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

Island Hopping Cruises Starting In May 2027, 2028 and 2029

Are you looking to embark on an island hopping cruise in May 2027, 2028 or 2029? Choose from 286 unique cruise itineraries and 7,326 departures from the world's leading cruise lines.
Filter Results
286 Cruises (7,326 Departures)
286 Cruises (7,326 Departures)
Departures
Duration
4 Days
45 Days
Regions
Ship Size
Interests
Show More...
Budget
Start & End Cities
Operators
Show More...
Price
$400pp
$143,710pp
Countries
Show More...
13 Day Leisurely Greek Islands - Rhodes, Crete, Santorini & Mykonos with Albatross Tours Featured
New ReleaseTour

13 Days Rhodes to Athens
Operator: Albatross
Departures: May 2027 to Sep 2027
Interests: Coach, Island Hopping
Visits: Greece
Exclusive Savings
From (Per Person)
A$17,137
Save 350
Per Person
View Trip
8 Day Idyllic Greece with Celestyal Cruises
Cruise

8 Days (7 Nights) Athens to Athens
Operator: Celestyal Cruises
Ship: Celestyal Journey
Departures: Apr 2027 to Oct 2028
Visits: Greece, Turkey
Exclusive Savings
Inside
$1,332
Oceanview
$1,655
Suite
$2,812
From (Per Person)
A$1,332
Save 40
Per Person
View Trip
8 Day Ancient Mediterranean Treasures with Viking Cruises
Cruise

8 Days (7 Nights) Athens to Istanbul
Operator: Viking
Ships: Viking Astrea, Viking Jupiter +11 more, Viking Libra, Viking Lyra, Viking Mars, Viking Mira, Viking Neptune, Viking Sea, Viking Sky, Viking Star, Viking Vega, Viking Vela, Viking Vesta
Departures: Nov 2026 to Jul 2029
Visits: Greece, Turkey
Exclusive Savings
Balcony
$4,258
Suite
$6,414
From (Per Person)
A$4,258
Save 1,389
Per Person
View Trip
8 Day Adriatic Coastal Cruise with Travelmarvel
Cruise
 (2)

8 Days (7 Nights) Dubrovnik to Zagreb
Operator: Travelmarvel
Ships: MV Princess Eleganza
Departures: Apr 2027 to Oct 2028
Visits: Croatia
Exclusive Savings
Oceanview
$4,221
From (Per Person)
A$4,221
Save 1,102
Per Person
View Trip
8 Day Adriatic Coastal Cruise with Travelmarvel
Cruise
 (2)

8 Days (7 Nights) Zagreb to Dubrovnik
Operator: Travelmarvel
Ships: MV Princess Eleganza
Departures: Apr 2027 to Oct 2028
Visits: Croatia
Exclusive Savings
Oceanview
$4,417
From (Per Person)
A$4,417
Save 1,090
Per Person
View Trip
10 Day Footsteps of Apostle Paul with Globus
Tour + Cruise
 (4)

10 Days Athens to Athens
Operator: Globus
Cruise Line: Celestyal Cruises
Departures: May 2027 to Sep 2027
Interests: Coach, Cruise, Island Hopping, Religious
Visits: Greece, Turkey
Exclusive Savings
From (Per Person)
A$5,272
Save 325
Per Person
View Trip
26 Day Northern Italy, Slovenia & Croatia with Bunnik Tours
Tour + CruiseFlights Included
 (6)

26 Days Milan to Dubrovnik
Operator: Bunnik Tours
Departures: Apr 2027 to Sep 2027
Interests: Coach, Small Group, Cruise, Island Hopping
Visits: Italy, Slovenia, Croatia
Exclusive Savings
From (Per Person)
A$18,923
Save 426
Per Person
View Trip
15 Day Greece & Aegean Islands Cruise with Cosmos
Tour + Cruise
 (15)

15 Days Athens to Athens
Operator: Cosmos
Cruise Line: Celestyal Cruises
Departures: Apr 2027 to Oct 2027
Interests: Coach, Cruise, Island Hopping
Visits: Greece, Turkey
Single Supplement Waivers
Exclusive Savings
From (Per Person)
A$5,512
Save 277
Per Person
View Trip
14 Day Country Roads of Croatia with Insight Vacations
Tour
 (13)

14 Days Zagreb to Dubrovnik
Operator: Insight Vacations
Departures: Apr 2027 to Oct 2027
Interests: Coach, Island Hopping
Visits: Croatia, Slovenia
Exclusive Savings
From (Per Person)
A$7,154
Save 1,210
Per Person
View Trip
14 Day Country Roads of Croatia with Trafalgar
Tour
 (13)

14 Days Zagreb to Dubrovnik
Operator: Trafalgar
Departures: Apr 2027 to Oct 2027
Interests: Coach, Island Hopping
Visits: Croatia, Slovenia
Exclusive Savings
From (Per Person)
A$7,154
Save 1,210
Per Person
View Trip
15 Day Grecian Fables Idyllic with Insight Vacations
Tour + Cruise
 (6)

15 Days Athens to Athens
Operator: Insight Vacations
Cruise Line: Celestyal Cruises
Departures: May 2027 to Sep 2027
Interests: Coach, Cruise, Island Hopping
Visits: Greece, Turkey
Exclusive Savings
From (Per Person)
A$9,642
Save 481
Per Person
View Trip
15 Day Grecian Fables Idyllic with Trafalgar
Tour + Cruise
 (6)

15 Days Athens to Athens
Operator: Trafalgar
Departures: May 2027 to Sep 2027
Interests: Coach, Cruise, Island Hopping
Visits: Greece, Turkey
Exclusive Savings
From (Per Person)
A$9,642
Save 481
Per Person
View Trip
13 Day Grand Hawaii Vacation with Globus
Tour
 (5)

13 Days Honolulu to Maui
Operator: Globus
Departures: Jan 2027 to Dec 2027
Interests: Coach, Island Hopping
Visits: USA
Exclusive Savings
From (Per Person)
A$9,980
Save 456
Per Person
View Trip
10 Day Greek Island Hopper with Globus
Tour
 (5)

10 Days Athens to Athens
Operator: Globus
Departures: Apr 2027 to Oct 2028
Interests: Coach, Island Hopping
Visits: Greece
Exclusive Savings
From (Per Person)
A$4,578
Save 309
Per Person
View Trip
24 Day Turkey & Greece with Bunnik Tours
Tour + CruiseFlights Included
 (5)

24 Days Istanbul to Athens
Operator: Bunnik Tours
Departures: Apr 2027 to Sep 2027
Interests: Coach, Small Group, Cruise, Island Hopping
Visits: Turkey, Greece
Exclusive Savings
From (Per Person)
A$16,272
Save 331
Per Person
View Trip
16 Day Classical Greece with Idyllic Aegean 7-night Cruise with Globus
Tour + Cruise
 (3)

16 Days Athens to Athens
Operator: Globus
Cruise Line: Celestyal Cruises
Departures: May 2027 to Sep 2027
Interests: Coach, Cruise, Island Hopping
Visits: Greece, Turkey
Exclusive Savings
From (Per Person)
A$8,012
Save 387
Per Person
View Trip
9 Day Dalmatian Elegance with Insight Vacations
Cruise
 (3)

9 Days (8 Nights) Split to Split
Operator: Insight Vacations
Departures: Apr 2027 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$5,380
Save 383
Per Person
View Trip
9 Day Dalmatian Elegance with Trafalgar
Cruise
 (3)

9 Days (8 Nights) Split to Split
Operator: Trafalgar
Departures: Apr 2027 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$5,380
Save 383
Per Person
View Trip
14 Day Greek Island Wanderer with Explore Worldwide
Tour
 (3)

14 Days Athens to Santorini
Operator: Explore
Departures: Apr 2027 to Oct 2027
Interests: Adventure, Island Hopping
Visits: Greece
Exclusive Savings
From (Per Person)
A$4,311
Save 373
Per Person
View Trip
30 Day Ultimate South America with Brazil's Amazon & Galapagos Cruise with Cosmos
Tour + Cruise
 (3)

30 Days Manaus to Guayaquil
Operator: Cosmos
Departures: Jan 2027 to Oct 2027
Interests: Coach, Cruise, Island Hopping, Wildlife
Visits: Brazil, Argentina, Peru, Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$18,459
Save 543
Per Person
View Trip
13 Day Classical Greece with Iconic Aegean 4-night Cruise with Globus
Tour + Cruise
 (2)

13 Days Athens to Athens
Operator: Globus
Cruise Line: Celestyal Cruises
Departures: Apr 2027 to Oct 2027
Interests: Coach, Cruise, Island Hopping
Visits: Greece, Turkey
Exclusive Savings
From (Per Person)
A$6,300
Save 355
Per Person
View Trip
7 Day Explore Croatia with Intrepid Travel
Tour
 (2)

7 Days Dubrovnik to Split
Operator: Intrepid
Departures: Apr 2027 to Oct 2028
Interests: Adventure, Small Group, Island Hopping
Visits: Croatia
Exclusive Savings
From (Per Person)
A$3,572
Save 227
Per Person
View Trip
9 Day Galapagos Discovery with Intrepid Travel
Tour
 (2)

9 Days Quito to Quito
Operator: Intrepid
Departures: Nov 2026 to Dec 2028
Interests: Adventure, Small Group, Island Hopping, Wildlife
Visits: Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$3,029
Save 389
Per Person
View Trip
11 Day Greek Island Hopping (Hotels) with Contiki
Tour
 (2)

11 Days Athens to Athens
Operator: Contiki
Departures: Apr 2027 to Sep 2027
Interests: 18-30's, Island Hopping
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,376
Save 73
Per Person
View Trip
8 Day Athens to Santorini (Hotels) with Contiki
Tour
 (1)

8 Days Athens to Santorini
Operator: Contiki
Departures: Apr 2027 to Sep 2027
Interests: 18-30's, Island Hopping
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,690
Save 57
Per Person
View Trip
10 Day Best of the Hawaiian Islands with Globus
Tour
 (1)

10 Days Honolulu to Maui
Operator: Globus
Departures: Jan 2027 to Dec 2027
Interests: Coach, Island Hopping
Visits: USA
Free Night Pre or Post
Exclusive Savings
From (Per Person)
A$7,876
Save 395
Per Person
View Trip
15 Day Classical Greece Plus Island Hopper with Globus
Tour
 (1)

15 Days Athens to Athens
Operator: Globus
Departures: Apr 2027 to Sep 2028
Interests: Coach, Island Hopping
Visits: Greece
Exclusive Savings
From (Per Person)
A$7,046
Save 386
Per Person
View Trip
11 Day Croatia & Its Islands with Collette
Tour + Cruise
 (1)

11 Days Zagreb to Dubrovnik
Operator: Collette
Departures: Oct 2026 to May 2028
Interests: Coach, Cruise, Island Hopping
Visits: Croatia
Exclusive Savings
From (Per Person)
A$7,888
Save 666
Per Person
View Trip
8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operator: Intrepid
Departures: May 2027 to Oct 2028
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,740
Save 209
Per Person
View Trip
8 Day Cycle the Dalmatian Coast with Explore Worldwide
Tour
 (1)

8 Days Kastel Kambelovac to Dubrovnik
Operator: Explore
Departures: May 2027 to Oct 2027
Interests: Adventure, Small Group, Cycling, Island Hopping
Visits: Croatia
Exclusive Savings
From (Per Person)
A$3,389
Save 281
Per Person
View Trip
Results: 1-29 of 286

No trips found. Try adjusting the search filters.




Cruises found! Scroll up to view.

Cruises

All Cruises Adriatic Cruises Aegean Cruises Africa Cruises Alaska Cruises Antarctic Cruises Arabian & Middle East Cruises Arctic Cruises Asia Cruises Australia Cruises Bahamas Cruises Bermuda Cruises Canada & New England Cruises Caribbean Cruises Central America Cruises China Cruises Croatia Cruises Cruises to the Falkland Islands Cruising Cape Horn Europe Cruises Hawaii Cruises Indian Ocean Cruises Japan Cruises Kimberley Tours & Cruises Mediterranean Cruises Mexico Cruises New Zealand Cruises Northern Europe & Baltic Cruises Northwest Passage Cruises Norway & Iceland Cruises Norwegian Fjords Cruises Patagonia Cruises South America Cruises South East Asia Cruises South Pacific Cruises Transatlantic Cruises UK Cruises USA Cruises Western Europe Cruises Worldwide Cruises

Trip Lengths

1 Month 10 Day 2 Week 3 Week 7 Day

Departure Months

October November December January February March April May June July August September

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.
    

Global Journeys | Terms & Conditions

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

Travel Industry Associations