The Cyclades · EVENING EXPERIENCES

15 Evening Experiences in Santorini Worth Booking Ahead

64 tours  ·  from $40 a head

A short list for a small island: 15 evening experiences worth the money, each with its price, the traveller verdict and the detail to check before you pay.

Santorini Wine Adventure with 12 Wine Tastings, Tapas and Sunset - Three wineries, with the lineup decided for you
Evening Experiences, Oia Sunset Tours, Santorini Tours, Santorini Wine Tours, Tour Reviews

Santorini Wine Adventure with 12 Wine Tastings, Tapas and Sunset

1.Santorini Wine Adventure with 12 Wine Tastings, Tapas and Sunset

★★★★★★★★★★5.0 · 1,715 reviews · 4 hours (approx.) · from $181Our pick

Tour three Santorini wineries with a local guide, taste 12 wines including Assyrtiko and Vinsanto, and sample local cheese and other snacks. The wineries vary, but Santo Wines is included. Choose the sunset option for a final tasting overlooking the caldera. Guides may include Elena, Angelo, Kristina, or others.

“Three wineries and twelve wine tastings, accompanied by plenty of snacks, as promised. Kristina provided some valuable insights into the unique wine production processes and challenges of Santorini. Clearly knowledgeable in wine production, but with added humour and fun. Also takes a great photo of the tour guests at teh various venues. Comfortable transport.”

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Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Red Beach and the southern coast
Evening Experiences, Oia Sunset Tours, Santorini Caldera Cruises, Santorini Tours, Tour Reviews

Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

2.Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

★★★★★★★★★★5.0 · 1,694 reviews · 5 hours (approx.) · from $181

Spend about five hours on a shared catamaran cruise along Santorini’s coast, with hotel pickup, two swimming stops, snorkel masks, towels, a Greek meal and drinks. Choose a morning or sunset departure. Luxury options add a longer route past Oia and Ammoudi Bay; the boat views those places from the water, not on foot.

“The onboard lunch has more options than advertised. Once you board, they ask if anyone has allergies and they accommodate your needs. The cheese for the salad is on the side, they made a gluten free pasta for a passenger with an allergy, and they gave you the option between pork or chicken.”

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Santorini Wine Stories: Sunset Tour with Tasting & Dinner - Wine tasting that works for beginners, too
Dining Experiences, Dinner Experiences, Evening Experiences, Oia Sunset Tours, Santorini Tours, Santorini Wine Tours, Tour Reviews, Tours

Santorini Wine Stories: Sunset Tour with Tasting & Dinner

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

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

Visit three traditional Santorini wineries with a sommelier-guide, taste 10 local wines including Assyrtiko and Vinsanto, and enjoy dinner with wine pairings. Round-trip pickup is included. The tour starts at 4:00 pm, lasts about five hours, and has space for up to eight people. Guides have included Nicholas, Constantine, and Rafael.

“Sunset Tours organised an excellent tour. Constantino our guide & sommelier was kind, helpful, articulate and very knowledgeable of the region, the wines and happy to answer any questions. Our tour was vibrant and happy through his expertise. Well done Constantino - you made our day so enjoyable.”

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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - Red Beach: a striking first swim
BBQ, Evening Experiences, Oia Sunset Tours, Santorini Caldera Cruises, Santorini Tours, Tour Reviews, VIP

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

4.Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

★★★★★★★★★★5.0 · 1,170 reviews · 5 hours (approx.) · from $133

Spend about five hours sailing Santorini aboard a catamaran for up to 20 people. Swim and snorkel near Red and White beaches, visit the volcanic hot springs, and enjoy a freshly prepared Greek barbecue with drinks. Choose the afternoon sailing to watch sunset from the water. Hotel transfers, towels, and snorkeling gear are included.

“The entire crew was incredible. This is an amazing way to see Santorini from a different perspective. Nichole was amazing, and prepared an outstanding meal for all of us on board”

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Santorini Day Tour with Sunset in Oia - Pyrgos views and the winery visit
Evening Experiences, Oia Sunset Tours, Oia Tours, Santorini Tours, Tour Reviews, Tours

Santorini Day Tour with Sunset in Oia

5.Santorini Day Tour with Sunset in Oia

★★★★★★★★★★4.5 · 1,130 reviews · 10 hours (approx.) · from $71

Spend about 10 hours crossing Santorini by air-conditioned bus, from the prehistoric ruins of Akrotiri to Emporio’s medieval lanes, Perissa’s black-sand shore and a local winery. The day ends with free time in Oia for sunset. A guide leads the main stops, but you’ll need to budget extra for Akrotiri’s €20 entry and bring a clear plan for your pickup and return points.

“Very nice day they pick up in time the lady explain everything about the tour top 100% Very recommended 👌👌👌”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Red Beach and the old lighthouse
BBQ, Evening Experiences, Oia Sunset Tours, Santorini Caldera Cruises, Santorini Sunset Cruises, Santorini Tours, Tour Reviews

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

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

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

Spend about five hours aboard a Santorini catamaran, with hotel pickup, swims near the hot springs and Red and White beaches, and a barbecue meal with wine, water, and soft drinks. Choose the later departure for a sunset cruise. The crew handles the route and meal; bring your own towel, and expect music as well as views.

“Amazing cruise - great crew, great atmosphere, the views, the stops at the bays and the food were all perfect. The wine was probably the only thing I didn’t rate too highly but not enough to put me off. The sunset was incredible - worth every penny to go o this trip! Definitely recommend.”

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Santorini: Sunset Guided Tour with Hotel Pickup - Red Beach: dramatic geology, short visit
Evening Experiences, Fira Tours, Guided, Oia Sunset Tours, Santorini Tours, Tour Reviews, Tours

Santorini: Sunset Guided Tour with Hotel Pickup

7.Sunset Guided Tour with Hotel Pickup

★★★★★★★★★★4.8 · 900 reviews · 5 hours · from $62Best value

See Santorini’s volcanic coast, Akrotiri Lighthouse, Profitis Ilias Monastery and the Three Bells of Fira, then get free time in Oia for the sunset. Hotel pickup, a guide, driver and bottled water are included. Guides such as Nikos and Irini lead the tour, and drivers including Vasilis and Billy handle the island’s winding roads.

“Irene (guide) was informative and friendly. We got to see 80% of Santorini, the hot spots, sunset and didn’t feel rushed. Would recommend! Thank you guys!”

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Santorini: Romantic Sunset Caldera Cruise with Dinner - Aboard the King Thiras
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Santorini: Romantic Sunset Caldera Cruise with Dinner

8.Romantic Sunset Caldera Cruise with Dinner

★★★★★★★★★★4.1 · 457 reviews · 1 day · from $76

Board the King Thiras at Athinios for a sunset cruise beneath Santorini’s caldera. You’ll get volcano views, onboard English or Greek commentary, a buffet dinner, and a bus transfer from a designated pickup point. Drinks cost extra, and the bar accepts cash only. Bring a jacket for the wind.

“a lovely cruise that was relaxing and under a cannot do we got the breeze but not the sun. the crew were nice and the food was very good. really a great price and we got excellent pictures of the sunset. I would definitely recommend this cruise!”

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Santorini Sunset Wine Tour with Santo Winery Views - What you’ll taste, and what you might not
Evening Experiences, Oia Sunset Tours, Santorini Tours, Santorini Wine Tours, Tour Reviews, Tours

Santorini Sunset Wine Tour with Santo Winery Views

9.Santorini Sunset Wine Tour with Santo Winery Views

★★★★★★★★★★5.0 · 342 reviews · 4 hours (approx.) · from $205

Spend about four hours visiting three Santorini wineries in a small group, with pickup, an English-speaking wine guide, 12 tastings and a cheese-and-meat platter at Santo Wines. The first winery may be Estate Argyros, Gavalas or Hatzidakis; Gaia and Santo follow. Guides have included Angelo, Marina, Vassi and Kristina.

“Wow, what a fabulous day my Wife and I had on this wine tour. Firstly, our guide and wine expert, Marina was amazing. Her knowledge and enthusiasm for the wines really made this a 5* experience. We were taken to 3 wineries; Estate Argyros, Gaia Winery and Santo Wines Winery. Each winery was different but all were fantastic. As well as tasting 12 amazing wines there was also delicious tapas provided at each location. When you factor in the free pick up and drop off service this is a great value tour and we totally recommend it.”

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Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks - Red Beach and the volcanic coast
Evening Experiences, Oia Sunset Tours, Santorini Caldera Cruises, Santorini Sunset Cruises, Santorini Tours, Tour Reviews

Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

10.Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

★★★★★★★★★★4.5 · 328 reviews · 5 hours (approx.) · from $114

Spend about five hours on a Santorini catamaran, with stops near Red Beach, White Beach and the volcanic hot springs. Swim or snorkel when conditions allow, then eat a Greek barbecue and watch the sun set near Oia. Hotel transfers, towels and an open bar with wine, beer and soft drinks are included.

“Very nice and courteous staff, amazing views, great food. I really enjoyed the experience. Highly recommend”

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Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer - Snorkeling off Red and White Beaches
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Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer

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

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

Set sail from Santorini for about five hours aboard the catamaran identified as the Ipanema 58. Swim near the hot springs, snorkel off Red and White Beaches, and eat a Greek barbecue with drinks on board. Hotel pickup and drop-off are included, and an English-speaking crew leads the trip.

“We had a lovely time! The crew was amazing and very hard workers. We were offered drinks at all times and the food was delicious :) Thank you for everything! Guada and Julian”

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Santorini Caldera Sunset Sailing Cruise with Dinner and Wine - Swim near Palea Kameni’s hot springs
Dining Experiences, Dinner Experiences, Evening Experiences, Oia Sunset Tours, Santorini Caldera Cruises, Santorini Sunset Cruises, Santorini Tours, Santorini Wine Tours, Tour Reviews

Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

12.Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

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

Spend about six hours on a shared Santorini boat trip, with a guided hike on the volcano, a swim near Palea Kameni’s hot springs, buffet dinner and wine, and sunset near Oia. Pickup is available if selected. Guides have included Tito and Cesar, but the crew and guide may vary.

“Loved swimming at the warm springs but it did ruin my white bathing suit. Pays to read the notes! Sober was delicious. Be aware that you do pay for all drinks other than wine at dinner.”

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Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers - Red Beach and the southern shoreline
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Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers

13.Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers

★★★★★★★★★★5.0 · 208 reviews · 5 hours (approx.) · from $133

Leave Vlychada Port at about 3 pm for a five-hour Santorini cruise with stops at Red Beach, the caldera hot springs and Mesa Pigadia. You’ll sail past White Beach, Indian Rocks and the Venetian Lighthouse, with a Greek dinner, BBQ and open bar included. Hotel transfers are offered by private minibus, and the group is capped at 20.

“Une expérience fabuleuse merci à l'équipage tout était parfait.la nourriture aussi .Le transfert aussi”

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Traditional Greek Night live Music & Dinner Show in Santorini - From buffet dinner to Greek dancing
Concerts, Dining Experiences, Dinner Experiences, Evening Experiences, Santorini Tours, Show, Tour Reviews

Traditional Greek Night live Music & Dinner Show in Santorini

14.Traditional Greek Night live Music & Dinner Show in Santorini

★★★★★★★★★★4.5 · 201 reviews · 3 hours (approx.) · from $73

At Dimitris Tavern in Kamari, settle in for a self-service Greek buffet and unlimited wine, beer, soft drinks, and water. Live musicians and costumed dancers take over at 9 pm, with folk dances, plate smashing, and chances to join in. You make your own way there; the evening lasts about three hours.

“Had a blast at this dinner! It was a lot of fun, everyone participated so you could really just get lost in the crowd and enjoy yourself! The food is incredible, definitely something for everyone and the wine was flowing! Not something I'd take kids to, as they would probably get lost in the crowd, but definitely all adults should do this!”

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Santorini: Wine Tour with Sunset in Oia - Inside the underground wine museum
Evening Experiences, Oia Sunset Tours, Oia Tours, Santorini Tours, Santorini Wine Tours, Tour Reviews, Tours

Santorini: Wine Tour with Sunset in Oia

15.Wine Tour with Sunset in Oia

★★★★★★★★★★4.6 · 199 reviews · 5 hours · from $129

Visit Hatzidakis Winery and Santorini Wine Museum for about eight local wine samples, with a guide explaining the island’s winemaking traditions. Then head to Sun Spirit in Oia for a glass of wine and sunset views. Hotel pickup and drop-off are included, and guides have included Mary, Susanna, Yiannis, and Akis.

“This was an amazing tour!!! Our guide was Ahki (sp?) and our driver was Thomas. We visited two wineries and all of the wine was delicious and all of our hosts at the wineries were excellent. Thomas is an excellent driver, (Santorini would be an intimidating drive for me) and Ahki has a wealth of knowledge pertaining to the history of Santorini and Greece itself. He also seems to be a bit of a local rockstar. He knows everyone and is happy to introduce his friends. It was really great. We also got to meet both owners of the wineries we visited, and, although it was cloudy most of the…”

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Out and about on Santorini

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