10 Best San Jose Multiday Tours in October 2027

Get a customized trip to San Jose in October 2027

Plan a multi-country or regional adventure across San Jose in October 2027, 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

Start planning your Trip

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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.

Exclusive Family Expedition in Paradise - October 2027

(6 reviews )

Trip customizable

Best price guaranteed

My wife and I just returned from an amazing 11-day trip to Costa Rica. Yuliana helped us to put together a private tour designed specifically for us. No amount of time and effort would have let us do it ourselves. We were most interested in the landscape and animals, and our private driver was able to take us to fabulous sights. We stayed in unusual accommodations including a tree house in the jungle and a villa at the Arenal volcano. We recommend Yuliana and her agency very highly and also our wonderful guide and driver, Roy.

WaterfallsZip lining

Tour Type

Group Tour

Age Range

4-70 yrs

Operated in

english

Destinations

La Fortuna, Monteverde Cloud For

La Fortuna, Monteverde Cloud Forest Biological Preserve, Tamarindo Beach, San Jose, Tamarindo, Guanacaste, La Paz Waterfall, Monteverde

Duration11 days

From

USD 2,415

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Super Sales

EPIC CENTRAL AMERICA 40 DAYS - October 2027

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

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25% OFF TODAY

Super Sales

One Week In Costa Rica - October 2027

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

25% OFF TODAY

Duration8 days

From

USD 695

USD 521

Saving

USD 174

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Costa Rica To Panama: Surf, Treks & Starry Skies - October 2027

10% OFF TODAY

Super Sales

Costa Rica to Panama: Surf, Treks & Starry Skies - October 2027

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

10% OFF TODAY

Duration13 days

From

USD 1,199

USD 1,079

Saving

USD 120

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All San Jose Tours in October 2027

Page 4 of 46 Trips in San Jose during October 2027 with 565 Reviews

Get a customized trip to San Jose in October 2027

Exclusive Family Expedition in Paradise - October 2027

EPIC CENTRAL AMERICA 40 DAYS - October 2027

One Week In Costa Rica - October 2027

Costa Rica to Panama: Surf, Treks & Starry Skies - October 2027

Page 4 of 46 Trips in San Jose during October 2027 with 565 Reviews

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All San Jose Tours in October 2027

Page 4 of 46 Trips in San Jose during October 2027 with 565 Reviews

Get a customized trip to San Jose in October 2027

Exclusive Family Expedition in Paradise - October 2027

EPIC CENTRAL AMERICA 40 DAYS - October 2027

One Week In Costa Rica - October 2027

Costa Rica to Panama: Surf, Treks & Starry Skies - October 2027

Page 4 of 46 Trips in San Jose during October 2027 with 565 Reviews