Be inspired by Molly and Will's romantic honeymoon of island hopping across Mykonos, Paros, Santorini, and Milos, followed by a quick stop in Athens!
Some of the links included may be affiliate; however, everything we feature has been independently selected and reviewed by our editorial team. When you make a purchase, we may receive revenue. Thank you for your support!
After their modern, elegant wedding in Washington, DC, Molly Bailey and Will Hutton traveled from New York City to Greece for a romantic honeymoon of island hopping across Mykonos, Paros, Santorini, and Milos, followed by a quick stop in Athens.
Having been on over 30 trips together, Molly and Will desired a honeymoon destination they could experience for the first time. Greece was just the destination. “We purposefully decided to start in Mykonos, which is known for its beautiful beaches, vibrant nightlife, restaurants, and shopping, since we knew we’d still be on a ‘high’ energy-wise from our wedding,” explains Molly. It was “the perfect way to keep the party going!” Will adds.
The newlyweds kicked off their honeymoon with three nights at Mykonos Grand Hotel & Resort, a luxury beachfront property. “We were in awe! Looking out over the beach from our private balcony was such an amazing feeling after planning a wedding for 16+ months,” Molly smiles. Since the resort is located outside of the main town of Mykonos, yet offers a complimentary shuttle service, the couple loved being able to explore and relax throughout their stay.
They started their mornings with the hotel’s delicious champagne buffet breakfast – “one of the best we’d had in all of Europe!” confirms Molly – before visiting island hot spots. Going to a lively beach club was at the top of Will’s wish list for the island, and Nammos located on Psarou Beach did not disappoint. The newlyweds also loved walking the winding streets of the main town (called Chora by locals), shopping along Matogianni Street, seeing the boats in the Old Port, as well as admiring the centuries-old Kato Mili windmills. “The restaurants and bars in Mykonos were another highlight,” she says of the vast array of eateries. “There were so many to choose from! Some of our favorites were Kastro’s, Negrita, Hippie Fish Bar, and Interni.”
Photo courtesy of Molly and Will Hutton
Dancing at Nammos Beach Club. “It was an all-day party – a perfect way to keep the wedding vibes going!”
Watching the sunset at Negrita. “In Little Venice right on the water, this small bar was an amazing place to watch the famous Mykonos sunset – with a DJ, a man playing drums, and people dancing on tables.”
Dining at Hippie Fish. “Known for seafood, Will loved picking out his whole fish with the chef and having them debone tableside.”
With plans to visit Santorini at some point along their journey, Paros offered a nice stopover by ferry between the two more famous islands. “After three nights in bustling Mykonos, we were ready for a more laid-back experience,” notes Molly, sharing that their two-night stay at Cosme, a Luxury Collection Resort, Paros provided the perfect opportunity to unwind – and use some of their Marriott points as a bonus.
Located just moments from the main whitewashed harbor town of Naoussa, the couple fell in love with the property’s architecture, décor, modern amenities, and sparkling pool overlooking the beach on the Aegean Sea. Though they took advantage of the hotel’s private beach club and the onsite Elios Spa that embraces the slow-paced Cycladic way of life, much of their stay was spent exploring the waterfront village.
They walked along the winding cobblestone streets, shopped for souvenirs at local stores, and visited the Church of Agios Nikolaos right on the harbor and the ancient Venetian fortress ruins. Continuing their epicurean delights, the newlyweds visited a fourth-generation family winery, dined on traditional Greek food at Yemeni, enjoyed a casual seaside lunch at Taverna Glafkos, and sipped cocktails at Barbarossa, which turns into a party scene at night, as well as Linardo, known for its vibrant hot pink-and-white façade – a “must-visit during the day for a photo and for an after-dinner nightcap,” suggests Molly.
Enjoying the spa. “We booked a couples massage, which was amazing! After, we took advantage of the private relaxation area with a Jacuzzi that was very romantic.”
Sampling traditional fare at Yemeni. “It was so authentic with a handwritten menu – we loved people watching, and the service was fantastic… one of the best places we visited!”
Visiting Moraitis Winery. “One afternoon, we enjoyed a tasting experience with wine flights and a charcuterie board while sitting in the vineyard’s floral courtyard.”
“Santorini was the most romantic island we visited, and Oia was just as picturesque as we’d seen in pictures when planning,” describes Molly. “The island is very spread out, but if you want the quintessential cave hotel rooms, whitewashed buildings with blue domes, views of the amazing sunset, and the best restaurants, Oia is the place to be.”
They spent four nights at Charisma Suites in a luxury honeymoon suite featuring a jetted tub, private veranda, and gorgeous views of the highly acclaimed Santorini sunsets. The honeymooners loved waking up to made-to-order breakfast on their balcony, soaking up the sun at the hotel’s pool, dining at the elegant onsite restaurant, and taking part in the property’s daily complimentary sunset toast.
They also hiked from Fira to Oia, wandered the 19th-century marble-lined main Nikolaou Nomikou Street, visited the Castle of Agios Nikolaos and many of the famed blue-domed churches, as well as dined at the romantic Ambrosia Restaurant. “This candlelight dinner on the cliffside terrace overlooking the famous caldera was magical,” adds Molly.
Additional highlights included taking a private wine tour with Platinum Travel Santorini, including two wineries and the underground Koutsogiannopoulos Wine Museum, as well as a private catamaran tour with Santorini Yachting Club. “Sipping wine while exploring the glistening Aegean Sea, swimming in the volcanic hot springs, seeing the famous white- and red-sand beaches, and enjoying a delicious chef-grilled BBQ lunch onboard was incredible,” Molly shares of their favorite excursion.
Hiking from Fira to Oia. “This 6.5-mile walk was absolutely breathtaking and the perfect way to visit some of the most popular sites along the way.”
Sailing the seas by catamaran. “Splurging on a private boat was at the top of Will’s honeymoon bucket list… and something we will never forget.”
Touring local wineries. “As a bonus, our guide was an amazing photographer and we did a sunset shoot at our final stop. The pictures are some of our favorites from the trip!”
The last island they visited was Milos. “We had heard the most amazing things about the beaches, snorkeling, and authentic vibe,” affirms Molly. “After staying in the bustling town of Oia, this felt like the perfect way to relax and enjoy our last island together!” They spent three nights at the brand-new Domes White Coast Milos, where they loved the “phenomenal” Makris fine-dining restaurant.
With so much to see, the couple recommends renting a car or ATV to explore the island – and also booking a catamaran cruise since many sites are only accessible by sea. Their full-day cruise with Polco Sailing included sightseeing in the bay of Adamas, seeing the colorful fishing village of Klima from the water, snorkeling Kleftiko, Sykia, and other remote beaches, and exploring the caves.
Other not-to-be-missed recommendations are a leisurely lunch at Medusa Restaurant and a visit to Sarakiniko Beach, known for its lunar-style landscape and cliff jumping. As for other restaurants, the couple enjoyed dinner right on the beach at Enalion in the town of Pollonia, as well as O! Hamos, a very popular local restaurant that doesn't take reservations so it's recommended to come early and have drinks on the beach while you wait.
Exploring Milos by ATV. “Will absolutely loved every minute. We drove around the island and went off-roading on sand dunes/beaches.”
Touring the island by catamaran. “The full-day tour was 100% the best way to see Milos, which is famous for its aqua-blue waters, caves, and rock formations.”
Dining at Medusa Restaurant. “You cannot miss this casual local restaurant on the water famous for octopus and fresh fish – you can even see fishermen lay out octopus to dry on fishing lines!”
Since they were flying home on a direct flight out of Athens, their romantic honeymoon concluded with 24 hours in the capital city. A one-night stay at King George, a Luxury Collection Hotel, Athens allowed them easy access to the sites. "The hotel was within walking distance to the Parthenon, the Acropolis hill, museums, upscale boutique shopping, and the vibrant street-food scene," says the bride. "Another perk that drew us to the King George is it was connected to the Grand Bretagne, its sister hotel, allowing us to use the amenities – including pool, spa, gym, cigar lounge, and rooftop – and restaurants and bars.
Since they were only in Athens for a short time, they spent their days seeing the sites, and also taking advantage of the dining at their hotel. They especially loved Alexander's Cigar Lounge for pre-dinner drinks and a cigar for Will, as well as the GB Rooftop Garden Restaurant, where they had their final meal, a romantic Mediterranean dinner with views of the Acropolis.
During the day, they explored Athens' street food and local specialties, including Lukumades’ loukoumades, Kostas’ souvlaki, and Zisis’ fish in a cone, as well as sampling koulouri (a Greek breakfast staple similar to a bagel) and peinirli (boat-shaped Greek pita pizza) from various street vendors and bakeries.
On the last morning of their honeymoon, the couple got up early to visit Will's wish list sites: the Parthenon, Acropolis Hill, and Museum – " a must-see piece of history in Athens," says Molly. "We purchased skip-the-line tickets, which was great given that we were short on time," she says. "Will has a picture of his parents visiting after they got married 30+ years ago, and he really wanted to recreate this for us as a family tradition," she smiles.
Making the most of their time. “We were only in Athens for ~24 hours, so we really packed it in, but I think 24-48 hours is all you need to see the highlights!”
Enjoying the cigar lounge. “Will found this hidden gem located in the interior garden of the Grand Brentagne hotel, which was the perfect spot to visit for pre-dinner drinks and a cigar (for Will).”
Having dinner on the rooftop. “We had dinner the romantic GB Rooftop Garden Restaurant on the last night of our honeymoon with upscale Mediterranean food and amazing views of the Acropolis – it was the perfect way to end the trip!”
“By combining the four islands, we got to have so many unique experiences – including our final stop in Athens to take in the history of the Acropolis!” shares Molly of the dream honeymoon. "This trip was all Molly," confirms Will. "She is like my own personal travel planner! Since our honeymoon, we've had so many friends reach out for our detailed Greece itinerary, so they can steal it for their own trips... [it was] above and beyond!"
“For beach clubs, make reservations in advance! We were late to the game in Mykonos but recommend reaching out in advance to get put on the walk-in waitlist and showing up right when they open.”
“Taxis can be hard to come by and Uber is not really a thing on the islands. Be prepared to arrange private car service, use the public bus system, or rent an ATV or scooter.”
“Paros restaurants were very hard to contact to make reservations in advance, so we recommend using your hotel concierge to make reservations!”
“Ferries are really the main mode of transportation between islands, and they are quite chaotic, so be prepared. We recommend downloading the Ferryhopper app to see the schedule, buy tickets in advance, and get status updates the day of – a life saver!”
“Milos is the place to rent an ATV. So much of the charm is exploring off the beaten path and public transportation is much less readily available… Make sure to get an International Driving Permit before your trip as many shops require it!”
"After spending time on the Greek islands, we were shocked by how hot it was in Athens. Plan to do outdoor activities early in the morning or in the evening to avoid the height of the heat in the summer months."
This story was originally published as a Travel Diaries feature in the Fall 2024 issue of Inside Weddings magazine. To order a copy of the Fall 2024 issue, visit our library of Inside Weddings back issues available for purchase.