Fly Southwest: RSW to Oakland, California

The radiant and warm Florida sun bid you farewell as you tighten your seatbelt and feel the familiar thrill coursing through you - you're on another adventure. Destination: the vibrant city of Oakland, a gem in the crown of California's Bay Area. This time, you are traversing the vast American skies with Southwest, renowned for its admirable mix of comfort, service, and affordability, its flight deals always reasonably within reach.

In planning your journey, the best time to book for the enticingly low Southwest fares emerges in your focus. The airline's dynamic airfare structure leans towards those who are early to reserve their seat, yet offers some comforts to the latter, spontaneous spirits with last-minute flights. Just a few clicks, and you'll be securing a one-way ticket from Fort Myers to Oakland. If you possess the traveler's nostalgia, you may opt for a round-trip ticket, confident in the return to the warm Florida embrace.

Southwest's array of flight schedules provides several choices between direct flights and connecting flights. Should you prefer a seamless journey, look for the non-stop option. Yet, should you wish for a pause to stretch and breathe – a layover – then a connecting flight can be quite relaxing. The balance between flight duration and comfort becomes easier with Southwest.

The next pivotal factor is the class of your ticket. Southwest offers simplicity in its class configuration; it’s economy all the way! However, the economy class does not lack the creature comforts. The aircraft's interior is spotless, seats ergonomically designed to cradle you in utmost comfort, and the warm, inviting smiles of cabin crew add to the experience. Even the frequent flyer can't resist the appeal of Southwest’s premium economy; this oft-taken route has become a beloved home amidst the clouds.

For the wary traveler who frets about the cost of luggage, Southwest's baggage allowance policy is like a cooling summer breeze on a humid day. Your first two check-ins are free, a rarity amongst domestic flights, allowing you to pack in a few extra essentials without worry.

Being part of Southwest's mileage program, Rapid Rewards, a peaceful journey begins to paint itself in your mind. You can accrue points on each travel leg, irrespective of how cheap flights were when booked, eventually translating them into future flights or upgrades - earning while flying never felt so satisfying.

Apart from generous legroom and warm cabin service, in-flight services on Southwest carry a distinct charm. From a range of snacks to a variety of entertainment options at your fingertips, time might just slip away before you realize.

There is also the tranquility that Southwest’s flight cancellation policy offers - a hassle-free reimbursement procedure or option to use the amount for future travel. Even a red-eye flight from Fort Myers to Oakland seems less daunting when you know how Southwest operates - placing its passengers' needs first.

In essence, the journey from the gorgeous beaches of Fort Myers to the lively streets of Oakland on Southwest is an embodiment of American spirit - warm, accommodating, and always looking forward. What more could a traveler ask for? So sit back and allow the anticipation to build. After all, at the heart of every travel shift lies not just the destination but the journey. And with such a supportive companion like Southwest to accompany you, no doubt the outlook is bright and exhilarating.