Proposal & Engagement Trips in Greece

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The best out of 75 deals in Greece - enter dates to check availability

Top Proposal & Engagement Trips in Greece

    Set sail from Alykanas for an unforgettable day cruise to South & Southeast Kefalonia. Discover breathtaking coastal landscapes and swim in pristine waters at iconic spots like Antisamos, Makria Petra, Ragia, Kako Lagkadi, Skala, and Mounta. Cruising as far as Karavomilos, you also have the unique optional opportunity to visit the magical Melissani Cave (extra transfer & entry fees apply). Enjoy comfort, freedom, and idyllic island scenery on this ultimate sea adventure!

    South/Southeast Kefalonia full day
    :
    US $1,973

    Live it up with an exclusive cruise catered entirely to your wishes. Swim, relax, party, our cruises offer the perfect backdrop for making memories that will last a lifetime. Relax, swim, discover, and eat on board a traditional wooden boat with a local captain navigating and explaining the history of the island. Let's enjoy a day making unforgettable memories. Best regards Captain Nikos

    Bachelor Cruise
    :
    US $717

    Set sail with family or friends and enjoy a relaxing 3.5-hour sunset cruise. The journey includes a stop at the beautiful Kallithea Springs, where you can swim and snorkel in crystal-clear waters. Onboard, savor fresh fruit and a selection of drinks including water, wine, beer, and soft refreshments—all included in the price.

    3,5 Hour – Private Sunset Tour
    :
    US $386

    Treat yourself to an unforgettable day of exploration and relaxation as we sail to the spectacular Balos Lagoon and Gramvoussa Island. A natural paradise of turquoise waters, white sandy beaches, and exotic beauty. One of the most iconic spots in Crete, where the shallow, warm waters invite you for a swim or simply to relax and take in the serene surroundings. Step back in time on Gramvoussa Island, home to a Venetian fortress perched atop a rocky hill. Swim in crystal-clear waters or explore the island.

    8 Hr – Balos Lagoon and Gramvoussa
    :
    US $970

    Enjoy a private 6-hour cruise around Mykonos, exploring crystal-clear waters and hidden beaches away from the crowds. Swim, relax, and discover beautiful spots or visit Rhenia, depending on the weather. During the trip, enjoy a freshly prepared light lunch cooked on board, along with Greek wine, soft drinks, and snorkeling equipment. An authentic, private experience filled with relaxation and unforgettable moments at sea, perfect for couples, families, or small groups, with a flexible and custom plan.

    6 Hour – Private Mykonos Cruise
    :
    US $683

    Explore Crete by sea with our T-Assos 450, a compact boat perfect for couples, families, or friends. Departing from Kasteli, you can visit Balos Lagoon's turquoise waters and Gramvousa Island's hidden beaches at your own pace. The boat comfortably fits up to 4 guests and includes a bimini shade, snorkelling gear, cooler, safety equipment, skipper, and fuel included in the price. Swim, sunbathe, and enjoy a private escape away from the crowded beaches.

    4 Hr – Kissamos to Balos/Gramvousa
    :
    US $243

    Set off from Kissamos on a private cruise to the iconic Balos Lagoon and the wild beauty of Gramvousa Island. Swim in crystal-clear turquoise waters, relax on white sandy shores, and enjoy breathtaking views of Crete's most famous coastline. Along the way, discover hidden coves and peaceful swimming spots like Agios Sozos, away from the crowded ferries, while enjoying a relaxing and personalized experience on board.

    Balos-Gramvousa from Kissamos / 4h
    :
    US $601

    Full-day private boat tour around Zakynthos, visiting the island's most iconic spots, including Marathonisi, the Keri Caves, Mizithres, Shipwreck Beach (Navagio), and the Blue Caves, with stops for swimming and snorkeling in crystal-clear waters.

    8 Hr – Zakynthos Private Boat Tour
    :
    US $1,102

    Experience Rhodes in true Italian style aboard the iconic Riva Aquariva 33. This private cruise is designed for couples, honeymooners, and guests seeking an elegant escape on one of the world's most beautiful wooden speedboats. Depart from Rhodes Marina and cruise along the medieval coastline before anchoring in the crystal-clear waters of Kallithea Springs or Anthony Quinn Bay for swimming and relaxation. Enjoy a bottle of chilled premium wine or champagne, seasonal fruit, soft drinks, and attentive serv

    Rhodes Riviera Escape
    :
    US $2,976
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What boaters said about Proposal & Engagement Trips

  • 5.0
    /5
    (3 Hr – Extended Cave & Snorkeling)

    Tony is the best!

    We had a genuinely lovely morning on the water with Tony. He’s a kind and very pleasant man to be around and he did everything he could to make our trip fun. Could not recommend more
    Will G.
    Will G.
    Reviewed on Sep 25, 2026
  • 5.0
    /5
    (6 Hour – Private Mykonos Cruise)

    This is a fantastic trip- Book it!!!

    My partner and I did the day cruise with Captain Grigoris. It was fantastic. From the food(canapés, cheeses, breadsticks and salad), wine, and beautiful day at Reneia Island. Snorkeling, diving and sailing around Mykonos. Book this trip, don’t hesitate!
    Emily-Kate R.
    Emily-Kate R.
    Reviewed on Sep 25, 2026
  • 5.0
    /5
    (2 Hr – Sunset Cruise)

    Fabulous experience

    Great experience end to end from booking and arranging special requirements to the trip itself. Captain Tony was absolutely brilliant. We had a lovely time. Thanks so much.
    Dawn J.
    Dawn J.
    Reviewed on Sep 23, 2026
  • 5.0
    /5
    (5.5 Hour – Shared Day Trip)

    Perfect day at sea

    Wonderful boat ride with Captain Georgios. 3 stop offs for swimming/snorkelling with plentiful Zythos beer (other options available), a fruit platter and Pastitsio and Greek salad. The Captain was friendly and professional and we had a great time. Would absolutely recommend this to anyone and we would definitely do again in the future.
    Dominique L.
    Dominique L.
    Reviewed on Sep 16, 2026
  • 5.0
    /5
    (8 Hour – Private Catamaran Cruise)

    Amazing Sunset Cruise

    We got married in Greece and did this as our "send off" and had our guest join us. The captain and Mary Lou were fantastic and the food they made.... phenomenal! I would 110% recommend. If you're thinking about it just do it.
    Hanna P.
    Hanna P.
    Reviewed on Sep 22, 2026