Check your sign...
Aries and Mars: activity, walking, biking, working...They need something to do! I know an Aries who insist to have active holidays. His Capricorn Ascendant leads him to mountain sides...
Taurus and Venus: lazy holidays, art and culture (drawing, painting), it is important for them to have good meals. I know a Taurus who doesn't leave without a bag full of food.
Gemini and Mercury: interesting places, trips with young folks, short trips and city trips, learning a foreign language abroad. It is important to have contact and often they need a dance floor or a dancing nearby.
Cancer and Moon: simple, not expansive and like at home (in a tent, caravan or in the house of relatives), back to the spot of last year again...Or why not stay at home or buy a home in another country (to feel at home wherever you are...). The Netherlands is a Cancer country with the highest number of caravans pro family in the world...
Leo and Sun: wants to have a party, glamour hotels and certainly not in a modest tent. Wants sunshine! Leo Ascendants like to give
Virgo and Mercury: useful trips to decent spots and virgin beaches, but why not to Switzerland (Virgo country)?
Libra and Venus: nice holidays with some luxury and comfort in beautiful areas.
Scorpio and Pluto: wild country sides, rough terrain, the challenging holiday, trips that require force or courage.
Sagittarius and Jupiter: country life (or on the balcony), exotic countries, educational trips or some place to brag about.
Capricorn and Saturn: climbing mountains, cold places, economic (...) holidays, crossing borders.
Aquarius and Uranus: group travel or with friends, city trips, something extraordinary or special (that no one else did before:), trip around the world.
Pisces and Neptune: swimming, sailing, cruises, indulging holidays but also: the trip to an isolated convent and ...going far, far away.
Signs and the position of Jupiter or placements in the houses of the movable signs (3, 6, 9, and 12) contain information about your preferences on vacation. I, for example, have Sun in Sagittarius, Moon in Aquarius and Pisces Ascendant conjunct Jupiter in 12. I am not surprised that I need to have at least a few days by or on the sea to feel that I hád a holiday. And when I have a holiday, I love to see cities, too.
I know a Capricorn boy who swears that he always wants to go to the mountains (ain't no mountain high enough!) and a Leo who refuses to sleep in a tent. How about you?
WHERE IS JUPITER?
Jupiter in 1: you could go alone or at least: find out how and what all by yourself (so you don't need this guide:)
Jupiter in 2: expenditure and value are important.
Jupiter in the houses 3, 4, 7 or 11: you prefer to go with others (family, friends) or others stimulate you to travel. While on your holiday spot, you want to have contact with other tourist or the locals.
Jupiter in 5: the pleasure of the kids is important, but... you love to travel a lot always.
Jupiter in 6: you need a purpose for a trip abroad and hygiene.
Jupiter in 8: risky and dangerous challenging trips...
Jupiter in 10: trips for your reputation or for your career or status
Jupiter in 12: going somewhere distant, incognito and whit a lot of privacy.
Of course there is more in the chart to help you select your (almost) perfect vacation. Here are some famous examples of the observations that you might take into consideration (like the ninth house, the house of traveling):
Michael Palin (the well known globetrotter) has Mars in the ninth house (work related journeys) and Jupiter in 12 in Cancer (distant travels but in a trusted environment). The ruler of Mars is Neptune in 3. The connection between the houses 3 and 9 is indicating education or publicity. It is very important to impress or be impressed (Pluto conjunct de Leo Ascendant). I wonder where he goes for holidays. I assume it will be in a secret place (12th house Jupiter) on a country side (Taurus Moon and Sun).
Princess Máxima of The Netherlands likes to make short trips to cities (Milano; Moon in Aquarius in 3). When she has a long stay abroad, she wants privacy (Jupiter in 12 in Sagittarius; she and her husband Prince William-Alexander sue AP for making pictures of them while they were skiing in Argentina) and goes far away, to exotic places (like Africa). With Neptune ruler 4 in 12 she lives in another continent since her marriage.
Agatha Christie loved to travel and she had Jupiter in the 5th house.
Angelina Jolie has Jupiter on Midheaven and the Moon in the 9th house of international traveling. She has houses (Moon) all over the world.
PS Maybe you developed a different style of traveling? Have a look at your progressive Sun sign, too, to see why. I for example had the progressed Sun in Capricorn since I was 10. The first trip that I booked was to the French Alps. (I wonder if I will do cruises only when the progressed Sun changes sign to Pisces:)
Whatever you do and wherever you go: take care and have a nice holiday to look forward to!