How to book your family vacation without breaking your bank account!

Based on the information provided to me by my host agency, KHM Travel Group and my experience booking my customers trips I will say:
 
Winter Months: From December 21 to March 19th 2018
 
If you don’t mind the cold weather this is the best time price wise to go to Europe and South America. In Europe it will be winter like here but in South America it is Summer and you can enjoy their beautiful beaches.
All the Caribbean will have great discounts during these months, some resorts offer 40%, 50% sometimes even more when running a promotion.

Peak travel
 

• Christmas: starts around December 18 and finishes around January 3
• Valentine’s Day: the week around February 14
• Martin Luther King Jr. Day
• President’s Day

 
Best value weeks for winter travel:

• First two weeks of January
• First week of February
• Last week of February

Spring Months: From March 20th to June 20th 2018

During the Spring months you can still have a very good value for your investment since you will be travelling before the peak season, that time here in America is all summer.
Europe and South America start their peak season in these months, to take advantage of the extra perks and good prices, make sure you book your trip at least 6 months prior to your trip.
Cruises offer great promotions, so it is probably the best time to go on one.

Peak Travel:

• Easter: this varies every year, sometimes it is in March and others in April. Since schools are out, it is a very high season for travelling. Don’t wait to the last minute to book, do it at least 4 months ahead to make sure that you have the option to choose the hotel that you want and your room category.

During this Spring Break there will be many promotions for the Caribbean but to take advantage, look for them around November or December to get the best value for your investment.
 
Summer months: From June 21st to September 21st

This is the busiest time of the year for travel. Book your family vacation at the end of December no later than February to make sure that you take advantage of the early bird discounts, kids stay free promotions and so on.

Peak travel:  All summer

Best value weeks:​

• First week of June
• Last week of July
• Second, third and fourth week of August

Fall months: From September 22nd to December 21st

After the summer peak season, hotels will have wonderful discounts and extra perks during this time, for me in particular is the best time of the year to take vacations with your friends and loved ones.

Peak travel:

• Labor Day
• Rosh Hashanah
• Halloween
• Thanksgiving Week

Best value weeks

• Second, third and fourth week of September
• First two weeks of October
• First two weeks of November
• First two weeks of December

Hurricane season June 1- November 30 

Reference:
Peak Season Calendar in Travel Agent Portal. Khm Consulting Inc.