14 days in United States & Caribbean Itinerary

14 days in United States & Caribbean Itinerary

Created using Inspirock trip itinerary maker

Make it your trip
Fly
1
Key Largo, United States
— 2 nights
Fly
2
Ocho Rios, Jamaica
— 1 night
Drive
3
Negril, Jamaica
— 2 nights
Fly
4
Oranjestad, Aruba
— 3 nights
Fly
5
Port-au-Prince, Haiti
— 1 night
Fly
6
Fort-de-France, Martinique
— 2 nights
+2
Drive to Martinique Aimé Césaire International Airport, Fly to L.F. Wade International International Airport, Drive to Hamilton Parish
7
Hamilton Parish, Bermuda
— 2 nights
Drive to L.F. Wade International International Airport, Fly to Louisville Muhammad Ali International Airport

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Key Largo, United States

— 2 nights

Diving Capital of the World

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Venture out of the city with trips to Marathon (Sombrero Beach & The Turtle Hospital). There's much more to do: see what you can catch with a fishing tour, identify plant and animal life at Spiegel Grove, sample the tasty concoctions at Islamorada Brewery & Distillery, and admire the majestic nature at John Pennekamp Coral Reef State Park.

To find photos, reviews, and other tourist information, use the Key Largo vacation planner.

Louisville to Key Largo is an approximately 6.5-hour flight. You can also drive; or do a combination of bus and shuttle. In May, Key Largo is a bit warmer than Louisville - with highs of 85°F and lows of 72°F. Cap off your sightseeing on the 25th (Tue) early enough to travel to Ocho Rios.

Things to do in Key Largo

Parks · Wildlife · Nature · Outdoors

Side Trips

Find places to stay May 23 — 25:

Ocho Rios, Jamaica

— 1 night
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Kick off your visit on the 26th (Wed): take in the dramatic scenery at Dunn's River Falls and Park, stroll around Konoko Falls, then admire the sheer force of Blue Hole, and finally pause for some serene contemplation at Our Lady of Fatima Catholic Church.

To see traveler tips, ratings, where to stay, and other tourist information, read our Ocho Rios road trip website.

Getting from Key Largo to Ocho Rios by flight takes about 8 hours. In May, daytime highs in Ocho Rios are 89°F, while nighttime lows are 77°F. Finish your sightseeing early on the 26th (Wed) so you can drive to Negril.

Things to do in Ocho Rios

Parks · Nature · Historic Sites
Find places to stay May 25 — 26:

Negril, Jamaica

— 2 nights
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Start off your visit on the 27th (Thu): relax and rejuvenate at some of the best spas, enjoy the sand and surf at Seven Mile Beach, and then surround yourself with nature on Kingsley's Take Care Tours - Day Tours.

Take the guesswork out of planning a Negril vacation by using our trip itinerary maker.

You can drive from Ocho Rios to Negril in 3 hours. Other options are to drive; or take a bus. In May, plan for daily highs up to 90°F, and evening lows to 75°F. On the 28th (Fri), you'll have the morning to explore before heading off to Oranjestad.

Things to do in Negril

Outdoors · Beaches · Parks · Wildlife
Find places to stay May 26 — 28:

Oranjestad, Aruba

— 3 nights
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Explore Oranjestad's surroundings by going to San Nicolas (Baby Beach & San Nicolas Community Museum). And it doesn't end there: kick back and relax at Eagle Beach, stroll through Aruba Ostrich Farm, visit a coastal fixture at California Lighthouse, and get a new perspective on things with Boat Tours & Water Sports.

For ratings, reviews, traveler tips, and tourist information, read Oranjestad trip itinerary builder.

Traveling by flight from Negril to Oranjestad takes 11.5 hours. You'll lose 1 hour traveling from Negril to Oranjestad due to the time zone difference. May in Oranjestad sees daily highs of 90°F and lows of 80°F at night. Finish your sightseeing early on the 31st (Mon) to allow enough time to fly to Port-au-Prince.

Things to do in Oranjestad

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay May 28 — 31:

Port-au-Prince, Haiti

— 1 night
Port-au-Prince, the capital of Haiti, gives most visitors their first taste of the country, along with all of its rugged and lively charm.
Start off your visit on the 1st (Tue): stop by Comite Artisanal Haitien, see the interesting displays at The Bureau of Ethnology, then see the interesting displays at Musee du Pantheon National Haitien, and finally hunt for treasures at Marche de Fer.

For photos, maps, traveler tips, and more tourist information, go to the Port-au-Prince trip maker tool.

Traveling by flight from Oranjestad to Port-au-Prince takes 6.5 hours. Traveling from Oranjestad to Port-au-Prince, you'll gain 1 hour due to the time zone difference. Expect a daytime high around 89°F in May, and nighttime lows around 78°F. Cap off your sightseeing on the 1st (Tue) early enough to travel to Fort-de-France.

Things to do in Port-au-Prince

Shopping · Museums
Find places to stay May 31 — Jun 1:

Fort-de-France, Martinique

— 2 nights
The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
Kick off your visit on the 2nd (Wed): steep yourself in history at Habitation Clement, take in the spiritual surroundings of St. Louis Cathedral, then get your bearings at Schoelcher Library, then take in nature's colorful creations at Jardin de Balata, and finally soothe aching muscles at Sylvie Esthetique.

For traveler tips, more things to do, reviews, and other tourist information, read Fort-de-France trip planner.

Fly from Port-au-Prince to Fort-de-France in 6.5 hours. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. Traveling from Port-au-Prince in June, you will find days in Fort-de-France are little chillier (87°F), and nights are about the same (77°F). Finish up your sightseeing early on the 3rd (Thu) so you can travel to Hamilton Parish.

Things to do in Fort-de-France

Historic Sites · Spas · Parks

Side Trips

Find places to stay Jun 1 — 3:

Hamilton Parish, Bermuda

— 2 nights
Hamilton Parish is one of the nine parishes of Bermuda. Start off your visit on the 4th (Fri): learn about wildlife with up-close encounters at Bermuda Aquarium, Natural History Museum & Zoo, enjoy the sand and surf at Horseshoe Bay Beach, and then kick back and relax at Warwick Long Bay Beach.

To find more things to do, where to stay, maps, and other tourist information, refer to the Hamilton Parish trip site.

The Route module can help you plan travel from Fort-de-France to Hamilton Parish. Traveling from Fort-de-France in June, you will find days in Hamilton Parish are little chillier (81°F), and nights are about the same (73°F). Wrap up your sightseeing by early afternoon on the 5th (Sat) to allow enough time to travel back home.

Things to do in Hamilton Parish

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trips

Find places to stay Jun 3 — 5:

United States travel guide

4.5
Specialty Museums · Beaches · Historic Sites
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.

Jamaica travel guide

4.1
Waterfalls · Beaches · Nightlife
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.

Aruba travel guide

4.3
Beaches · Scuba & Snorkeling · Gift & Specialty Shops
Happy Island
A Dutch outpost in the Caribbean, sun-drenched Aruba provides a mix of modern seaside resorts and quiet coastal areas ideal for those wishing to escape the crowds. Vacations in Aruba, known affectionately as the "Happy Island," generally combine water-based activities with tours of the untamed backcountry, where you can discover unusual rock formations, historic churches, ostrich farms, and animal sanctuaries. Island capital Oranjestad offers some of the finest shopping and cultural sightseeing in Aruba, with an eco-friendly electric streetcar providing quick access to all of the city's major attractions, including numerous shops, restaurants, and hotels.

Martinique travel guide

4.4
Beaches · Gardens · Scuba & Snorkeling
The mountainous island of Martinique offers travelers everything from stunning natural landscapes, to vibrant towns and enticing cuisine. The island's varied scenery includes numerous scenic beaches, lush forests, and a majestic volcano that towers over the St. Pierre harbor. A range of activities await you on your Martinique holiday, allowing you to spend your days lounging on the sand and enjoying the azure waters, sampling gastronomic delicacies, or frequenting the shops, clubs, and cafes in the capital city of Fort-de-France.

Bermuda travel guide

4.1
Beaches · Caves · Scenic Walking Areas
The tropical "island" of Bermuda is actually a number of islands connected by road bridges and surrounded by numerous islets and cays. With access to everything from upscale resorts and quaint seaside inns, to tranquil pink-sand beaches and secluded snorkeling spots, a holiday in Bermuda appeals to most vacationers, regardless of age or budget. Although known as a place to relax, you'll find plenty of things to do in Bermuda. Partake in dynamic nightlife of the capital city, explore scenic hiking trails, or roam the narrow streets of St. George, the oldest British town in the New World.