The 15 Best Island Hopping Sailing Trips in Greece

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion’s Venetian Harbour to protected Dia Island aboard a comfortable yacht with a maximum of 14 people. Swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. Afternoon departures can include a beautiful sunset sail back.

“It was amazing experience. Definitely a highlight of my vacation. Mariana and Manos was fun and helpful. Good food and beautiful views.”

Check availability →Read our full review

2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Best value

Choose a shared half-day sail to Dia Island with lunch, wine, soft drinks, snorkeling gear, paddleboards, and fishing equipment, or book a private trip. A one-hour coastal option stays near Heraklion and includes drinks but no lunch or water activities.

“It takes a conciderable while to get to the island and there isn't a lot to look at in the meantime, I wish the boat was faster. The island looks nice upclose, but it's unfortunatelly not allowed to take a look around from a hill - you can only stay on the beach and visit an old... church? On the other hand, staying in the water is perfectly fine, as it's crystall clear, you can see the sea floor and there's a lot of fish around. While I recommend bringing your own snorkel, the equipment is provided. Good thing they also have flippers. Beware the see urchins - the shore…”

Check availability →Read our full review

3.Corfu Island Sailing Trip with Snack and Soft Drinks

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

Set out from Gouvia with a skipper such as Ari, Savvas, or Tasos for about five hours along Corfu’s northeast coast. Swim at three clear-water spots, try a cliff jump, visit a blue cave, and enjoy sandwiches, fruit, and soft drinks aboard a small yacht for up to 12 people.

“The activity was great! Beautiful Sailing Boat with a lot of space for everyone. Been to 3 different spots and to a small Cave on the way back. All in one an absolut amazing trip!”

Check availability →Read our full review

4.Sailing Cruise to Dia Island with Drinks and Meal

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

Spend six hours sailing from Heraklion to uninhabited Dia Island with a certified crew, snorkeling and SUP gear, fishing equipment, drinks, and a Greek meal. You can join the sailing, swim in clear water, hike, or simply relax on deck. Hotel pickup is available.

“Lovely chilled boat cruise with two swimming stops… the island is uninhabited just some goats but it’s all about boat life!! Lush food, beer and wine and soft drinks flowing all day and raki shots for the hard-core”

Check availability →Read our full review

5.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion’s Venetian harbor to uninhabited Dia Island with a small crew, usually including Ernesto or George. Swim in clear bays, snorkel, paddleboard, and enjoy wine, soft drinks, and either seafood pasta or a lighter half-day meal.

“A really enjoyable and relaxing day. The group was small and everyone chatted with eachother and also with the two crew who were great. It was my first time on a sailing boat which I really enjoyed as well. Would highly recommend!”

Check availability →Read our full review

6.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

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

Set sail from Agios Ioannis with the Greece Sailing by Chios Yachting team for a six-hour trip to Delos and Rhenia. Explore Delos on foot or with a paid guide, then swim, snorkel, and eat a fresh Greek BBQ aboard a spacious yacht. Hotel transfers and Delos entry cost extra.

“Wonderful crew and the food was fantastic. We enjoyed the entire trip and would highly recommend this activity for anyone who wants to spend a day relaxing in the sun while enjoying good food, views and swimming.”

Check availability →Read our full review

7.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 small crew of up to 18 people. Swim, snorkel, paddleboard, eat Greek food, and watch the sunset on the return journey. The crew, including guides such as Andreas and Ianos on some departures, adjusts the plan to wind and sea conditions.

“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 availability →Read our full review

8.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, about an hour offshore, then anchor near Saint George Bay for swimming, snorkeling, SUP, fishing, and lunch. The crew, including captains such as Petros and Yannis, provides equipment, drinks, and a shrimp-linguine meal for up to 14 people.

“Very pleasant cruise out to Dia Island. The crew was wonderful and provided excellent service. We did have to wait to dock, but it was pleasant to chat with other passengers while waiting. Would definitely recommend this trip.”

Check availability →Read our full review

9.Sailing Trip to Dia Island with Lunch & Swimming

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

Sail six nautical miles from Heraklion to Dia Island with Captain George, George the Fisherman, Panos, or Vaso. Swim in Saint George Bay, use the SUP and snorkel gear, and enjoy shrimp or vegetarian pasta, Greek salad, fruit, and unlimited drinks aboard a small yacht.

“We had a lovely experience and enjoyed every moment! The food was amazing and we had some lovely couples with us on the boat. The water was crystal clear and we did some snorkelling. A truly lovely day.”

Check availability →Read our full review

10.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours

Cruise privately from Heraklion to Dia Island with a two-person crew, stopping in Saint George Bay for swimming, snorkeling, fishing, paddleboarding, and lunch if added. The 4.5-hour trip includes drinks, wine, fruit, gear, and plenty of deck space for up to eight people.

“Amazing! We chose to be picked up from our resort, communication and transport great! The boat was private, with only the 5 of us plus Marius and Marisa (the two captains) and had lots of space. The ride was lovely, and when we got to Dia Island, we had over 2 and a half hours to swim, snorkel, and ate lovely fresh salad and sandwiches (made by the captains) which were incredible. They were so welcoming and made us feel so welcome. Amazing value for money, especially for such a private trip with a lovely, modern boat. Would 100% recommend and do it again.”

Check availability →Read our full review

11.Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

★★★★★★★★★★5.0 · 143 reviews · 5 hours 30 minutes (approx.) · from $145

Sail from Heraklion to Dia Island aboard a luxury catamaran with a certified English-speaking crew. You get a seafood Mediterranean lunch, Cretan snacks, unlimited local wine and beer, plus snorkeling, SUP, fishing, canoe boards, and a peaceful three-hour stop in the bay.

“The best caramaran in the port and I'm sure is the crew. Amazing captain, chef and assistant. Beautiful and tasteful food, with dinner and snacks before and after. Everything is thought of, even SUPs and snorkel equipments. Captain anchored us in the best spot in the bay, close to the shore. Amazing experience, would reccomend to anyone.”

Check availability →Read our full review

12.Santorini Catamaran Charter Cruise with a skipper

★★★★★★★★★★5.0 · 136 reviews

You and up to nine companions can sail from Santorini aboard a Lagoon catamaran, choosing your Aegean route with a skipper and hostess. Expect private cabins, four bathrooms, snorkeling gear, a dinghy, and flexible stops across the Greek islands. Fuel, meals, marina fees, and WiFi cost extra.

“I cannot recommend this company enough, but mainly because of one person: Peter. My wife, friends and I had the good fortune of meeting Peter in Oia, and writing this review I do so knowing I cannot do justice to how wonderful he is. Never in my life have I met someoRead more”

Check availability →Read our full review

13.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★5.0 · 126 reviews · 6 hours 30 minutes (approx.) · from $181

Join an English-speaking crew aboard a luxury catamaran from Heraklion for a 6.5-hour trip to Dia Island. Captain Spiro, George, Alexandra, Thomas, Anise, and other crew members have been praised for friendly service. Expect swimming, snorkeling, paddleboarding, fishing, fresh lunch, and drinks in a bay of clear water.

“Lovely relaxing day out visiting dia island , hosts were friendly and meal cooked onboard was exceptional. Whilst on board you can use snorkeling equipment, sup boards and floats. Highly recommend for a chilled day out Only issues we found was that a few clips were broken on the front of the boat seats at knee level...a few of us got scratched as they're quite sharp so could do with being replaced along with a lock on the toilet door which was missing”

Check availability →Read our full review

14.Half Day Cruise on a Sailing Yacht in Corfu Island

★★★★★★★★★★5.0 · 108 reviews · 4 hours (approx.)

Sail Corfu’s northeast coast aboard a private yacht for up to 10 people. Your crew takes you to bays such as Barbati, Kalami, Kerasia, or Strogylo for swimming, snorkeling, SUP, snacks, and drinks. Past crews have included Captain Takis, Panos, Tannos, Athena, and Andromachi.

“Beautiful boat. Lovely crew- Tannos and Athena did a wonderful job. A highlight of our trip. This was a favorite outing for our group of adults. Snorkeling, drinks and great snacks. We enjoyed the blue caves and private snorkel area along the coastline.”

Check availability →Read our full review

15.Private Sailing Cruise from Heraklion to Dia Island

★★★★★★★★★★5.0 · 22 reviews · 6 hours (approx.)

Join Captain Greg and first mate Demetri for a private sailing trip from Heraklion to Dia Island. Swim in clear water, use the paddleboard and snorkel gear, explore an ancient harbor site, and enjoy fruit, snacks, drinks, and lunch on the longer cruise option.

“Very good sailing trip. Personalized for our group of four people. Relaxing, and activities when we arrived at Dia Island. Lunch was very good.”

Check availability →Read our full review