Sunny holiday for September - no idea where to start

[NotMeNoNo]

I'm looking at going on holiday with my 20 yo son in mid-September this year. We want a beach holiday, maybe Greece/Spain? We don't really want a huge crowded hotel or Ibiza-esque nightclubs but somewhere a bit more quiet we can explore the countryside/heritage - DS is ND and gets a bit anxious. Ideally self catering or B&B and some sort of accommodation with 2 rooms like a small apartment. I know all about camping and UK holidays but we've never done a package holiday.
Our nearest airport is East Midlands. I've looked on Jet2 and Tui but there is just too much choice and information. How do you narrow it down to a resort or hotel? What is a realistic budget - could we get a week for under £1500 for both of us? Should I try a travel agent?

I narrow it down based on these factors:

• trip advisor 4 plus
• 5 star hotel
• flight time
• transfer time (some times they are 2 hour transfer which we refuse to do after a flight)
• al carte restaurants if going half board or more
• beach front

i think it’s worth working out what you want and none negotiables and maybe seeing a travel agent. I will reduce to a 4 star hotel if our price range doesn’t match but might as well start high 😂

if you prefer self cating have you looked at Airbnb? We used it for a trip to France.

When i have looked before I haven’t found many all inclusive to Italy, most are bed and breakfast. That could be a good place to look.

I narrow it down by
Flight departure time
Flight return time
Length of flight
Distance from destination airport to resort / hotel
4.5 minimum on TripAdvisor
Hotel room must have sea view

Do you want to hire a car? If not and you want to sightsee then look at the local transport network

It would be better to choose the country at least. So if you chose Spain that narrows it down a bit!

£1500 is realistic yes.

Are you bothered about journey time? If so, non Canaries Spain is about an hour and a half closer than Greece, so that might be one way to narrow it down.

Is it important to be close to the sea? That's another thing to consider. If you want eg a 5 minute walk max it'll rule a lot out.

Also, will you hire a car or would you want to explore using public transport and booked excursions? If you need proximity to a bus stop then that also narrows it down.

Lastly, I wouldn't rule Ibiza out! Especially if you're going towards the end of September. Some quieter places on the north coast in particular. Cliff walks, little villages inland, that type of thing. Just avoid the really buzzy places like San Antoni.

There are plenty of apartments on jet2, you can still book package for peace of mind. Will you want to hire a car to explore? If not you'll need to work out how to get around.

Mallorca is lovely, fly to Palma, have a couple of nights there then take the train to Port De Soller. I think you will find everything you hope for and within your budget.

Look at Paphos area of Cyprus. We went last September using Villa Select.

https://www.booking.com/hotel/es/apartamentos-los-alisios.en-gb.html?label=en-gb-booking-mobile-ItlRyWOkYEZAOpVWzsYMmQSM652796016126%3Apl%3Ata%3Ap1%3Ap2%3Aac%3Aap%3Aneg%3Afi%3Atikwd-334108349%3Alp9045119%3Ali%3Adem%3Adm&aid=2311236&ucfs=1&arphpl=1&checkin=2025-09-15&checkout=2025-09-22&dest_id=92968&dest_type=hotel&group_adults=2&req_adults=2&no_rooms=1&group_children=0&req_children=0&hpos=1&hapos=1&sr_order=popularity&srpvid=334695e7288d050d&srepoch=1750108753&all_sr_blocks=9296804_88193345_0_0_0&highlighted_blocks=9296804_88193345_0_0_0&matching_block_id=9296804_88193345_0_0_0&sr_pri_blocks=9296804_88193345_0_0_0__62370&from_sustainable_property_sr=1
We have stayed here a couple of times and had lovely holidays. 15 minutes from the airport, 10 minute walk to the beach and literally hundreds of restaurants.

I've not done this yet myself but have heard from a couple of friends that they had a good experience going into a travel agents....no more expensive than online and an actual person to guide you...rather than endless scrolling. Good luck!

Thanks this is all helpful!

Just came back to say, thanks we have booked with TUI in Rethymno, Crete. Filtered by 4* reviews and found a 9 days holiday in an apartment with 25% off. It's quite a long transfer from the airport but will be on Tui's coach and I presume everyone checks in even if we arrive in the middle of the night? Really looking forward to something different now.

Only question is that DS wants to be able to do sports, there isn't an activity program as such but I guess we can play table tennis or use the local sports clubs or kick around on the beach.

Rethymnon is a lovely town.
Just watch out when swimming in the sea. I haven't been for many years but do remember very strong currents /rip tides and no lifeguards or flags, they probably have those now.

Amazing, hope you have a lovely time

DS isn't a confident swimmer so I guess the sea will be for paddling if anything, hotel has pools too.

Also I'm hoping - knowing no Greek language won't be a problem? And we will be able to find suitable food for someone who has eaten the same tuna sandwich lunch and about 5 dinners on rotation for the last 3 years. We are on B&B with a kitchenette.