View Gallery

Santorini & Crete Multi-Adventure Tour

Sun-Splashed Mythical Greek Isles

With its beaches and deep mountain gorges, Crete is a gift from the vacation gods. Pair this ancient isle with the enchanting vistas of Santorini for an active adventure of mythological proportions.

6 days, 5 nights

Luxury Hotels

Activity Levels 1-3

Couples, Friends & Solos

Also Available for:

From $6,499 - $7,499/person

Itinerary Where You’ll Stay What to Know Bikes Reviews

Compare

Saved

Save

View Dates & prices

Snapshots from the Trip

Trip at a Glance

Highlights

Mamma mia! It’s an Aegean dream trip as you pair fascinating Crete, with its rich culture, and iconic Santorini, the jewel of the Cyclades
Bike between rugged mountains and silvery olive groves on Crete
Hike through the iconic blue-and-white cliffside cottages of Santorini and watch the sunset from the terrace of our heavenly hotel
Journey back in time on the sleepy islet of Thirasia, facing Santorini across the waters of what was once a volcanic caldera
Savor regional wines, fresh-caught seafood and incredible Greek recipes made from the kitchen gardens of our many incredible hosts

Hike/Walk

Bike

Yoga

Sample itinerary. Trip details may vary by departure.

Start Heraklion Airport & Travel Details

Start your active journey in Crete biking past tiny villages and olive groves
Sip a glass of wine and learn a traditional Cretan dance
Soak up the sun over lunch at a local eatery
Cool off with a swim in the dazzling sea or relax in the pool at our resort
Hike tranquil paths through soaring gorges and an idyllic Mediterranean countryside
Explore the ancient ruins at Lato, a well-preserved archaeological site with extraordinary panoramic views of Crete’s mountains and valleys
Take in tranquil vistas of Spinalonga Island from a traditional sailboat
Bike quiet roads from the island’s rugged interior to the Aegean Sea
Visit the Areti Monastery in Karydi and discover the legend behind this fortified site
Sample regional dishes and enjoy Cretan hospitality at a local taverna
Find your balance in a yoga class or opt to pamper yourself at the spa.

Cayo Exclusive Resort & Spa

(Luxury Hotel, 3 nights)

Activity Options & Terrain

Night view of Cayo resort entrance with hills and ocean in the background.

Luxury resort pool area surrounded by tropical landscaping, lounge chairs, and private cabanas. Outdoor dining seating sits beside the pool, with views toward the ocean through the trees in the background.

A hotel pool with many lounge chairs overlooks the Mediterranean sea.

Restaraunt overlooking the mediterranean sea.

Nights 1-3

Cayo Exclusive Resort & Spa

Plaka

Luxury Hotel

Eco-friendly design mixes tile, stone, wooden verandas and minimalist sensibilities into a rustic-chic whole. But the location steals the show, with the whole property sweeping down a vast slope to a crystal-clear beach, surrounded by wild rocky mountainsides and overlooking the ancient fortified islet of Spinalonga across the bay. (pool, spa)

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.

Ferry across the jewel-toned Sea of Crete to awe-inspiring and alluring Santorini
Wander through picturesque mazelike walkways, past the island’s signature blue-and-white buildings that climb uphill like an architectural bougainvillea
Hike one of Santorini’s most scenic volcanic trails
Step into the past as you explore the quiet island of Thirasia
Sample crisp, volcanic soil-grown local wines
Luxuriate in the elegant simplicity of Santo Pure Oia Suites & Villas, a Greek Isle oasis
Capture the beauty of the Cyclades during a sunrise walk for a perfect lasting memento.

Santo Pure Oia Suites & Villas

(Luxury Hotel, 2 nights)

Activity Options & Terrain

Overlook of Santo Pure Oia with rolling hills and a distant bay.

Open air restaraunt with a pool and the ocean in the background.

Pool with underlit loungers and clear water.

Infinity pool with loungers and the ocean on the horizon.

Nights 4-5

Santo Pure Oia Suites & Villas

Santorini

Luxury Hotel

This enchanting oasis embodies the Santorini-chic aesthetic that has become synonymous with Greek daydreams the world over: whitewashed patios, rustic stone walls, dazzling indoor-outdoor spaces and sinuous infinity pools suspended over infinite views of the Aegean. (pool, spa)

Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.

End Santorini Airport & Travel Details

Start
End
Overnight stay
Trip direction

View & Download

This trip has an activity level range of 1-3

Route & Terrain Notes

The biking routes on this trip are primarily on the quiet roads of Crete, passing olive groves, villages and coastline. The terrain is hilly, with some steep climbs and exhilarating descents. Some of our routes follow winding roads with little or no shoulder, and there are some sections with rough pavement. Hiking terrain on this trip includes narrow trails through gorges and cliffside coastal paths. Trails cover rocky uneven terrain and volcanic soil; sturdy hiking shoes are appropriate.

Day 1

Biking

Level 2

12 miles

900 ft. gain

Level 2

14 miles

1400 ft. gain

Day 2

Hiking & Walking

Level 2

3 miles

400 ft. gain

Level 3

4 miles

500 ft. gain

Other

Tour of Lato Archaeological Site (45 minutes)

Spinalonga Island Cruise (1.5 hours)

Day 3

Biking

Level 1

11 miles

400 ft. gain

Level 1

16 miles

1400 ft. gain

Level 2

22 miles

2200 ft. gain

Level 3

26 miles

2400 ft. gain

Yoga

(1 hour)

Day 4

Hiking & Walking

Level 2

3 miles

400 ft. gain

Level 3

6 miles

900 ft. gain

Day 5

Hiking & Walking

Level 1

3 miles

400 ft. gain

Level 1

3 miles

900 ft. gain

Level 2

5 miles

1100 ft. gain

Level 3

8 miles

1200 ft. gain

Other

Thirasia Island Visit (half day)

Day 6

Other

Sunrise Walking Tour (1 hour)

View Dates & Prices From $6,499/person

What to Know

What's Included

See Everything Included

Straight Talk

We want to make sure you're on the trip that's right for you. Every Backroads trip is unique and this one is no exception.

Shuttle Time

In order to access the most scenic biking routes and significant points of interest on this trip, strategic shuttles are incorporated into several days of our itinerary. Most will be limited to an hour or so at a time, but on some days you can expect to spend a bit more time in the shuttle. Please note that we have planned our itinerary to make the most of our time on these spectacular islands.

Ferry Crossing

We travel by public ferry across the Aegean Sea from Crete to Santorini Island. Bring seasickness medication if you think you’ll need it; this crossing can be subject to strong winds and rough seas. On the rare occasion that our ferry does not run as scheduled, we will need to adjust our itinerary. This may include changing our port of departure, extending our stay on the first island or leaving earlier than scheduled for the second. Should this be the case on your trip, your Trip Leaders are equipped with alternate activities and will share more details about what to expect.

Summer Heat & Crowds

Crete and Santorini are popular tourist destinations with busy peak seasons, especially during the summer months and on national holidays. We’ve planned our itinerary to take you off the beaten path, but crowds are common on these islands. And keep in mind that summer heat can make biking and hiking more challenging.

FAQs

This trip is best suited for adults who enjoy multi-adventure travel with easy to moderately challenging activity options each day. It's ideal for those who want to experience two distinct Greek islands by bike, on foot and by boat while exploring ancient sites, dramatic coastlines and local culture. E-bikes available.

This is a Level 1–3 Multi-Adventure trip, with hikes of roughly 3–8 miles and up to 1,200 feet of gain, plus bike rides of around 10–25 miles and up to 2,400 feet. A typical day includes multiple flexible route choices—see this trip’s Activity Options & Terrain in the itinerary for day-by-day details or learn more about Backroads’ activity levels.

Crete and Santorini offer two distinct sides of Greece. Crete features rugged mountains, traditional villages and a slower-paced island culture, while Santorini is known for its iconic whitewashed villages, caldera views and lively atmosphere. Together, they combine authentic local traditions with some of Greece's most famous scenery.

The trip combines biking, hiking and cultural exploration across Crete and Santorini. Guests bike through rural villages and olive groves, hike coastal and caldera trails, visit ancient sites and explore historic towns while experiencing the distinct character of each island.

Boat travel is a regular part of the itinerary, including a ferry ride of about 1.5 hours between Crete and Santorini. The trip also includes a short boat ride to the quiet island of Thirasia, offering a different perspective on Santorini away from the crowds.

Trusted by Travelers Since 1979

7,000+ 5-star reviews.
Your Day, Your Way

Route and activity options to match your pace and preferences.
24/7 Local Support

Experienced leaders on every trip backed by a dedicated service team.
Never Outsourced

Expert trip design rooted in five decades of local knowledge and relationships.
Small Groups

More access, flexibility and connection, with an average of 14 guests.