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.

Cancun to San Jose Travel Pass - Winter tours

No booking fees

Best price guaranteed

Embark on an unforgettable adventure from Cancun to San Jose, uncovering the vibrant cultures and stunning landscapes of Central America. Experience thrilling activities like exploring ancient Mayan ruins, snorkeling in crystal-clear Caribbean waters, and hiking lush rainforests. Delight in local cuisine, lively nightlife, and charming colonial towns. This meticulously crafted travel itinerary offers unique experiences and seamless transportation, ensuring a hassle-free, exhilarating journey perfect for culture enthusiasts and natural beauty seekers. Discover the hidden gems of Mexico, Belize, Guatemala, and Costa Rica.

Trekking and HikingZip lining

Tour Type

Group Tour

Accommodation

Hostel, Home-stay, Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

San Jose, Cancún, Belize City, S

San Jose, Cancún, Belize City, San Ignacio, Flores, Rio Dulce, Lanquin, Panajachel, San Jorge La Laguna, Playa Del Carmen, Antigua, Copán Ruinas, El Tunco, Leon, Granada, San Jorge, Ometepe, San Juan Del Sur, Monteverde, Manuel Antonio, Tulum, Bacalar, Chetumal, Caye Caulker

Duration39 days

From

USD 2,656

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San Jose to Cancun Travel Pass - Winter tours

No booking fees

Best price guaranteed

Embark on an unforgettable Central America adventure with a travel pass connecting San Jose to Cancun. This journey offers diverse experiences from exploring lush Costa Rican rainforests and discovering ancient Mayan ruins to relaxation on pristine Mexican beaches. Highlights include vibrant local markets, culturally-rich towns, and thrilling activities like zip-lining and snorkeling in crystal-clear waters. Ideal for adventure seekers and culture enthusiasts, this route promises an immersive blend of nature, history, and vibrant local flavors. Book your tropical escapade now!

Active and outdoor

Tour Type

Group Tour

Accommodation

Hostel, Home-stay, Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

San Jose, Cancún, Leon, El Tunco

San Jose, Cancún, Leon, El Tunco, Copán Ruinas, Antigua, Panajachel, San Jorge La Laguna, Lanquin, Monteverde, Flores, Belize City, Caye Caulker, Chetumal, Bacalar, Tulum, Playa Del Carmen, Liberia City, San Juan Del Sur, Granada

Duration33 days

From

USD 2,273

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San Jose to Antigua Travel Pass - Winter tours

No booking fees

Best price guaranteed

Embark on an unforgettable journey from San Jose to Antigua with a travel pass designed for adventure lovers. This route offers rich cultural experiences, scenic landscapes, and thrilling activities. Explore iconic attractions like Arenal Volcano, Monteverde Cloud Forest, and the picturesque colonial streets of Antigua. Enjoy zip-lining, hot springs, and guided tours through lush rainforests. Perfect for solo travelers, couples, and groups seeking immersive adventures in Central America's most stunning destinations.

Adventure

Tour Type

Group Tour

Accommodation

Home-stay, Hostel

Age Range

18-99 yrs

Operated in

english

Destinations

San Jose, Antigua, San Jorge La

San Jose, Antigua, San Jorge La Laguna, Ometepe, San Jorge, Granada, Leon, El Tunco, Copán Ruinas, Manuel Antonio National Park, Manuel Antonio, Monteverde, Liberia City, San Juan Del Sur

Duration21 days

From

USD 1,632

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Cancun to Panama City Travel Pass - Winter tours

No booking fees

Best price guaranteed

Embark on an unforgettable Central American adventure, exploring pristine beaches, vibrant cities, and lush jungles. This travel pass takes you from Cancun to Panama City, offering immersive experiences like snorkeling in Belize’s Blue Hole, discovering Mayan ruins in Guatemala, and hiking Costa Rica’s volcanoes. Enjoy local cultures, authentic cuisines, and breathtaking landscapes. Perfect for thrill-seekers and culture enthusiasts, this journey provides incredible opportunities to make lasting memories while venturing through this diverse and captivating region.

Active and outdoor

Tour Type

Group Tour

Accommodation

Hostel, Home-stay, Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Panama City, Cancún, Belize City

Panama City, Cancún, Belize City, Flores, Rio Dulce, Lanquin, Panajachel, San Jorge La Laguna, Playa Del Carmen, Antigua, Copán Ruinas, El Tunco, Leon, Granada, San Jorge, San Juan Del Sur, Monteverde Cloud Forest Biological Preserve, Manuel Antonio National Park, San Jose, Tulum, Tortuguero, Puerto Viejo De Sarapiqui, Bocas Del Toro, San Blas Islands, Bacalar, Chetumal, Caye Caulker

Duration48 days

From

USD 4,231

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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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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 6,885

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Super Sales

EPIC CENTRAL AMERICA 40 DAYS - Winter tours

No booking fees

Best price guaranteed

Volcanic eruptions, ancient Mayan heritage, the world’s second-largest barrier reef, and an abundance of wildlife – Central America truly has it all! Embark on our 40 day adventure through this natural wonderland, where you'll hike, snorkel, and indulge in the local food, plus some epic unique local experiences that will take you off the beaten path. From the lively streets of Mexico City to the palm-lined shores of the Yucatán Peninsula, one day you’ll be marvelling at towering volcanoes, and the next soaking up the sun and sea in beach towns. Oh, and did we mention you’ll be doing all this with an experienced group leader and an instant crew of new mates? The trip of a lifetime just got even better. The jungle awaits…

Local cultureHot springs

Tour Type

Group Tour

Accommodation

Home-stay, Hotel

Age Range

18-55 yrs

Operated in

english

Destinations

Mexico City, San Jose, Isla Holb

Mexico City, San Jose, Isla Holbox, Playa Del Carmen, Chichen Itza, Tulum, Bacalar, Caye Caulker, Hol Chan Marine Reserve, Flores, Tikal, Coban, Semuc Champey, Chichicastenango, San Juan La Laguna, Antigua, Acatenango, La Fortuna, Oaxaca, Arenal, Rincon de la Vieja Volcano National Park, Playa Samara, Esterillos, Manuel Antonio National Park, Tehuantepec, San Cristobal De Las Casas, Cancún

Duration40 days

From

USD 7,099

USD 6,886

Saving

USD 213

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Super Sales

Costa Rica Adventure - Winter tours

(1 review )

No booking fees

Best price guaranteed

Just finished my Costa Rica Trip and had the best time ever!! If you are considering it DO IT!!! I’ve been on many many group tours and this was by far the best I have done to date! The group leader - Elmer, honestly made the trip and just went above and beyond in every possible way to ensure we were having a good time! Will definitely be booking another Intro trip soon as it was the best two weeks ever!

Hot springsWalking

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-55 yrs

Operated in

english

Destinations

San Jose, Esterillos, Manuel Ant

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

Duration13 days

From

USD 2,199

USD 2,133

Saving

USD 66

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Super Sales

CENTRAL AMERICA ADVENTURE - Winter tours

No booking fees

Best price guaranteed

Volcanic eruptions, ancient Mayan heritage, the world’s second-largest barrier reef, and an abundance of wildlife – Central America truly has it all! Embark on our 30 day adventure through this natural wonderland, where you'll hike, snorkel, and indulge in the local food, plus some epic unique local experiences that will take you off the beaten path. One day you’ll be marvelling at towering volcanoes, and the next soaking up the sun and sea in beach towns. Oh, and did we mention you’ll be doing all this with an experienced group leader and an instant crew of new mates? The trip of a lifetime just got even better. The jungle awaits…

Hot springsNational parks

Tour Type

Group Tour

Accommodation

Home-stay, Hotel

Age Range

18-55 yrs

Operated in

english

Destinations

San Jose, Playa Del Carmen, Coba

San Jose, Playa Del Carmen, Coban, Semuc Champey, Lake Atitlan, San Juan La Laguna, Antigua, Acatenango, La Fortuna, Chichen Itza, Arenal Volcano, Rincon de la Vieja Volcano National Park, Playa Samara, Esterillos, Manuel Antonio National Park, Tulum, Bacalar, Caye Caulker, Hol Chan Marine Reserve, Flores, Tikal

Duration30 days

From

USD 5,324

USD 5,164

Saving

USD 160

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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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Super Sales

One Week In Costa Rica - Winter tours

No booking fees

Best price guaranteed

Calling all nature lovers, solo travellers and young adventurers! Spend a week in Costa Rica beginning in San Jose – the thriving urban centre with colourful markets, vibrant nightlife and spontaneous art fairs. Explore Monteverde’s Cloud Forest at your own pace, keeping your eye out for sloths and the elusive quetzal bird. Head to La Fortuna, shadowed by the immense Arenal Volcano, and enjoy free time to chase waterfalls and soak away your worries in the natural thermal hot springs. Explore Cahuita National Park with a hike and a swim, then enjoy some beach time on the Caribbean coast in Puerto Viejo. If you're lucky, spot sloths, hummingbirds, iguanas, monkeys, toucans, coatimundis, quetzals and racoons, then take a cooking class to learn the local cuisine. With a local leader with insider knowledge and a likeminded group of travellers – what better way to dive into Costa Rica?

Adventure

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

San Jose, Monteverde, La Fortuna

San Jose, Monteverde, La Fortuna, Puerto Viejo de Talamanca

Duration8 days

From

USD 650

USD 631

Saving

USD 20

View Tour

All San Jose Tours in Winter

Page 5 of 79 Trips in San Jose with 179 Reviews

Page 5 of 79 Trips in San Jose with 179 Reviews

Cancun to San Jose Travel Pass - Winter tours

San Jose to Cancun Travel Pass - Winter tours

San Jose to Antigua Travel Pass - Winter tours

Cancun to Panama City Travel Pass - Winter tours

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

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

EPIC CENTRAL AMERICA 40 DAYS - Winter tours

Costa Rica Adventure - Winter tours

CENTRAL AMERICA ADVENTURE - Winter tours

7 Days: Highlights of Costa Rica - Winter tours

One Week In Costa Rica - Winter tours

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All San Jose Tours in Winter

Page 5 of 79 Trips in San Jose with 179 Reviews

Page 5 of 79 Trips in San Jose with 179 Reviews