Trips with Casual Hotels

From $4,499/person

Arizona's Red-Rock Deserts & the Iconic South Rim

Guest on red-rock clifftop, overlooking Utah valley.

Archway shot of guest hiking down trail, towards rock face.

Large valley of gravel hills and mountains

Dramatic landscape shot of mountain range in AZ

Multi-Adventure

Couples, Friends & Solos

Sedona & Grand Canyon Multi-Adventure Tour

6 days

Levels 1-3

Deluxe & Casual Hotels

2026: Apr-May, Sep-Oct

From $4,599/person

Rugged Peaks, Emerald Lakes & Wildlife

Group of people walking down a gravel trail on a hill, surrounded by tall trees

Flowers surrounded by large boulders, with mountains in the distance

People walking up stairs in the middle of a forest towards the top of a mountain

Dirt trail on top of a hill, with a large valley in the distance

NEW

Hiking & Walking

Couples, Friends & Solos

Rocky Mountain National Park Hiking & Walking Tour

5 days

Levels 2-4

Casual Hotels

2026: Jun-Sep

From $3,299/person

Breton Cliffs to D-Day Beaches

Man and woman smiling while walking through a dirt trail

Rustic homes by the oceanside, with large crop valleys in the distance

Two people behind a table full of chocolate desserts and croissants

Castle-like cathedral building on an island, surrounded by ponds of water

Small town next to a beach and large cliffs

NEW

Hiking & Walking

Couples, Friends & Solos

Brittany & Normandy Hiking & Walking Tour

6 days

Levels 1-3

Casual Hotels

From $4,199/person

Waterfalls, Volcanic Craters & Lush Island Landscapes

Sky view of a long path that sits on top of a long, grass-covered cliff

Three men walking on a beach, with a large cliff in the background

Capela de Nossa Senhora das Vitorias Church next to Volcano Crater on Sao Miguel, Azores, Portugal.

Two men on a kayak, paddling in a river by a bridge

Multi-Adventure

Families with 20s & Beyond

Portugal's Azores Family Multi-Adventure Tour

6 days

Levels 1-3

Casual & Deluxe Hotels

2026: May-Aug

From $5,199/person

Coastal Adventures, Seaside Bike Paths & Provincetown

Boy on the beach, playing with the sand and a scooper

Young guest on small backroad with bike.

Person riding their bike on a road next to the beach

Woman riding a bike on an empty road, with a marsh in the distance

NEW

Biking

Families with Kids & Teens

Cape Cod Family Bike Tour

5 days

Levels 1-3

Casual Hotels

2026: Jun-Aug

From $3,899/person

Atlantic Beaches, Seaside Bike Paths & Provincetown

Two white chairs on an outdoor patio, looking out to a large valley

Bridge over a small river, with plants surrounding the river

NEW

Biking

Couples, Friends & Solos

Cape Cod Bike Tour

5 days

Levels 1-3

Casual Hotels

2026: May-Oct

From $3,549/person

Waterfalls, Volcanic Craters & Lush Island Landscapes

Three people walking on a dirt path that is on top of a hill, with a large valley in the background

Active waterfall in the middle of a forest, with a pond on the grand floor

Pineapples grown on a plantation on the island Sao miguel, Azores

Man walking on a beach, with grassy mountains in the background

NEW

Multi-Adventure

Families with Kids & Teens

Portugal's Azores Family Multi-Adventure Tour

6 days

Levels 1-3

Deluxe Hotels

2026: Jun-Aug

From $4,899/person

Sapphire Waters of the Dalmatian Coast

Bird's eye shot of Korcula during sunset.

Two guests in bike gear on bench, overlooking Dalmatian Coast.

Guest in bike gear at meal, smiling at camera.

Shot of Croatian hillside town, Prosek, and 'Olive Oil" sign.

Biking

Couples, Friends & Solos

Croatia Bike Tour

6 days

Levels 2-4

Casual Hotels

From $5,299/person

Mountains & Rugged Coast from Christchurch to Queenstown

Woman surrounded by sheep in New Zealand

Woman hiking on mountainous, glacial trail in New Zealand.

3 Men Talking and Drinking Wine in New Zealand

Biking with Mountain and Water View in Japan

Shape of a kiwi bird spray painted on a road in New Zealand

Multi-Adventure

Couples, Friends & Solos

New Zealand South Island Multi-Adventure Tour

9 days

Levels 1-3

Casual Hotels

2026: Oct-Dec

2027: Jan-Apr

From $6,699/person

Island-Hopping in the Adriatic from Split to Dubrovnik

Shot of the coastal Dubrovnik City Walls.

Six guests in window, drinks in hand, smiling at camera.

Shot of different varieties of bell peppers.

Multi-Adventure

Couples, Friends & Solos

Croatia Multi-Adventure Tour

6 days

Levels 2-4

Casual Hotels*

From $5,099/person

Historic Lunenburg & Bay of Fundy

Guest cycling down road, large lake or river in background.

Shot of numerous different styles and colors of buoys.

Rocky ocean shore in foreground, two-story fishing house in background.

Guests receiving D5 leader brief, ocean in background.

Biking

Couples, Friends & Solos

Nova Scotia Bike Tour

6 days

Levels 2-4

Casual Hotels

2026: Jun-Sep

From $3,899/person

A Taste of Italy from Pienza to Siena & Chianti

Guest cycling down lone, tree-lined road.

Four guests at dinner, talking wine with local.

Guests cycling in front of red flower bushes, hills in distance.

Wide shot of Brunelleschi's dome and it's surrounding city.

Biking

Couples, Friends & Solos

Tuscany Bike Tour

6 days

Levels 2-5

Casual & Deluxe Hotels

2026: May-Oct

From $4,299/person

Epic Peaks, Lakes & Glaciers

Three guests walking over orange rocks, snowy peaks in distance.

Point of view shot of guests on horseback, heading towards beach.

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

Hiking & Walking

Couples, Friends & Solos

Argentina's Patagonia Hiking Tour

7 days

Levels 3-5

Casual Hotels

2026: Mar, Nov-Dec

2027: Jan-Apr

From $5,399/person

Waterfalls, Volcanic Craters & Lush Island Landscapes

Aerial view of Lagoa das Furnas located on the Azorean island of Sao Miguel, Azores, Portugal. Lake Furnas (Lagoa das Furnas) on Sao Miguel, Azores, Portugal from the Pico do Ferro scenic viewpoint.

View of Sete Cidades - Boca do Inferno, Sao Miguel, Azores, Portugal

Man smiling at the camera while holding up a glass of wine

Man and woman inside of a kayak, paddling in the middle of a lake

Multi-Adventure

Couples, Friends & Solos

Portugal's Azores Multi-Adventure Tour

6 days

Levels 1-3

Casual & Deluxe Hotels

2026: Apr-Nov

From $4,899/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

World War II Landmarks & Majestic Mont-St-Michel

Woman in pink, biking in front of a green tank with flags waiving in the background

Man and woman biking in front of a stone cathedral

Two Backroads Guests High Fiving on Beach with Bicycles

Biking

Couples, Friends & Solos

Brittany & Normandy Bike Tour

6 days

Levels 1-4

Casual & Deluxe Hotels

From $4,199/person

Spain's Castile & León to Portugal's Northern Coast

Man riding bike on a road with crops in the distance

Crop fields with a road cutting through the grassy fields

Three people riding bikes on a concrete road

Ancient building courtyard with pillars and a fountain

Biking

Couples, Friends & Solos

Madrid to Porto Bike Tour

6 days

Levels 2-5

Casual & Deluxe Hotels

2026: Mar-Jun, Aug-Oct

From $4,199/person

From Mountains & Glaciers to Prince William Sound

Backroads guests relaxing and enjoying a drink

River flowing through a forest in Alaska

Multi-Adventure

Couples, Friends & Solos

Alaska's Wilderness & Fjords Multi-Adventure Tour

6 days

Levels 2-4

Casual Hotels*

2026: Jun-Sep

From $4,699/person

Charming Villages, Cozy Pubs & Celtic Coastline

Biking

Couples, Friends & Solos

Ireland's County Cork & Kerry Bike Tour

6 days

Levels 2-4

Casual Hotels

From $4,299/person

Path of the Gods, Idyllic Capri & Ischia

Six guests on boat, three looking at one of their phones.

Wide shot of Amalfi Coast, boats dotting the crystal blue water.

Pier on the Amalfi Coast, boast littering the water's edge.

Hiking & Walking

Couples, Friends & Solos

Italy's Amalfi Coast Hiking & Walking Tour

6 days

Levels 2-4

Casual Hotels

From $5,299/person

Mountains, Coastal Trails & Graceful Traditions from Nikko to Kyoto

Woman smiling while walking through an outdoor garden full of plants and pink flowers

Japanese-style building surrounded by red and green trees

Man and woman smiling while walking along a Japanese shrine

Tree-covered cliff by the edge of the ocean

NEW

Hiking & Walking

Couples, Friends & Solos

Japan Hiking & Walking Tour

8 days

Levels 2-4

Deluxe & Casual Hotels

2026: May-Jun, Sep-Nov

2027: Apr-Jun, Sep-Nov

From $7,899/person

Storybook Châteaux & French Countryside

The North West Façade of the Chateau de Chambord

Biking

Couples, Friends & Solos

Loire Valley Bike Tour

6 days

Levels 1-4

Casual & Deluxe Hotels

2026: May-Jun, Aug-Oct

From $4,299/person

From Medieval Villages of the Czech Republic to the Vineyards of Austria's Danube River

Beautiful view of church and castle in Cesky Krumlov, Czech republic

Bikers riding through a city in Czech Republic.

Forest landscape in Mostviertel, lower Austria.

Young men doing an Austrian traditional folk dance.

Biking

Couples, Friends & Solos

Prague to Vienna Bike Tour

6 days

Levels 1-4

Casual & Premiere Hotels

From $4,499/person

1698 Dates

Sort: Date

2026

January 2026

Three guests on hillside trail, one pointing towards something off-frame.

Hiking & Walking

Couples, Friends & Solos

Chile's Patagonia & Fjords Cruise Hiking & Walking Tour

9 days

1-3

Premiere Hotels & Casual Ship

$13,199/person

(+$4,000 for optional single occ.)

Jan 16, 2026

Friday

Jan 24, 2026

Saturday

Sky view of a large lake, surrounded by tall mountains and trees

Multi-Adventure

Couples, Friends & Solos

Argentina's Patagonia Lake District Multi-Adventure Tour

7 days

2-4

Casual Hotels

$5,399/person

(+$750 for optional single occ.)

Request to Book

Jan 19, 2026

Monday

Jan 25, 2026

Sunday

Hiking & Walking

Couples, Friends & Solos

Chile's Patagonia & Fjords Cruise Hiking & Walking Tour

9 days

1-3

Premiere Hotels & Casual Ship

$12,799/person

(+$4,000 for optional single occ.)

Jan 24, 2026

Saturday

Feb 1, 2026

Sunday

Biking

Couples, Friends & Solos

Cuba Bike Tour

6 days

2-4

Casual & Deluxe Hotels

$5,749/person

(+$500 for optional single occ.)

Request to Book

Jan 25, 2026

Sunday

Jan 30, 2026

Friday

Multi-Adventure

Couples, Friends & Solos

Argentina's Patagonia Lake District Multi-Adventure Tour

7 days

2-4

Casual Hotels

$5,349/person

(+$750 for optional single occ.)

Request to Book

Jan 26, 2026

Monday

Feb 1, 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

Hiking & Walking

Couples, Friends & Solos

Chile's Patagonia & Fjords Cruise Hiking & Walking Tour

9 days

1-3

Premiere Hotels & Casual Ship

$12,799/person

(+$3,950 for optional single occ.)

Feb 1, 2026

Sunday

Feb 9, 2026

Monday

Hiking & Walking

Couples, Friends & Solos

Chile's Patagonia & Fjords Cruise Hiking & Walking Tour

9 days

1-3

Premiere Hotels & Casual Ship

$12,599/person

(+$4,000 for optional single occ.)

Feb 9, 2026

Monday

Feb 17, 2026

Tuesday

Guests riding down desert road during sunset.

Biking

Couples, Friends & Solos

Death Valley Bike Tour - 4-Day Getaway

4 days

2-4

Casual Hotels

$4,249/person

(+$1,100 for optional single occ.)

Request to Book

Feb 12, 2026

Thursday

Feb 15, 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

Two groups of families on green rafts, paddling in a river

Multi-Adventure

Families with Kids & Teens

Costa Rica Rain Forest & Pacific Family Multi-Adventure Tour

6 days

1-2

Casual & Deluxe Hotels

$4,899/person

(+$850 for optional single occ.)

Request to Book

Feb 16, 2026

Monday

Feb 21, 2026

Saturday

Biking

Couples, Friends & Solos

Death Valley Bike Tour - 4-Day Getaway

4 days

2-4

Casual Hotels

$4,249/person

(+$1,100 for optional single occ.)

Request to Book

Feb 19, 2026

Thursday

Feb 22, 2026

Sunday

Multi-Adventure

Couples, Friends & Solos

Argentina's Patagonia Lake District Multi-Adventure Tour

7 days

2-4

Casual Hotels

$5,399/person

(+$750 for optional single occ.)

Request to Book

Feb 23, 2026

Monday

Mar 1, 2026

Sunday

Two women ascending a rocky trail with large canyons in the background

Hiking & Walking

Women's Adventures

Death Valley Women's Hiking & Walking Tour

4 days

1-3

Casual Hotels

$4,049/person

(+$1,250 for optional single occ.)

Available

Feb 23, 2026

Monday

Feb 26, 2026

Thursday

Hiking & Walking

Couples, Friends & Solos

Chile's Patagonia & Fjords Cruise Hiking & Walking Tour

9 days

1-3

Premiere Hotels & Casual Ship

$12,799/person

(+$3,000 for optional single occ.)

Feb 25, 2026

Wednesday

Mar 5, 2026

Thursday

Biking

Couples, Friends & Solos

Death Valley Bike Tour - 4-Day Getaway

4 days

2-4

Casual Hotels

$4,149/person

(+$1,100 for optional single occ.)

Request to Book

Feb 26, 2026

Thursday

Mar 1, 2026

Sunday

March 2026

Hiking & Walking

Couples, Friends & Solos

Sedona Hiking & Walking Tour - 4-Day Getaway

4 days

1-3

Deluxe Hotels

$3,699/person

(+$1,000 for optional single occ.)

Going fast! 2 spaces left

Mar 1, 2026

Sunday

Mar 4, 2026

Wednesday

Multi-Adventure

Couples, Friends & Solos

Argentina's Patagonia Lake District Multi-Adventure Tour

7 days

2-4

Casual Hotels

$5,249/person

(+$750 for optional single occ.)

Available

Mar 2, 2026

Monday

Mar 8, 2026

Sunday

Two people standing on top of a large, orange canyon looking at larger canyons

Hiking & Walking

Couples, Friends & Solos

Death Valley Hiking & Walking Tour

4 days

1-3

Casual Hotels

$4,149/person

(+$1,250 for optional single occ.)

Available

Mar 2, 2026

Monday

Mar 5, 2026

Thursday

Hiking & Walking

Couples, Friends & Solos

Argentina's Patagonia Hiking Tour

7 days

3-5

Casual Hotels

$5,749/person

(+$700 for optional single occ.)

Request to Book

Mar 8, 2026

Sunday

Mar 14, 2026

Saturday

Multi-Adventure

Families with Kids & Teens

Costa Rica Rain Forest & Pacific Family Multi-Adventure Tour

6 days

1-2

Casual & Deluxe Hotels

$4,949/person

(+$850 for optional single occ.)

Available

Mar 9, 2026

Monday

Mar 14, 2026

Saturday

Hiking & Walking

Couples, Friends & Solos

Death Valley Hiking & Walking Tour

4 days

1-3

Casual Hotels

$4,049/person

(+$1,250 for optional single occ.)

Available

Mar 9, 2026

Monday

Mar 12, 2026

Thursday

Hiking & Walking

Couples, Friends & Solos

Argentina's Patagonia Hiking Tour

7 days

3-5

Casual Hotels

$5,699/person

(+$850 for optional single occ.)

Request to Book

Mar 10, 2026

Tuesday

Mar 16, 2026

Monday

Hiking & Walking

Couples, Friends & Solos

Chile's Patagonia & Fjords Cruise Hiking & Walking Tour

9 days

1-3

Premiere Hotels & Casual Ship

$12,199/person

(+$3,000 for optional single occ.)

Mar 13, 2026

Friday

Mar 21, 2026

Saturday

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