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New York City to Boston Discovery

Find out what makes New York, Rhode Island, Cape Cod and Boston some of the USA’s most beloved destinations on this six-day state-spanning adventure. Walk in the shoes of a New Yorker on a tour of Brooklyn’s family-run businesses and eateries, cruise the scenic waterways of Rhode Island’s Providence, let the charm of Cape Cod’s beaches and quaint towns wash over you, and uncover the old and new sides of Boston. Throw in wine tasting, picnics and a whole bunch of friendly locals and you’ll never want to leave the East Coast.

6 days, from


per person


13 people max


Trip code: STKN
Style: Comfort
Theme: Explorer
Print itinerary


Countries Visited:  United States Of America
Accommodation: Hotel (5 nights)
Transportation: Private vehicle
Meals: 1 dinners, 5 breakfasts
Group size: Minimum 1, Max 13

  • New York City is calling – see it through the eyes of a local as you join a New Yorker for a walking tour of Brooklyn, checking out local family-run businesses and eateries.

  • Get on the road to Rhode Island and explore the charming city of Providence by cruising its waterways while your leader shares local stories and history.

  • Coastlines don’t get much prettier than Cape Cod – spend two days discovering the beaches, lighthouses and quaint towns of this much-loved summer spot, including a sand dune tour and sunset clam bake. 

  • Visit a local family-run vineyard in Truro, sip five different fabulous wines and learn about wine production in Cape Cod.

  • Let a local show you the best of Boston, from the historic sites along the famous Freedom Trail to lesser-known local hangouts.


Show Full Itinerary

Day 1: New York

Welcome to New York, New York! Your East Coast adventure begins at 9.30 this morning with a welcome meeting at your hotel. Meet your local leader and the other travellers joining you on your adventure, then head out to explore one of the world’s most exciting cities. Join a local New Yorker to get to know Brooklyn, a borough known for its trendy residents, multicultural eateries and tight-knit community. What really sets Brooklyn apart from the rest of New York is the prevalence of family-run ‘mom and pop’ businesses, many of which have been open for generations. Support these local establishments by popping in to sample the delicious treats they have on offer, and visit some creative new eateries serving up daring dishes. Once you’ve seen Brooklyn through the eyes of a local, the rest of the afternoon is free for your own explorations. Get back together in the evening for an optional dinner (at your own expense) with your group and leader at a local restaurant.

Day 2: Providence

Get on the road to Rhode Island, but first make a pit stop at a famous local pizza joint in New Haven, Connecticut for lunch. In the early afternoon arrive in Providence, Rhode Island's state’s capital and most populous city. The best way to get to know this inviting city is by cruising its waterways, so hop aboard a riverboat and navigate the channels as your leader points out important landmarks, like Waterplace Park and the Providence River, while sharing stories of the city. Once you disembark the rest of the day is yours to uncover more of the city’s charms – the downtown area is perfect for strolling and brimming with trendy bars and creative restaurants.

Day 3: Provincetown

Cross from Rhode Island to Massachusetts, first stopping off in the quaint little town of Chatham where you’ll have the chance to wander around its pleasant streets. Continue to the Cape Cod National Seashore, a stunning stretch of coastline made up of sandy beaches, marshes and uplands. Visit the Nauset Lighthouse, one of the most photographed landmarks in Cape Cod, and learn about the efforts to preserve this important piece of maritime history. Then it’s time to head towards the northern tip of Cape Cod where you’ll find the town of Truro and a fantastic family-run vineyard. Taste five of the wonderful wines produced at the vineyards, and you may have the chance to chat to one of the owners about the work they do here. Continue to nearby Provincetown, a flourishing and creative town in the northernmost tip of Cape Cod, where you’ll spend the night.

Day 4: Provincetown

The day is yours to get better acquainted with Cape Cod. A popular holiday destination for visitors from all over the USA, there’s no shortage of good times to be had here. You may like to take a tour with Anne Hutchison, a spiritual advisor who was banished from her Puritan community. While the real Anne died 400 years ago, her drag queen reincarnation lives on, and she puts on quite the tour! Perhaps take a stroll or cycle down the Cape Cod Rail Trail, head out on a whale watching tour, or get active with some kayaking. The Racepoint Lighthouse, Pilgrim Monument and JFK Museum are all well worth a visit. Whatever your interests, your leader will be on hand to help plan out a perfect day here. Regroup late in the afternoon for a sand dune tour where you'll learn about Cape Cod's unique ecology. Finish at the beach and view one of the most magnificent sunsets on the East Coast while tucking into a delicious clam bake dinner.

Day 5: Boston

Say goodbye to Cape Cod and travel to Boston, the capital of Massachusetts and most populous city in the whole of New England. This thriving city is famed for its food scene, passionate sports fans (and excellent teams, of course) and hundreds of years of history. Dive straight into the city with a walking tour lead by a Boston local, covering some of the city’s most significant historical sites and local hotspots. Take a walk along Boston’s famous Freedom Trail, a 3.7-mile stretch of road dotted with 16 significant historical locations. Your guide will then take you off the well-trodden track to check out some of Boston’s more modern sights, plus some favourite local hangouts. The balance of the day is free to enjoy Boston – ask your leader for tips on the best places to grab a bite to eat tonight.

Day 6: Boston

Your adventure comes to an end this morning. Not ready to go home? Get in touch ahead of time and we’d be happy to arrange additional accommodation at your hotel in Boston (subject to availability).

6 days, from $1,920

to book call 1-844-205-6226

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