MedSailors guests pose for a photo in front of Dubrovnik Old Town

Gallery

Island Hopping Sailing Tours for 20-39 Year Olds

The ultimate island-hopping sneak peek

From jumping off the deck into turquoise bays to exploring stunning islands and sharing laughs over dinner with your crew, get a taste of what it’s like to live the yacht life. Scroll through, get inspired, and start picturing yourself in the middle of all this magic. Your island-hopping adventure is calling!

MedSailors guests pose for a photo together

Two friends on a hill above Dubrovnik Old Town

Group of people jump off a catamaran into the water in Croatia

Three people cycling in Mljet National Park

Group of people at Massimo's cocktail bar in Croatia

MedSailors yachts rafted together in Korcula

MedSailors yachts rafted together in a bay in Croatia

Two people sit looking at the view over Hvar Town

Group dancing at Hula Hula bar at sunset

Friends having a drink together in Croatia

Group of friends pose for a photo on a yacht

Group of cyclists at Mljet National Park

MedSailors yachts anchored in a bay in Croatia

Man learning to sail on a MedSailors yacht

4.9/ 5

based on 682 reviews

Had the absolute best week of my life with MedSailors! I chose the Ionian route because of the beautiful pictures I saw online. Greece had been at the top of my bucket list my whole life, so the bar was set pretty high on what I was expecting! Not only were my expectations met, but they were exceeded! Medsailors takes the time to pair you with alike people on your boat, so I was extremely lucky to be put on an all girls boat where the other girls and I got very close very fast! 2 weeks later and we’re still all talking and plan on taking future trips together with MedSailors, so if you’re solo traveling, no need to worry about meeting people!
Our skipper Philly was amazing. Not only was she extremely knowledgeable about the route, amazing at sailing, and an incredible chef, but she was also extremely friendly and welcoming and was a huge contributor on why my experience was as good as it was! Instead of feeling like I was on a structured tour of the islands, I just felt like I was sailing with my closes friends the whole week, even though we had all just met! Philly is one of the main reasons I will be recommending MedSailors to everyone I know!
Our GEL Sara was also amazing! She always took it upon herself to make sure we knew what was in store for us that day, and she was always there to answer any questions we had! She even came to chat and have breakfast on our boat one morning! Sara is another main reason I will be recommending MedSailors to everyone I know!
If you’re thinking about booking a trip with this amazing company, definitely do it! You will have one of the best weeks of your life!

Mikayla Gifford

SEPT 2024

Our week with Med Sailors was nothing short of AMAZING! The whole week is planned out so well by the company (time for swimming/snorkeling, stand up paddle boarding, personal island and national park explore time, socialisation time with other med sailor boats in the convoy, and down time on the boat when sailing between locations). The trip is executed and resourced so incredibly well and the staff were all so fun and easy going (all the skippers and the head wellbeing/social coordinator of our trip, Marion, made the trip the best experience). My 2 friends and I were on the monohull sail boat and were really happy with the 5 other girls that the company had coordinated/selected to be on this boat with us, I have made some friends for life. A special call out to our skipper, Maggie, who went above and beyond to cook a delicious breakfast and lunch for us each day, got us safely from A to B each day, taught us LOTS about sailing and allowed us to get as involved as we each would like to be in learning how to sail, and just hung out and became an awesome friend with the girls and I!!

Chloe Penn

AUG 2024

Adolf was amazing! His skipper ability cannot be explained in words. He was great with letting us know about stops, picking off itinerary swim spots that were gorgeous, fitting in with the vibe of the boat. Always accommodating, never leaving anyone left out. He was a lot of fun! Made it so that I'm worried I'll never have a sailing trip this good ever again. Phily was also on our boat for a bit and was such a treat!

Kennedyeb 16

JULY 2024

Well what an incredible week!! Hugh and Marion you are just such wonderful people!! You really made the holiday special. Thank you so much!!
We could not have been teamed up with a nicer group of girls. We definitely became boat friends. I Would definitely recommend booking MedSailors for an unforgettable holiday.
So many good memories!!