Call us 9am - 9pm Mon - Sun Tralee 066 7164410
Dublin 01 6649900

Search

Self-Drive Boston to New York by the Beaches

8 Nights Tour from €1,589 per Person Including Flights

Click here for Pricing & Dates

Overview

This self-drive tour starts in the historic city of Boston, journeying to one of the world’s most famous summer vacation destinations, Cape Cod and its magnificent beaches. You’ll ferry over to Martha’s Vineyard, explore Mystic Seaport and venture to the grand old mansions of Long Island, before ultimately reaching your final destination: New York City.

Further reading: Top 10 coastal towns in New England

Highlights

  • Take in spectacular views of Boston and visit iconic historic sites like Plymouth Rock
  • Stroll the sand dunes, tour lighthouses and watch for whales on Cape Cod
  • Explore the famous gingerbread cottages, ride the world’s oldest carousel and dine on fresh lobster you just watched the lobstermen bring in on Martha’s Vineyard
  • Visit Mystic Seaport, the largest maritime museum in the world and enjoy wine tasting along Long Island’s North Fork Wine Route
  • See the historic Hamptons mansions, browse the shops and art galleries that line Main Street Southampton, and relax on pristine white sand beaches

Details

Day 1

Boston, MA

Arrive into Boston and check into your hotel – if time and energy allow, take in one of the best views of the city from the 50th floor of Prudential Tower. See the sailboats gliding across the Charles River, the gold of the Massachusetts State House glistening in the sun, the Harbor Islands in the distance, and even down into Fenway Park.

Standard Hotel: Boston Park Plaza

Day 2 & 3

Yarmouth, MA (169 miles)

Today’s journey will take you to Cape Cod, but you’ll want to stop at the village of Plymouth first. Founded in 1620, it’s most famous as the site of the landing of the Pilgrims, with Plymouth Rock purportedly marking the very spot they disembarked. Explore more history by visiting Plimouth Plantation, a living history museum, and the Mayflower, a full-scale replica of the ship, complete with costumed guides. Enjoy time on the water by taking a Hyannis Harbor Cruise in Hyannis before reaching your final destination of Yarmouth. Your second day on The Cape will be filled with beautiful beaches along the Cape Cod National Seashore, lighthouses and whales. Take a stroll across the dunes, tour one of the five historic Cape Cod lighthouses, open to the public, and then watch for whales by joining a tour from Provincetown, with humpbacks and other marine life frequently spotted.

Standard Hotel: Blue Water on the Ocean

Day 4 & 5

Martha’s Vineyard, MA (28 miles)

Your morning begins with a short and scenic ferry ride to Martha’s Vineyard, an island just seven miles from the Cape Cod coast. The busy main port, Vineyard Haven, offers great shopping for sea glass jewellery and other treasures, and in Menemsha, you can watch the lobstermen unload their catch. Oaks Bluff, renowned for its unique, vibrant-coloured gingerbread cottages that give the town a storybook feel, is home to the world’s oldest carousel, while Edgartown is considered one of the island’s most picturesque villages, with its brick paths and grand old captain’s homes. Before the day is done, capture the grandeur of an island sunset from the stunning terra cotta-hued clay Gay Head Cliffs overlook. Spend your second day on Martha’s Vineyard taking part in outdoor adventures, like horseback riding or renting a bike and exploring the island on two wheels, or visiting many idyllic stretches of sand. Protected, shallow, clear waters can be found at beaches on the northern and eastern sides of the island.

Standard Hotel: Kelley House

Day 6

Mystic, CT (133 miles)

Return to the Cape via ferry, and then drive to Mystic, a fabulous coastal town home to Mystic Seaport, the nation's leading maritime museum. It features a working preservation shipyard, a recreated 19th-century seafaring village, fascinating exhibits, a planetarium and four National Historic Landmark vessels, including the last wooden whaleship in the world.

Standard Hotel: Hilton Mystic

Day 7 & 8

Riverhead, NY (108 miles)

Drive to New London, where you’ll take the Orient Ferry to Long Island. Travel the North Fork toward the north shore town of Riverhead - this popular wine route features a bounty of vineyards for tasting and touring, like Jamesport Vineyards which also offers complimentary olives and cheeses to help fortify the afternoon.

The Hamptons is world-renowned for its beaches with fine white sands, gorgeous sunsets and top-notch eateries. On your second day here, take time to explore the best it has to offer, spending time at the Village of Southampton’s main beach, where you can rent and chair and an umbrella, tossing your cares away. Afterwards, take time to stroll the especially charming village of Southampton, with its wide, tree-lined Main Street lined with boutiques and art galleries before taking a tour of the island’s iconic, extravagant mansions.

Standard Hotel: Hyatt Place

Day 9

New York City marks the end of the tour – or, it could be the beginning of yet another adventure. Either way, be sure to experience some of its highlights, like walking through Central Park, riding the lift to the top of the Empire State Building and exploring the Metropolitan Museum of Art. Just ask to add a few nights on in New York.

 

  • Return transatlantic flights
  • Hotel accommodation as show or of a similar standard
  • Car hire for the duration of the trip included fully inclusive insurance
  • Flydrive directions and information pack delivered to your first hotel

The weather information shown below refers to the first stop on the tour, call us and speak to one of our travel experts for the most up-to-date forecasts and weather details for your tour.

TODAY 18ºC
THU 22ºC
FRI 20ºC
SAT 18ºC
SUN 16ºC
Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
Average Temperature (Celsius) Average Rainfall (Inches)
3ºC
2ºC
5ºC
9ºC
14ºC
18ºC
22ºC
22ºC
18ºC
14ºC
9ºC
4ºC
0
0
0
0
0
0
0
0
0
0
0
0

Average Temperature (Celsius) Average Rainfall (Inches)

Jan
3ºC
0
Feb
2ºC
0
Mar
5ºC
0
Apr
9ºC
0
May
14ºC
0
Jun
18ºC
0
Jul
22ºC
0
Aug
22ºC
0
Sep
18ºC
0
Oct
14ºC
0
Nov
9ºC
0
Dec
4ºC
0

Book today

Talk to our travel experts for more information and to book or tailor-make your holiday.

Tralee 066 7164410

Dublin 01 6649900

9am - 9pm Mon - Sun

Jackie

American Sky also recommends

Self-Drive New England Explorer

7 Nights Tour from €1,199 Including Flights

A great little tour of the highlights of New England, starting in Boston. You'll experience the beautiful coastal regions of Cape Code and Maine, climb into the mountains of Vermont and New Hampshire and enjoy a stay in the Connecticut River Valley.

More Details

Car Hire Offer

Self-Drive Best of New England

11 Nights Tour from €1,359 Including Flights

From the glamorous mansions of Newport, the lighthouses of the New England coast, and the majestic mountains of the New England interior, this spectacular tour offers a vast variety of experiences that truly capture the unique flavour of the Northeast.

More Details

Fairmont Copley Plaza

 

3 nights from €669 Including Flights

Located in historic Back Bay a symbol of Boston’s rich history and elegance recently renovated and restored to shine more brightly than ever before. Rich with heritage, The Fairmont Copley Plaza epitomizes the culture and traditions of Boston.

More Details


Back to Top

Get exclusive offers & deals delivered to your inbox

Tell us your holiday preferences and receive special deals and exclusive offers straight to your inbox.