Home > Cruises > Luxury Cruises > Island Hopping Cruises & Sailing Trips > May

Luxury Island Hopping Trips Starting In May 2027 and 2028

Are you looking to embark on a luxury island hopping trip in May 2027 or 2028? Choose from 41 unique trip itineraries and 178 departures from the world's leading touring operators.
Filter Results
41 Trips (178 Departures)
41 Trips (178 Departures)
Departures
Duration
8 Days
31 Days
Regions
Trip Styles
Start & End Cities
Operators
Show More...
Price
$2,400pp
$80,995pp
Countries
Show More...
8 Day Mediterranean Enchantment with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Dubrovnik to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia +2 more, Emerald Raiya, Emerald Sakara
Departures: Jul 2027 to Oct 2028
Visits: Croatia, Montenegro, Albania, Greece
Exclusive Savings
Inside
-
Oceanview
$8,099
Balcony
-
Suite
$10,867
From (Per Person)
A$8,099
Save 2,225
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
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,526
From (Per Person)
A$7,526
Save 158
Per Person
View Trip
15 Day An Extended Journey From The Shores Of Athens To The Island Of Mykonos with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 10 May 2027
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$14,778
From (Per Person)
A$14,778
Save 302
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
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,221
Suite
$17,738
From (Per Person)
A$10,221
Save 4,679
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
Visits: Turkey, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,526
From (Per Person)
A$7,526
Save 154
Per Person
View Trip
17 Day Greece & Croatia Combination Cruise: Rhodes, Santorini & Hvar with Azamara Cruises
Cruise
 (4)

17 Days (16 Nights) Athens to Venice
Cruise Line: Azamara
Ship: Azamara Journey
Departure: 06 May 2028
Visits: Greece, Turkey, Montenegro, Croatia, Italy
Azamara Always Included
Exclusive Savings
Inside
$7,170
Oceanview
$7,749
Balcony
$9,483
Suite
$13,295
From (Per Person)
A$7,170
Per Person
View Trip
8 Day Greece Intensive Cruise: Syros, Patmos & Rhodes with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Athens to Athens
Cruise Line: Azamara
Ships: Azamara Journey, Azamara Onward
Departures: Sep 2026 to May 2028
Visits: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$3,186
Oceanview
$3,451
Balcony
$4,206
Suite
$5,881
From (Per Person)
A$3,186
Save 49
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
Departure: 15 May 2027
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,408
Suite
$15,925
From (Per Person)
A$9,408
Save 2,592
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
Visits: Greece, Croatia, Italy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,174
From (Per Person)
A$7,174
Save 169
Per Person
View Trip
8 Day Croatian Coast and the Best of the Adriatic with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Venice to Dubrovnik
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia +2 more, Emerald Raiya, Emerald Sakara
Departures: Jul 2026 to Oct 2028
Visits: Italy, Croatia
Exclusive Savings
Inside
-
Oceanview
$8,498
Balcony
-
Suite
$11,267
From (Per Person)
A$8,498
Save 2,661
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
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,333
Suite
$14,896
From (Per Person)
A$6,333
Save 5,417
Per Person
View Trip
8 Day Greek Islands & Turkish Coastlines with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) Athens to Athens
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 29 May 2027
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$12,831
From (Per Person)
A$12,831
Save 1,739
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
Visits: Turkey, Greece, Montenegro, Croatia, Slovenia, Italy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$18,262
Suite
-
From (Per Person)
A$18,262
Save 352
Per Person
View Trip
9 Day Croatian Island Discovery with APT
Cruise

9 Days (8 Nights) Dubrovnik to Zagreb
Cruise Line: APT
Ship: MV Lady Eleganza
Departures: May 2027 to Oct 2027
Visits: Croatia
Exclusive Savings
Inside
-
Oceanview
$8,732
Balcony
-
Suite
-
From (Per Person)
A$8,732
Save 1,273
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: Jul 2026 to Sep 2027
Visits: Croatia, Bosnia Herzegovina, Montenegro
Exclusive Savings
Inside
-
Oceanview
$10,064
Balcony
-
Suite
-
From (Per Person)
A$10,064
Save 3,181
Per Person
View Trip
8 Day San Cristóbal to San Cristóbal with Silversea
Cruise

8 Days (7 Nights) Quito to Guayaquil
Cruise Line: Silversea
Ship: Silver Origin
Departures: Jul 2026 to Mar 2028
Visits: Ecuador, Galapagos
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,749
Suite
$29,106
From (Per Person)
A$14,749
Save 5,486
Per Person
View Trip
8 Day Hidden Gems Of Turkey & Greece with Seabourn
Cruise

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2027 to Oct 2027
Visits: Turkey, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,172
Suite
$12,004
From (Per Person)
A$7,172
Save 172
Per Person
View Trip
26 Day Best of South America with Galápagos Cruise with APT
New ReleaseTour + Cruise

26 Days Rio de Janeiro to Guayaquil
Cruise Line: APT
Departures: Apr 2027 to Nov 2028
Trip Styles: Small Group, Cruise, Island Hopping, Wildlife, Scenic
Visits: Brazil, Argentina, Chile, Peru, Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$33,435
Save 2,118
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
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,876
Suite
$21,197
From (Per Person)
A$13,876
Save 314
Per Person
View Trip
14 Day Croatia & the Dalmatian Coast with Luxury Gold
Tour + Cruise

14 Days Zagreb to Dubrovnik
Operator: Luxury Gold
Departures: Sep 2026 to Sep 2027
Trip Styles: Coach, Small Group, Cruise, Island Hopping, Scenic
Visits: Croatia
Exclusive Savings
From (Per Person)
A$12,347
Save 1,935
Per Person
View Trip
8 Day Greek Islands & Turkish Coastlines with Emerald Cruises
Cruise

8 Days (7 Nights) Athens to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya, Emerald Sakara
Departures: Jul 2026 to Oct 2028
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
$8,249
Balcony
-
Suite
$10,401
From (Per Person)
A$8,249
Save 3,497
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
Visits: Turkey, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,864
Suite
$12,891
From (Per Person)
A$7,864
Save 160
Per Person
View Trip
15 Day An Extended Journey Through Greek Splendour, Byzantine History & Timeless Piazzas with Explora Journeys
Cruise

15 Days (14 Nights) Venice to Athens
Cruise Line: Explora Journeys
Ship: Explora I
Departures: May 2028 to Aug 2028
Visits: Italy, Slovenia, Croatia, Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$13,891
From (Per Person)
A$13,891
Save 290
Per Person
View Trip
31 Day Best of South America with Belmond Andean Explorer Train and Galápagos Cruise with APT
New ReleaseTour + Cruise

31 Days Rio de Janeiro to Guayaquil
Cruise Line: APT
Departures: May 2027 to Oct 2028
Trip Styles: Small Group, Cruise, Island Hopping, Wildlife, Scenic
Visits: Brazil, Argentina, Chile, Peru, Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$42,257
Save 3,126
Per Person
View Trip
22 Day Greek Isles, Evening At Ephesus, Croatia & Slovenia with Seabourn
Cruise

22 Days (21 Nights) Athens to Venice
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Jul 2028
Visits: Greece, Turkey, Montenegro, Croatia, Slovenia, Italy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$20,506
Suite
$31,796
From (Per Person)
A$20,506
Save 440
Per Person
View Trip
23 Day Mediterranean Mosaic: Greek Isles, Ephesus & Croatia with Seabourn
Cruise

23 Days (22 Nights) Athens to Venice
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 22 May 2027
Visits: Greece, Turkey, Montenegro, Croatia, Slovenia, Italy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$28,934
Suite
-
From (Per Person)
A$28,934
Save 560
Per Person
View Trip
11 Day Adriatic Gems & Greece with Oceania Cruises
Cruise

11 Days (10 Nights) Trieste to Athens
Cruise Line: Oceania
Ship: Oceania Allura
Departure: 11 May 2028
Visits: Italy, Croatia, Montenegro, Greece
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,108
Suite
$9,891
From (Per Person)
A$6,108
Save 2,172
Per Person
View Trip
8 Day San Cristóbal to San Cristóbal with Silversea
Cruise

8 Days (7 Nights) Quito to Guayaquil
Cruise Line: Silversea
Ship: Silver Origin
Departures: Aug 2026 to Mar 2028
Visits: Ecuador, Galapagos
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$15,504
Suite
$27,440
From (Per Person)
A$15,504
Save 7,096
Per Person
View Trip
11 Day Yachting the Less-travelled Greek Isles, Mykonos and Turkey with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Athens to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: Sep 2027 to Oct 2028
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
$11,051
Balcony
-
Suite
$14,726
From (Per Person)
A$11,051
Save 3,251
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
Visits: Turkey, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$19,389
Suite
$23,270
From (Per Person)
A$19,389
Save 5,909
Per Person
View Trip
Results: 1-30 of 41

No trips found. Try adjusting the search filters.




Trips found! Scroll up to view.

Luxury Travel

Luxury Tours Luxury Cruises Luxury River Cruises Luxury Small Group Tours

Luxury Trips By Region

Africa Alaska Amazon Arctic Argentina Asia Australia Balkans Botswana Brazil Cambodia Canada & Alaska Central America Central Europe Chile Corsica Costa Rica Croatia Denmark Eastern Europe Eastern Med Ecuador Egypt England Europe Finland France Galápagos Germany Greece Greenland Iceland India Indonesia Ireland Italy Japan Jordan Kenya Latin America Malta Mexico Middle East Morocco New South Wales New Zealand Northern Ireland Northern Italy Norway Patagonia Peru Portugal Queensland Sardinia Scandinavia Scotland Sicily Slovenia South America South Australia South East Asia South Korea Southern Italy Spain Spain & Portugal Sweden Switzerland Tanzania Turkey UK & Ireland USA Vietnam Western Australia Western Europe

Cruise Themes

Adults Only Cruises Christmas & New Year Cruises Expedition Cruises Family Cruises Island Hopping Cruises Luxury Cruises Northen Lights Cruises Sailing Trips Short Cruises Last Minute Cruise Deals

© 2010-2026. Global Journeys. You're viewing our site in Australian dollars.

    

Global Journeys | Terms & Conditions

Global Journeys Pty Ltd. Accredited Member of The Australian Travel Industry Association (ATIA). No. A11351.

Travel Industry Associations