Greece · ISLAND HOPPING SAILING TRIPS

15 Island-Hopping Sailing Trips Worth the Whole Day

73 sailing trips  ·  from $35 a seat

Two or three islands between breakfast and sunset, with the crossings doing the work a ferry timetable normally ruins. These 15 are compared on how far they actually go, how long you get ashore and what a seat costs.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - The One-Hour Sail to Dia Island
Greece Sailing Trips, Heraklion Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Heraklion, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Heraklion, Swim Stop & Beach Sailing Trips, Tour Reviews

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Number one

Spend 5.5 hours sailing from Heraklion’s Old Venetian Harbour to protected Dia Island. With no more than 14 people aboard, you’ll swim, snorkel, paddleboard, eat shrimp linguini and Greek salad, and enjoy unlimited drinks. Crew members may include Mariana, Manos, Sofia, Giannis, or Captain Petros.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

Check dates →Read our review →

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Finding the boat at Heraklion Port
Crete Sailing Trips, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Crete, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Cheapest deck

Sail from Heraklion with an experienced crew on a luxury yacht, choosing a shared half-day trip to Dia Island, a private cruise, or a one-hour coastal sail. The island option includes swimming, snorkeling, fishing gear, paddleboards, lunch, fruit, and unlimited drinks. Crew members such as Stavroula and Dennis are noted for warm, capable service.

“Nice shorter activity 4 hr, Friendly crew! Good lunch with plenty of water and wine! Beautiful day! ❤️🥂”

Check dates →Read our review →

Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Barbati Beach is the first chance to cool off
Corfu Sailing Trips, Greece Sailing Trips, Island Hopping Sailing Trips, Sailing Trips with an Open Bar, Tour Reviews

Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

3.Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Sail from Gouvia Marina along Corfu’s northeast coast with a skipper such as Ari, Savvas, or Thassos. Swim at Barbati and Gialiskari, snorkel among fish, try a supervised cliff jump, and visit a blue cave. Sandwiches, fruit, and soft drinks are included, while snorkeling gear and alcoholic drinks cost extra.

“We absolutely loved this boat trip, very chilled and relaxed and beautiful views, our guide (Ari) was brilliant and fun too😁”

Check dates →Read our review →

Mykonos: Yacht Cruise to Rhenia and Guided Tour of Delos - Setting sail from Mykonos
Greece Sailing Trips, Guided, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Mykonos, Luxury Yacht Cruises, Luxury Yacht Cruises in Mykonos, Mykonos Sailing Trips, Tour Reviews, Tours

Mykonos: Yacht Cruise to Rhenia and Guided Tour of Delos

4.Yacht Cruise to Rhenia and Guided Tour of Delos

★★★★★★★★★★4.8 · 802 reviews · 1 day · from $141

Spend a full day sailing from Mykonos to Delos and Rhenia with Sunfos Alessia Yachting. A licensed guide, including guides such as Helen or Alexis on some departures, leads the Delos visit, while the crew serves pasta, Greek salad, fruit, wine, and soft drinks. Expect swimming, snorkeling, sun, and a potentially windy ride.

“We had such a great day! The boat was so nice and a very small group so we all got our own space to sunbathe or relax. The guide for Delos was very informative however it was very hot so make sure you bring something to cover up as it’s around 1 hr 30. Make sure to bring treats for the cats too, there are plenty there! :) Food was delicious which we had after our swim spot, keep your swimwear on as the journey back you can get a little wet. Highly recommend!”

Check dates →Read our review →

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Dia Island gives you room to choose your own pace
Greece Sailing Trips, Heraklion Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Heraklion, Sailing Trips with an Open Bar, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Heraklion, Tour Reviews

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

5.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Spend about six hours sailing from Heraklion’s Old Venetian Harbor to Dia Island with an experienced crew, often including Stelios, Celia, or Captain Nick. Swim, snorkel, paddleboard, fish, hike, and eat a Greek meal aboard. Hotel pickup is optional, and afternoon departures can finish with a sunset sail.

“Literally so nice, personable and professional. We made friends with others on the tip facilitated by the captain. Not been cheesy but we will be lifelong friends.”

Check dates →Read our review →

Heraklion: Dia Island Sailing Cruise with Snorkeling - Reaching quiet Dia Island
Greece Sailing Trips, Heraklion Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Heraklion, Sailing & Snorkeling Trips, Tour Reviews

Heraklion: Dia Island Sailing Cruise with Snorkeling

6.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Join Ernesto, George, and the Sailing Crete crew for a small-group cruise from Heraklion’s Venetian harbor to Dia Island. Sail for about an hour, then swim, snorkel, paddleboard, and eat onboard in a quiet bay. Choose a half-day or full-day trip, with hotel transfers available outside central Heraklion.

“The team,the activities snd spots with clear water”

Check dates →Read our review →

Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Starting at Agios Ioannis Diakoftis
Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Mykonos, Mykonos Sailing Trips, Semi-Private Sailing Cruises, Tour Reviews

Shared Mykonos Sail Cruise to Delos and Rhenia Islands

7.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151Highest rated

Spend about six hours sailing from Agios Ioannis to Delos and Rhenia aboard a spacious gulet. Explore Delos with a self-guided walk or paid guide, then swim, snorkel, and enjoy a fresh barbecue buffet with drinks. Hotel transfers and Delos admission are optional extras.

“Loved our trip and snorkeling in these beautiful areas! Food was good, the staff was great - a fun way to spend the day in Mykonos! And they were able to arrange transportation for us from our cruise ship! Highly recommend!”

Check dates →Read our review →

Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks - Lunch onboard with wine and a view
Greece Sailing Trips, Guided, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Mykonos, Mykonos Sailing Trips, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Mykonos, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Mykonos, Tour Reviews, Tours

Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

8.Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

★★★★★★★★★★4.5 · 608 reviews · 6 hours (approx.) · from $145

Spend six hours sailing from Mykonos to Rhenia and Delos with Sunfos Alessia Yachting. Swim from the yacht, use free snorkeling gear, eat lunch onboard, then tour Delos with an English-speaking guide such as Fanny. Expect open-sea views, changing weather, and a group of up to 35 people.

“The Delos architecture tour with a qualified guide and early arrival was worth the whole trip. Food was a little bit depressing and the pick-up fees a bit high. Still loved the day, would recommend, make sure to align your expectations on space and other passengers.”

Check dates →Read our review →

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - What makes Dia Island worth the crossing
Evening Experiences, Greece Sailing Trips, Heraklion Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Heraklion, Sailing & Snorkeling Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Heraklion, Tour Reviews

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

9.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island with a professional crew such as Andreas, Manos, or George. Swim and snorkel in a quiet bay, use the paddleboard, eat Greek food onboard, and sail home at sunset. Shared and private options are available, with hotel pickup offered from selected areas.

“This was one of the best experiences I’ve ever had!! Stella and Elena are two wonderful hosts who did everything to make the trip amazing! Thank you to them! We had a delicious dinner with pasta, salad, and fruit, the chance to enjoy the beauty of the sea, and saw an incredible sunset! I highly recommend it to everyone!”

Check dates →Read our review →

Sailing Cruise to Dia Island with Meal and Water Activities - Why Dia Island feels different from a beach outing
Greece Sailing Trips, Heraklion Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Heraklion, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Heraklion, Tour Reviews

Sailing Cruise to Dia Island with Meal and Water Activities

10.Sailing Cruise to Dia Island with Meal and Water Activities

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $96

Sail from Heraklion to uninhabited Dia Island on a yacht or catamaran with a maximum of 14 people. You get about three hours in a sheltered cove for swimming, snorkeling, paddleboarding, and fishing, plus shrimp linguine, Greek salad, Cretan appetizers, fruit, beer, wine, and soft drinks. Captains such as Petros, Yannis, and Pedro adjust the route when wind or waves change.

“This was one of the best tours we booked! Amalia was amazing! We had a blast swimming, snorkeling and paddle boarding in the beautiful area of Dia Island!”

Check dates →Read our review →

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Leaving Heraklion Port
Greece Sailing Trips, Heraklion Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Heraklion, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Heraklion, Swim Stop & Beach Sailing Trips, Tour Reviews

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

11.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Join a small group of up to 10 people for a six-hour sail from Heraklion to Dia Island. Captains George, Panos, and Vaso bring local stories and good humor, while you swim, snorkel, paddleboard, fish, and enjoy shrimp or vegetarian pasta with Greek salad, fruit, and unlimited drinks.

“George and Marco were friendly and informative and made the trip very enjoyable. We spent a good amount of time snorkelling using the equipment they provided and enjoyed a nice lunch of pasta, salad and fruit. It’s a small group of 10 so the boat isn’t overcrowded and you get to know the people well. Highly recommend”

Check dates →Read our review →

Heraklion: Private Half-Day Sailing Trip to Dia Island - The One-Hour Sail to Dia Island
Crete Sailing Trips, Greece Sailing Trips, Half-Day, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Private Sailing Charters, Private Sailing Charters in Crete, Tour Reviews

Heraklion: Private Half-Day Sailing Trip to Dia Island

12.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459 per boat

Sail privately from Heraklion to Dia Island with a two-person crew, then spend 2.5 hours at Saint George Bay swimming, snorkeling, fishing, and using a paddleboard. Water, soft drinks, wine, fruit, and equipment are included. Add hotel transfers or an onboard meal for extra convenience.

“Sailing trip was great, guides gave a lot of explanation concerning the boat, island and history.”

Check dates →Read our review →

Best of Milos and Poliegos Catamaran snorkelling Cruise with BBQ - Poliegos and the Blue Lagoon at Galazia Nera
Catamaran Cruises, Catamaran Cruises in Milos, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Milos, Milos Sailing Trips, Sailing & Snorkeling Trips, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Milos, Tour Reviews

Best of Milos and Poliegos Catamaran snorkelling Cruise with BBQ

13.Best of Milos and Poliegos Catamaran snorkelling Cruise with BBQ

★★★★★★★★★★5.0 · 460 reviews · 9 hours (approx.) · from $241

Spend about nine hours aboard POLCO Sailing’s Lagoon 440, cruising from Adamantas to Poliegos, Kleftiko, Gerakas, Kalogries, and more. Expect swimming, snorkeling, paddleboarding, Greek tapas, a BBQ lunch, drinks, Wi-Fi, and underwater GoPro photos. The crew may include Yannis, Dina, Flo, Elena, or other POLCO team members.

“Tour was on Sept. 9, 2024. What an amazing tour! The staff members were fantastic, very friendly and chatty. The food was delicious and exceeded expectations. It really was freshly prepared on the catamaran. One of the best things was that this wasn't a "drink your face off" party boat. There was music playing but it wasn't loud at all. It really was a relaxed and enjoyable experience. Highly recommend.”

Check dates →Read our review →

Dia Sailing Cruise With All-inclusive Meal And Drinks - Four hours around Dia Island
Greece Sailing Trips, Heraklion Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Heraklion, Sailing Trips with an Open Bar, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Heraklion, Tour Reviews

Dia Sailing Cruise With All-inclusive Meal And Drinks

14.Dia Sailing Cruise With All-inclusive Meal And Drinks

★★★★★★★★★★4.6 · 422 reviews · 5.5 hours · from $76

Sail from Heraklion’s Old Venetian Port to Dia Island aboard a comfortable yacht with captains such as Alex, Nikolas, Fabio, and Mel. Spend four hours swimming, snorkeling, paddleboarding, eating fresh pasta and Greek salad, and sipping unlimited wine and soft drinks. Choose a daytime or sunset departure, with hotel pickup available by arrangement.

“This was the highlight of our vacation!! The drive was funny and relaxing and the food amazing!! They got all the things for snorkeling and to SUP around and it felt more like a friend outing than a payed tour, since they made you feel so comfortable. I would highly recommend to anyone who‘s thinking about it!!!”

Check dates →Read our review →

Agios Nikolaos: Spinalonga and Kolokytha Catamaran with Meal - Seeing Spinalonga Without Going Ashore
Agios Nikolaos Sailing Trips, Catamaran Cruises, Greece Sailing Trips, Island Hopping Sailing Trips, Sailing Trips with Lunch & BBQ, Tour Reviews

Agios Nikolaos: Spinalonga and Kolokytha Catamaran with Meal

15.Spinalonga and Kolokytha Catamaran with Meal

★★★★★★★★★★4.8 · 381 reviews · 5.5 hours · from $141

Join an English-speaking crew, often including Christos and Marina, for a relaxed catamaran cruise from Agios Nikolaos. Sail past Elounda and Spinalonga, swim in clear bays, use SUP boards and snorkels, then enjoy fresh pasta, Cretan appetizers, fruit, and unlimited drinks. Spinalonga is viewed from the water only.

“This was a really enjoyable day trip. The catamaran was comfortable, and the crew were friendly and professional. The cruise to Spinalonga was smooth, and the guide gave a good overview of the island’s history without it feeling rushed. After the visit, we anchored near Kolokytha for a swim, which was a highlight — the water was crystal clear and calm. The meal on board was simple but tasty, and there was plenty for everyone. It felt relaxed and well-paced, with enough time to explore, swim, and just enjoy being out on the water. If you’re looking for a mix of history, scenery, and some downtime at sea, this trip…”

Check dates →Read our review →

Just added in Island Hopping Sailing Trips

★ 3.9Spinalonga and Kolokitha Island Sailing TripFrom $848 per boat3 reviews
★ 5.0Antiparos: Private Sailing Cruise with Swim Stops and LunchFrom $1,885 per boat3 reviews
★ 5.06 Hours Tour to Delos and Rhenia Islands with Sailing YachtFrom $1583 reviews
★ 4.5Private Sailing Cruise to Dia Island with Meal & Water ActivitiesFrom $951 per boat10 reviews
★ 5.0Dia Island Private Sailing Cruise with Full MealFrom $931 per boat6 reviews
★ 4.8Private sailing to Dia Island with LunchFrom $471 per boat16 reviews
★ 4.7Dia Island: Semi-Private Full Day Sailing Trip with mealFrom $10019 reviews
★ 4.5Private Luxury Sailing Trips to Dia IslandFrom $639 per boat25 reviews
★ 4.5Small group 5,5h Sunset Sailing trip to Dia IslandFrom $8426 reviews
★ 5.0Catamaran Cruise to Dia IslandFrom $14126 reviews
★ 4.5Heraklion | Half day Sailing cruise to Dia IslandFrom $8030 reviews
★ 5.0Catamaran Cruise to Dia with Sunset, Meal & BarFrom $15030 reviews
★ 5.0Ag. Nikolaos Catamaran to Spinalonga – Gourmet Meal & Water ToysFrom $15033 reviews
★ 5.0Full Day Cruise on Sailing Yacht in Corfu IslandFrom $1,442 per boat33 reviews
★ 4.3Thassos Island: Sailing Day Cruise Beer & SnackFrom $8830 reviews

Other kinds of day

Private Sailing Charters83Luxury Yacht Cruises35Semi-Private Sailing Cruises38Catamaran Cruises172
Scroll to Top

Pick a coast, then pick a boat

Every island we sail from, and every kind of day that leaves it.

The Cyclades

SantoriniMilosMykonosNaxosParos

Crete

CreteHeraklionChaniaAgios NikolaosRethymno

Mainland and Ionian

AthensCorfuNafplioHalkidikiThessaloniki

Kinds of day

Catamaran DaysSunset SailsPrivate ChartersIsland HoppingCrewed Yachts