Naxos and Lesser Cyclades Romantic Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by William Keller
  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Flight and Romantic hotel deals in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.
MILEO Mykonos

MILEO Mykonos

CA $1,871
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Mykonos (JMK)
10/10 Exceptional! (55 reviews)
Mileo Mykonos is a GEM. We were looking for somewhere we could complete unwind and Mileo offered exactly this. The hotel is located a 5 minute walk to the beach and the beautiful Aegean Sea and the views from our room and from the bar area were gorgeous. The room was modern but warm, luxurious with a comfortable bed, large shower and the option of both air con and fan cooling. We had a room with sea view and private pool and this did not disappoint. The rooms were cleaned daily, often whilst we ate breakfast which was great as we came back to a spotless room. The gym is small but well appointed and the spa/sauna area is great for a bit of relaxation out of the sun. The breakfast has plenty of choice with little changes each day and we found the lunch menu food really hit the spot (chicken club is the one!!). Staff couldn’t do enough for you too - incredibly helpful. Being able to use Whatsapp to ask questions was very convenient and nothing was ever too much to ask. Only downside is that the hotel, whilst close to the beach and some other hotel restaurants, is on the more isolated part of the island - without a car it gets very pricey to get around/get to Mykonos via taxis so if you are looking to explore maybe it’s not ideal, but we were looking for a retreat and this is exactly what we got. Would 100% stay here again!

Reviewed on Aug 10, 2026

Tropicana Suites & Villas

Tropicana Suites & Villas

CA $2,136
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Mykonos (JMK)
9.8/10 Exceptional! (754 reviews)
Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

CA $5,500
per person
Sep 15 - Sep 21
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.8/10 Exceptional! (143 reviews)
The room service meals were so good!! No need to even go out to a restaurant when you can be in the privacy, comfort of your own room with a balcony and the best views ever, I had the blue domes views, could see the ocean, all the beautiful white buildings, no need to deal with packed, busy restaurants crowded with people. Both are cool options! But I loved just eating in and being comfy with peaceful quietness. The hotel staff were so accommodating!! Even helped me find a photoshoot with the super long satin dress & the blue domes as my background. The immediate hotel transportation that I accidentally last minute requested, they were right on it! Helped carry our huge suitcases up tons of stairs. Constantly kept our room stocked & clean! Love this hotel soo much, I’d recommend to everyone seriously! The room & everything they supplied in the room was great. Thank you so much for making my Santorini trip the best ever.

Reviewed on Aug 1, 2026

Art Maisons Oia Castle

Art Maisons Oia Castle

CA $4,115
per person
Oct 16 - Oct 22
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.6/10 Exceptional! (123 reviews)
Everything was amazing!

Reviewed on Jul 27, 2026

Million Stars Mykonos

Million Stars Mykonos

CA $2,186
per person
Sep 17 - Sep 22
just found
Roundtrip flight included
Toronto (YYZ) to Mykonos (JMK)
10/10 Exceptional! (3 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Naxos and Lesser Cyclades
View all trips

5* Romantic holidays in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.
Tropicana Suites & Villas

Tropicana Suites & Villas

CA $2,136
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Mykonos (JMK)
9.8/10 Exceptional! (754 reviews)
Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

CA $5,500
per person
Sep 15 - Sep 21
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.8/10 Exceptional! (143 reviews)
The room service meals were so good!! No need to even go out to a restaurant when you can be in the privacy, comfort of your own room with a balcony and the best views ever, I had the blue domes views, could see the ocean, all the beautiful white buildings, no need to deal with packed, busy restaurants crowded with people. Both are cool options! But I loved just eating in and being comfy with peaceful quietness. The hotel staff were so accommodating!! Even helped me find a photoshoot with the super long satin dress & the blue domes as my background. The immediate hotel transportation that I accidentally last minute requested, they were right on it! Helped carry our huge suitcases up tons of stairs. Constantly kept our room stocked & clean! Love this hotel soo much, I’d recommend to everyone seriously! The room & everything they supplied in the room was great. Thank you so much for making my Santorini trip the best ever.

Reviewed on Aug 1, 2026

Art Maisons Oia Castle

Art Maisons Oia Castle

CA $4,115
per person
Oct 16 - Oct 22
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.6/10 Exceptional! (123 reviews)
Everything was amazing!

Reviewed on Jul 27, 2026

Don't see what you're looking for?
See all available trips from Columbus to Naxos and Lesser Cyclades
View all trips

3 Night Romantic holidays in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.
Grand Ambassador Santorini Hotel

Grand Ambassador Santorini Hotel

CA $2,010
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Thira (JTR)
9.4/10 Exceptional! (256 reviews)
Hotel isn’t very modern. For guests who stay out of the country, you have to bring your own outlet to charge your things or do your hair (women). Also, the upstairs part of the room (where the bed is) is SUPER HOT! A/c isn’t strong enough. We stayed there 5 days and on night 3, the hot water to shower wasn’t working and everyday we showered, the drain didn’t drain quick enough so I was standing in my own dirty shower water. Had to rinse my feet at the end. Also, free breakfast was mid. The 2 times we had breakfast there, the waiter would forget something that I had ordered and had to remind him again.

Reviewed on Aug 6, 2026

Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

CA $2,481
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Thira (JTR)
9.8/10 Exceptional! (143 reviews)
The room service meals were so good!! No need to even go out to a restaurant when you can be in the privacy, comfort of your own room with a balcony and the best views ever, I had the blue domes views, could see the ocean, all the beautiful white buildings, no need to deal with packed, busy restaurants crowded with people. Both are cool options! But I loved just eating in and being comfy with peaceful quietness. The hotel staff were so accommodating!! Even helped me find a photoshoot with the super long satin dress & the blue domes as my background. The immediate hotel transportation that I accidentally last minute requested, they were right on it! Helped carry our huge suitcases up tons of stairs. Constantly kept our room stocked & clean! Love this hotel soo much, I’d recommend to everyone seriously! The room & everything they supplied in the room was great. Thank you so much for making my Santorini trip the best ever.

Reviewed on Aug 1, 2026

Volcano View Hotel Santorini

Volcano View Hotel Santorini

CA $2,177
per person
Nov 3 - Nov 5
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Thira (JTR)
9.4/10 Exceptional! (1,002 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Naxos and Lesser Cyclades
View all trips

4 Night Romantic holidays in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.
Aria Suites

Aria Suites

CA $2,642
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Thira (JTR)
10/10 Exceptional! (317 reviews)
Loved our stay at Aria Suites. Very friendly and helpful staff. Amazing view and villa. Stacy and her team is fantastic. Highly recommend!

Reviewed on Aug 13, 2026

Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

CA $3,458
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Thira (JTR)
9.8/10 Exceptional! (143 reviews)
The room service meals were so good!! No need to even go out to a restaurant when you can be in the privacy, comfort of your own room with a balcony and the best views ever, I had the blue domes views, could see the ocean, all the beautiful white buildings, no need to deal with packed, busy restaurants crowded with people. Both are cool options! But I loved just eating in and being comfy with peaceful quietness. The hotel staff were so accommodating!! Even helped me find a photoshoot with the super long satin dress & the blue domes as my background. The immediate hotel transportation that I accidentally last minute requested, they were right on it! Helped carry our huge suitcases up tons of stairs. Constantly kept our room stocked & clean! Love this hotel soo much, I’d recommend to everyone seriously! The room & everything they supplied in the room was great. Thank you so much for making my Santorini trip the best ever.

Reviewed on Aug 1, 2026

Grand Ambassador Santorini Hotel

Grand Ambassador Santorini Hotel

CA $2,735
per person
Oct 6 - Oct 9
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.4/10 Exceptional! (256 reviews)
Hotel isn’t very modern. For guests who stay out of the country, you have to bring your own outlet to charge your things or do your hair (women). Also, the upstairs part of the room (where the bed is) is SUPER HOT! A/c isn’t strong enough. We stayed there 5 days and on night 3, the hot water to shower wasn’t working and everyday we showered, the drain didn’t drain quick enough so I was standing in my own dirty shower water. Had to rinse my feet at the end. Also, free breakfast was mid. The 2 times we had breakfast there, the waiter would forget something that I had ordered and had to remind him again.

Reviewed on Aug 6, 2026

Don't see what you're looking for?
See all available trips from Columbus to Naxos and Lesser Cyclades
View all trips

Plan unforgettable romantic Naxos and Lesser Cyclades vacations

What are some of the benefits of booking a romantic Naxos and Lesser Cyclades vacation?

When booking a romantic Naxos and Lesser Cyclades vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in South Aegean.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Naxos and Lesser Cyclades destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in Naxos and Lesser Cyclades?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,871 and can enjoy savings of up to 37 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in Naxos and Lesser Cyclades?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Naxos and Lesser Cyclades certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Naxos and Lesser Cyclades.

Can I book a romantic Naxos and Lesser Cyclades vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Naxos and Lesser Cyclades search.

Can I book a romantic trip to Naxos and Lesser Cyclades that is fully refundable?

Several romantic Naxos and Lesser Cyclades vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.