29 days in Massachusetts, California & Florida Itinerary

29 days in Massachusetts, California & Florida Itinerary

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Route & dates

29 days in Massachusetts, California & Florida Itinerary

Start: New York City
Drive:  4​h 45​min
1
Falmouth
— 2 nights
Drive:  1​h 15​min
2
Eastham
— 3 nights
Drive:  1​h 45​min
3
Boston
— 3 nights
Fly:  7​h 15​min
4
San Francisco
— 4 nights
Fly:  3​h 45​min
5
Los Angeles
— 4 nights
Drive:  2​h 15​min
6
San Diego
— 4 nights
Fly:  7​h 45​min
7
Orlando
— 3 nights
Fly:  4​h 15​min
8
Key West
— 4 nights
Fly + bus:  6​h
End: New York City

2
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Get out of town with these interesting Falmouth side-trips: Heritage Museums & Gardens (in Sandwich), Plymouth Rock (in Plymouth) and Flying Horses Carousel (in Oak Bluffs). The adventure continues: stroll through Shining Sea Bikeway, enjoy the sea views from Nobska Point Lighthouse, explore the world behind art at Highfield Hall & Gardens, and enjoy the sand and surf at Old Silver Beach.

For where to stay, maps, other places to visit, and tourist information, use the Falmouth vacation tool .

New York City to Falmouth is an approximately 5-hour car ride. You can also do a combination of bus and flight; or do a combination of flight and bus. Expect a bit cooler temperatures when traveling from New York City in July; daily highs in Falmouth reach 80°F and lows reach 64°F. Finish your sightseeing early on the 10th (Fri) to allow enough time to drive to Eastham.

Things to do in Falmouth

Parks Outdoors Museums

Side Trips

Sandwich, Plymouth Rock, Edgartown Lighthouse, Flying Horses Carousel
Highlights from your plan
Highfield Hall & Gardens ©
Highfield Hall & Gardens
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum

3
nights
Eastham

Eastham ©
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Explore Eastham's surroundings by going to Provincetown (Long Point & Pilgrim Monument & Provincetown Museum). The adventure continues: kick back and relax at Cape Cod National Seashore, trek along Cape Cod Rail Trail, take an in-depth tour of Chatham Marconi Maritime Center, and stroll through Marconi Beach.

For ratings and other tourist information, read Eastham trip itinerary maker website .

Getting from Falmouth to Eastham by car takes about 1.5 hours. Other options: take a bus. July in Eastham sees daily highs of 79°F and lows of 65°F at night. Wrap up your sightseeing on the 13th (Mon) to allow time to drive to Boston.

Things to do in Eastham

Outdoors Parks Beaches

Side Trips

Provincetown, Cape Cod, Marconi Beach, Chatham Marconi Maritime Center
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Cape Cod National Seashore ©
Cape Cod National Seashore

3
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Explore Boston's surroundings by going to Edward Gorey House (in Yarmouth Port), Dolphin & Whale Watching (in Gloucester) and Corporation Beach (in Dennis). Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, explore the different monuments and memorials at Mount Auburn Cemetery, take in nature's colorful creations at Boston Public Garden, and stroll around Rose Kennedy Greenway.

To see traveler tips, where to stay, more things to do, and more tourist information, use the Boston online sightseeing planner .

Drive from Eastham to Boston in 2 hours. Alternatively, you can take a bus; or do a combination of bus and ferry. In July, plan for daily highs up to 83°F, and evening lows to 67°F. Finish your sightseeing early on the 16th (Thu) so you can travel to San Francisco.

Things to do in Boston

Museums Outdoors Parks

Side Trips

Brewster Gardens, Corporation Beach, Edward Gorey House, Mount Auburn Cemetery, Dolphin & Whale Watching
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Dolphin & Whale Watching

4
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
San Francisco is known for nature, museums, parks, nightlife, and shopping. Your plan includes some of its best attractions: take in the views from Golden Gate Bridge, take in nature's colorful creations at Japanese Tea Garden, learn the secrets of beer at a beer tour and tasting, and head off the coast to Alcatraz Island.

For maps and more tourist information, use the San Francisco trip itinerary planner .

You can fly from Boston to San Francisco in 7.5 hours. Other options are to do a combination of flight and train; or drive. You'll gain 3 hours traveling from Boston to San Francisco due to the time zone difference. Plan for slightly colder temperatures traveling from Boston in July, with highs in San Francisco at 73°F and lows at 57°F. Wrap up your sightseeing on the 20th (Mon) early enough to travel to Los Angeles.

Things to do in San Francisco

Parks Tours Museums
Highlights from your plan
Golden Gate Bridge ©
Golden Gate Bridge
Alcatraz Island ©
Alcatraz Island
Fisherman's Wharf ©
Fisherman's Wharf

4
nights
Los Angeles

Los Angeles ©
Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Get out of town with these interesting Los Angeles side-trips: Anaheim (Disneyland Park & Disney California Adventure Park). Next up on the itinerary: find something for the whole family at Universal Studios Hollywood, experience the excitement of Harry Potter and the Forbidden Journey, don't miss a visit to Santa Monica Pier, and put a fun spin on your tour with Fantastic Race.

To find more things to do, ratings, reviews, and more tourist information, use the Los Angeles online route planner .

Traveling by flight from San Francisco to Los Angeles takes 4 hours. Alternatively, you can do a combination of train and flight; or drive. Prepare for somewhat warmer weather when traveling from San Francisco in July: high temperatures in Los Angeles hover around 83°F and lows are around 66°F. Finish up your sightseeing early on the 24th (Fri) so you can go by car to San Diego.

Things to do in Los Angeles

Theme Parks Museums Fun & Games

Side Trips

Anaheim, Santa Monica Pier
Highlights from your plan
Diorama-museum of Bhagavad-gita ©
Diorama-museum of Bhagavad-gita
Disneyland Park ©
Disneyland Park
Universal Studios Hollywood ©
Universal Studios Hollywood

4
nights
San Diego

San Diego ©
Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
Step out of San Diego with an excursion to Self Realization Fellowship Hermitage & Meditation Gardens in Encinitas--about 30 minutes away. There's still lots to do: get to know the resident critters at San Diego Zoo, browse the exhibits of Maritime Museum of San Diego, glide through the air with a parasailing or paragliding tour, and pause for some photo ops at Cabrillo National Monument.

To find reviews, other places to visit, where to stay, and more tourist information, go to the San Diego travel route planner .

Getting from Los Angeles to San Diego by car takes about 2.5 hours. Other options: take a bus; or fly. Traveling from Los Angeles in July, expect nights in San Diego to be about the same, around 68°F, while days are a bit cooler, around 77°F. Wrap up your sightseeing on the 28th (Tue) early enough to travel to Orlando.

Things to do in San Diego

Parks Zoos & Aquariums Fun & Games

Side Trip

Self Realization Fellowship Hermitage & Meditation Gardens
Highlights from your plan
AxeVentures ©
AxeVentures
San Diego Zoo ©
San Diego Zoo
USS Midway Museum ©
USS Midway Museum

3
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Orlando is known for theme parks, nightlife, fun & games, shopping, and museums. Your plan includes some of its best attractions: get in on the family fun at Universal's Islands of Adventure, make an unforgettable trip to Happily Ever After Fireworks, make a trip to Cinderella Castle, and get your game on at The Escape Game Orlando.

For photos, maps, other places to visit, and other tourist information, you can read our Orlando travel itinerary planner .

Traveling by flight from San Diego to Orlando takes 8 hours. Alternatively, you can drive; or take a bus. The time zone difference moving from Pacific Standard Time (PST) to Eastern Standard Time (EST) is 3 hours. Plan for somewhat warmer temperatures traveling from San Diego in July, with highs in Orlando at 91°F and lows at 75°F. Finish up your sightseeing early on the 1st (Sat) so you can travel to Key West.

Things to do in Orlando

Theme Parks Fun & Games Museums

Side Trip

Charles Hosmer Morse Museum of American Art
Highlights from your plan
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort

4
nights
Key West

Key West ©
Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Step out of Key West to go to Big Pine Key and see Bahia Honda State Park, which is approximately 50 minutes away. Next up on the itinerary: see the interesting displays at The Ernest Hemingway Home and Museum, get engrossed in the history at Truman Little White House, don't miss a visit to Duval Street, and see majestic marine mammals with a dolphin and whale watching tour.

For other places to visit, photos, where to stay, and tourist information, read our Key West trip itinerary maker site .

Getting from Orlando to Key West by flight takes about 4.5 hours. Other options: drive; or take a bus. In August, plan for daily highs up to 90°F, and evening lows to 81°F. Finish your sightseeing early on the 5th (Wed) so you can travel back home.

Things to do in Key West

Outdoors Tours Wildlife

Side Trip

Bahia Honda State Park
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

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