After arriving in Naxos, take a pre-arranged taxi to Naxos Island Hotel in Agios Prokopios—about 10–15 minutes from the port, usually €20–€30. September is calmer than high summer, but it is still worth confirming your transfer and asking the hotel to hold your luggage if the room is not ready. Keep this first afternoon deliberately unstructured: settle in, use the pool, and allow roughly two hours for a spa treatment or an easy drink overlooking the beach. The hotel is directly by Agios Prokopios Beach, so there is no need to organize another outing today.
Around 5:30–6:00 p.m., take a taxi into Naxos Town; allow 10–15 minutes, depending on traffic, and ask to be dropped near the waterfront or Grotta area. Walk across the causeway to Palatia Islet for Portara, the enormous marble gateway and Naxos’s best first-evening viewpoint. The walk is easy but uneven in places, and the islet is exposed, so bring sandals with a secure strap and a light layer for the breeze. Sunset in mid-September is around 7:25 p.m.; arrive 30–40 minutes beforehand, then linger briefly after the sun drops rather than rushing straight to dinner.
From Portara, stroll along the waterfront toward Meltemi Restaurant, allowing about 15–20 minutes at an unhurried pace. Reserve ahead and request a harbor-side table; dinner here is a relaxed introduction to local Greek cooking rather than a late-night occasion. Plan on €35–€60 per person with wine, and allow about 90 minutes. Afterward, take a taxi back to Naxos Island Hotel—roughly €20–€30—or arrange the return through the hotel, since taxis can be less immediate later in the evening. Don’t add more sightseeing tonight; the point is to arrive gently and start the anniversary trip feeling rested.
Start with an easy morning at Agios Prokopios Beach, just steps from Naxos Island Hotel. Arrive around 9:00, before the beach becomes busier, and settle on the broad sandy stretch near the central promenade. The water is usually calm and exceptionally clear here, making this a day for swimming, reading, and doing very little rather than moving from cove to cove. Sun loungers and umbrellas are available from beach operators, generally around €15–€25 for a set in September, though prices vary; bring some cash and ask your hotel whether it has a preferred section.
Around 12:30, take a short walk inland to Anatoli for a relaxed Greek lunch. Order simply—grilled fish or calamari, a village salad, local cheese, and perhaps a carafe of house wine—and expect roughly €25–€45 per person. Lunch here is best treated as a proper pause rather than a quick beach stop; allow about 90 minutes, and call ahead if you want a shaded table, as September hours can change slightly after the summer peak.
After lunch, take a taxi south to Agia Anna Beach—about 5 minutes and usually €8–€12—or walk in roughly 20–25 minutes along the coastal road if you feel like stretching your legs. Spend the late afternoon swimming from the smaller sandy beach, then wander slowly beside the little harbor as the light softens. For dinner, settle into Spiridakos Taverna near the waterfront around sunset; reserve a seaside table if possible, particularly for an anniversary meal. Allow about 1½ hours and budget €30–€50 per person for grilled seafood, Greek specialties, and wine. A taxi back to Agios Prokopios takes approximately 5–10 minutes, so ask the taverna to call one rather than relying on finding one late in the evening.
Take a morning KTEL Naxos bus from Agios Prokopios toward Chora; the ride usually takes 15–25 minutes and costs roughly €2–€3. Get off near the waterfront and walk uphill into Naxos Kastro, allowing about 1½ hours to wander without rushing. Enter through the old gates and follow the quiet lanes around the Venetian mansions, small chapels, and shaded stairways. Comfortable shoes help—the marble paths are uneven, and the slopes are more noticeable in the midday heat.
Pause at Kastro Café for coffee and a light breakfast, budgeting approximately €8–€18 per person. It is a good place to linger rather than simply refuel, so give yourselves an hour before continuing to the Archaeological Museum of Naxos, usually open from morning into the afternoon, though September hours can vary. Allow about an hour inside; the collection is compact and especially rewarding for its Cycladic figurines and finds from ancient Naxos. Check the posted hours before ordering coffee, as seasonal museum schedules occasionally change.
After the museum, come downhill through the back lanes toward the old harbor area—roughly a 10-minute walk, with plenty of tempting stops along the way. Settle into Kitron Café Cocktail Bar for a relaxed afternoon drink and try a cocktail or digestif made with local kitron, the island’s distinctive citrus liqueur. Plan on €10–€20 per person and give yourselves an hour; this is a good point to slow the day down, especially if the afternoon is warm. If you want to browse, stay around the waterfront and narrow streets rather than adding another formal sight.
Walk or take a short taxi ride back toward central Naxos Town for dinner at To Elliniko, a polished but welcoming choice centered on traditional Naxian produce. Reserve ahead for an evening table and expect approximately €35–€60 per person, depending on wine and shared dishes. Order slowly—local cheeses, vegetables, and island meats are best enjoyed family-style—and leave room for a final stroll through the softly lit lanes of Chora before returning to Agios Prokopios by bus or pre-arranged taxi.
Arrange a taxi from Naxos Island Hotel to Naxos Town Harbor for around 8:00–8:30, allowing roughly 20–25 minutes and a little extra time for traffic and finding the correct meeting point. Your private boat with Naxos Sea Club should depart in the morning and run for about seven hours, with the exact route adjusted for wind and sea conditions. Bring a light layer, reef-safe sunscreen, water shoes, and a dry bag; the southern coast is wonderfully quiet, but facilities are nonexistent once you leave the harbor. Private-charter pricing varies widely by boat size and inclusions, so confirm whether fuel, crew, drinks, towels, and lunch provisions are included.
The cruise toward Rina Cave is the real luxury today: open water, dramatic limestone coastline, and no need to hurry between stops. Plan about an hour here for swimming directly from the boat in exceptionally clear water. The cave and surrounding shoreline are best enjoyed from the sea, and your skipper will choose the safest place to enter depending on swell and wind. If the water is calm, linger on deck afterward rather than adding another stop—the spacious, unstructured rhythm is exactly what makes this a better anniversary day than a packed sightseeing cruise.
Continue south to Kalados Bay, where you can spend roughly two hours anchored in a peaceful, undeveloped setting. Have lunch on board or unpack provisions arranged through the charter; this is not the place to rely on finding a restaurant or shop. Swim, read in the shade, and let the crew handle the timing. The bay can feel especially remote in September, though wind exposure may change quickly, so follow the skipper’s advice about swimming and anchoring. Keep some energy for the ride back rather than trying to squeeze in additional beaches.
After returning to Naxos Town Harbor, take a taxi back to the hotel to freshen up, or remain by the harbor if you still feel comfortable in saltwater clothes. For dinner, choose a well-reviewed seafood restaurant along the waterfront, reserving ahead and requesting an outdoor table if available. Expect approximately €35–€60 per person for a relaxed meal with wine, depending on the catch and the day’s selections. Keep the evening low-key: a short stroll beside the harbor is enough after seven hours at sea, and heading back before you are overtired will make tomorrow’s resort day feel genuinely restful.
Keep today deliberately unstructured after yesterday’s boat charter. At 18 Grapes Hotel, settle into the pool area after breakfast and let the morning unfold slowly—September sun is still warm, while the atmosphere is noticeably calmer than in July and August. Reserve loungers in advance if the hotel requires it, and book a late-morning spa treatment rather than trying to fit in several activities. Allow roughly four hours for swimming, a massage or facial, and an unhurried lunch at the hotel; expect approximately €20–€35 per person for a light meal, with spa treatments commonly starting around €80–€120 depending on duration. Keep your afternoon free rather than returning to the beach—this is the restorative pause in the itinerary.
If you feel like leaving the hotel pool, take a short taxi ride or walk—depending on your exact hotel entrance and the heat—to Aqua Fun Water Park, also in Agios Prokopios, for about 1½ hours. Treat it as a casual swim and drinks stop, not a major outing; the complex generally operates seasonally and hours can shorten in September, so confirm same-day opening times before going. Entry prices vary by season and package, but budget roughly €15–€25 per person. If the park feels too lively or the weather is windy, simply remain at the hotel instead; the day works perfectly without this optional stop.
For dinner, choose a traditional taverna along the Agios Prokopios waterfront and walk there from the hotel, or ask reception to arrange a short taxi if you prefer not to walk after dark. Look for grilled fish, local cheeses, tomato keftedes, and slow-cooked lamb rather than a formal tasting menu; a relaxed meal should take about 1½ hours and cost approximately €25–€45 per person with wine. Arrive around 19:30, when the light is soft and tables are easier to find, then return to 18 Grapes Hotel for one final quiet drink by the pool. Keep luggage and tomorrow’s ferry arrangements simple tonight, but avoid turning the evening into a planning session.
Take an early direct ferry from Naxos Port to Parikia, ideally between 8:00 and 10:00, so the crossing—usually about an hour—doesn’t take over the day. With disembarkation and the drive north, allow roughly 45–60 minutes from Parikia to Naousa. A pre-booked taxi is the easiest option with luggage; expect approximately €35–€50 for the road transfer, depending on the vehicle and season. Ferry times can change, so confirm the sailing the evening before and arrive at the port 30–45 minutes early.
After checking in at Parilio, a Member of Design Hotels, in the Kolymbithres area, resist the temptation to start sightseeing. Leave your bags, have something cool by the pool, and let the arrival day become part of the holiday. The hotel is beautifully positioned for a quiet first afternoon; allow about two hours to settle in, swim, and arrange dinner reservations. If your room is not ready, the hotel can usually store luggage while you use the pool and lounge areas.
Around 5:00, take a short taxi to Naousa Old Port—roughly 10–15 minutes from Parilio, depending on traffic—or ask the hotel to arrange a transfer. Wander slowly along the fishing harbor and through the whitewashed lanes behind it, where the evening light is especially lovely and September feels noticeably calmer than August. Keep this walk unstructured: pause for a drink, browse the small jewelry and design shops, and avoid trying to “cover” the whole village. A taxi back to the hotel later is sensible, as local buses and taxis can become less predictable after dinner.
Have dinner at Barbossa Restaurant, right on the harbor, around 7:30 or 8:00. Reserve ahead and request a waterside table, while remembering that the harbor frontage is lively rather than completely quiet. Budget approximately €45–€75 per person before wine; seafood, modern Greek dishes, and a bottle of local Paros wine make an easy celebratory first-night combination. After dinner, take one final unhurried turn around the harbor before returning to Parilio—this is a night for enjoying your new setting, not squeezing in another stop.
Have Parilio arrange a taxi to Monastiri Beach, allowing about 20–25 minutes from Naousa. Leave around 9:00–9:30 to enjoy the protected bay before the warmest part of the day; a taxi should cost roughly €25–€35 each way, though confirm the September rate and return pickup in advance. The road ends at the beach area, where you can settle in for an unhurried swim and several hours on the sand. The cove is sheltered and usually gentler than the more exposed beaches, but bring water, sunscreen, and a little cash—facilities are limited outside the beach restaurant.
Stay at Monastiri Restaurant for lunch rather than packing up and moving elsewhere. Its setting directly above the bay makes this an easy anniversary-day choice: order slowly, linger over a Greek salad, grilled fish, or a light pasta, and expect approximately €25–€45 per person before drinks. September hours can vary with the season, so ask the hotel to confirm that the kitchen is serving lunch and reserve a table around 13:30. Afterward, take a proper break in the shade before walking.
From the restaurant, follow the easy coastal path through Paros Park toward the lighthouse. Allow about 1½ hours at a relaxed pace, with time to pause on the rocky viewpoints and watch the light change across the water. Wear sandals with a secure sole rather than smooth flip-flops, and carry water; the terrain is manageable but exposed, with little shade. If you prefer not to walk the full route, simply do the first section and return to the beach area for your taxi.
Arrange pickup from Monastiri for around 18:45–19:00, giving you time to reach Naousa before the old harbor becomes lively. Finish at Sante Cocktail Bar, tucked into the harbor-side lanes, for one drink rather than turning the evening into another full outing. Cocktails generally run about €12–€20 per person. The walk through Naousa Old Harbor is especially pleasant after sunset, but keep the evening short if you are tired: returning to Parilio by taxi usually takes 10–15 minutes, and your hotel can call one when you are ready.
Ask Parilio to confirm the exact departure point for your Mykonos On Board private charter the evening before; Naousa is most convenient if offered, while Pounda requires roughly 25–30 minutes by taxi. Plan to arrive around 8:45–9:00 for a 9:00–9:30 departure, allowing time for the skipper’s weather briefing and provisions. A private cruise of about seven hours typically includes fuel, a skipper, water, and basic equipment, but confirm whether towels, snorkeling gear, and lunch are included. September can bring a fresh meltemi, so the skipper may adjust the route for calmer water—this is a day to follow local judgment rather than insist on a fixed itinerary.
Cruise toward Lageri Beach on Paros’s northeastern coast, where the boat can anchor off a quieter stretch away from the organized beach areas. Give yourselves about 1½ hours here for an unhurried swim and time on deck; the sand is beautiful, but arriving by boat is the more peaceful experience. There are very few useful facilities in this area, so bring sunscreen, water, and anything you may want for a light lunch. Keep valuables aboard and use the boat’s swim ladder—the shoreline can be less convenient for a barefoot landing than it looks from offshore.
Continue south toward the Blue Lagoon, between Paros and Antiparos, for another roughly 1½-hour stop if the sea is calm. The shallow water is exceptionally clear and ideal for snorkeling, though the brilliant color depends heavily on sun and wind conditions. Afterward, head toward Despotiko, where your skipper can point out the undeveloped island and the ancient sanctuary area from the water. Allow about an hour here rather than forcing a shore visit; the charm is the silence, low rocky coastline, and sense of isolation. Keep lunch simple on board—fruit, salads, sandwiches, and chilled wine are easier than arranging a formal meal during a seven-hour charter.
Return to Naousa in the late afternoon, usually around 4:00–5:00 depending on sea conditions, and leave the evening intentionally light. After a shower and perhaps a quiet drink at Parilio, walk or take a short taxi ride to Tsantali Restaurant for dinner. Expect approximately €30–€50 per person for a relaxed meal, depending on seafood and wine; reserve ahead and ask for a table away from the busiest passage if possible. Keep the order uncomplicated—grilled fish, local salads, and a few shared dishes suit the day better than a long tasting menu. Exact charter timing and stops remain weather-dependent, so confirm the final plan with the skipper that morning.
Begin with an unhurried walk through Naousa Village around 9:30, before the harbor cafés and boutiques fill up. Wander beyond the waterfront into the quieter lanes around Aghios Nikolaos, where whitewashed houses, small galleries, and independent boutiques feel more relaxed than the main quay. Allow about two hours, but keep it loose—this is a good morning for browsing linen, jewelry, and ceramics rather than following a sightseeing checklist. Wear comfortable sandals: the old lanes are uneven, and there is very little shade.
Stop at Ragoussis Bakery for coffee and a pastry, ideally before lunch crowds arrive. It is a practical, casual pause rather than a formal café stop; choose something local such as a cheese pie, bougatsa, or a sweet made with almonds and honey. Budget roughly €6–€15 per person, and allow 45 minutes. Opening hours can vary in September, but the bakery generally opens from the morning into the evening. From the quieter lanes, it is an easy walk back toward central Naousa.
After a relaxed lunch or some pool time at Parilio, take a taxi to Moraitis Winery for an afternoon tasting. The short ride from Naousa is usually around 10 minutes, with a typical fare of approximately €10–€15 each way; have the hotel reserve both the taxi and tasting time, as appointments are preferable. Set aside about 1½ hours for Parian varietals such as Monemvasia and Mandilaria, served in a calm cellar setting rather than a hurried tour. Tastings generally cost €20–€35 per person, and the late-afternoon slot is especially pleasant. Arrange your return taxi before you begin—the service can be limited outside the village.
Finish at Siparos Restaurant in Santa Maria, a polished seaside choice just outside Naousa. Leave around 7:00–7:30, before the roads darken and dinner traffic builds; the drive is roughly 10–15 minutes by taxi, usually about €15–€25 each way. Reserve a waterfront table and let dinner unfold slowly over local seafood, seasonal vegetables, and chilled Parian wine. Expect approximately €45–€75 per person before extra drinks, depending on how generously you order. Ask the restaurant to arrange the return taxi to Parilio, since Santa Maria is not a place you want to navigate on foot after dinner.
Have Parilio arrange a taxi to Kolymbithres Beach, allowing roughly 20–25 minutes from Naousa. Leave around 9:00 so you can enjoy the unusual granite formations and clear, shallow water before the beach boats and day-trippers arrive. The small coves are reached by walking over uneven rock, so wear sandals with a secure sole; the water is often calm, but there is little shade directly beside the most scenic formations. Sunbeds and umbrellas are limited and seasonal, so bring water and confirm September availability with the hotel. If you prefer not to arrange a return taxi immediately, the local water taxi from Naousa may operate between the harbor and Kolymbithres, though schedules become less frequent outside peak summer.
After about three relaxed hours, continue by taxi toward Krios Beach, west of Parikia—allow approximately 25–30 minutes, depending on traffic and the driver’s route. This is a good final beach stop because it feels more spacious and low-key than the busier coves, with clear water and a few casual facilities for drinks or a simple lunch. Settle in for the afternoon rather than trying to fit in another sight; September light is especially lovely here, and the western outlook makes the late afternoon feel unhurried. Ask the driver to return around 17:00, or have Parilio coordinate a pickup, as taxis can be less readily available from the beach later in the day.
Freshen up and return to Parikia for dinner at Mario Restaurant, allowing roughly 1½ hours and budgeting about €45–€75 per person depending on wine and seafood. Reserve ahead and request a waterfront table, particularly for an anniversary dinner; a seating around 19:30–20:00 gives you time to dine slowly without making the evening feel late. Afterwards, take a gentle 45-minute walk along the Parikia waterfront promenade, watching the ferries and enjoying one last view across the Aegean. Keep the walk intentionally short and relaxed—this is a lovely place to end the trip without adding another taxi ride or a final sightseeing commitment.