I voted Shire with Bilbo, figuring he would be a jolly and knowledgeable companion who could show me everything at a leisurely pace and give me lots of backstory/gossip wherever we went, plus he'd know all the good pubs AND how to avoid people like the Sackville-Bagginses. But, I could be happy with many other options.
Perfect relaxation for mind, body and spirit! Every day would include: waking to the sound of falling water and bird song; some hours of study in Elrond's archives; wandering in the hills and valley, with afternoon swims to cool off in streams and waterfall pools; scrumptious picnic lunches after said swims; scrumptious evening meals with the Elves and their music, stories, laughing and singing in the Hall of Fire; and, finally, starlight and moonlight and the sound of falling water sending me off to peaceful sleep.
Faramir would be the perfect companion - able to find his own amusements and then excitedly share what he's learned that day; chivalrous and happy to hike the hills at my (I'm sure) slower pace and carry the lunch; a poet and song writer adding an intelligent human element to the evening festivities.
time, but I could have gone on juggling and arranging for ages. (Shagrat, the Orchards of Mordor.) Yes, you're right, Bilbo is the most well-rounded choice. Frodo would be busy philosophizing, and Sam dragging us to every garden in sight, while Lotho made of with the luggage.
Rivendell with Thorin - hm, no, we'd be spending all the time in the smithies.
Moria with the Balrog - he'd certainly know places to visit which not even the Dwarves know about, but I'd be concerned about things getting a bit too "hot".
Moria with Eowyn - no, an Orc-hunt is not exactly my idea of a vacation.
Lorien with Gollum - too fattening, I'd be eating all the food they offered him.
Ithilien with Sam - now there's a thought, he'd give a tour of herbs and herb-lore and we'd have fresh-cooked coney stew!
Rohan with Ghân-Buri-Ghân - this would be a hiking tour, for sure, on all the very-little-known forest paths. But I have the feeling the native foods might not be to my liking, probably a bit too raw.
Bree with Merry - we'd visit every pub and restaurant.
Bree with Bill the Pony - we'd visit every apple orchard.
Fangorn with Treebeard - nope, I'd be dozing off constantly with his sonorous descriptions.
Fangorn with Legolas - nope, I'd be dozing off constantly as he tried to make friends with each tree.
Hm, ah, hoom. I think I'd like the Ithilien trip with Sam. Back-packing for a week, in the Springtime, with lots of rest stops along the way to simply sit and take in the visual and olfactory delights. With breakfasts and dinners cooked by Master Chef Sam, and simple lunches of the local fruits and sandwiches made with tomatoes and left-over nice, crispy bacon and just-plucked herbs. With a special two-night visit to the Window on the West (now a hostel)!
My vacation package specifies a twilight arrival accompanied by a choir of elves tra-la-la-lallying to customised nonsensical lyrics guaranteed to amaze and annoy, followed by a sprinkling of rude remakes such as, "Just look! Lissuin the old lady on a pony, my dear! Isn't it delicious!" As long as there are bright lanterns waiting as I lead my pony across the bridge over the river to find the doors of the Last Homely House flung wide, they can sing any silly old thing they like!
Even though we had no ponies and found our own way over miles of rock and scree (but, disappointingly, no skull avalanches). We did escape unscathed, and I don't think we starved, did we? We made it! There are, indeed, many definitions of "vacation", and one's choice of companion is not an unimportant element to its success. Cheers, mate!
I was conflicted between that and a trip to the Shire with Bilbo as my guide, but I just love Rivendell and Elves too much to pass up on an opportunity like that. There would be fine music, incredible scenery, places of historical interest, museums, art, gardens, libraries, fine dining - everything I could possibly want. Aragorn would be an excellent tour guide, too.
Though I wouldn't mind stopping in at Thranduil's Caverns with Legolas, either - I've always wanted to know more about the realm of the Wood Elves.