Spend one day on land and two “at sea” for an authentic Maine experience that encapsulates today’s urban sophistication and seafaring history of Portland, Maine.  Enjoy a luxurious night at Portland Harbor Hotel in the Old Port District, offering proximity to the city’s working waterfront, eclectic shops, art galleries and historic treasures, with dinner and a full breakfast at BlueFin. After exploring the mainland, our town car will pick you up and take you to dock where a ferry will whisk you away for a short sail across scenic Casco Bay to car-free Great Diamond Island. Once there, enjoy two nights’ accommodations and dinner at the Inn at Diamond Cove, a member of the Historic Hotels of America. Relax as you indulge in a resort experience that offers an outdoor pool with cabana, miles of hiking and biking, and more – all to be followed by an elegant dinner for two at Diamond’s Edge, the island’s acclaimed waterfront restaurant with marina.

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