Three words: take me back! I feel so lucky Bridge and I finally got to go on the honeymoon I’d been planning for what felt like forever. It was truly the best trip we’ve ever taken and the longest we’ve been away from home. Below I’m sharing our full itinerary for anyone who wants it. I planned the entire trip myself—no travel agent—because I love researching and collecting recommendations. I included many of the suggestions you shared in posts and DMs; please let me know in the comments if I missed anything. Overall, I wouldn’t change a thing. We absolutely loved every island we visited—each one is unique. Amsterdam was our last stop; the last time Bridge and I were there was 2018 and we only had 48 hours. It’s stayed on our minds ever since and remains one of our favorite cities.
I hope you save this itinerary for your next trip to Greece. We made so many memories and can’t wait to return.
Random tips:
– Bridge and I each packed one checked bag, one small carry-on, and one smaller personal bag for this trip. I worried it might be a hassle, but it wasn’t—drivers and hotels helped with luggage to and from properties.
– People always ask, “If you could pick only two islands from the four you visited, which would they be?” It depends on what you want. Paros is more relaxed: rent a car, beach hop, stroll village streets and enjoy dinner nightly. Milos is more adventurous: cliff jumping, dune buggies, private boat trips to Kleftiko, and hiking to sunset viewpoints. Mykonos and Santorini can feel touristy, but we loved both and are glad we went. Next time we’d like to explore a few smaller islands.
– Best travel window: late May through the end of September for reliably warm weather and open businesses. July and August are the busiest months; June and September offer great weather with fewer crowds.
MYKONOS
180-degree Sunset Bar
FLIGHTS: We flew Seattle → Athens → Mykonos (30-minute flight). Ferries are an option (about 2.5 hours), but I prefer flying because I get seasick and ferries can be delayed.
4 nights, 5 days – a great length for Mykonos. The island is known for parties, but you can balance exploring with relaxation at your hotel.
HOTEL: Soho Roc House (members only)
TRANSPORTATION: Rent a car for a day or two to explore. Scooters and ATVs can be risky on narrow, winding roads; our driver recommended a car. If you rent through a hotel, an international driver’s permit usually isn’t required, but many private rentals and Airbnb hosts will ask for one.
(*) indicates places we visited
FOOD & BARS
*180 Degree Sunset Bar – a must. Book your exact seat on their website the day before; you can choose the table and pay a minimum that’s covered by food and drinks. We sat on the main terrace.
Hippie Fish
Kiki’s Tavern – remote but worth it if you have a car; fresh seafood and a swim-while-you-wait beach.
*Jimmie’s – best gyros
*Rhapsody Bar – Mykonos Town, great coffee/drinks and windmill views
Interni
Nikolas Taverna
*Scorpios – difficult to book but excellent day-to-night beach club with dining and live DJs (and a great massage). Order the octopus.
*Spilia Seaside Restaurant – tucked on the water; try their cheesecake.
Zuma
*Souvlaki Story
Lotus
Remezzo
Kastro’s – classic waterfront seating and views
Taverna Petra
Pepper
Sakis Grill House – fast, good gyros
Buddha Bar at Santa Marina hotel
I Scream and Vincy’s – ice cream
Nice N Easy
Sea Satin
ACTIVITIES
Petra Kouzina – cooking class
Mykonian Spiti – cooking class
Negrita or *Caprice in Little Venice – go early for sunset to get the best views of the windmills and water. Many waterfront restaurants have minimums for prime tables, applied to food and drinks.
Day trip to Syros
BEACHES & BEACH CLUBS
Alemagou
Principote
Psarrou Beach (Nammos) – upscale beach club and cove for swimming
Agia Anna – combine with lunch at Spilia
Panormos
Solymar or Lohan Beach Club – day beds and dinner at Spilia afterward
SantaAnna Mykonos
Super Paradise Beach Club
PAROS
Town of Naousa
FERRY: Mykonos → Paros was quick and easy: about 45 minutes.
3 nights, 4 days – we arrived midday and left late on the fourth day. Three nights is the minimum I’d recommend for Paros.
HOTEL: Parilio, a Member of Design Hotels — a stunning property about five minutes from town and close to several beaches. Highly recommended.
TRANSPORTATION: Rent a car for your whole stay to explore the island and beach hop; we rented through our hotel.
FOOD & BARS
*Stilvi – exceptional dinner; arrive around 7pm for an open table
*Sigi Ikthios – outstanding seafood and service in Naousa
*Barbarossa – another Naousa favorite (try the crispy zucchini)
*Souvlakia Kargas – best gyros on the island
*Vrohas Cafe – found during a road trip, next to a small marina; try the Greek yogurt with fruit and granola
Agosti – drinks before or after dinner
Siparos – reserve ahead
Comeback Paros – drinks
Mario
Tsachpinis Ouzeri
Captain Pipinos
Sousouro – great breakfast and avocado toast
Sativa Music Bar
ACTIVITIES
Margarita Studios – cooking classes (check opening days)
Book a boat day with Michael Zeppos around Antiparos
Drive your rental to Antiparos on the short ferry from Pounta (very affordable even with a car). Visit Kedros Beach and the town for shopping and swimming — a highlight.
Antiparos nightlife: dancing at Lionardi
BEACHES
*Piperi Beach (near Naousa)
*Kolimpithres
Monastiri
Santa Maria
*Golden Beach
Punda Beach Club
Fanari Beach Club
MILOS
Sarakiniko Beach
FERRY: Mykonos → Milos took about 1 hour 45 minutes on a smaller vessel. Ferries can run late and be sensitive to waves; expect delays.
3 nights, 4 days – I would have added another night. We arrived late due to a delayed ferry and only had two full days to explore; more time would be ideal.
HOTEL/AIRBNB: Terra Mare Suites – we stayed in a holiday home on the water and loved it. It was centrally located: about 10–15 minutes from the port and 12 minutes to Pollonia and Sarakiniko Beach.
TRANSPORTATION: Rent a dune buggy — highly recommended. We used [email protected]. Note: an international driver’s permit may be required for rentals from private hosts.
FOOD & BARS
Pollonia restaurants are great.
*Deck – excellent breakfast (try the Greek yogurt with fruit and honey)
Medusa – popular waterside spot in Firopotamos (check hours)
Enalion in Pollonia
*De Milos – tasty food in Pollonia
*Garden the Juice Bar – frequent stop for coffee and matcha
Avli
*Archontoula
Ergina
O! Hammos
*Gyros of Milos – fantastic gyros
*Aggeliki – ice cream and breakfast
Astakas in Klima
Psaravolada – seaside dining
Aragosta
Akrotiri
Hanabi
Gialos
ACTIVITIES
Visit Klima village on the water
*Spend time at Sarakiniko Beach for cliff jumping and photos; it’s lunar and stunning
Hike to the castle for sunset—arrive early to enjoy most of the view, then head down for dinner at Archontoula or Avli before crowds arrive
Rent a small boat (Blue Mile) to Kleftiko for swimming, snorkeling, and cave exploration (bring snorkels and snacks)
Day trip to Kimolos
Kostantakis winery visit
Explore Papafragas caves and the ancient theater
BEACHES
*Sarakiniko – moon-like rocks and clear water; great for photos and cliff jumping
Tsigrado – accessed via a ladder, worth the effort
Firiplaka
*Firopotamos – best earlier in the day for photos
Papafragas caves
*Paparodi Shore – near our rental with cool caves to jump and swim under
SANTORINI
In the town of Oia
FERRY: If I could change one thing, I would have flown from Milos to Santorini instead of taking the ferry. Our ferry was delayed and stormy, turning a 1 hour 40 minute trip into over three hours.
4 nights, 5 days – the right amount for Santorini. The island is larger and has more to explore, so allow time.
HOTEL: Santo Maris — recommended by my sister and a great base. It’s just outside the busiest part of Oia with spacious grounds, a pool, spa, and superb sunset views. Request room 302 for a lovely placement.
TRANSPORTATION: Rent ATVs for a couple of days to visit the Black, Red, and White beaches and to reach Fira. We booked ours through the hotel.
FOOD & BARS
Ammoudi Bay – a charming fishing village below Oia with several restaurants; it’s steep to reach but worth multiple visits. Dimitri’s was one of our favorite meals. Avoid overpriced options with mediocre service.
Sunset Ammoudi
*Dimitri’s in Ammoudi Bay – excellent dishes: tomato fritters, grilled seabass, tzatziki, hummus
*Pitogyro – in our opinion the best gyro in Greece; opens at noon and often busy. Great for takeaway to enjoy on a balcony at sunset.
*Fanari Restaurant – amazing sunset views and food
Apsithia – for Greek salad and fava while shopping in Oia
The Good Heart
*Solo Gelato – must after sunset
Oia Vineyard
The Athenian House
Ambrosia
Floga Restaurant
La Maison Restaurant
Mellitini – tapas
Nocturna – underrated sunset view and baklava
Passagio – smoothies
Pyrgos restaurants
Rastoni – ask for the top seating
Skiza Café – pizza
Pelekonos Restaurant
Yogi Gyros
Lucky Gyros in Fira
Catch
Fino – no view, exceptional food
Metaxi Mas – highly recommended cheesecake
PK Cocktail Bar in Fira
Volcan on the Rocks – outdoor movie nights (Mamma Mia and other classics)
Roka and Pacman
Salt & Pepper in Fira
Theros Wave Bar – south coast
ACTIVITIES
Rent ATVs for island cruising and beach visits (Black Sand / Kamari beaches are about 45 minutes from Oia). Dining at beachfront restaurants often includes use of chairs for guests.
Archaeological Museum and Museum of Prehistoric Thera
Sunset cruises from Ammoudi Bay are highly recommended if you’re comfortable at sea; many recommend catamarans for the evening
Profitis Ilias – highest point on Santorini for panoramic views
*Watch the sunset in Oia — widely regarded as one of the best in the world
Hike from Fira to Oia if you have time (3–6 hours) and bring water
Day passes at clifftop hotel pools for views and fruit platters
Boat tour of the caldera and hot springs
BEACHES
*Black Sand Beach – many restaurants offer free chair access when you dine; we ate at The Acropolis and enjoyed the beach
Red Beach – short walk down from the cliff; bring snacks
White Beach
*Ammoudi cliff jumping spot – a hidden gem and one of my favorite experiences. Walk past the restaurants and follow the path to a ~20–25ft cliff for swimming and jumps. Go mid-morning, bring towels and snacks, and finish with lunch at Dimitri’s.
AMSTERDAM
FLIGHT: We flew Santorini → Amsterdam (about 3.5 hours). Amsterdam is a convenient gateway for the return flight to Seattle.
HOTEL: Soho Amsterdam (members only)
FOOD & BARS
*Bakers & Roasters – breakfast
*CT + Coffee and Coconuts – breakfast and lunch
Soup en Zo – cozy soup spot; one of my favorite rainy moments in Amsterdam was sitting on the bench outside with a warm bowl
*Winkel 43 – famous Dutch apple pie, a must
The Butcher – burgers
Foodhallen – an indoor food market akin to Chelsea Market
The Avocado Show – avocado-forward menu
Omelegg
*Pluk – bakery and café
Back to Black – coffee
MarQt – healthy grocery and food stalls
Dignita
*SLA – build-your-own salads
Hummus bistro and Sir Hummus
Little Collins
Stroopwafel from a street cart (best fresh)
Betty Blue – café near Waterlooplein
Café Walem – open-faced sandwiches
De Kas – farm-to-table in a glasshouse
ACTIVITIES
*Buy Anne Frank House tickets at least a month in advance
Reserve Van Gogh Museum tickets ahead of time
*Rent bikes and ride through Vondelpark
Canal cruise
*Shop around De Negen Straatjes (The Nine Streets)