Anytime we have flown Southwest, you do not have a seat number, passengers choose their seating as they board. Make sure you board when they announce family boarding and while you are waiting, I would suggest that you wait near the door for your flight.
NO.
No, the OP does not need to board when family boarding is announced, unless they happen to have children
under whatever age the gate attendants specify (usually
under five, but to/from Orlando, frequently reduced to
under three - due to the vast number of parties with young children). It appears from the OP's signature that their party consists of two adults in their twenties, no children of any age, making them ineligible for family boarding.
Never ever ever wait near the door for your flight. EVER. Unless "near the door" means "seated in the correct gate area". PLEASE. This only clogs the process and delays boarding. The Gate Agents know what they're doing. Listen to the announcements and follow the instructions.
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Speaking of instructions: Southwest's boarding is unique in that they don't preassign seats. They DO, however, have a very organized procedure.
You will get a boarding pass with a boarding letter
AND NUMBER on it. The letter will be A, B, or C - as Southwest has been doing for many years. The numbers will be 1-60 on the A boarding passes, 1-60 on the B boarding passes, and 1-whatever the remaining number of seats are on the C boarding passes. Note that this is for originating flights only. Continuing flights will have fewer open seats, so the BPs will naturally be divided into smaller groups.
There are numbered posts in the gate area. Each post is numbered by fives: 1-5, 6-10, 11-15, etc. At boarding time, medical need travelers and business travelers board first. Then the A boarding pass holders will be asked to line up next to the appropriately-numbered pole
in numerical order. They board and choose seats.
Then the
immediate families with small children who did not have "A" boarding passes board. Following them, the "B" boarding pass holders line up next to their number posts like the "A" bp holders did, followed by the "C"s, followed by any latecomers.
Yes, you can check in for your return flight from your mobile device. There may be an app, but just accessing Southwest's mobile website is fine. If you're staying in almost any Disney resort (two exceptions, one is OKW, reason for both exceptions is lack of luggage storage space) you can use RAC to check in for your Southwest flight and check your luggage through to your home airport
even if you're not using Magical Express to get to the airport. See the RAC counter for more information.
If you're not staying onsite, or you're staying at one of the exception resorts, you can go to Lobby Concierge at any resort or Guest Relations at any park 24 hours before your flight and they'll check you in. Be sure to have your reservation information.