The Caribbean
TV hosts
Classic games by the piece
Precipitation
Hotel elite
400

The capital of the Bahamas is this city

Nassau

400

The Voice; Country singer (guy)

Blake shelton

400

Five armies of varying color

Risk

400

Falls in the summer; ice 

Hail

400

The first hotel listed on the Marriott chain family of brands. It is listed even above St. Regis and Ritz Carlton. 

Edition

800

The Virgin Islands are divided into the British Virgin Islands and what

USVI or US Virgin Islands 

800

The tonight show

jimmy fallon

800

Rook

Chess

800

Falls in the winter; ice 

Sleet

800

The Willard in Washington DC is an example of this upper class IHG hotel.

Intercontinental

1200

This island east of Florida is home to Virgin Voyages beach club and resorts world.

Bimini

1200

Today with ...

Hoda (Kotb) and Jenna (Bush)

1200

Pop-arazzi. Also lists and sheets with columns.

Scattergories

1200

Falls in the winter; rain then ice(upon contact)

Freezing rain

1200

This upper class IHG hotel shares the same name as my school besides one letter.

Regent

1600

the capital of Cuba 

Havana

1600

Wheel of fortune(2)

Pat seajack  and Vana white

1600

Draw two (+2)

Uno

1600

Falls in the winter; fun to play in; soft; white

snow

1600

The highest listed Hilton hotel.

Waldworf Astoria

2000

The island with Haiti and the Dominican Republic is called what?

Hispaniola

2000

Fixer upper

Chip and Joanna Gaines

2000

metal minifigurines;boardwalk

Monopoly

2000

Falls year round; wet

Rain

2000

The top hotel on the Sonesta chain is basically a  Sonesta given a more glorified title.

Royal Sonesta