Light blue windowsill, overlooking blue and white Mediterranean domed houses.
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Santorini & Crete Family Multi-Adventure Tour

Sun-Splashed Mythical Greek Isles

Quiet seaside roads and rugged terrain make Crete a gift from the vacation gods. From here, journey across the Aegean to enjoy world-class luxury in Santorini. This family odyssey is nothing short of legendary. 

6 days, 5 nights
Luxury Hotels
5 nights, Luxury Hotels

Learn more about where you'll stay.

Activity Levels 1-3
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We rate our trips based on a range of activity levels from 1-5.

Activity Levels None (White)

See this trip's Activity Options & Terrain for more details.

Families with Teens & 20s

This trip is for:

  • Families with Teens & 20s – Best for ages 16+ (min. age 14)

Also available for:

  • Couples, Friends & Solos – Adults 18+
  • Families with Kids & Teens – Best for ages 9-17 (min. age 4)
Best for ages 16+ (min. age 14)
Also Available for:

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

Itinerary Where You’ll Stay What to Know Bikes Reviews

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Snapshots from the Trip

Trip at a Glance

Highlights

  • Pair bike routes on rugged and mountainous Crete with panoramic hikes on Santorini   
  • Cruise the glittering Aegean aboard a traditional sailboat
  • Follow scenic trails past Santorini’s famous blue-and-white houses and end the day with sunset views from our hotel’s terrace
  • Explore the island of Thirasia, a hidden gem overlooking the deep-blue waters that separate it from Santorini’s iconic caldera cliffs
  • Feast on recipes passed down through generations cooked with fresh local ingredients
Hike/Walk
Bike
Yoga

Sample itinerary. Trip details may vary by departure.

Start Heraklion, Crete Airport & Travel Details

  • Start your family journey on Crete, biking past tiny villages and olive groves
  • Sip coffee or raki alongside locals in Plaka
  • Learn a traditional Cretan dance
  • Soak up the sun over lunch at a local eatery
  • Cool off with a swim in the dazzling sea at a white pebble beach or relax by the pool at our resort
  • Follow serene hiking paths through soaring gorges and idyllic Mediterranean countryside
  • Discover the ancient ruins at Lato, a well-preserved archaeological site with panoramic views of Crete’s peaks and valleys
  • Take in tranquil vistas of Spinalonga Island from a traditional sailboat
  • Bike quiet roads to the Aegean Sea from the island’s rugged interior
  • Visit the Areti Monastery in Karydi and discover the legend behind the origins of this fortified site
  • Taste regional dishes and enjoy Cretan hospitality at a local taverna
  • Consider a yoga class or 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.
Open air resort restaraunt terrace.
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
  • Arrive in awe-inspiring and alluring Santorini, where signature blue-and-white buildings climb uphill like an architectural bougainvillea
  • Wander through the island’s picturesque mazelike walkways
  • Hike one of Santorini’s most scenic volcanic trails
  • Step into the past as you explore peaceful Thirasia island
  • Sample crisp, volcanic soil-grown local wines
  • Immerse yourself in the elegant simplicity of Santo Pure Oia Suites & Villas, a Greek Isle oasis
  • A sunrise walk shows off the beauty of the Cyclades—the perfect way to complete this family adventure.
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.
Santo Pure Oia resort view.

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

This trip has an activity level range of 1-3

Activity level range
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

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