37 days in Caribbean Itinerary

37 days in Caribbean Itinerary

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Route & dates

37 days in Caribbean Itinerary

Start: Cairo, Egypt
drive:  18​h 30​min
1
San Juan, Puerto Rico
— 7 nights
Fly:  2​h
2
Isla de Vieques, Puerto Rico
— 4 nights
Fly:  4​h 15​min
3
The Bottom, Saba
— 2 nights
+2
Drive + Fly + Drive:  45​min
4
Philipsburg, St. Maarten-St. Martin
— 7 nights
Fly:  4​h 15​min
5
Punta Cana, Dominican Republic
— 6 nights
Fly:  8​h 30​min
6
Seven Mile Beach, Cayman Islands
— 3 nights
Fly:  2​h
7
Havana, Cuba
— 6 nights
Fly:  19​h
End: Cairo, Egypt

7
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Visit Old San Juan and Sitio Histórico de San Juan for their historical value. Head to Coqui International and El Alcazarfor some retail therapy. Change things up with these side-trips from San Juan: El Yunque Rain Forest (in El Yunque National Forest), Estudio de Arte Samuel Lind (in Loiza) and Maji Lina Gallery & Art Center (in Palmer). There's lots more to do: browse the different shops at Plaza Las Americas, view the masterpieces at The Poet's Passage, revel in the low prices at Puerto Rico Premium Outlets, and stroll through Condado Beach.

To see other places to visit, where to stay, traveler tips, and tourist information, use the San Juan road trip site .

Cairo, Egypt to San Juan is an approximately 18.5-hour flight. You can also do a combination of flight and car; or do a combination of flight and shuttle. The time zone difference moving from Eastern European Time to Atlantic Standard Time is minus 6 hours. While traveling from Cairo, expect somewhat warmer days and warmer nights in San Juan, ranging from highs of 34°C to lows of 28°C. Wrap up your sightseeing on the 10th (Tue) early enough to travel to Isla de Vieques.

Things to do in San Juan

Shopping Museums Historic Sites

Side Trips

Rio Grande, San Patricio Plaza, El Yunque Rain Forest, Puerto Rico Premium Outlets, Estudio de Arte Samuel Lind
Find places to stay Dec 3 — 10:
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
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.
For shopping fun, head to Fish Market or Serenity Point Yoga & Visionary Arts Space. Get some historical perspective at Puerto Ferro Lighthouse and El Hombre de Puerto Ferro. The adventure continues: take in the exciting artwork at Siddhia Hutchinson Fine Art Gallery, take in the waterfront at Mosquito Pier, tour the pleasant surroundings at Vieques National Wildlife Refuge, and stop by Isla Vida.

To find other places to visit, maps, traveler tips, and more tourist information, you can read our Isla de Vieques trip itinerary planning site .

Traveling by flight from San Juan to Isla de Vieques takes 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. In December, daily temperatures in Isla de Vieques can reach 34°C, while at night they dip to 28°C. Finish your sightseeing early on the 14th (Sat) to allow enough time to travel to The Bottom.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Dec 10 — 14:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Scuba & Snorkeling
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge

2
nights
The Bottom, Saba

The Bottom ©
The Bottom is the capital and largest town of the island of Saba, the Caribbean Netherlands, and is the first stop on the way from Saba's Port in Fort Bay towards the rest of the island. Your day-by-day itinerary now includes The Bottom. Kick off your visit on the 15th (Sun): contemplate the waterfront views at Saba National Marine Park and then explore the activities along Tide Pools at Flat Point. On the 16th (Mon), you'll have a packed day of sightseeing: get a taste of the local shopping with Saba Trail Shop, stroll through Mount Scenery, and then take in the architecture and atmosphere at Sacred Heart Church.

To see more things to do, reviews, where to stay, and other tourist information, you can read our The Bottom holiday planner .

You can fly from Isla de Vieques to The Bottom in 4.5 hours. Alternatively, you can do a combination of flight and ferry. Prepare for little chillier weather when traveling from Isla de Vieques in December: high temperatures in The Bottom hover around 26°C and lows are around 24°C. Finish up your sightseeing early on the 16th (Mon) so you can travel to Philipsburg.

Things to do in The Bottom

Parks Nature Wildlife

Side Trips

Saba, Windwardside, Saba National Marine Park
Find places to stay Dec 14 — 16:
Highlights from your plan
The Bottom ©
The Bottom
Saba National Marine Park ©
Saba National Marine Park
Saba Trail Shop ©
Saba Trail Shop

7
nights
Philipsburg, St. Maarten-St. Martin

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Shop till you drop at Caribbean Gems and Gingerbread Gallery. When in Philipsburg, make a side trip to see Cupecoy Bay Beach in Cupecoy Bay, approximately 30 minutes away. There's lots more to do: get some thrills on the water with a speed boat tour, make a trip to Frontstreet, kick back and relax at Dawn Beach, and contemplate the waterfront views at Mullet Bay Beach.

For other places to visit and more tourist information, refer to the Philipsburg trip itinerary planner.

Traveling by combination of car and flight from The Bottom to Philipsburg takes an hour. Alternatively, you can ride a ferry. Expect somewhat warmer temperatures when traveling from The Bottom in December; daily highs in Philipsburg reach 34°C and lows reach 28°C. Finish your sightseeing early on the 23rd (Mon) so you can travel to Punta Cana.

Things to do in Philipsburg

Outdoors Parks Wildlife

Side Trips

Saint-Martin, Sint Maarten, Maho, Simpson Bay, Cupecoy Bay Beach
Find places to stay Dec 16 — 23:
Highlights from your plan
Caribbean Gems ©
Caribbean Gems
Speed Boats Tours
Loterie Farm ©
Loterie Farm

6
nights
Punta Cana, Dominican Republic

Punta Cana ©
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Head to La Perla Dominicana and Downtown Punta Canafor plenty of shopping. Explore the numerous day-trip ideas around Punta Cana: Scuba & Snorkeling (in Bayahibe) and Altos de Chavon (in La Romana). Spend a day of island exploring on the 27th (Fri) at Saona Island. Spend the 29th (Sun) spotting exotic species with a safari tour. There's much more to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, enjoy the sand and surf at Bavaro Beach, browse the different shops at Palma Real Shopping Village, and make a trip to Jesus Maestro Parish.

Planning Punta Cana trip won't be overwheling when you use's Insprock itinerary maker.

You can do a combination of flight and shuttle from Philipsburg to Punta Cana in 4.5 hours. Another option is to fly. In December in Punta Cana, expect temperatures between 34°C during the day and 26°C at night. Finish your sightseeing early on the 29th (Sun) so you can travel to Seven Mile Beach.

Things to do in Punta Cana

Outdoors Wildlife Tours

Side Trips

Altos de Chavon, Scuba & Snorkeling
Find places to stay Dec 23 — 29:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Safaris

3
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
Shop till you drop at Guy Harvey Gallery and Shoppe and Davinoff's Concrete Sculpture Garden.

Plan my day in Seven Mile Beach using traveler tips and tourist information provided by Inspirock.

You can fly from Punta Cana to Seven Mile Beach in 8.5 hours. Another option is to do a combination of shuttle and flight. The time zone difference when traveling from Punta Cana to Seven Mile Beach is minus 1 hour. December in Seven Mile Beach sees daily highs of 34°C and lows of 28°C at night. Finish your sightseeing early on the 1st (Wed) so you can travel to Havana.

Things to do in Seven Mile Beach

Parks Wildlife Outdoors

Side Trips

Grand Cayman, George Town, Davinoff's Concrete Sculpture Garden, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Dec 29 — Jan 1:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Scuba & Snorkeling

6
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Get some historical perspective at Malecón of Havana and Fortaleza de San Carlos de la Cabana. Head to L'Antigua Habana and Yuniel Delgado Studiofor some retail therapy. Get out of town with these interesting Havana side-trips: Cayo Largo (Playa Paraiso & Sea Turtle Hatchery). Next up on the itinerary: get to know the fascinating history of Old Havana, get the lay of the land with Walking tours, make a trip to Plaza de la Catedral, and take in the exciting artwork at Estudio Taller Santacana.

To see other places to visit, photos, traveler tips, and more tourist information, use the Havana sightseeing planner.

You can fly from Seven Mile Beach to Havana in 2 hours. Traveling from Seven Mile Beach in January, expect a bit cooler with lows of 19°C in Havana. Finish your sightseeing early on the 7th (Tue) so you can travel back home.

Things to do in Havana

Historic Sites Parks Shopping

Side Trips

Cayo Largo, L'Antigua Habana
Find places to stay Jan 1 — 7:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)

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