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Luxury Island Hopping Trips Starting In May 2026, 2027 and 2028

Are you looking to embark on a luxury island hopping trip in May 2026, 2027 or 2028? Choose from 41 unique trip itineraries and 190 departures from the world's leading touring operators.
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41 Trips (190 Trip Departures)
11 Day The Eternal Aegean with Ponant
Cruise
 (2)

11 Days (10 Nights) Valletta to Istanbul
Cruise Line: Ponant
Ship: Le Boreal
Departure: 14 May 2026
Visit: Malta, Sicily, Italy, Greece, Turkey
Inside
-
Oceanview
-
Balcony
$9,970
Suite
-
From
US$9,970
Per Person
View Trip
8 Day Greek Islands & Turkish Coastlines with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Athens to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: Jun 2026 to Oct 2027
Visit: Greece, Turkey
Preferred Fare + Bonus Savings
Select Fare
Exclusive Savings
Inside
-
Oceanview
$5,450
Balcony
-
Suite
$7,498
From
US$5,450
Save 1,926
Per Person
View Trip
8 Day A Journey Of Aegean Allure & Ancient Echoes with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 17 May 2027
Visit: Turkey, Greece
Inside
-
Oceanview
-
Balcony
-
Suite
$4,670
From
US$4,670
Per Person
View Trip
11 Day The Eternal Aegean with Ponant
Cruise
 (2)

11 Days (10 Nights) Valletta to Istanbul
Cruise Line: Ponant
Ship: Le Boreal
Departure: 14 May 2026
Visit: Malta, Sicily, Italy, Greece, Turkey
Inside
-
Oceanview
$9,470
Balcony
$9,970
Suite
$21,310
From
US$9,470
Per Person
View Trip
8 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departures: May 2027 to Sep 2027
Visit: Greece, Turkey
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,900
Suite
$8,900
From
US$4,900
Save 2,500
Per Person
View Trip
8 Day A Journey from Sunlit Cyclades to Adriatic Elegance with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2027 to Jul 2027
Visit: Greece, Croatia, Italy
Inside
-
Oceanview
-
Balcony
-
Suite
$4,590
From
US$4,590
Per Person
View Trip
10 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

10 Days (9 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departure: 29 May 2027
Visit: Greece, Turkey
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,500
Suite
$12,100
From
US$7,500
Save 1,500
Per Person
View Trip
15 Day An Extended Journey Of Island Light & Adriatic Horizons with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Jun 2026
Visit: Greece, Italy, Croatia
Inside
-
Oceanview
-
Balcony
-
Suite
$11,440
From
US$11,440
Per Person
View Trip
8 Day A Journey Of Lush Landscapes & Golden Enchantment with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Oct 2026
Visit: Greece, Croatia, Italy
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,840
From
US$5,840
Per Person
View Trip
8 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departures: May 2027 to Sep 2027
Visit: Greece, Turkey
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,900
Suite
$8,800
From
US$4,900
Save 2,500
Per Person
View Trip
15 Day An Extended Journey of Marble Cities & Sapphire Seas with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Oct 2026
Visit: Greece, Croatia, Italy, Montenegro
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$11,590
From
US$11,590
Per Person
View Trip
15 Day An Extended Journey Of Quiet Shores & Endless Blue with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Venice to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 18 May 2026
Visit: Italy, Croatia, Montenegro, Greece
Inside
-
Oceanview
-
Balcony
-
Suite
$10,980
From
US$10,980
Per Person
View Trip
8 Day A Journey Through Mythical Isles & Captivating Shores with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Istanbul
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Inside
-
Oceanview
-
Balcony
-
Suite
$4,670
From
US$4,670
Per Person
View Trip
15 Day An Extended Journey Of Island Rhythms & Adriatic Echoes with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Jul 2026
Visit: Greece, Italy, Croatia
Inside
-
Oceanview
-
Balcony
-
Suite
$10,370
From
US$10,370
Per Person
View Trip
15 Day Gardens of the Italian Lakes, Slovenia & Croatian Islands Cruise with APT
Tour + Cruise

15 Days Milan to Dubrovnik
Operated By: APT
Ship: MV Lady Eleganza
Departures: May 2027 to Oct 2027
Visit: Italy, Slovenia, Croatia
Inside
-
Oceanview
$12,595
Balcony
-
Suite
-
From
US$12,595
Per Person
View Trip
16 Day Hidden Galapagos & Peru with Tauck
Tour + Cruise

16 Days Lima to Guayaquil or Lima to Quito
Operated By: Tauck
Ships: Silver Origin
Departures: Sep 2026 to Oct 2027
Visit: Peru, Ecuador, Galapagos
Inside
-
Oceanview
-
Balcony
$16,990
Suite
$29,235
From
US$16,990
Per Person
View Trip
15 Day Peru & the Galapagos Islands with Tauck
Tour + Cruise

15 Days Lima to Guayaquil
Operated By: Tauck
Departures: May 2026 to Oct 2027
Visit: Peru, Ecuador, Galapagos
From
US$14,690
Per Person
View Trip
14 Day Croatia & the Dalmatian Coast with Luxury Gold
Tour + Cruise

14 Days Zagreb to Dubrovnik
Operated By: Luxury Gold
Departures: May 2026 to Sep 2026
Visit: Croatia
From
US$9,150
Per Person
View Trip
8 Day Yacht Harbors Of The Aegean Sea with Seabourn
Cruise

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Sep 2028
Visit: Turkey, Greece
Inside
-
Oceanview
-
Balcony
$5,499
Suite
$9,299
From
US$5,499
Per Person
View Trip
12 Day Ancient Empires: Istanbul to Athens with Scenic
New ReleaseCruise

12 Days (11 Nights) Istanbul to Athens
Cruise Line: Scenic
Ship: Scenic Ikon
Departures: May 2028 to Aug 2028
Visit: Turkey, Greece
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$15,093
Suite
$17,654
From
US$15,093
Save 2,370
Per Person
View Trip
16 Day Hidden Gems Of Turkey, Greece, Croatia & Slovenia with Seabourn
Cruise

16 Days (15 Nights) Istanbul to Venice
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 29 May 2027
Visit: Turkey, Greece, Montenegro, Croatia, Slovenia, Italy
Yours to Explore
Inside
-
Oceanview
-
Balcony
$15,299
Suite
-
From
US$15,299
Per Person
View Trip
11 Day Aegean & Turkish Awakening with Oceania Cruises
Cruise

11 Days (10 Nights) Athens to Istanbul
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 07 May 2026
Visit: Greece, Turkey
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,549
Suite
$8,649
From
US$5,549
Save 5,549
Per Person
View Trip
13 Day Spring In The Aegean with Regent Seven Seas
Cruise

13 Days (12 Nights) Istanbul to Istanbul
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 22 May 2026
Visit: Turkey, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$16,899
From
US$16,899
Save 16,899
Per Person
View Trip
11 Day Wonders of the Greek Islands & Aegean Riviera with Scenic
New ReleaseCruise

11 Days (10 Nights) Athens to Athens
Cruise Line: Scenic
Ship: Scenic Ikon
Departure: 27 May 2028
Visit: Greece, Turkey
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,765
Suite
$16,093
From
US$13,765
Save 2,230
Per Person
View Trip
10 Day Treasures of the Aegean with Tauck
Tour + Cruise

10 Days Athens to Athens
Operated By: Tauck
Departures: Jul 2026 to Aug 2026
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visit: Greece, Turkey
From
US$9,990
Per Person
View Trip
15 Day Greek Isles & Ephesus with Seabourn
Cruise

15 Days (14 Nights) Athens to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Yours to Explore
Inside
-
Oceanview
-
Balcony
$10,799
Suite
$18,799
From
US$10,799
Per Person
View Trip
15 Day Crete, Evening At Ephesus & Aegean Yacht Harbors with Seabourn
Cruise

15 Days (14 Nights) Athens to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Aug 2028
Visit: Greece, Turkey
Inside
-
Oceanview
-
Balcony
$9,899
Suite
$16,499
From
US$9,899
Per Person
View Trip
14 Day Croatia in Depth with APT
Cruise

14 Days (13 Nights) Zagreb to Dubrovnik
Cruise Line: APT
Ship: MV Lady Eleganza
Departures: May 2026 to Sep 2027
Visit: Croatia, Bosnia Herzegovina, Montenegro
Exclusive Savings
Inside
-
Oceanview
$4,795
Balcony
-
Suite
-
From
US$3,795
Save 4,200
Per Person
View Trip
8 Day Crete, Mykonos & Ephesus with Seabourn
Cruise

8 Days (7 Nights) Athens to Istanbul
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Yours to Explore
Inside
-
Oceanview
-
Balcony
$5,999
Suite
$11,444
From
US$5,999
Per Person
View Trip
29 Day Mediterranean Medley: Italy, Greece & Ephesus with Seabourn
Cruise

29 Days (28 Nights) Rome to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 08 May 2027
Visit: Italy, Sicily, Malta, Croatia, Montenegro, Greece, Turkey
Yours to Explore
Inside
-
Oceanview
-
Balcony
$30,699
Suite
-
From
US$30,699
Per Person
View Trip
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