31 days in Caribbean Itinerary

31 days in Caribbean Itinerary

Created using Inspirock Caribbean sightseeing planner

This plan was created by another user.  Make it your plan

Route & dates

31 days in Caribbean Itinerary

Start: Toronto, Canada
Fly + bus:  9​h 45​min
1
Saint Joseph Parish, Barbados
— 2 nights
bus + Fly:  5​h 15​min
2
Philipsburg, St. Maarten-St. Martin
— 5 nights
Fly:  3​h
3
Isla de Vieques, Puerto Rico
— 7 nights
Fly:  2​h
4
San Juan, Puerto Rico
— 5 nights
Fly:  30​min
5
Culebra, Puerto Rico
— 4 nights
Fly:  7​h 45​min
6
Seven Mile Beach, Cayman Islands
— 2 nights
Fly:  2​h
7
Havana, Cuba
— 5 nights
Fly:  6​h 30​min
End: Toronto, Canada

2
nights
Saint Joseph Parish, Barbados

Saint Joseph Parish ©
Lush Saint Joseph Parish has a particularly rugged aspect to it down by the sea, so much so that it has gained the nickname 'Scotland District'.
Kick off your visit on the 2nd (Mon): tour the pleasant surroundings at Bottom Bay, examine the collection at Sunbury Plantation House, then contemplate the long history of Andromeda Botanic Gardens, then take in nature's colorful creations at Hunte's Gardens, and finally explore the fascinating underground world of Harrison's Cave.. Keep things going the next day: stroll through Carlisle Bay, then savor the flavors at St. Nicholas Abbey, and then kick back and relax at Soup Bowl.

Plan my Saint Joseph Parish trip by asking Inpirock to come up with tips and suggestions.

Toronto, Canada to Saint Joseph Parish is an approximately 10-hour combination of flight and car. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. Expect warmer temperatures when traveling from Toronto in December; daily highs in Saint Joseph Parish reach 34°C and lows reach 28°C. Finish your sightseeing early on the 3rd (Tue) to allow enough time to travel to Philipsburg.

Things to do in Saint Joseph Parish

Parks Beaches Outdoors

Side Trips

Saint Philip Parish, Harrison's Cave., St. Nicholas Abbey, Carlisle Bay
Find places to stay Dec 1 — 3:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Harrison's Cave. ©
Harrison's Cave.
Bottom Bay ©
Bottom Bay

5
nights
Philipsburg, St. Maarten-St. Martin

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Philipsburg is known for shopping, wildlife, beaches, adventure, and museums. Your plan includes some of its best attractions: enjoy the sand and surf at Maho Beach, try to win big at Casino Royale, contemplate the waterfront views at Mullet Bay Beach, and tour the pleasant surroundings at Dawn Beach.

To see maps, reviews, where to stay, and other tourist information, go to the Philipsburg online trip itinerary maker .

Traveling by combination of bus and flight from Saint Joseph Parish to Philipsburg takes 5.5 hours. In December, daytime highs in Philipsburg are 34°C, while nighttime lows are 28°C. Finish your sightseeing early on the 8th (Sun) so you can travel to Isla de Vieques.

Things to do in Philipsburg

Outdoors Parks Beaches

Side Trips

Maho, Sint Maarten, Saint-Martin, Cupecoy Bay Beach, WAKE N' GLISSE
Find places to stay Dec 3 — 8:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Orient Bay Beach ©
Orient Bay Beach

7
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Isla de Vieques is known for nature, beaches, adventure, wildlife, and nightlife. Your plan includes some of its best attractions: explore the activities along Sun Bay Beach, enjoy the sand and surf at La Chiva, have fun at Vieques Gun Club & Sporting Clays, and stroll through Media Luna Beach.

Planning Isla de Vieques trip won't be overwheling when you use's Insprock itinerary maker.

Getting from Philipsburg to Isla de Vieques by flight takes about 3 hours. In December, daily temperatures in Isla de Vieques can reach 34°C, while at night they dip to 28°C. Cap off your sightseeing on the 15th (Sun) early enough to travel to San Juan.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Dec 8 — 15:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
Media Luna Beach ©
Media Luna Beach

5
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Explore the numerous day-trip ideas around San Juan: El Yunque Rain Forest (in El Yunque National Forest), Museo de Arte de Ponce (in Ponce) and Museo del Tabaco Caguas (in Caguas). There's much more to do: wander the streets of Old San Juan, tour the pleasant surroundings at Condado Beach, get to know the fascinating history of Sitio Histórico de San Juan, and make a trip to Plaza de la Catedral.

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

You can fly from Isla de Vieques to San Juan in 2 hours. Other options are to do a combination of ferry and car; or do a combination of ferry and shuttle. In December, plan for daily highs up to 34°C, and evening lows to 28°C. Wrap up your sightseeing on the 20th (Fri) early enough to fly to Culebra.

Things to do in San Juan

Parks Outdoors Nature

Side Trips

Luquillo Beach, Museo del Tabaco Caguas, El Yunque Rain Forest, Museo de Arte de Ponce, Bosque Nacional El Yunque
Find places to stay Dec 15 — 20:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

4
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, nature, outdoors, and adventure. Your plan includes some of its best attractions: tour the pleasant surroundings at Flamenco Beach, enjoy the sand and surf at Tamarindo Beach, visit a coastal fixture at Culebrita Lighthouse, and step off the mainland to explore Culebrita Island.

To see ratings, other places to visit, and tourist information, go to the Culebra tour itinerary planner .

Culebra is just a short distance from San Juan. In December, plan for daily highs up to 34°C, and evening lows to 28°C. Finish up your sightseeing early on the 24th (Tue) so you can travel to Seven Mile Beach.

Things to do in Culebra

Parks Beaches Outdoors
Find places to stay Dec 20 — 24:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

2
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
On the 25th (Wed), kick back and relax at Seven Mile Beach, then brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, and then tour the pleasant surroundings at Stingray City Grand Cayman. Keep things going the next day: see some colorful creatures with a scuba or snorkeling tour, try out the rides at Cayman Turtle Centre: Island Wildlife Encounter, and then don't miss a visit to Hell Gift Store.

For maps, photos, traveler tips, and more tourist information, refer to the Seven Mile Beach holiday site .

Traveling by flight from Culebra to Seven Mile Beach takes 8 hours. Alternatively, you can do a combination of ferry, shuttle, and flight. Traveling from Culebra to Seven Mile Beach, you'll gain 1 hour due to the time zone difference. In December, daily temperatures in Seven Mile Beach can reach 34°C, while at night they dip to 28°C. Finish up your sightseeing early on the 26th (Thu) so you can travel to Havana.

Things to do in Seven Mile Beach

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Cayman Turtle Centre: Island Wildlife Encounter, Cayman Spirits Co. Distillery
Find places to stay Dec 24 — 26:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

5
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Take a break from Havana with a short trip to Playa Paraiso in Cayo Largo, about 2 hours away. Next up on the itinerary: appreciate the extensive heritage of Malecón of Havana, contemplate the long history of El Morro, take in the local highlights with Walking tours, and take an in-depth tour of Museum of the Revolution (Museo de la Revolucion).

For where to stay, ratings, more things to do, and more tourist information, read Havana trip maker website .

Fly from Seven Mile Beach to Havana in 2 hours. Traveling from Seven Mile Beach in December, you can expect nighttime temperatures to be a bit cooler in Havana, with lows of 20°C. Cap off your sightseeing on the 31st (Tue) early enough to travel back home.

Things to do in Havana

Historic Sites Museums Tours

Side Trip

Playa Paraiso
Find places to stay Dec 26 — 31:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

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