DISCLAIMER: The Professor's wonderful characters don't belong to me; I just get to think about them day and night.
Author notes: Appendix B of The Return of the King states, "…the tradition is handed down from Elanor that Samwise passed the Towers, and went to the Grey Havens, and passed over Sea, last of the Ring-bearers." Although it's assumed that Sam sailed from Middle-earth the same way Frodo did, the Professor doesn't exactly say that, does he?
My view of why and how Bilbo is still alive and well in the West can be found in "Sing Me Home" (chapter 5) and "The Path to Healing" (chapters 1 and 7). A description of the hobbits' home on Tol Eressëa is in "The Path to Healing" (chapter 1). There are lines in Chapter One of this story from The Hobbit and The Silmarillion.
Chapter 1: One Fine Day On Tol Eressëa
Sam had long ago made up his mind that, though boats were maybe not as dangerous as he had been brought up to believe, they were far more uncomfortable than even he had imagined. 'The Great River', The Fellowship of the Ring
Frodo awoke to a room awash in light, the warm sun streaming through his window. He heard Bilbo whistling, as he did when especially pleased about something. Bilbo's so happy here, Frodo thought contentedly, and he's still eager to greet each new day, which is all that matters. Sam used to whistle like that. I wonder how much time has passed in Middle-earth? I wonder what he'll decide to do, when his time comes?
"Make whatever decision brings you peace, dear Sam," Frodo said quietly, then smiled at his foolishness; he often spoke to Sam as if his friend was at his side, and had been doing so quite a bit recently. He sat up and stretched, unsurprised that he had slept so late. He had walked for miles along the sand until nearly dawn, feeling strangely restless.
After washing up, and donning his favorite soft blue tunic and a pair of fawn-brown breeches, he entered the airy kitchen to find Gandalf sitting at the round table in one of the large guest-chairs. The wizard still came and went "exactly when he meant to," as he had declared long ago. He traveled with Shadowfax far and wide, welcomed wherever he went. 'Gandalf' he remained to the hobbits, as well as the Elves who had known him in Middle-earth. He laughed often, and gave wise counsel when asked.
"Good morning," the wizard said, his eyes twinkling.
Frodo grinned mischievously.
"Do you wish me a good morning, or mean that it is a good morning whether I want it or not; or that you feel good this morning; or that it is a morning to be good on?"
Gandalf threw back his head and laughed. "What am I to do with you Bagginses?"
"Enjoy our company," Frodo said cheerily. "I heard Bilbo outside in the orchard; we're planning to bake pies for our birthday." He went to the stove where a kettle of water nearly always sat on heated bricks, and began to prepare one of the fragrant local teas he had grown to love. "Have you eaten?"
"Your uncle has stuffed me to the bursting point," Gandalf assured him. "You're looking well."
"I need a haircut… again!" Frodo sighed. His hair, and Bilbo's, seemed to grow as quickly as the vegetables in their garden, and he often tied it back with a thin strip of leather.
Gandalf observed Frodo for a long moment. His fair skin was lightly freckled now from the sun, and there were laugh-crinkles at the corners of his remarkable eyes. Although still-glossy black curls were now laced with silver, the years had thus far touched him very gently.
"Sit down, dear lad. There is something I need to discuss with you."
"Hardly a lad any longer," Frodo smiled, still bustling about the stove. Bilbo had left a stack of hotcakes warming for him. "I must be older than eleventy-one by now; I'll have to work it out sometime."
"One hundred fourteen, to be precise," the wizard said, "but still a youngster, as the Elves measure time."
Frodo began loading hotcakes onto a plate. "It's wonderful to see you. What did you want to talk about?"
"Oh!" Frodo's heart raced in sudden fear. "He hasn't… I mean, he's not--"
"No, he's not," Gandalf assured him. "Sam is fine, Frodo."
Frodo sat down hurriedly, his enormous eyes never leaving the wizard's face.
"Rose has passed on," Gandalf said gently, "and Sam has made the decision to join you here."
Frodo was silent for a few moments, remembering how happy Sam and Rose had been. His heart ached for his friend.
"I've been thinking about him so much recently," he said at last. "He'll find all the healing he needs in this wonderful place. When does the ship dock?"
"That is what I wish to talk with you about," Gandalf said. "As you experienced first-hand, mortal flesh unaided cannot travel the Straight Way. Do you remember how Elrond and I were with you and Bilbo when the Bent Seas were left behind?"
"Of course," Frodo said, confused. "But Sam--"
"There are Elf-lords still in Middle-earth, but none who are ready to sail at this time… none who have the skill to ease his passage."
"But he must sail, before it's too late!" Frodo said in distress. "I promised him!"
"And sail he will," Gandalf said. "I know this may sound quite incredible, but... Eärendil himself will be bringing him most of the way."
"What?" Frodo gasped, dropping his fork with a clatter. "But his ship travels among the stars. Won't Sam freeze to death? How will he breathe? How would he get up there in the first place? I don't--"
Gandalf held up his hand to stop the torrent of questions.
"It has all been arranged."
Frodo stared at him in amazement, completely forgetting about his breakfast cooling in front of him.
"Does Bilbo know?"
"I told him this morning. I believe he is already composing a new poem."
"That explains why I heard him whistling so joyously," Frodo said, still trying to absorb the news. "But how will Sam know what's being planned, and what he needs to do? I don't want him to be afraid."
"Everything will be explained to him, by those whom he will welcome and trust," Gandalf assured him.
"And who will explain it to me?" Frodo asked in good-natured frustration, causing Gandalf to chuckle quietly. "When is all this to happen?"
The wizard closed his eyes. After a moment, he nodded to himself.
"Today?" Frodo gasped.
"Near enough." Gandalf opened his eyes. "We have much to prepare, my friend. There has already been quite a flurry of communication between Lord Manwë's messengers."
"There has?" Tears filled Frodo's eyes. "Such great beings are doing this… for us?"
"Indeed they are," Gandalf said fondly. "Every measure is taken to assure that mortals permitted to live here will arrive safely, however they travel… and that they will be cherished for as long as they live."
"So that's the only reason you keep such a close eye on Bilbo and me," Frodo teased. "Because Lord Manwë decrees it."
"Of course! Why else would I have entwined my life and heart with hobbits?" Gandalf held out his arms, and Frodo left his chair to embrace him.
"Sailing through the sky," Frodo murmured, shaking his head in wonder.
"For Samwise, perhaps the best way of all," Gandalf smiled. "As I recall, he loves not water craft."
"He doesn't," Frodo said firmly. "Or, at least, he didn't. Oh, I have so much to ask him about the years we've been apart."
"The one thing he will not be able to tell you about is his journey here," Gandalf said solemnly. "He will be put into a sleep for the passage; it is not for mortal eyes to see from the vaults of heaven."
Frodo nodded up at Gandalf earnestly.
"He wouldn't be able to see anything anyway, with that great jewel blazing just a few feet away."
"Plain hobbit sense," Gandalf nodded sagely. "Surely the only thing the Blessed Realm was lacking."
"Perhaps so!" Frodo agreed. He returned to his seat, his face glowing with excitement.
"Now, tell me everything!" he insisted, digging into the pile of hotcakes.
** TBC **