The Winter Holiday You&#039;ve Been Waiting For

Manuel Antonio National Park to Nicoya Peninsula

A father and son Kayaking in Costa Rica on a Backroads multisport trip

Six young guests in hot tub, looking up at camera.

Multi-Adventure

Families with Kids & Teens

Costa Rica Beaches & Wildlife Family Multi-Adventure Tour

6 days

Levels 1-2

Premiere Hotels*

2026: Feb-Apr, Jul-Aug, Nov-Dec

2027: Jan-Apr, Jun-Aug

From $5,649/person

Biking, the Big Five & Luxury Game Lodges

Four people hike up a sandy beach front road

Leopard laying on its side, looking at camera

A man holds his hand up to handprints on a stone wall

Multi-Adventure

Couples, Friends & Solos

South Africa & Botswana Active Safari

11 days

Levels 1-3

Premiere Hotels

2026: Jun-Dec

2027: Mar-Apr, Jun-Dec

From $16,499/person

Arenal Volcano to the Osa Peninsula

Tall hill covered in grass, with trees on the ground level

Biking

Couples, Friends & Solos

Costa Rica Bike Tour

6 days

Levels 2-4

Premiere & Deluxe Hotels

2026: Jan-Apr, Nov-Dec

2027: Jan-Apr

From $5,699/person

Sacred Valley, Cusco & Machu Picchu

Man and women holding hands, with sights of Machu Picchu in the background

Nighttime photo of a hummingbird flying to treebranch.

Guests hiking up stone trail, Machu Picchu ruins behind them.

Wide shot of South American city, mountain range in distance, large cathedral in foreground.

Fancy platter of seedy beverage and small chocolates.

Hiking & Walking

Couples, Friends & Solos

Peru Hiking & Walking Tour

7 days

Levels 2-4

Premiere Hotels

2026: Mar, May-Dec

2027: Feb-Dec

From $5,999/person

Rugged Coast & Mountains from Christchurch to Queenstown

Waterfall flowing into a crystal clear river

Asia & Pacific Kayaking on River with Mountain View

Two people posing next to a stream in New Zealand

Winding path among large rocks and boulders in New Zealand

Hiking & Walking

Couples, Friends & Solos

New Zealand South Island Hiking & Walking Tour

9 days

Levels 1-4

Casual Hotels

2026: Oct-Dec

2027: Jan-Apr

From $6,699/person

Sacred Valley, Cusco & Machu Picchu

Two women smiling and pointing towards the sky, with large stone ruins in the background

Group of men and women with walking poles, walking through stone ruins

Colorful pile of textiles, numerous different patterns and colors.

Hiking & Walking

Families with Teens & 20s

Peru Family Hiking & Walking Tour

7 days

Levels 2-4

Premiere Hotels

2026: Jun-Aug, Dec

2027: May-Aug, Dec

From $6,099/person

Ancient Northern Kingdoms to Southern Island Hideaways

Two woman with bikes walking through a decorated town square

Large gold Buddha statue on top of building

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

Levels 1-3

Premiere & Casual Hotels

2026: Jan-Feb, Nov-Dec

2027: Jan-Feb

From $7,249/person

Journey from Halong Bay to Majestic Angkor Wat

Spread of Vietnamese food, fried rice, meat, seafood, veggies, etc.

Guest in front of large painted longevity symbol.

Person exploring the temple of Angkor Wat in Cambodia

Hiking & Walking

Couples, Friends & Solos

Vietnam & Cambodia Hiking & Walking Tour

10 days

Levels 1-2

Premiere Hotels & Casual Ship

2026: Feb, Oct-Dec

From $8,049/person

Lakes, Volcanoes & Pampered Pleasures

Large, open valley with an empty road in the center

Mountain with a large lake in front and pink skies

Man and woman riding bikes with views of large mountains in the distance

Woman walking under a group of people with their arms sticking out

Biking

Couples, Friends & Solos

Chile Bike Tour

7 days

Levels 2-4

Premiere Hotels

2026: Jan, Mar, Oct-Dec

From $6,749/person

Sacred Temples, Tropical Waters & Luxurious Retreats

Man and woman biking on a road with jungle in the background

Two men and one women wearing traditional gowns in front of temple ruins

Group of people smiling and paddling in a raft in a river

Monkey eating a pastry next to a statue of two monkeys

Multi-Adventure

Couples, Friends & Solos

Bali Multi-Adventure Tour

7 days

Levels 2-4

Premiere Hotels

2026: May, Sep-Oct, Dec

2027: Jan-Feb, Apr-Jun, Sep-Oct, Dec

From $6,199/person

Cultural Connections & Havana Highlights

Group Photo Valle Nuevo National Park Sign

Multi-Adventure

Couples, Friends & Solos

Cuba Multi-Adventure Tour

6 days

Levels 2-4

Casual & Deluxe Hotels

2026: May, Nov-Dec

2027: Jan-Jun

From $4,399/person

Arenal Volcano to Manuel Antonio National Park

Multi-Adventure

Families with Teens & 20s

Costa Rica Rain Forest & Pacific Family Multi-Adventure Tour

6 days

Levels 1-2

Casual & Deluxe Hotels

2026: Jun-Jul, Dec

2027: Feb-Mar, Jun-Aug

From $4,649/person

Coastal Fjords & Alpine Trails from Milford Sound to Queenstown

Large valley with mountains in the background

Woman descending a mountain with large mountains in the background

Silhouette of woman with her arms open with the stars in the sky

Large lake with mountains in the background

NEW

Hiking & Walking

Couples, Friends & Solos

New Zealand South Island Fiordland Hiking Tour

7 days

Levels 3-5

Deluxe & Casual Hotels

2026: Nov-Dec

2027: Jan-Apr

From $8,699/person

The Coffee Triangle, Caribbean Coast & Cartagena

Man and woman walking on a dirt trail, with hills in the background

Man and woman walking in an alley surrounded by tall apartment buildings

Hiking & Walking

Couples, Friends & Solos

Colombia Hiking & Walking Tour

days

Levels 2-4

Casual Hotels

2026: Jan-Mar, Dec

From $4,799/person

Maya Temples to the Caribbean

Multi-Adventure

Families with Teens & 20s

Belize & Guatemala Family Multi-Adventure Tour

7 days

Levels 1-3

Premiere Hotels

2026: Dec

2027: Feb-Apr

From $6,199/person

Towering Peaks & Luxurious Vineyard Escapes

people biking down a road by a mountain range

red mountain range reflected on water below it

Multi-Adventure

Couples, Friends & Solos

Argentina's Mendoza Wine Country & Andes Multi-Adventure Tour

7 days

Levels 2-4

Premiere & Deluxe Hotels

2026: Mar-Apr, Nov-Dec

2027: Mar-May

From $7,199/person

Vibrant Buenos Aires to Wine Country and the Coast

Sky view of small town by the ocean, with cars parked along the beach

Four guests in BR gear, all smiling, talking.

Man smiling while picking purple wine grapes from a vine

Beach with a wooden staircase and a lighthouse in the background

Road with large, European-style apartment buildings on either side

NEW

Biking

Couples, Friends & Solos

Uruguay's Wine Country to the Ocean Bike Tour

7 days

Levels 2-4

Premiere Hotels

2027: Feb-Apr, Oct-Nov

From $6,599/person

Mystical Angkor Wat, Ancient Citadels & Lantern-Lit Villages

Bikers cycling through red and yellow temples

Biking

Families with Teens & 20s

Vietnam & Cambodia Family Bike Tour

8 days

Levels 1-3

Premiere Hotels

2026: Dec

From $8,649/person

The Coffee Triangle, Caribbean Coast & Cartagena

Woman smiling while ascending a trail surrounded by tall plants

Two women smiling and laughing with arms around their shoulders, holding wine glasses

Green plant with fruits over a red floor

Woman in a green shirt, smiling while petting a horse

NEW

Hiking & Walking

Women's Adventures

Colombia Women's Hiking & Walking Tour

7 days

Levels 2-4

Casual Hotels

2026: Dec

From $4,799/person

Sacred Valley, Cusco & Machu Picchu

Woman and man walking on a dirt trail, smiling and looking out towards large hills

Two men and one women climbing up stairs with a view of a town in the distance

Boy in traditional attire, smiling with a group of other boys behind him

Hiking & Walking

Families with 20s & Beyond

Peru Family Hiking & Walking Tour

7 days

Levels 2-4

Premiere Hotels

2026: May-Aug

From $6,399/person

Vibrant Buenos Aires to Wine Country and the Coast

Two guests on e-bikes riding past vineyard.

Exterior view of orange building with a small tree in front

Man and woman holding wine glasses, smiling while looking at each other

NEW

Biking

Couples, Friends & Solos

Uruguay's Wine Country to the Ocean Easygoing E-bike Tour

7 days

Levels 1-3

Premiere Hotels

2027: Feb, Apr, Oct

From $6,599/person

Epic Peaks, Lakes & Glaciers

Wide shot of sunset vista, mountain, river, meadow, small horse all visible.

Close-up of dry yerba mate infusion pot and gourd.

Shot of shepherd on horse, herd of sheep under them.

Hiking & Walking

Women's Adventures

Argentina's Patagonia Women's Hiking & Walking Tour

8 days

Levels 2-4

Premiere Hotels

2026: Dec

2027: Feb-Mar

From $7,299/person

Cultural Connections & Havana Highlights

Fruit stand with pink walls and fruit on a shelf

Man standing while raising a glass, with a person sitting on a hammock also raising their glass

Exterior view of large palace building with old school cars in front

NEW

Multi-Adventure

30s & 40s

Cuba Multi-Adventure Tour

6 days

Levels 2-4

Casual & Deluxe Hotels

2026: Nov

2027: Jan

From $4,799/person

435 Dates

Sort: Date

2026

January 2026

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

1-3

Premiere & Casual Hotels

$7,999/person

(+$2,000 for optional single occ.)

Request to Book

Jan 10, 2026

Saturday

Jan 18, 2026

Sunday

Biking

Couples, Friends & Solos

Costa Rica Bike Tour

6 days

2-4

Premiere & Deluxe Hotels

$6,349/person

(+$1,300 for optional single occ.)

Request to Book

Jan 11, 2026

Sunday

Jan 16, 2026

Friday

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

1-3

Premiere & Casual Hotels

$7,999/person

(+$2,000 for optional single occ.)

Request to Book

Jan 24, 2026

Saturday

Feb 1, 2026

Sunday

Biking

Couples, Friends & Solos

Chile Bike Tour

7 days

2-4

Premiere Hotels

$6,749/person

(+$2,300 for optional single occ.)

Available

Jan 24, 2026

Saturday

Jan 30, 2026

Friday

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

1-3

Premiere & Casual Hotels

$7,999/person

(+$2,000 for optional single occ.)

Request to Book

Jan 31, 2026

Saturday

Feb 8, 2026

Sunday

Hiking & Walking

Couples, Friends & Solos

Colombia Hiking & Walking Tour

days

2-4

Casual Hotels

$5,599/person

(+$950 for optional single occ.)

Request to Book

Jan 31, 2026

Saturday

Feb 7, 2026

Saturday

February 2026

Biking

Couples, Friends & Solos

Costa Rica Bike Tour

6 days

2-4

Premiere & Deluxe Hotels

$6,299/person

(+$1,300 for optional single occ.)

Request to Book

Feb 1, 2026

Sunday

Feb 6, 2026

Friday

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

1-3

Premiere & Casual Hotels

$7,949/person

(+$2,000 for optional single occ.)

Request to Book

Feb 7, 2026

Saturday

Feb 15, 2026

Sunday

Biking

Couples, Friends & Solos

Costa Rica Bike Tour

6 days

2-4

Premiere & Deluxe Hotels

$6,299/person

(+$1,200 for optional single occ.)

Request to Book

Feb 8, 2026

Sunday

Feb 13, 2026

Friday

Hiking & Walking

Couples, Friends & Solos

Bhutan Hiking & Walking Tour

8 days

1-4

Premiere Hotels

$10,449/person

(+$2,100 for optional single occ.)

Request to Book

Feb 10, 2026

Tuesday

Feb 17, 2026

Tuesday

Hiking & Walking

Couples, Friends & Solos

Vietnam & Cambodia Hiking & Walking Tour

10 days

1-2

Premiere Hotels & Casual Ship

$9,349/person

(+$2,500 for optional single occ.)

Request to Book

Feb 12, 2026

Thursday

Feb 21, 2026

Saturday

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

1-3

Premiere & Casual Hotels

$7,949/person

(+$2,000 for optional single occ.)

Request to Book

Feb 14, 2026

Saturday

Feb 22, 2026

Sunday

Hiking & Walking

Couples, Friends & Solos

Colombia Hiking & Walking Tour

days

2-4

Casual Hotels

$5,449/person

(+$950 for optional single occ.)

Request to Book

Feb 14, 2026

Saturday

Feb 21, 2026

Saturday

Multi-Adventure

Families with Kids & Teens

Costa Rica Beaches & Wildlife Family Multi-Adventure Tour

6 days

1-2

Premiere Hotels*

$6,349/person

(+$1,400 for optional single occ.)

Request to Book

Feb 15, 2026

Sunday

Feb 20, 2026

Friday

Hiking & Walking

Couples, Friends & Solos

Vietnam & Cambodia Hiking & Walking Tour

10 days

1-2

Premiere Hotels & Casual Ship

$9,199/person

(+$2,600 for optional single occ.)

Request to Book

Feb 17, 2026

Tuesday

Feb 26, 2026

Thursday

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

1-3

Premiere & Casual Hotels

$7,799/person

(+$2,000 for optional single occ.)

Available

Feb 21, 2026

Saturday

Mar 1, 2026

Sunday

Biking

Couples, Friends & Solos

Costa Rica Bike Tour

6 days

2-4

Premiere & Deluxe Hotels

$6,049/person

(+$1,300 for optional single occ.)

Unplugged

Available

Feb 22, 2026

Sunday

Feb 27, 2026

Friday

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

1-3

Premiere & Casual Hotels

$7,799/person

(+$2,300 for optional single occ.)

Available

Feb 23, 2026

Monday

Mar 3, 2026

Tuesday

Hiking & Walking

Couples, Friends & Solos

Vietnam & Cambodia Hiking & Walking Tour

10 days

1-2

Premiere Hotels & Casual Ship

$9,349/person

(+$2,600 for optional single occ.)

Request to Book

Feb 26, 2026

Thursday

Mar 7, 2026

Saturday

Biking

Couples, Friends & Solos

Thailand Bike Tour

9 days

1-3

Premiere & Casual Hotels

$7,799/person

(+$2,000 for optional single occ.)

Available

Feb 28, 2026

Saturday

Mar 8, 2026

Sunday

March 2026

Biking

Couples, Friends & Solos

Costa Rica Bike Tour

6 days

2-4

Premiere & Deluxe Hotels

$6,199/person

(+$1,300 for optional single occ.)

Request to Book

Mar 1, 2026

Sunday

Mar 6, 2026

Friday

Biking

Couples, Friends & Solos

Costa Rica Bike Tour

6 days

2-4

Premiere & Deluxe Hotels

$6,199/person

(+$1,300 for optional single occ.)

Available

Mar 8, 2026

Sunday

Mar 13, 2026

Friday

Multi-Adventure

Couples, Friends & Solos

Argentina's Mendoza Wine Country & Andes Multi-Adventure Tour

7 days

2-4

Premiere & Deluxe Hotels

$7,649/person

(+$2,500 for optional single occ.)

Going fast! 8 spaces left

Mar 8, 2026

Sunday

Mar 14, 2026

Saturday

Biking

Couples, Friends & Solos

Chile Bike Tour

7 days

2-4

Premiere Hotels

$8,049/person

(+$1,700 for optional single occ.)

Unplugged

Solo Room Savings

Available

Mar 14, 2026

Saturday

Mar 20, 2026

Friday

Hiking & Walking

Couples, Friends & Solos

Colombia Hiking & Walking Tour

days

2-4

Casual Hotels

$5,399/person

(+$900 for optional single occ.)

Available

Mar 14, 2026

Saturday

Mar 21, 2026

Saturday