Greece · SWIM STOP & BEACH SAILING TRIPS

15 Greek Sailing Trips Built Around the Swimming

29 sailing trips  ·  from $88 a seat

Some boats sail and stop once. These 15 are the other kind: three or four anchorages, a ladder down at each, and enough time in the water to be worth the sunscreen. Priced, timed and clear on how many stops you get.

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: 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

2.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 →

Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise - Leaving Kissamos with breakfast and a safety briefing
Catamaran Cruises, Chania Sailing Trips, Greece Sailing Trips, Swim Stop & Beach Sailing Trips, Tour Reviews

Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise

3.Balos & Gramvousa Luxury Catamaran Sailing Cruise

★★★★★★★★★★4.9 · 516 reviews · 7 - 8.5 hours · from $229

Sail from Kissamos to Balos Lagoon and Gramvousa Island aboard a modern catamaran limited to 22 people. The crew, often including Giannis, Dimitri, Jessica, Peter, or Spiros, serves Cretan food, beer, wine, and soft drinks while you swim, snorkel, paddleboard, or relax on deck. Transfers are available from Georgioupoli to Kissamos.

“We really enjoyed the full day sailing - the beaches were beautiful, the food served on board was delicious, we felt like there was sufficient time at each beach to really enjoy ourselves, and the boat was luxurious and nice. Our only grievance was that Kissamos (where the tour started) is an expensive cab ride away from Chania, where everyone was coming from, and it would have been nice if the tour provided transportation or at least helped everyone coordinate cabs to save money.”

Check dates →Read our review →

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch - Leaving Kissamos for the western coast
Crete Sailing Trips, Greece Sailing Trips, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Swim Stop & Beach Sailing Trips, Tour Reviews

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

4.Balos Gramvousa Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 257 reviews · 7.5 hours · from $229

Sail from Kissamos with an experienced skipper to Balos Lagoon and Gramvousa Island. You’ll have time to swim, snorkel, hike to the Venetian castle, and eat a fresh Cretan lunch cooked aboard. Small-group and private options are available, with beer, soft drinks, fruit, towels, and snorkeling gear included.

“Was great overall experience. Crew were amazing. Lunch was delicious. Would do it again!!!”

Check dates →Read our review →

Nydri: Sailing Through History. Daily Cruise with Beach BBQ - Boarding Odysseia in Nydri at 8:30 AM
Greece Sailing Trips, Historical Tours, Sailing Trips with Lunch & BBQ, Swim Stop & Beach Sailing Trips, Tour Reviews

Nydri: Sailing Through History. Daily Cruise with Beach BBQ

5.Nydri: Sailing Through History. Daily Cruise with Beach BBQ

★★★★★★★★★★4.9 · 253 reviews · 8 hours · from $88Cheapest deck

Join the local family crew aboard Odysseia for an eight-hour cruise from Nydri. Hear stories of Odysseus and ancient Greek sailing, visit Spartochori and its 300-year-old church, swim in Papanikolis Cave, snorkel in clear bays, and eat a beach BBQ with wine and soft drinks.

“Amazing crew and one of the most beautiful boats I’ve seen. Oldies but goldies experience. Love, love, love”

Check dates →Read our review →

Kissamos: Balos & Gramvousa Luxury Catamaran Cruise - Starting at Kissamos Port
Catamaran Cruises, Chania Sailing Trips, Greece Sailing Trips, Swim Stop & Beach Sailing Trips, Tour Reviews

Kissamos: Balos & Gramvousa Luxury Catamaran Cruise

6.Balos & Gramvousa Luxury Catamaran Cruise

★★★★★★★★★★4.6 · 240 reviews · 7 hours · from $190

Sail from Kissamos to Gramvousa and Balos on a modern catamaran with a small-group feel. You get time to swim, visit Gramvousa Fortress, use SUP and snorkeling gear, and enjoy shrimp linguine, Greek salad, Cretan appetizers, and unlimited drinks. Crew members including Tina, Yannis, Stellios, and Michael help make the day easy and friendly.

“We had such a wonderful time on this sailing trip! The atmosphere on board was great, with a fun group of people. Yannis and Olga were very friendly and welcoming, and it was lovely to talk with them throughout the day. The food was delicious, and they regularly offered drinks, making sure everyone felt comfortable. The stops at Gramvousa and Balos were absolutely beautiful. Thanks to Yannis’ advice on timing, we were able to enjoy the places before the big tourist boats arrived, which made the experience even more special. Overall, an unforgettable day and a truly fantastic experience. We highly recommended!”

Check dates →Read our review →

Naxos: Catamaran Cruise with Swim Stops, Food, and Drinks - Boarding the Danae, Rena, Anassa, or Steve π
Catamaran Cruises, Food, Food & Drink, Greece Sailing Trips, Naxos Sailing Trips, Sailing Trips with an Open Bar, Swim Stop & Beach Sailing Trips, Tour Reviews

Naxos: Catamaran Cruise with Swim Stops, Food, and Drinks

7.Catamaran Cruise with Swim Stops, Food, and Drinks

★★★★★★★★★★4.8 · 235 reviews · 150 - 390 minutes · from $194

Spend 150 to 390 minutes aboard a Naxos Yachting catamaran, with the captain choosing sheltered coves according to the weather. Swim, snorkel, sunbathe, and enjoy onboard coffee, fruit, local wine, beer, raki, and a traditional lunch. Boats include Danae, Rena, Anassa, and Steve π, with English and Greek-speaking crews.

“Truly an amazing day! Anna and Panos were overall fantastic - helpful, friendly, fun, and professional. The boat, food, and everything else was top-notch. Highly recommend!”

Check dates →Read our review →

Athens Riviera Catamaran tour with fresh Meal Drinks and Swimming - The ride to Prasoniso Island
Athens Sailing Trips, Catamaran Cruises, Catamaran Cruises in Athens, Greece Sailing Trips, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Athens, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Athens, Swim Stop & Beach Sailing Trips, Tour Reviews, Tours

Athens Riviera Catamaran tour with fresh Meal Drinks and Swimming

8.Athens Riviera Catamaran tour with fresh Meal Drinks and Swimming

★★★★★★★★★★5.0 · 210 reviews · 5 hours (approx.) · from $157Highest rated

Spend about five hours aboard a catamaran from Alimos Marina, with stops at Vouliagmeni Bay and Prasoniso Island. Swim, snorkel, and enjoy a Greek meal prepared on board, with Captain Roberto and the crew guiding the trip in several languages. Choose a morning cruise or a sunset sailing.

“This was one of our favorite days on our trip to Athens. It was so relaxing and scenic. Ada and the rest of the crew showed us a great time. We especially enjoyed the swim/snorkeling at the second spot. The homemade lunch was absolutely delicious!”

Check dates →Read our review →

Kos: Small Group Full-Day Sailing with Meal, Drinks, & Swim - The first bay, clear water and easy swimming
Full-Day, Greece Sailing Trips, Kos Sailing Trips, Sailing Trips with an Open Bar, Sailing Trips with Lunch & BBQ, Semi-Private Sailing Cruises, Swim Stop & Beach Sailing Trips, Tour Reviews

Kos: Small Group Full-Day Sailing with Meal, Drinks, & Swim

9.Small Group Full-Day Sailing with Meal, Drinks, & Swim

★★★★★★★★★★4.8 · 162 reviews · 7 hours · from $170

Sail from Kos Harbor on a comfortable 20-meter Greek sailing boat with an English-speaking crew, including Nikki and the captain. You’ll stop at two quiet swim and snorkel spots, visit Pserimos, and eat a fresh Greek-style lunch on board. Recent departures have often carried only 10 to 12 people, though the boat may vary by date.

“We had the most amazing time on the boat, we were so well looked after, the food was amazing, the views incredible, the sea was crystal clear and everything about the trip was five star”

Check dates →Read our review →

Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner - Sailing past five famous Mykonos beaches
Dining Experiences, Dinner Experiences, Evening Experiences, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Mykonos, Mykonos Sailing Trips, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Mykonos, Sunset Sailing Cruises, Swim Stop & Beach Sailing Trips, Tour Reviews

Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner

10.Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner

★★★★★★★★★★4.8 · 122 reviews · 5 hours · from $111

Spend five hours on a sailing yacht off Mykonos, passing Ornos, Psarou, Platis Gialos, Paraga, and Paradise beaches before swimming and snorkeling from the boat at quiet Rhenia. Your crew serves a Greek buffet, wine, beer, soft drinks, and a farewell shot. Captain Stelios and crew member Anastasis have earned warm praise, though the boat size varies.

“Such lovely staff, everyone was very well looked after, beautiful sunset and views !!”

Check dates →Read our review →

Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos - Greek Snacks and Drinks on the Way
Catamaran Cruises, Catamaran Cruises in Crete, Crete Sailing Trips, Greece Sailing Trips, Swim Stop & Beach Sailing Trips, Tour Reviews

Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

11.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

★★★★★★★★★★5.0 · 116 reviews · 7 hours 30 minutes (approx.) · from $235

Set sail from Kissamos with an English-speaking crew such as Dimitri, Yannis, and Jessica, and reach Balos before the big ferries. Swim, snorkel, paddleboard, and enjoy Greek snacks, a Mediterranean lunch, beer, wine, and soft drinks aboard a catamaran limited to 22 people.

“This is the best Boat Tour we have ever been on. From the start of the trip to the end, you are treated by Dimitri and Jessica like you are so special. The homecooked Greek meal created by Jessica was stupendous. Meanwhile, Dimitri made personal contact with every member of the passengers on board. The scenery was wonderful too,especially snorkeling in the aqua waters.”

Check dates →Read our review →

Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks - Rhenia: two hours of swimming from the yacht
Dining Experiences, Dinner Experiences, Evening Experiences, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Mykonos, Mykonos Sailing Trips, Safari, 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, Sunset Sailing Cruises, Swim Stop & Beach Sailing Trips, Tour Reviews

Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

12.Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

★★★★★★★★★★4.5 · 116 reviews · 5 hours (approx.) · from $114

Set sail from Agios Ioannis along Mykonos’ famous south coast, then spend about two hours swimming and snorkeling from the yacht near uninhabited Rhenia. The crew serves a Greek buffet with wine, beer, soft drinks, and coffee or tea before the return sail at sunset. Pickup costs extra.

“Unbelievable trip, fantastic crew, great sites, everything was top notch. So much fun and great Greek meal included as well. Highly recommend!”

Check dates →Read our review →

Paros: Catamaran Cruise with Swimming, Meal and Drinks - Faneromeni Beach and the southern side of Antiparos
Catamaran Cruises, Greece Sailing Trips, Paros Sailing Trips, Sailing Trips with an Open Bar, Sailing Trips with Lunch & BBQ, Swim Stop & Beach Sailing Trips, Tour Reviews

Paros: Catamaran Cruise with Swimming, Meal and Drinks

13.Catamaran Cruise with Swimming, Meal and Drinks

★★★★★★★★★★5.0 · 108 reviews · 9 hours · from $318

Spend a full day aboard a spacious catamaran with a crew such as Angeli, Yoti, and Jo. From Paros, you’ll reach Antiparos, Despotiko, and Panteronisi, stopping for swimming, snorkeling, paddleboarding, snacks, and a freshly cooked Greek lunch. Hotel pickup, towels, equipment, and unlimited drinks are included.

“The days was so good!! Angeli the captain ! Yoti and Jo were so accommodating and professional!! Loved the whole day.”

Check dates →Read our review →

Kos: Small Group Full-Day Sailing with Meal, Drinks, & Swim - The first bay, clear water and easy swimming
Full-Day, Greece Sailing Trips, Kos Sailing Trips, Sailing Trips with an Open Bar, Sailing Trips with Lunch & BBQ, Semi-Private Sailing Cruises, Swim Stop & Beach Sailing Trips, Tour Reviews

Kos: Small Group Full-Day Sailing with Meal, Drinks, & Swim

14.Small Group Full-Day Sailing with Meal, Drinks, & Swim

★★★★★★★★★★5.0 · 82 reviews · 7 hours (approx.) · from $174

Join Arthur and Niki aboard a small sailing boat from Kos for a seven-hour cruise toward Pserimos. You’ll swim and snorkel at quiet boat-access-only spots, enjoy a freshly prepared Greek lunch, and have coffee, iced tea, and snacks included. The group is limited to 14 people, with teenagers aged 12 and older welcome.

“This was the most amazing day we have had during our holiday so far. Both Arthur and his wife Niki were amazing host from the moment we boarded till we left. Made us feel like family. Food was amazing too. 100% recommended without a doubt. The locations we went too were amazing to swim at and there was enough wind to sail back for most of the ride. So much room to lay down.”

Check dates →Read our review →

Semi-Private :Full-Day Sailing Tour Swim, Snacks & Drinks - Why the flexible route matters
Full-Day, Greece Sailing Trips, Naxos Sailing Trips, Private Sailing Charters, Sailing Trips with an Open Bar, Sailing Trips with Lunch & BBQ, Semi-Private Sailing Cruises, Swim Stop & Beach Sailing Trips, Tour Reviews, Tours

Semi-Private :Full-Day Sailing Tour Swim, Snacks & Drinks

15.Semi-Private :Full-Day Sailing Tour Swim, Snacks & Drinks

★★★★★★★★★★4.3 · 72 reviews · 9 hours · from $188

Join skipper George aboard the small yacht Annabella for a nine-hour sailing day from Naxos. Depending on wind and passenger wishes, you may visit Rina Cave, Kalados Bay, Schinoussa, Irakleia, Paros, the Blue Lagoon, or Holed Cave. Swim, snorkel, learn basic sailing, enjoy homemade snacks, and return to Naxos around 18:00.

“A great sailing experience. If you're looking to sail with an experienced, local sailor, this is for you!”

Check dates →Read our review →

Just added in Swim Stop & Beach Sailing Trips

★ 4.9Private Day Catamaran Cruise with Swimming and MealFrom $2,121 per boat12 reviews
★ 5.0Antiparos: Private Sailing Cruise with Swim Stops and LunchFrom $1,885 per boat3 reviews
★ 5.0Adamantas: Kleftiko Sailing Cruise with Meal and Swim StopsFrom $21211 reviews
★ 4.9Catamaran Day Cruise – Swim, Snorkel, Food & Drinks!From $21218 reviews
★ 5.0Private Sailing Cruise, Balos and Gramvousa with meal and drinks.From $947 per boat38 reviews
★ 5.0Catamaran Balos Sunset Cruise with Sushi & DrinksFrom $14741 reviews
★ 4.8Balos and Gramvousa Private Sailing Trip with MealFrom $931 per boat41 reviews
★ 5.0Santorini Catamaran Cruise with Swimming, Meal and Open BarFrom $12941 reviews

Other kinds of day

Island Hopping Sailing Trips73Sea Cave & Cove Sailing Trips27Sailing & Snorkeling Trips16Caldera & Volcano Sailing Trips21
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