4 Sunset Cruises in Santorini to Build a Day Around

1.Santorini Wine Stories: Sunset Tour with Tasting & Dinner

★★★★★★★★★★5.0 · 1,285 reviews · 5 hours (approx.) · from $209Our pick

Visit three Santorini wineries with a sommelier guide such as Nicholas, Constantine, or Rafael, tasting 10 local wines including Assyrtiko and Vinsanto. You’ll tour cellars, learn how volcanic soil shapes the island’s wines, enjoy dinner with Greek dishes, and finish with a sunset view. Pickup and drop-off are included.

“Rafael was absolutely the most delightful and knowledgeable guide and host on this thoroughly enjoyable evening. So much fun, unbelievable scenery and meeting new friends was just magical!”

Check availability →Read our full review

2.Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $95Best value

Spend about five hours aboard a catamaran with hotel pickup, swimming stops at the hot springs, Red Beach, and White Beach, plus a BBQ, wine, soft drinks, and music. Captain Sakis and crew members Giannis and Orestis have been praised for their friendly service. Choose the later departure if seeing sunset near Oia matters most.

“Overall it was ok. The food was good along with the views. Music was load and it could’ve been shorter. Those looking for a quiet ride around seeing the sites this is not for you.”

Check availability →Read our full review

3.Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer

★★★★★★★★★★5.0 · 310 reviews · 5 hours (approx.) · from $157

Spend about five hours aboard the Ipanema 58, a spacious Santorini catamaran limited to 20 people. Swim near the hot springs, snorkel by Red and White Beaches, eat a Greek barbecue, and watch the sunset. Pickup, drinks, towels, snorkeling gear, and an English-speaking crew are included.

“The crew was AMAZING!! The catamaran was a highlight of our vacation!! Gorgeous view, delicious food and an awesome crew!!!”

Check availability →Read our full review

4.Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

★★★★★★★★★★4.5 · 208 reviews · 6 hours (approx.) · from $96

Spend about six hours sailing Santorini’s caldera, hiking the volcano, swimming near Palea Kameni, eating a Greek buffet, and watching sunset near Oia. Guides such as Tito and Cesar have led the trip, while the shared boat, swim noodles, pickup option, and lively return ride make this a social outing rather than a quiet private cruise.

“We had an amazing time! Staff and crew were very nice and knowledgeable. One of the staff members got us all to join him in dancing at the end. We really enjoyed our day.”

Check availability →Read our full review