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6 month journey starting SE Asia, ending in Spain

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My wife and I are taking a 6 month journey through SE Asia and Spain. Should I post our list of places we are visiting in each specific forum related to the country?

We start in mid March and end in mid August

1) Singapore
2) Bus to Kuala Lumpur
3) Bus to Penang
4) Fly to Phuket - beginning of April
5) Ferry to Koh Phi Phi
6) Fly to Koh Samui
7) Ferry to Ko Phang nan
8) Ferry to Ko Tao
9) Flight to Bangkok (from Koh Samui)
10) Fly to Vienna - beginning of May
11) Train to Zagreb
12) Bus to Plitivce
13) Bus to Zadar/Sibenik
14) Bus to Split
15) Ferry to Hvar Island
16) Ferry to Vis
17) Ferry back to Split, bus to Dubrovnik
18) Ferry to Mljet and Korcula
19) Ferry back to Dubrovnik
20) Dreaded overnight ferry from Dubrovnik to Bari, train to Sorrento
21) Train to Rome
22) Train to Florence
23) Train back to Rome, flight to Santorini - mid June
24) Santorini then ferry to Crete
25) Crete for a week
26) Flight to Thessaloniki


27) Drive to Meteora (not sure how long to stay or if it's just a days visit to see monasteries)
28) Drive to Pelion (how many days?)
29) Drive to Delphi
30) Drive to Galaxidi
31) Drive to Nafpaktos
32) Drive to Olympia
33) Drive to Lakonia
34) Drive to Navplion
35) Drive to Athens
36) Fly out from Athens to Barcelona - mid to late July


Based on the timeline, we want to finish in Spain/Portugal (I have not done so much research on Spain yet so not sure if train or buses are best way to get around the cities)

37) Barcelona
38) Train to Valencia
39) Granada
40) Seville
41) Lagos
42) Lisbon..fly home from Lisbon

General questions:

1) We had to include SE Asia due to the "Schengen" zone and not being able to stay there for more than 90 days, no way around this right?

2) I have a shellfish allergy. Is it possible to still survive in SE Asia? I'm getting a laminted card in Thai language to demonstrate this

3) Do you need a car on Phuket? or will a scooter suffice?

4) How do we go about getting travellers insurance?
38)

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