Review: Santorini Caldera Morning Cruise With Sunset Oia
Review: Santorini Caldera Morning Cruise With Sunset Oia
Figuring out where to stay in Santorini was the hardest part of planning our trip here.
Luckily, figuring out what to actually do once you’re there is much easier. Santorini is a place best experienced slowly. Take in the landscape, eat well, and give yourself time to just relax and enjoy just being.
For the adventurous, you can go scuba diving or horseback riding on a black pebble beach. But the one experience you should make time for is getting out on a sailing boat in the volcanic caldera and see Santorini from the waters.
You get the cliffs, the volcanic formations, and the sandy beaches, all while sunbathing and enjoying the breeze with a glass of wine and fresh fish grilling off the back of the boat. We decided to do a 5-hour morning sailing with Sunset Oia, one of the most established sailing companies on the island. Their fleet is massive, but they also offer luxury small group sailings. We picked the Diamond Morning Cruise, on their flagship catamaran that takes only up to 20 guests. We had 16.
Morning Cruise or Sunset Cruise Better In Santorini?
We did both. You can read about our sunset cruise sailing to Thirassia Island here.
Sailing at sunset and watching the fiery sky change colors while floating in the Caldera is pretty amazing. But we also opted for a morning cruise on one of the days, and here’s why it made sense.
- We visited during shoulder season. The late morning and early afternoon are still warm and perfect for swimming, while the wind starts to pick up in the afternoon.
- With a morning cruise from 9:30 AM to 2:30 PM, we still had a full afternoon and evening to explore and relax.
- We were staying in Oia and had a great sunset view from our private plunge pool. We didn’t want to waste this.
If golden hour on the sea is important to you, the sunset cruise may be the better fit. But if you’re looking for ideal swim and tanning weather, fewer crowds, and the chance to enjoy your hotel views in the evening, consider sailing in the morning.
The Route
Most cruises follow a similar route around the caldera and southern coast. Each stop sort of blends into the next. This isn’t about ticking off a list of attractions. Swim, tan, lounge, eat, and just enjoy the coastline.
Note that none of these cruises can stop off at the beaches. They anchor off shore where you can swim.
Stop 1: Hot Springs near Nea Kameni
The name might suggest a steamy soak, but it’s more a cove where the water gets slightly warmer than the surrounding sea due to the underwater volcanic activity. Rich in sulfur, iron, and manganese, the water here is supposed to have therapeutic properties. There’s a pretty little white church that stands out against the volcanic black rocks.
Tip: Take off your jewelry and opt for dark swimwear since the sulfur in the water can tarnish precious metals.
Stop 2: Red Beach
Anchor off the cliffs of Red Beach, named for its iron-rich sandstone. We stopped nearby for swimming and snorkeling. While you see people on the beaches, it’s not generally recommend to sunbathe at Red Beach due to the falling rocks from the cliffs. Nicer to see the formation from a distance.
Tip: Snorkeling masks are provided, but I would recommend bring your own mask. Currently, I use the Hollis M1, but if you’re on a budget, the Cressi F1 was a solid mask I had for years. But the biggest surprise is the cheap Aqua A diving mask, which has a generous view and rarely ever fogs up.
Stop 3: White Beach
This was our longest stop and where we had lunch. We swam to shore and then floated back to the boat to the smell of smoky grilled fish in the air.
Sailing The Caldera
Some of the best views come from simply watching the layers of volcanic rock rise above you. You pass landmarks like the Akrotiri Lighthouse, Indian Rock, and Aspronisi along the way.
Our Thoughts On The Sunset Oia Diamond Cruise
Boarding and First Impressions
We were picked up right at a nearby access point in Oia and taken down to Amoudi Bay. Pick-up was smooth and on time. The port was busy with people, highlighting the popularity of the activity. Dozens of vans, passengers, and boats were moving in and out, but the crew was efficient and organized.
We spotted the big boats with upwards of 50 people being boarded. Seeing our luxury yacht anchored in the waters validated our decision to take the premium Diamond option.
A small motorboat served as a tender between the dock and our boat. We dropped our shoes into a storage box and boarded the clean and modern Ipanema 58 catamaran.
With a small group and plenty of space, there was no stress or rush to claim a spot.
We boarded quickly, sat for a quick safety briefing and then spread out comfortably with a cold drink almost immediately.
Onboard Atmosphere and Layout
The vibe was relaxed and friendly. Funny enough, everyone onboard (except us) just happened to be married with kids, and most were on vacation without them. We chatted with a couple also living in Portugal. It was easygoing and social, and we had plenty of time to ourselves to just tan and read.
We started on the upper deck where there were padded mats and some shade coverage. It was breezy and perfect for lounging. Later we moved to the front on some of the other padded sunbeds to tan. People moved around naturally, and there was no scramble for space. The inside cabin was spotless and modern, with clean bathrooms downstairs.
Lunch and Drinks
Lunch was grilled on the back of the boat while we were swimming.
The menu included: Grilled fresh fish, chicken and pork chops, shrimp saganaki, Greek salad with feta, dolmas (stuffed vine leaves), pasta, and Tzatziki with pita bread. For dessert, we had Greek yogurt with berry compote.
Drinks included soft drinks, beer, local white wine, soft drinks and water. Everything was prepared fresh on board. We filled our plates and ate while taking in the sun.
Different Boat Options and Pricing Breakdown
Sunset Oia has a range of private and shared cruises at different comfort levels and prices depending on the season. Here’s how the shared options compare.
During Peak Season, if you are looking the lowest price, then consider the budget-friendly, but crowded Red option. If you want the most luxurious catamaran experience from the boat to the food as well as starting and returning to the same port, go with the Diamond option. Otherwise, the Platinum or the Santorini Gems Cruise will be fine depending on if you have a preference for the type of boat.
During other times, the price differences are not as big, so opt for the best option within your budget.
Diamond Cruise
The top of the line option on one of their flagship Lagoon 560 or Ipanema 58 luxury catamaran. Takes up to 20 people. Towels, blankets, and snorkels are included. Beer, local wine, and a cocktail is included as well.
Peak Season (May 16 – Sept 30): €230
High Season (Apr 15 – May 15 & Oct 1 – Oct 25): €165
Low Season (Mar 15 – Apr 14 & Oct 26 – Nov 20): €130
Note: Start and return from the same port. Most luxurious and newest boats with the most space. If budget is not an issue, this is what I recommend.
Book Diamond Sailing here with free cancellation up to 24 hours before sailing.
Platinum Cruise
An alternative option that sails one way from Amoudi Port and ends at Vlychada Port on the morning cruise and the other way around on the sunset cruise. Transportation is provided, but the drive back takes about an hour between the two ports. Takes up to 14 people on a Lagoon 450 catamaran. Towels, blankets, and snorkels are included. Beer and local white wine included as well.
Peak Season (May 16 – Sept 30): €195
High Season (Apr 15 – May 15 & Oct 1 – Oct 25): €130
Note: Start and ends at a different port. Smaller catamaran than the Diamond Cruise’s Lagoon 560 or Ipanema 58. If you want an intimate experience and don’t mind ending in a different port with a longer minibus transfer back, this is slightly less expensive.
Book Platinum Sailing here and get free cancellation up to 24 hours before sailing.
Santorini Gems Cruise
I’d consider this the most standard option. It takes 20 people, but on a smaller boat. It also starts from Amoudi Port and ends at Vlchada Port for the morning option and the other way around to see the sunset near Oia for the afternoon option. Towels, blankets, and snorkels are included. Beer and local white wine included as well.
Morning Cruise
Peak Season (May 16 – Sept 30): €130
High Season (Mar 15 – May 15 & October 1 – Nov 20): €110
Sunset Cruise
Peak Season (May 16 – Sept 30): €159
High Season (Mar 15 – May 15 & October 1 – Nov 20): €110
Book Santorini Gems here and get free cancellation up to 24 hours before sailing.
Red Cruise
The most budget friendly option, but with at larger crowd up to 55 people on either the 74-foot Ocean Voyager or the 80-foot Tahiti catamaran. For larger groups and families. Starts at Amoudi Port and ends in Athinios Port or vice versa. Towels and beer are not included with this option.
Morning Cruise
Peak Season (May 16 – Sept 30): €89
High Season (Apr 15 – May 15 & Oct 1 – Oct 25): €79
Sunset Cruise
Peak Season (May 16 – Sept 30): €159
High Season (Apr 15 – May 15 & Oct 1 – Oct 25): €79
Book Red Cruise here and get free cancellation up to 24 hours before sailing.
Final Thoughts
The five hours passed quickly, but it felt like the perfect amount of time. We swam in warm clear waters, ate well, made new friends, and enjoy Santorini away from the crowds. The route itself may be similar across companies, but what you’re looking for is the vibe and experience, as well as the type of boat you’ll be sailing on.
The Diamond cruise is as close as you’ll get to a much more expensive private rental.
Updated on September 12, 2025
