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.

I have experienced all the facets of traveling with children. I have traveled with my few months old baby, with a toddler, preschooler and with a school age kid. All of them are different, each requiring attention to detail to make sure that you have a good family vacation from the moment you start to the time you return.

Traveling with Babies: I would consider a baby from new born to 2 years old

• Make sure that when you pack their luggage you have plenty pacifiers on hand and their favorite stuffed toy or blanket that he/she likes to sleep with. Pack plenty clothes to change them, favorite toys to make them feel at home. If you are heading to the beach: hats, sunglasses, sun screen and mosquito repellent for sure.

• When the airplane is taking off, make sure that you feed the baby, the sucking action prevents ear ache due to the change in air pressure. If baby does not need food, use a pacifier, this will make them more comfortable.

 

• I would recommend to have with you on the airplane a bag just with the baby items: baby formula, bottle of water, (check the TSA web for details https://www.tsa.gov/travel/special-procedures/traveling-children) change of clothes, baby snacks,  toys, diapers, pacifiers, cream for  diaper rash , wet wipes, and any medication that your child might be taking.

Traveling with Toddlers: I would consider a toddler from 2 to 4 years old

• Toddlers are more independent and very active, so make sure that you have their favorite toys, clothes and planned activities to keep them occupied while they wait in the airport, in the check-in line at the hotel and so. Some kids love electronics (tablets, phones) but some love to color, read or play with toys; choose something that your child will enjoy and make you feel more relaxed during all this process.

 

• Make sure that you pack for them: tooth brush, tooth paste, comb, plenty clothes because they will need to change clothes many times. Of course if you are heading for the beach, they need the same items that babies need.

 

• They will still look for their favorite blanket or stuffed toy to sleep with so make sure you bring it with you

 

• Plenty snacks to keep them well feed to prevent tantrums

​Traveling with young kids: I would consider kids from 5 to 7 years old on this group.

• At this age they are already going to school so they are more tolerant with the waiting time at airports and hotels but still need to be distracted. At this age I would say it is very important to have either a book to read or a tablet where they can play video games appropriate to their age.

 

• You won’t need to pack extra clothes since they don’t get as dirty as toddlers, but make sure that they choose the clothes that they are taking. They show more their personality at this range of age and they like to dress in their own style.

 

• Bring their favorite snack, their favorite hat, dress, shirt or short. This lets them feel special and close to home. Travelling is always a stressful time for all of us, so let’s make it easy on our kids with little details from home.

​Traveling with older kids: I would consider kids from 8 to 18 years old on this group.

• This group age for sure will pack their own luggage, make sure that they don’t carry too much, that everything is in compliance with TSA if it is a carry-on or that is within the weight limits per luggage.

 

• Plan activities ahead of time, excursions that appeal to them, let them be involved in the process of choosing them so they feel that they are contributing to make this trip memorable for all the members of the family.

 

• Give them their own space, this means set hours per day where they will choose what to do. Resorts in the Caribbean have many Arcades and activities for kids this age, the same with cruises. This is a time for them to meet other kids their age and interact with them, this is crucial for kids that do not have siblings.

 
Happy travels!

​According to Cruise Critic families have the following categories to choose from:

Best cruises for Romance:
​
1.-Windstar cruises: Their three intimate motor-sail-yatchs offer luxurious touches like fine dining, fine linens, L’occitane toiletries, personal service and  itineraries in the Caribbean and French Polynesia with plenty time in ports that allow honeymooners to have a great time discovering the marvels of each one.
Their three regular yachts (with no sails) offer itineraries in Panama Canal, Europe and Asia
 
2. - Paul Gauguin Cruises: They specialize in the idyllic South Pacific Islands such as Tahiti, Fiji, Cook Islands. They cruise all year around and are the favorite line for honeymooners, couples celebrating anniversaries or looking for a romantic escape. Their itineraries offer stops in remote islands with plenty time to lie in the tropical sun.
 
3.- Princess Cruises:  Well-known cruise line for the  Love Boat TV show, offers couples seeking romance, alfresco balcony dinners for two, several dinning venues for a date night and adults-only  sun decks with spa-like atmospheres.

Best for families with young kids:

1.- Disney Cruise Line: They offer nurseries for babies starting at 3 months old, themed play space for preschoolers and school-age kids; plenty Disney character interaction and cabins that cater to families with split baths ( with tubs), extra berths, room dividing curtain, child proof balcony locks.

2. - Carnival Cruise Line: Their kids program starts at 2 years old, plenty food options for kids, water slides and aqua parks. They also offer the interactive “Hasbro, the Game show”, “Seuss at the Sea” and some of the largest standard cabins in the industry for families.
​
3. - Royal Caribbean International: Another favorite line among families. This cruise line is a leader with innovative kid programming and expansive youth facilities. Their partnership with Dream Works brings the characters that the little ones love to parties, parades and photos.

Best for families with older kids:

Royal Caribbean International: Teens have rock climbing walls, on board surfing, DJ classes. Zip lines, shows, and teen’s clubs.

Norwegian Cruise Line: Teens appreciate no set dining times, no strict dress code, plenty choices in entertainment and food. Teen’s club offers game stations, exclusive parties, water parks, outdoor sports, Musical venues and shows.

Carnival Cruise Line: They offer separate tween and teens clubs, shore excursions just for 12 to 17 year old chaperoned by the youth staff. They also have water parks, mini golf and outdoor movie screens.

Best Cruises for seniors:

1.-Holland America: Has midsize ships and appeals to mature travelers with their traditions like: Afternoon tea, ballroom dancing, gentlemen host and with their focus on cooking and technology classes.

2.-Cunard Line: Is a line for a classic cruising. They offer the only regular season of transatlantic crossings on its flagship Queen Mary 2. This is full of ballroom parties, formal dinners, jazz concerts and so on.


Resource: cruisecritic.com. Cruising 101. How to pick a cruise line by Roxanne Wells, updated on December 11 2017