, mole, and big energy — then it’s full speed ahead through mountains, jungles, highlands, beaches, and islands. You’ll snorkel in Belize, boat across Lake Atitlán, crash with a local fam on Nicaragua’s Ometepe Island, and dance the night away in Panama City. Whether you’re soaking in cloud forest vibes in Costa Rica or chilling barefoot on the San Blas Islands, this trip is the ultimate way to see it all. From street eats to off-the-grid retreats, it’s two months of pure adventure — and it’s calling your name.

Explorer

Tour Type

Small Group Tour

Accommodation

Guest House, Home-stay, Hostel, Hotel, Hut

Age Range

18-39 yrs

Operated in

english

Destinations

Mexico City, Panama City, Bacala

Mexico City, Panama City, Bacalar, Valladolid, Tulum, Playa Del Carmen, Caye Caulker, San Ignacio, Flores, Rio Dulce, Antigua, Panajachel, San Juan La Laguna, Oaxaca, Copan, Suchitoto, La Libertad, Leon, Granada, Isla De Ometepe, Monteverde, La Fortuna, San Jose, Puerto Viejo de Talamanca, Bocas Del Toro, San Cristobal De Las Casas, Boquete, Valle De Antón, San Blas Islands, Palenque

Duration62 days

From

USD 6,199

USD 6,013

Saving

USD 186

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Essential Mexico, Guatemala & Costa Rica - 20 days - Winter tours

No booking fees

Best price guaranteed

GROUP TOUR (FOR AGES 18 - 55): Travel from Mexico City to San Jose in Costa Rica on this 20-day group tour of Central America, also taking in the best of Mexico and Guatemala and staying in hostels and dorm accommodation. Learn to surf in Puerto Escondido, visit Chichen Itza and embark on a cycling tour of Tulum. In Guatemala, enjoy a memorable 2-day hike to the Acatenango Volcano, relax in Antigua and opt for kayaking in San Pedro La Laguna. Fly to San Jose for exploration of La Fortuna, zip lining in Monteverde and a sunset catamaran cruise in Manuel Antonio National Park. Enhance your adventure with lots of optional activities, or further explore at your own pace.

Explorer

Tour Type

Group Tour

Accommodation

Hostel

Age Range

18-55 yrs

Operated in

english

Destinations

Mexico City, San Jose, San Pedro

Mexico City, San Jose, San Pedro La Laguna, Antigua, La Fortuna, Manuel Antonio, Puerto Escondido, Oaxaca, Tulum

Duration20 days

From

USD 8,765

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Mexico to Costa Rica Youth Adventure - 30 days - Winter tours

No booking fees

Best price guaranteed

GROUP TOUR (FOR AGES 18 to 39): Journey from Playa del Carmen on Mexico's Yucatan Peninsula to San Jose in Costa Rica on this 30-day tour that also takes in Belize and Guatemala. Take in some of Central America's best ancient treasures, including Chichen Itza, Tulum and Tikal. Hike up the Arenal and Acatenango volcanoes, spot wildlife in national parks like Manuel Antonio, Rio Celeste and Rincon de la Vieja. Cruise Lake Atitlan, meet local families across the region, and enjoy guided sightseeing in cities like San Jose, Antigua. With plenty of time for relaxation and swimming on the beaches of Playa del Carmen, Caye Caulker, Samara and more!

Explorer

Tour Type

Group Tour

Accommodation

Home-stay, Hotel

Age Range

18-39 yrs

Operated in

english

Destinations

San Jose, Playa Del Carmen, Coba

San Jose, Playa Del Carmen, Coban, Panajachel, San Juan La Laguna, Antigua, La Fortuna, Rincon de la Vieja Volcano National Park, Playa Samara, Esterillos, Bacalar, Caye Caulker, Flores

Duration30 days

From

USD 6,855

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Central America Youth Expedition - 40 days - Winter tours

No booking fees

Best price guaranteed

GROUP TOUR (FOR AGES 18-39): Explore Mexico, Guatemala, Belize, and Costa Rica on this 40-day tour, starting in Mexico City with its Aztec heritage, and moving through Oaxaca's markets and mezcal distilleries. Journey through Sumidero Canyon and San Cristobal de las Casas, then visit Isla Holbox's beaches and Mayan sites like Chichen Itza and Tulum. Continue to Bacalar's lagoon, Belize's reefs, and Caye Caulker for snorkelling, before experiencing Mayan cooking in Guatemala and exploring Tikal and the Candelaria Caves. Embark on a 4x4 adventure into the highlands, followed by a hike and swim in blue pools, with a traditional Mayan lunch. Visit Chichicastenango and Panajachel by Lake Atitlán, then take a boat to San Marcos and San Juan La Laguna. Hike Mayan Face Mountain at sunrise, then trek Acatenango volcano before heading to Costa Rica. Explore San Jose, La Fortuna, Arenal Volcano, Rio Celeste, and Rincon de la Vieja, before visiting Liberia, a pottery village, and Samara’s beaches. Conclude with a visit to Esterillos, Manuel Antonio National Park, the Crocodile Bridge, and San Jose.

Explorer

Tour Type

Group Tour

Accommodation

Camping, Home-stay, Hotel

Age Range

18-39 yrs

Operated in

english

Destinations

Mexico City, San Jose, Isla Holb

Mexico City, San Jose, Isla Holbox, Playa Del Carmen, Chichen Itza, Bacalar, Caye Caulker, Flores, Coban, Panajachel, San Juan La Laguna, Antigua, Acatenango, La Fortuna, Oaxaca, Rincon de la Vieja Volcano National Park, Playa Samara, Esterillos, Tehuantepec, San Cristobal De Las Casas, Cancún

Duration40 days

From

USD 9,345

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Super Sales

Solo-ish Costa Rica - Winter tours

(4 reviews )

No booking fees

Best price guaranteed

Excellent trip with Gracie, I did things I never would have tried by myself such as rappelling down waterfalls and ziplining 1.5km. Saw some amazing wildlife and met some great people.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-100 yrs

Operated in

english

Destinations

San Jose, Manuel Antonio Nationa

San Jose, Manuel Antonio National Park, Arenal, La Fortuna, Monteverde, Manuel Antonio

Duration8 days

From

USD 1,399

USD 1,357

Saving

USD 42

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Rainforest, volcano and beach - Winter tours

Trip customizable

Best price guaranteed

Embark on a leisurely journey through Costa Rica's most iconic national parks: Tortuguero and Manuel Antonio national parks. This privacy-focused trip allows ample time for exploration while ensuring you don't miss out on the natural wonders each destination offers. Begin in Tortuguero, a remote paradise dubbed the "Amazon of Costa Rica." Here, immerse yourself in lush rainforests, winding waterways, and pristine beaches. Witness the nesting of endangered sea turtles, a rare spectacle found in few places around the globe. Next, head to Manuel Antonio National Park, known for its breathtaking beaches and abundant wildlife. Explore the trails of park, where monkeys swing through trees and colorful birds soar overhead. Relax on tranquil coves or venture into azure waters for a refreshing swim. Throughout your journey, enjoy the freedom to explore at your own pace, ensuring a truly unforgettable experience filled with privacy, tranquility, and the beauty of Costa Rica's national parks.

Trekking and HikingVolcanoes

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

1-79 yrs

Operated in

English

Destinations

Manuel Antonio National Park, To

Manuel Antonio National Park, Tortuguero National Park, Arenal Volcano, San Jose, Tortuguero, Arenal, Manuel Antonio

Duration9 days

From

USD 2,153

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Volcanoes Adventure - Winter tours

Trip customizable

Best price guaranteed

Immerse yourself in the essence of Costa Rica on this exciting 9-day journey that will take you to explore the natural beauty and majesty in the surrounding areas of four of the country's most prominent volcanoes: the imposing Irazú Volcano in Cartago, the majestic Arenal Volcano in La Fortuna area, thee intriguing Rincón de la Vieja Volcano in Guanacaste, and the famous Poás Volcano. Get ready to embark on this adventure as you enjoy the landscapes full of biodiversity that only Costa Rica can offer. In this volcano adventure trip, you will have the opportunity to visit some destinations with different volcano landscapes and hikes within the national parks.

Trekking and HikingVolcanoes

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

5-79 yrs

Operated in

english, spanish

Destinations

San Jose, Arenal Volcano, Rincon

San Jose, Arenal Volcano, Rincon de la Vieja Volcano National Park, Poas Volcano, Irazú Volcano, Arenal, La Paz Waterfall, Juan Santamaria

Duration9 days

From

USD 1,948

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7 Days: Highlights of Costa Rica - Winter tours

Trip customizable

Best price guaranteed

Embark on a captivating journey through Costa Rica's diverse landscapes and vibrant culture with this meticulously crafted itinerary. Begin your adventure with a private transfer from Juan Santamaria International Airport to your hotel in San Jose, where you'll receive a warm welcome and an introduction to the country's rich heritage. Explore Costa Rica's cosmopolitan capital, San Jose, home to bustling streets, iconic landmarks, and a myriad of gastronomic delights. Next, venture into the misty cloud forests of Monteverde, where exhilarating horseback riding tours and guided walks through the renowned Monteverde Cloud Forest Reserve await. Immerse yourself in the breathtaking natural beauty and abundant wildlife of this verdant region. Continue your journey to Manuel Antonio, a paradise of unspoiled beaches and lush rainforests. Spend your days snorkeling, hiking, or simply basking in the sun-kissed tranquility of this coastal haven. With a variety of optional tours available, including mangrove boat tours, horseback riding adventures, and guided walks through national parks, there's something for every adventurer to enjoy. As your unforgettable Costa Rican odyssey draws to a close, bid farewell to this enchanting country and its warm-hearted people with a private transfer back to Juan Santamaria International Airport for your departure. Prepare to be captivated by the beauty, biodiversity, and boundless adventure that await you in Costa Rica.

AdventureTrekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

1-79 yrs

Operated in

english, spanish

Destinations

San Jose, Manuel Antonio Nationa

San Jose, Manuel Antonio National Park, Monteverde Cloud Forest Biological Preserve, Monteverde, Manuel Antonio

Duration7 days

From

USD 2,230

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Pacuare Raging Rapids & Jungle Adventure 2D/1N - Winter tours

No booking fees

Best price guaranteed

Embark on an exhilarating Costa Rican white-water rafting adventure along the scenic Pacuare River, renowned for its Class III-IV rapids. Immerse yourself in lush jungle landscapes, spotting vibrant wildlife and cascading waterfalls. This tour offers adrenaline-pumping thrills, guided nature hikes, and serene moments at eco-friendly riverside lodges. Ideal for nature enthusiasts and adventure seekers, this unforgettable Costa Rica experience promises both excitement and relaxation amidst one of the world's most captivating rainforests.

AdventureExplorer

Tour Type

Small Group Tour

Accommodation

Lodge

Age Range

18-99 yrs

Operated in

english

Destinations

San Jose, Pacuare River

Duration2 days

From

USD 338

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Antigua to Panama City Travel Pass - Winter tours

No booking fees

Best price guaranteed

Embark on an unforgettable Central America adventure with Bamba’s travel pass taking you from Antigua to Panama City. This immersive journey offers diverse experiences including exploring ancient Mayan ruins, soaking up the sun on pristine beaches, and hiking lush rainforests. Thrill-seekers can revel in adrenaline-pumping activities like volcano treks and zip-lining. Discover vibrant cultures, delicious cuisine, and captivating landscapes. Ideal for solo travelers and groups alike, this adventure ensures a seamless and memorable travel experience across stunning destinations.

Explorer

Tour Type

Group Tour

Accommodation

Home-stay, Hotel, Hostel

Age Range

18-99 yrs

Operated in

english

Destinations

Panama City, Antigua, Panajachel

Panama City, Antigua, Panajachel, El Tunco, Leon, Granada, San Jorge, Ometepe, San Juan Del Sur, Liberia City, San Jorge La Laguna, Monteverde, Manuel Antonio, San Jose, Tortuguero, Puerto Viejo de Talamanca, Bocas Del Toro, San Blas Islands, Lanquin, Copán Ruinas

Duration35 days

From

USD 3,471

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Classic Costa Rica Youth Adventure - 13 days - Winter tours

No booking fees

Best price guaranteed

GROUP TOUR (FOR AGES 18 - 39): Take in the best of Costa Rica on this 13-day group tour, which starts and ends in the capital, San Jose. Hike around the Arenal Volcano in La Fortuna, hike in the jungle after dark, explore Rincon de la Vieja National Park and unwind on the beaches of Samara. Take in the lesser-visited beach town of Esterillos and end with a visit to Manuel Antonio National Park, the country's most popular wildlife reserve.

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-39 yrs

Operated in

english

Destinations

San Jose, Esterillos, La Fortuna

San Jose, Esterillos, La Fortuna, Rincon de la Vieja Volcano National Park, Playa Samara

Duration13 days

From

USD 2,960

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All San Jose Tours in Winter

Page 4 of 59 Trips in San Jose with 381 Reviews

Get a customized trip to San Jose in Winter

Page 4 of 59 Trips in San Jose with 381 Reviews

Central and South American Adventure: From Costa Rica to Colombia - Winter tours

Panama: Craters, Coasts & Highland Mountains - Winter tours

Costa Rica to Panama: Surf, Treks & Starry Skies - Winter tours

Total Central America: Two Months of Wild - Winter tours

Essential Mexico, Guatemala & Costa Rica - 20 days - Winter tours

Mexico to Costa Rica Youth Adventure - 30 days - Winter tours

Central America Youth Expedition - 40 days - Winter tours

Solo-ish Costa Rica - Winter tours

Rainforest, volcano and beach - Winter tours

Volcanoes Adventure - Winter tours

7 Days: Highlights of Costa Rica - Winter tours

Pacuare Raging Rapids & Jungle Adventure 2D/1N - Winter tours

Antigua to Panama City Travel Pass - Winter tours

Classic Costa Rica Youth Adventure - 13 days - Winter tours

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All San Jose Tours in Winter

Page 4 of 59 Trips in San Jose with 381 Reviews

Get a customized trip to San Jose in Winter

Page 4 of 59 Trips in San Jose with 381 Reviews