30 days in Mississippi & Jamaica Itinerary

30 days in Mississippi & Jamaica Itinerary

Created using Inspirock sightseeing planner

Make it your trip
Drive
1
Biloxi, United States
— 3 nights
Drive
2
Natchez, United States
— 3 nights
Drive
3
Vicksburg, United States
— 3 nights
Drive
4
Tupelo, United States
— 2 nights
Drive to Memphis International Airport, Fly to Kingston
5
Kingston, Jamaica
— 2 nights
Drive
6
Port Antonio, Jamaica
— 2 nights
Drive
7
Ocho Rios, Jamaica
— 5 nights
Bus to Discovery Bay, Drive to Saint Elizabeth Parish
8
Saint Elizabeth Parish, Jamaica
— 1 night
Drive
9
Negril, Jamaica
— 3 nights
Drive
10
Montego Bay, Jamaica
— 5 nights
Fly

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Biloxi, United States

— 3 nights

Playground of the South

A busy city on the Gulf Coast, Biloxi is one of the nation's oldest communities, first settled by Europeans in 1699.
Change things up with a short trip to Saint Rose de Lima Catholic Church in Bay Saint Louis (about 48 minutes away). The adventure continues: get a new perspective on things with Boat Tours & Water Sports, take in the spiritual surroundings of St. Michael's Catholic Church, meet the residents at The Institute for Marine Mammal Studies, and stop by Sharkheads.

To see traveler tips, ratings, more things to do, and tourist information, go to the Biloxi journey planner.

Montgomery to Biloxi is an approximately 4-hour car ride. You can also take a bus; or fly. Expect a daytime high around 88°F in June, and nighttime lows around 74°F. Cap off your sightseeing on the 4th (Fri) early enough to go by car to Natchez.

Things to do in Biloxi

Historic Sites · Parks · Fun & Games · Casinos

Side Trips

Find places to stay Jun 1 — 4:

Natchez, United States

— 3 nights
Natchez is the county seat and only city of Adams County, Mississippi, United States. Natchez is known for historic sites, nature, and nightlife. Your plan includes some of its best attractions: pause for some serene contemplation at St. Mary Basilica, stroll around Bluff Park, admire the masterpieces at Stratton Chapel Gallery, and contemplate the long history of Stanton Hall.

To find photos, traveler tips, where to stay, and other tourist information, refer to the Natchez trip itinerary planner.

Getting from Biloxi to Natchez by car takes about 4.5 hours. Other options: do a combination of bus, train, and car; or do a combination of flight and taxi. In June in Natchez, expect temperatures between 87°F during the day and 70°F at night. Finish your sightseeing early on the 7th (Mon) so you can drive to Vicksburg.

Things to do in Natchez

Historic Sites · Museums · Parks · Wineries
Find places to stay Jun 4 — 7:

Vicksburg, United States

— 3 nights
Vicksburg is the only city and county seat of Warren County, Mississippi, United States. Step out of Vicksburg to go to Port Gibson and see Windsor Ruins, which is approximately 48 minutes away. There's lots more to do: take a tour of U.S.S. Cairo Museum, take an in-depth tour of Old Court House Museum - Eva W. Davis Memorial, steep yourself in history at Martha Vick House, and stroll the grounds of Vicksburg National Cemetery.

To see other places to visit, more things to do, photos, and more tourist information, refer to the Vicksburg trip planner.

You can drive from Natchez to Vicksburg in 1.5 hours. In June in Vicksburg, expect temperatures between 88°F during the day and 70°F at night. Wrap up your sightseeing on the 10th (Thu) early enough to drive to Tupelo.

Things to do in Vicksburg

Historic Sites · Museums · Scenic Drive · Parks

Side Trip

Find places to stay Jun 7 — 10:

Tupelo, United States

— 2 nights
Tupelo is the county seat and the largest city of Lee County, Mississippi. On the 11th (Fri), steep yourself in history at Elvis Presley Birthplace & Museum, then cruise along Natchez Trace Pkwy, and then stop by Margaretes Fine Chocolates.

Make your Tupelo itinerary with Inspirock to find out what to see and where to go.

Drive from Vicksburg to Tupelo in 5 hours. Alternatively, you can fly; or take a bus. In June, daytime highs in Tupelo are 89°F, while nighttime lows are 69°F. Wrap up your sightseeing by early afternoon on the 12th (Sat) to allow time for travel to Kingston.

Things to do in Tupelo

Museums · Scenic Drive · Outdoors · Historic Sites
Find places to stay Jun 10 — 12:

Kingston, Jamaica

— 2 nights
The country's capital, Kingston offers all the excitement of a lively and storied city, while also housing the services and facilities travelers need to get around and see the rest of the island.
On the 13th (Sun), don't miss a visit to Two Sisters Cave, take in the waterfront activity at Port Royal, then stop by Chocolate Dreams, and finally appreciate the history behind Devon House. Here are some ideas for day two: steep yourself in history at Bob Marley Museum, then enjoy the scholastic atmosphere at University Of The West Indies - Mona, then browse the different shops at Morgans Creek Ltd, and finally walk around Emancipation Park.

To see ratings, maps, traveler tips, and more tourist information, go to the Kingston trip planner.

Use the Route module to find suitable travel options from Tupelo to Kingston. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Plan for somewhat warmer nights when traveling from Tupelo in June since evenings lows in Kingston dip to 78°F. Finish up your sightseeing early on the 14th (Mon) so you can go by car to Port Antonio.

Things to do in Kingston

Parks · Historic Sites · Museums · Shopping

Side Trip

Find places to stay Jun 12 — 14:

Port Antonio, Jamaica

— 2 nights
A coastal getaway from coastal getaways, Port Antonio offers a break from the more touristy retreats in the west of the island.
Kick off your visit on the 15th (Tue): kick back and relax at Winifred Beach, explore the activities along Blue Lagoon, and then kick back and relax at Frenchman's Cove. On the next day, explore the activities along Long Bay (Northeast), then admire the sheer force of Reach Falls, and then browse the fresh offerings at Boston Jerk Centre.

Plan my day in Port Antonio using traveler tips and tourist information provided by Inspirock.

Traveling by car from Kingston to Port Antonio takes 2.5 hours. Alternatively, you can take a bus. In June, daytime highs in Port Antonio are 90°F, while nighttime lows are 78°F. Finish up your sightseeing early on the 16th (Wed) so you can go by car to Ocho Rios.

Things to do in Port Antonio

Parks · Nature · Beaches · Outdoors

Side Trip

Find places to stay Jun 14 — 16:

Ocho Rios, Jamaica

— 5 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Explore the numerous day-trip ideas around Ocho Rios: Joe James Gallery (in Rio Bueno), Bob Marley Museum (in St. Ann's Bay) and Green Grotto Caves (in Runaway Bay). Pack the 20th (Sun) with family-friendly diversions at Rainforest Adventures. There's still lots to do: take in the dramatic scenery at Dunn's River Falls and Park, fulfill a lifelong dream with a swim-with-the-dolphins experience, pause for some serene contemplation at Bethel Tabernacle United Pentecostal Church, and trot along with a tour on horseback.

To see reviews, more things to do, maps, and other tourist information, read our Ocho Rios online trip itinerary builder.

You can drive from Port Antonio to Ocho Rios in 2 hours. Alternatively, you can take a bus. June in Ocho Rios sees daily highs of 90°F and lows of 78°F at night. Wrap up your sightseeing on the 21st (Mon) early enough to travel to Saint Elizabeth Parish.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Theme Parks

Side Trips

Find places to stay Jun 16 — 21:

Saint Elizabeth Parish, Jamaica

— 1 night
Ecotourism and beach break activities dominate most Saint Elizabeth Parish itineraries, as this wild and relatively undeveloped region offers a wealth of natural environments.
Kick off your visit on the 22nd (Tue): admire the sheer force of YS Falls and then indulge in some personalized pampering at Shirley's Steam Bath & Massage.

To see ratings, more things to do, reviews, and more tourist information, you can read our Saint Elizabeth Parish trip planner.

Do a combination of bus and car from Ocho Rios to Saint Elizabeth Parish in 3 hours. Alternatively, you can drive; or take a bus. June in Saint Elizabeth Parish sees daily highs of 91°F and lows of 77°F at night. Wrap up your sightseeing on the 22nd (Tue) early enough to drive to Negril.

Things to do in Saint Elizabeth Parish

Nature · Parks · Spas
Find places to stay Jun 21 — 22:

Negril, Jamaica

— 3 nights
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Go for a jaunt from Negril to Pennycooke to see Original Mayfield Falls Jamaica about 1h 5 min away. There's much more to do: kick back and relax at Seven Mile Beach, get a new perspective on things with Boat Tours & Water Sports, explore the striking landscape at Negril Cliffs, and indulge in some personalized pampering at some of the best spas.

To find where to stay, traveler tips, ratings, and tourist information, read Negril tour itinerary maker tool.

You can drive from Saint Elizabeth Parish to Negril in 2 hours. Another option is to take a bus. In June in Negril, expect temperatures between 91°F during the day and 77°F at night. Finish up your sightseeing early on the 25th (Fri) so you can go by car to Montego Bay.

Things to do in Negril

Parks · Nature · Outdoors · Beaches

Side Trips

Find places to stay Jun 22 — 25:

Montego Bay, Jamaica

— 5 nights
The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Get out of town with these interesting Montego Bay side-trips: Tryall Golf Course (in Sandy Bay) and Boat Tours & Water Sports (in Falmouth). Spend the 27th (Sun) wandering through the wild on a nature and wildlife tour. There's lots more to do: enjoy the sand and surf at Doctor's Cave Beach, contemplate the long history of Rose Hall Great House, take an exotic tour of Rastasafari Experience, and contemplate the waterfront views at Martha Brae Rafting Village.

To find other places to visit, reviews, more things to do, and more tourist information, use the Montego Bay attractions website.

Getting from Negril to Montego Bay by car takes about 1.5 hours. Other options: take a bus. In June in Montego Bay, expect temperatures between 91°F during the day and 77°F at night. On the 30th (Wed), you'll have the morning to explore before heading back home.

Things to do in Montego Bay

Outdoors · Tours · Wildlife · Golf

Side Trips

Find places to stay Jun 25 — 30:

Mississippi travel guide

3.5
Casinos · Historic Sites · History Museums
The Magnolia State
Still relatively unspoiled by mass tourism, Mississippi epitomizes rich history and offers warm hospitality to those who vacation here. The Mississippi River forms most of its western border, so it's no surprise that this mighty waterway shapes the lives of people calling the "Magnolia State" their home. The river influences everything from the food they eat to the music they listen to. Perhaps the easiest way to discover Mississippi is to take a drive on the 715 km (444 mi) long national parkway, which follows a route used since pre-colonial times that's famous for its scenic beauty and attractions of historical interest. At the end of the parkway sits a town packed with nearly 600 antebellum homes.

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.