Home > Cruises > Island Hopping Cruises & Sailing Trips

Island Hopping Cruises

Embark on the island hopping adventure of a lifetime on a sun-kissed cruise or sailing voyage. Revel in the golden hues of Aegean sunsets in Greece, plunge into the crystal-clear waters off Croatia's coast, uncover Turkey's quaint and hidden coastal gems, or sail smoothly across Thailand's shimmering white sands. Tailored for every traveller, this is your passport to paradise.

Quick Search Search 9,069 Island Hopping Cruises

Popular Cruises View all

Greece & Aegean Islands Cruise

15 Days Athens to Athens

Operator: Cosmos

From 3,703pp

Save 405pp

Country Roads of Croatia

14 Days Zagreb to Dubrovnik

Operator: Insight Vacations

From 4,536pp

Save 424pp

Grecian Fables - Idyllic

15 Days Athens to Athens

Operator: Insight Vacations

From 5,433pp

Save 371pp

Greek Island Explorer

10 Days Athens to Athens

Operator: Costsaver

From 3,132pp

Save 564pp

Island Hop Your Way View all

18-30 Somethings Trips — 18-30 Somethings

Discover Island-Hop Across the Oceans, Choose Your Own Adventure

Island-Hoppers Unleashed!
Gather your mates or form new friendships as you sail your way through the Med. Hop through the Greek Islands, skip over to Santorini and 'OPA!' you're ready to party.

Indulge in Luxury
Cruise in unparalleled luxury on a small-ship island hopping journey. Indulge in lavish suites, gourmet dining, and personalised service, all while exploring enchanting island destinations.

Authentic Adventures
Sail turquoise waters and pristine atolls on an authentic Dhoni cruise through the Maldives. Explore coral reefs, relax on sandy shores, and soak up this tropical paradise.

Spotlight on Thailand
Experience Thailand's island lifestyle on your next island-hopping adventure. Savour the delicious local cuisine, kick off your sandals and sink into pristine beaches, or join in the vibrant and iconic island nightlife with a Sabai Sabai or two.

Sail Croatia
Sail Croatia's stunning Adriatic Coast, exploring historic towns, hidden coves, and crystal-clear waters. Perhaps visit Hvar, boasting the largest piazza in Dalmatia, and Korcula which is said to be the birthplace of Marco Polo.

LATEST REVIEWS WHAT OUR CLIENTS ARE SAYING ABOUT THEIR ISLAND HOPPING ADVENTURES

Amazing Greek Island Wanderer Katherine, MD, United States, Oct 2025

Kaitlyn was a great help booking and answering questions. She always answered email in a timely manner. I am planning another trip with Kaitlyn.

Galapagos Adventure: Snorkelling & Sea Lions Galápagos Adventure: Snorkelling & Sea Lions David, NC, United States, Sep 2025

The tours and activities were great! Really enjoyed our leader. Felt like he was very knowledgeable and he was very personable. One complaint-breakfasts were way too small. Nina from Global Journeys was extremely helpful. Especially since I made arrangements kind of last minute.

Great cruise Istanbul And Greek Islands L&M, QLD, Australia, Sep 2025

15 day cruise from Barcelona with Cunard. Great cruise line, food was excellent as were the staff. Ephesus was a highlight. Cruised through the Dardanelles strait to Istanbul. The Turkish bazaar’s are fantastic. Would highly recommend.

Wonderful walking tour of 4 Greek Islands Greek Island Wanderer Denise, QLD, Australia, Sep 2025

This was my 4th tour with Explore. Another enjoyable tour with a fantastic young Greek tour leader: very professional, friendly and organised who led us on our walks and organised us with getting on and off ferries and using local buses. A great group of 11 travellers from UK, USA and 1 other Australian. We enjoyed great food and wine at restaurants read more