16-day car-free East Coast itinerary, Boston to Miami, October 11–26, with Everglades airboat and paddling tours picked up from Miami

Phase 1 — Boston
Oct 11–13 · 3 days · Fenway, universities, city life
Day 1
Oct 11, Sat
Arrive Boston — Freedom Trail + Allston
Morning arrival. Drop bags at HI Boston hostel (great location, near South End). Walk the Freedom Trail — 2.5-mile red brick line connecting 16 free historic sites through the city. Evening in Allston, Boston's student neighbourhood — cheap eats, live music, packed bars any night of the week.
Arrival dayFreedom TrailAllston nightlife
Day 2
Oct 12, Sun
Harvard + MIT campus walk + comedy night
Take the T (Red Line) to Harvard Square. Walk Harvard Yard and the Natural History Museum (glass flowers exhibit is genuinely strange and beautiful). 20-min walk to MIT — the Stata Center and MIT Museum are both free. Back to Cambridge for dinner. Evening: The Comedy Studio or ImprovBoston — cheap or free Sunday nights.
Harvard + MITFree to visitComedy night
Day 3
Oct 13, Mon
Amtrak Northeast Regional · Boston → NYC · ~4 hrs · ~$35–60
Phase 2 — New York City
Oct 14–17 · 4 days · City, culture, Woodbury Common outlets
Day 4
Oct 14, Tue
Arrive NYC — Brooklyn Bridge, DUMBO, Lower East Side
Morning Amtrak from Boston. Check into a hostel in Williamsburg or Brooklyn — cheaper and more interesting than Manhattan. Walk the Brooklyn Bridge on foot (free, stunning). DUMBO neighbourhood for skyline views. Evening on the Lower East Side — dense bar and restaurant scene, very student-friendly prices.
Brooklyn BridgeDUMBO viewsLES nightlife
Day 5
Oct 15, Wed
Central Park, MoMA (free Fri → go Thursday eve), Columbia
Morning in Central Park — rent a bike or just walk. Afternoon at Columbia University's beautiful Morningside Heights campus (free to walk). Lunch in Harlem — best soul food in the city and very cheap. Evening: bouldering day pass at Cliffs of ID in Brooklyn — great way to meet locals and burn energy.
Central ParkColumbia uniHarlem foodBouldering
Day 6
Oct 16, Thu
Day 7
Oct 17, Fri
SoHo, High Line, MoMA free evening
Morning in SoHo — boutique browsing and street art. Walk the High Line (elevated park above the West Side, completely free, beautiful in October fall colours). Late afternoon: head to MoMA — free entry from 5:30pm on Fridays, arrive at 5pm to beat the queue. Dinner in Hell's Kitchen after.
High LineMoMA freeSoHo shopping
Amtrak · NYC → Washington D.C. · ~3 hrs · ~$30–60
Phase 3 — Washington D.C.
Oct 18–19 · 2 days · Free Smithsonians, monuments, Georgetown
Day 8
Oct 18, Sat
National Mall + monuments + Smithsonians
Amtrak from NYC. Drop bags at HI Washington D.C. hostel (excellent location near the Mall). Walk the National Mall — Lincoln Memorial, Vietnam Veterans Wall, Washington Monument. Smithsonians are all free and world-class: Air & Space is the obvious first stop (real Moon rocks, Wright Brothers plane). Dinner in Dupont Circle.
All freeAir & SpaceNational Mall
Day 9
Oct 19, Sun
Georgetown, Natural History Museum, Adams Morgan
Morning at Georgetown University's beautiful campus — the oldest Jesuit university in the US, free to walk. Natural History Museum after lunch (free — the Hope Diamond is genuinely impressive). Evening in Adams Morgan — D.C.'s most eclectic neighbourhood, great bars and live music, very international crowd.
Georgetown uniNatural HistoryAdams Morgan
Fly D.C. (DCA) → Miami (MIA) · ~3 hrs · ~$60–120 · book ahead
Phase 4 — Cocoa Beach surf
Oct 20–24 · 5 days · Fly into Miami, bus to Cocoa Beach
Day 10
Oct 20, Mon
Fly to Miami → bus to Cocoa Beach, first session
Morning flight from DCA to Miami. From Miami Airport, take the Greyhound or FlixBus to Cocoa Beach (~3.5 hrs, ~$25). Check into a beach motel near the pier. Rent a foamie from Ron Jon Surf Shop (open 24/7) and get a first feel for the water before sunset. Book a lesson for tomorrow morning.
First paddleRon Jon rental
Day 11
Oct 21, Tue
Surf lesson + afternoon free surf
2-hour beginner lesson with Cocoa Beach Surf School — sandy bottom, warm water, very forgiving. By the afternoon you'll be catching small waves solo. Evening on the pier for food and a cold drink watching the sunset over the lagoon side.
Surf lesson ~$70Beginner-friendly
Day 12
Oct 22, Wed
Morning surf + Kennedy Space Center
Early dawn session (waves glassier in the morning). Then take a rideshare or the Space Coast Area Transit bus to Kennedy Space Center — 10 min away. Shuttle Atlantis, the Saturn V hall, launch pad views. Student discount ~$65. Check if there's an upcoming SpaceX launch — watching one from the beach at night is free and unforgettable.
Kennedy Space CenterStudent discount
Day 13
Oct 23, Thu
New Smyrna Beach day trip + full surf day
Take the SunRail or a rideshare north to New Smyrna Beach (~45 min) — Florida's most consistent surf town, slightly different breaks from Cocoa. Great for building on your skills. Long beachside lunch, then back to Cocoa for an evening session. By now you should be reading waves and timing pop-ups comfortably.
New SmyrnaProgress day
Day 14
Oct 24, Fri
Final surf session + Canaveral National Seashore
Last morning surf at Cocoa. Afternoon at Canaveral National Seashore — 24 miles of undeveloped Atlantic coast, sea turtles nesting, zero crowds. Free with America the Beautiful pass ($20 student). Take the evening Greyhound or FlixBus to Miami (~3.5 hrs) — arrive late, check into a Wynwood or South Beach hostel.
Canaveral SeashoreFree with pass
Greyhound/FlixBus · Cocoa Beach → Miami · ~3.5 hrs · ~$25
Phase 5 — Miami + Everglades
Oct 25–27 · 3 days · Wynwood, Art Deco, airboat + paddling
Day 15
Oct 25, Sat
Day 16
Oct 26, Sun
Wynwood Walls + Little Havana + South Beach
Morning in Wynwood — the outdoor street art district is completely free and one of the best in the world. Grab a coffee at a Wynwood café. Afternoon in Little Havana: walk Calle Ocho, eat a Cuban sandwich, watch the domino players in Máximo Gómez Park. Evening stroll through the Art Deco Historic District on Ocean Drive — free self-guided walking tour, most beautiful at dusk.
Wynwood WallsLittle HavanaArt Deco District
Day 17
Oct 27, Mon
South Beach morning + fly home to Europe
Easy morning. Walk Ocean Drive one last time, swim if the flight allows. Miami connects directly to most European capitals — British Airways, Iberia, Lufthansa, and KLM all fly direct. Head to MIA airport by early afternoon for an evening departure, arriving in Europe Monday morning.
Departure dayMIA → Europe direct
Total days
17
Oct 11 → Oct 27
Surf days
5
Cocoa Beach
Est. daily spend
$80–110
Hostel + food + entry
No rental car
Trains
Amtrak + bus + rideshare
Key transports: Amtrak Northeast Regional Boston→NYC→D.C. (book 2–3 weeks ahead for cheapest fares). Budget flight D.C.→Miami (check Spirit, Frontier, or Southwest — often under $80). Greyhound/FlixBus for Cocoa Beach leg. Everglades tour with Miami pickup — book at least a week ahead for October weekends.
Student savings: America the Beautiful pass ($20) covers Canaveral Seashore. Amtrak student fares save 15%. MoMA free Fridays. All D.C. Smithsonians always free. HI USA hostels in Boston, NYC and D.C. are excellent value at $35–50/night.